Rescission

As kids playing ball, we learned about the “do-over” rule, pursuant to which the player in question was allowed to try again, without penalty, whatever it was that they were doing.  As we got older and our games changed, some of us learned about “taking a mulligan,” again without penalty.[i]  It may not come as a surprise, therefore, that a variation of this principle has found its way into the tax law.  It is called the “rescission doctrine,” and although it has been recognized for many years, it has been applied only in limited circumstances.

However, as we entered the final month of 2018, I found myself facing two situations in which the application of the rescission doctrine afforded the only solution for avoiding some adverse tax consequences.

Requirements

In general, the tax law treats each taxable year of a taxpayer as a “separate unit” for tax accounting purposes, and requires that one look at a particular transaction on an “annual basis,” using the facts as they exist at the end of the taxable year; in other words, one determines the tax consequences of the transaction at the end of the taxable year in which it occurred, without regard to events in subsequent years.

It is this basic principle of the annual accounting concept that underlies the rescission doctrine, and from which is derived the requirement, set forth below, that the rescission occur before the end of the taxable year in which the transaction took place.[ii]

According to the IRS,[iii] the legal concept of “rescission” (i) refers to the canceling or voiding of a contract or transaction, that (ii) has the effect of releasing the parties from further obligations to each other, and (iii) restores them to the relative positions they would have occupied had no contract been made or transaction completed.

A rescission may be effected by mutual agreement of the parties, by one of the parties declaring a rescission of the contract without the consent of the other (if sufficient grounds exist), or by applying to the court for a decree of rescission.

It is imperative, based on the annual accounting concept, that the rescission occur before the end of the taxable year in which the transaction took place.

If these requirements are satisfied, then the rescinded transaction is ignored for tax purposes – it is treated as though it never occurred.

Thus, a sale may be disregarded for federal income tax purposes where the sale is rescinded within the same taxable year that it occurred, and the parties are placed in the same positions as they were prior to the sale.[iv]

If the foregoing requirements are not satisfied, the rescission will not be respected, the tax consequences of the original transaction will have to be reported, and the “unwinding” of the original transaction will be analyzed as a separate event that generated its own tax consequences.

Why Rescind?

Whether the IRS will accept the parties’ claimed rescission of a particular transaction will, of course, depend upon the application of the above criteria to the facts and circumstances of the particular case.

Although the IRS has stated that it is studying the issue of rescission, and it has not issued letter rulings on the subject since 2012,[v] there are a number of earlier rulings to which taxpayers may turn for guidance regarding the IRS’s views.

These rulings illustrate some of the reasons for rescinding a transaction, as well as some of the means by which the rescission may be effectuated.

For example, the IRS has accepted the rescission of a transaction where the transaction was undertaken for a bona fide business reason, but without a proper understanding of the resulting tax consequences. When the parties realized what they had done, they sought to rescind the transaction and thereby avoid the unexpected adverse tax consequences;[vi] in one ruling, the parties not only rescinded the transaction, but then “did it over” so as to achieve the desired result.[vii]

The IRS has also looked favorably on the rescission of a transaction where, due to changed circumstances, the business purpose for the transaction no longer existed.[viii]

Thus, it appears that either a legitimate tax purpose or a bona fide business purpose may be the motivating factor for a rescission.

Restoring Pre-Transaction Status

Of the foregoing requirements for a successful rescission, the most difficult to satisfy may be the restoration of the parties to their pre-transaction status. The difficulty is compounded where events have occurred during the period preceding the rescission which may prevent, or which appear inconsistent with, an unwinding of the transaction.

Closely related to this requirement is the manner in which the rescission is effectuated; i.e., the steps that are taken to return the parties to their earlier positions.[ix]

For example, in one case, a taxpayer instructed their broker to sell $100,000 worth of a publicly-traded stock, but the broker instead sold 100,000 shares of such stock. In order to reverse this event, at the taxpayer’s direction, the broker reacquired over 96,000 shares in the same corporation. The court found that there was no rescission because the broker was not the buyer of the shares that were sold originally; that buyer was not returned to their original position.[x]

Common Representations

Regardless of the reasons for the rescission, the parties must be prepared to demonstrate that the requirements set forth above have been satisfied, including the requirement that the rescission restored, in all material respects, the legal and financial arrangements among the parties that would have existed had the transaction never occurred.

The taxpayers who were parties to the rescission transactions, for which the above-referenced rulings were requested, represented to the IRS – for the purpose of supporting their claim that they had been restored to their pre-transaction status – that, among other things: (i) no party took or would take any material position inconsistent with the position that would have existed had the rescinded transaction not occurred, (ii) no activities occurred prior to the rescission, or would occur after the rescission, that were materially inconsistent with the rescission, (iii) the purpose and effect of the rescission was to restore in all material respects the legal and financial arrangements among the parties that would have existed had the transaction never occurred, (iv) the legal and financial arrangements between the parties were identical in all material respects, from the date immediately before the rescinded transaction, to such arrangements that would have existed had the transaction not occurred, (v) the parties would take all reasonable actions necessary to effectuate those purposes, (vi) the parties would mutually agree to each of the steps to implement the rescission, (vii) all material items of income, deduction, gain, and loss of each party would be reflected on their respective income tax returns as if the transaction had not occurred, (viii) during the period between the transaction and the rescission, no material changes to the legal or financial relationships between parties occurred that would not have occurred if the transaction had not occurred, and (ix) the rescission would not involve any party that was not involved in the transaction.

Our Transactions

As indicated above, I was presented with two separate transactions that had to be rescinded in December of 2018. Both had occurred several months earlier during 2018.

In one transaction, a C corporation had distributed a minority interest in a subsidiary corporation to one of its shareholders in complete redemption of the shareholder’s stock in the distributing corporation. For some inexplicable reason, both parties believed that the distribution was not a taxable event to either of them; the corporation did not consider Sec. 311(b) and the former shareholder did not consider Sec. 302(a).[xi]

The redemption distribution was rescinded by having the “former” shareholder return to the distributing corporation the stock in the subsidiary and re-issuing stock in the distributing corporation to the shareholder. Between the date of the transaction and its rescission, no dividend distributions were made by either the corporation or the subsidiary, and no other event occurred that was inconsistent with the rescission of the redemption distribution.

In the second transaction, a partnership had contributed a wholly-owned disregarded entity (an LLC) to a newly-formed, and wholly-owned, C corporation subsidiary of the partnership. The partnership erroneously believed that it could obtain loans more easily through a corporation. The LLC membership interests were returned to the partnership in rescission of the contribution. As in the first case, there were no distributions by either the corporation or the LLC, nor did any other events occur that were inconsistent with the rescission.

A Useful Tool

In general, the best way to avoid a situation that calls for the rescission of a transaction is to refrain from undertaking the transaction without first vetting it in consultation with one’s tax and corporate advisers.

That being said, there will be instances in which unforeseen post-transaction events may defeat the purpose for the transaction, or may cause the transaction to be unduly expensive from an economic perspective.

In those cases, the taxpayer should bear in mind the possibility of rescinding the transaction, and they should be aware that they have only a limited period in which to exercise the rescission option.


[i] I am not a golfer, and never will be, though I do enjoy the dinners that follow many golf outings.

[ii] The rescission allows the taxpayer to view the transaction “using the facts as they exist at the end of the taxable year” – i.e., as though the transaction never occurred.

[iii] Rev. Rul. 80-58.

[iv] Stated simply: the property is returned to the seller and the cash is returned to the buyer.

[v] Rev. Proc. 2012-3. This no-ruling policy was reaffirmed in Rev. Proc. 2019-3.

[vi] See, e.g., PLR 200309009 (rescinding a distribution of property that would have disqualified taxpayers from the low income housing credit). Moreover, it does not appear to matter whether the transaction to be rescinded was undertaken between unrelated persons or within a group of related taxpayers.

[vii] PLR 201211009 (rescinded a stock sale that did not qualify for a Sec. 338(h)(10) election; substituted a new buyer for which the election would be available).

[viii] See, e.g., PLR 200923010 (rescinding a spin-off where changes in the business environment and in management subsequent to the distribution negated the benefit of the spin-off).

[ix] For example, how might taxpayers rescind a merger? If you’re facing this issue, feel free to contact me.

[x] Hutcheson v. Commissioner, T.C. Memo 1996-127.

[xi] Under IRC Sec. 311(b), a distribution of appreciated property by a corporation to its shareholders is treated as a sale of such property by the corporation. Under IRC Sec. 302(a) and 302(b)(3), the redemption of a shareholder’s entire equity in a corporation is treated as a sale of such equity by the shareholder.

Home for the Holidays?

Our last post considered the division of a business between family members as a means of preempting the adverse consequences that will often follow disagreements within the family as to the management or direction of the business. https://www.taxlawforchb.com/2018/12/business-purpose-and-dividing-the-family-corporation-think-before-you-let-it-rip/.

This week, as family members return to work – after having come together to celebrate the holidays and renew their commitment to one another – we turn to a recent IRS ruling that considered a situation that presents the proverbial “trap for the unwary,” and that arises more often than one might think in the context of a business that is plagued by family discord. https://www.irs.gov/pub/irs-wd/201850012.pdf.

Another Family Mess

Corp was formed by Dad, who elected to treat it as an S corporation for federal tax purposes.[i] Immediately prior to the events described in the ruling, Dad owned more than 50% of Corp’s non-voting shares, but less than 50% of Corp’s voting shares. Mom and Daughter owned the balance of Corp’s issued and outstanding shares.

Following Mom’s death, Daughter – who was also the CEO of the business – received a testamentary transfer of all of Mom’s voting shares, resulting in Daughter’s owning a majority of Corp’s voting shares.

For reasons not set forth in the ruling, Daughter subsequently terminated Dad’s employment with Corp. In response, Dad filed a lawsuit against Corp and Daughter (the “Litigation”) in which he alleged shareholder oppression and breach of fiduciary duties. Dad asked the court to enter an order requiring Daughter and/or Corp to buy Dad’s shares in Corp (“Dad’s Shares”), or an order requiring Dad to purchase Daughter’s shares.[ii]

Within three months after Dad initiated the Litigation, Corp and Daughter filed a notice under the Litigation (the “Election”) for Corp to purchase Dad’s Shares (the “Proposed Transaction”). Dad filed a motion to nullify the Election.[iii] The court denied Dad’s nullification motion, and ruled that the Election was valid.

Proposed Buyout

Dad died before the Litigation could be resolved and his shares in Corp purchased. His revocable trust (the “Trust”) – which became irrevocable upon his death – provided that Dad’s Shares would pass to Foundation, a tax-exempt charitable organization that was created and funded by Mom and Dad, and that was treated as a private foundation under the Code. [iv]

Pursuant to the terms of the Trust, the trustee had the power and authority to sell any stock held by or passing to the Trust, including Dad’s Shares.[v] However, because of the Litigation, Foundation did not receive Dad’s Shares from the Trust; nor could the Trust sell Dad’s Shares to anyone other than Corp during the Litigation.[vi]

The court in the Litigation was required by state law to determine the “fair value” of Dad’s Shares as of the date the Litigation was initiated, or such other date the court deemed appropriate. The Foundation represented to the IRS that the Litigation court could determine the fair value of Dad’s Shares to be less than their fair market value after marketability and control discounts were applied.[vii]

The administration of the Trust was overseen by a probate court, not the court in which the Litigation was ongoing. The probate court had the responsibility to ensure that Foundation received the full value of Dad’s Shares, and was required to approve the valuation of Dad’s Shares and the Proposed Transaction. According to the Foundation, if the probate court approved the Proposed Transaction, the Litigation court would honor the probate court’s decision.

Self-Dealing

The foregoing may seem innocuous to most persons – just a buyout of a decedent’s shares in a corporation. Fortunately, Foundation recognized that Corp’s redemption of Dad’s Shares could be treated as an act of “self-dealing” under the Code, which could in turn result in the imposition of certain penalties (i.e., excise taxes) on the “self-dealer” and on the “foundation managers.”

The Code imposes a tax on acts of self-dealing between a “disqualified person”[viii] and a private foundation.[ix] The tax with respect to any act of self-dealing is equal to 10% of the greater of the amount of money and the fair market value of the other property given or the amount of money and the fair market value of the other property received in the transaction.[x] In general, the tax imposed is paid by any disqualified person who participated in the act of self-dealing.

The term “self-dealing” includes any direct or indirect sale or exchange of property between a private foundation and a disqualified person. For purposes of this rule, it is immaterial whether the transaction results in a benefit or a detriment to the private foundation; the act itself is prohibited.

An “indirect sale” may include the sale by a decedent’s estate (or revocable trust),[xi] to a disqualified person, of property that would otherwise have passed from the estate to the private foundation pursuant to the terms of the decedent’s will; in other words, property in which the foundation had an expectancy.

However, the term “indirect self-dealing” does not include a transaction with respect to a private foundation’s interest or expectancy in property held by a revocable trust, including a trust which became irrevocable on a grantor’s death, and regardless of when title to the property vested under local law, provided the following conditions are satisfied:

(i) The trustee of the revocable trust has the power to sell the property;

(ii) The transaction is approved by a court having jurisdiction over the trust or over the private foundation;

(iii) The transaction occurs, in the case of a revocable trust, before the trust is considered a “non-exempt charitable trust”;[xii]

(iv) The trust receives an amount which equals or exceeds the fair market value of the foundation’s interest or expectancy in the property at the time of the transaction; and

(v) The transaction results in the foundation receiving an interest or expectancy at least as liquid as the one it gave up.[xiii]

The IRS Ruling

Foundation conceded that Dad was a disqualified person (a “substantial contributor”) as to Foundation while he was alive, having funded Foundation with Mom.[xiv] Daughter was a disqualified person as to Foundation because her father (a “member of her family”) was a substantial contributor to Foundation. Corp was also a disqualified person as to Foundation because Daughter owned more than 35% of Corp’s voting shares.[xv]

Because Corp was a disqualified person as to Foundation, and because of Foundation’s expectancy interest in receiving Dad’s Shares from the Trust, the proposed sale of Dad’s Shares by the Trust to Corp pursuant to the Litigation court’s order (the Proposed Transaction) could be an act of indirect self-dealing.

Foundation requested a ruling from the IRS that Corp’s purchase (i.e., redemption) of Dad’s Shares – which were held by the Trust – would satisfy the indirect self-dealing exception, described above, and would not be treated as an act of self-dealing for which a penalty could be imposed.

The IRS reviewed each of the requirements for the application of the exception.

First, a trustee must have the power to sell the trust’s property. Pursuant to the trust agreement that created Trust, Trust’s trustee had the power to sell any Trust assets, including Dad’s Shares. Thus, the Proposed Transaction met the first requirement.

Second, a court with jurisdiction over the trust must approve the transaction. Foundation sought, and was waiting to obtain, the approval of the Proposed Transaction from the probate court that had jurisdiction over, and was overseeing administration of, the Trust. Thus, the Proposed Transaction would meet the second requirement upon the Trust’s receipt of the probate court’s approval of the proposed sale.

Third, the Proposed Transaction must occur before the Trust became a non-exempt charitable trust. Foundation represented that because of the active and on-going status of the Litigation, the Trust’s trustees were, and would continue to be, unable to complete the ordinary duties of administration necessary for the settlement of Trust prior to the date of the sale of Dad’s Shares. Thus, the Trust would not be considered a non-exempt charitable trust prior to the date of the sale of Dad’s Shares; until then, the trustee would still be performing the ordinary duties of administration necessary for the settlement of the Trust.

In addition, before the sale of Dad’s Shares, the Trust will have made those other distributions required to be made from the Trust to any beneficiary other than Foundation, which would then be the sole remaining beneficiary.

Thus, if the Trust were not considered terminated for Federal income tax purposes prior to the Proposed Transaction, the Proposed Transaction would meet the third requirement.

Fourth, the Trust must receive an amount that equals or exceeds the fair market value of the foundation’s interest or expectancy in such property at the time of the transaction. The Litigation court was tasked with valuing Dad’s Shares. Foundation would endeavor to ensure that the Litigation court ordered the sale of Dad’s Shares to Corp at a price that was not less than the fair market value at the time of the Proposed Transaction. Thus, the Proposed Transaction would meet the fourth requirement if Dad’s Shares were sold to Corp at no less than their fair market value at the time of the transaction.

Fifth, the sale of Foundation’s interest or expectancy must result in its receiving an interest as liquid as the one that was given up. Pursuant to the trust agreement, Foundation had the expectancy of receiving Dad’s Shares, which were illiquid. Upon the completion of the Proposed Transaction, Foundation would receive the money that Corp paid Trust for Dad’s Shares. Thus, the Proposed Transaction would meet the fifth requirement if Foundation received the money proceeds from the Proposed Transaction.

Based on the foregoing, the IRS ruled that Corp’s purchase of Dad’s Shares held by the Trust would satisfy the “probate exception” from indirect self-dealing provided the following contingencies occurred:

  1. The probate court approved the Proposed Transaction;
  2. The Trust did not become a non-exempt charitable trust prior to the date of the sale of Dad’s Shares by the Trust; and
  3. The Trust received from the sale of Dad’s Shares to Corp an amount of cash or its equivalent that equaled or exceeded the fair market value of Corp’s Shares at the time of the transaction.

Trap for the Unwary?

Some of you may be thinking that the issue presented in the ruling discussed above, although somewhat interesting, is unlikely to arise with any regularity and, so, does not represent much of a trap for the unwary.[xvi]

I respectfully disagree. The fact pattern of the ruling is only one of many scenarios of indirect self-dealing that are encountered by advisers whose practice includes charitable planning for the owners of a closely held business.

There are two major factors that contribute to this reality: (i) the owner’s business will likely represent the principal asset of their estate, and (ii) the owner may have established a private foundation that they plan to fund at their demise (and thereby generate an estate tax deduction), either directly or through a split-interest trust.[xvii]

It is likely that the owner’s spouse, or some of their children, or perhaps a trust for their benefit, will be receiving an interest in the family business (an illiquid asset). It is also possible that the foundation will be funded with an interest in the business.

In these circumstances, the foundation may have to divest its interest in the family business in order to avoid the imposition of another private foundation excise tax (the one on “excess business holdings”).[xviii] Because of the limited market for such an interest, the foundation (or the owner’s estate or revocable trust) will probably have to sell its interest to the business itself (a redemption, as in the ruling above) or to another owner – each of which may be a disqualified person, thereby raising the issue of self-dealing. https://www.taxlawforchb.com/2018/10/private-foundations-and-business-ownership-a-new-day/.

In other circumstances, the divergent interests of the foundation to be funded, on the one hand, and of the individual beneficiaries of the owner’s estate or trust, on the other, may require that the foundation’s interest in the business be eliminated. For example, the foundation will need liquidity in order to engage in any charitable grant-making, while the other owners may prefer that the business reinvest its profits so as to expand the business; the foundation may prefer not to receive shares of stock in an S corporation, the ownership of which would result in the imposition of unrelated business income tax;[xix] or the foundation may be managed by individuals other than those operating the business, thereby setting the stage for a shareholder dispute as in the above ruling.

Bottom line:  It behooves the owners of the closely held business to consider these issues well before they arise. In many cases, it will be difficult to avoid them entirely, but the relevant parties should plan a course of action that is to be implemented after the demise of an owner.[xx] In this way, they may be able to avoid the personal, financial, and business disputes that may otherwise arise.

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[i] IRC Sec. 1361; IRC Sec. 1362.

[ii] The ruling does not disclose the jurisdiction under the laws of which Corp was formed.

In New York, the holders of shares representing 20% or more of the votes of all outstanding shares of a corporation may present a petition of dissolution on the ground that the directors or those in control of the corporation are guilty of oppressive acts toward the complaining shareholders. In determining whether to proceed with involuntary dissolution, the court must take into account whether liquidation of the corporation is the only feasible means by which the petitioners may reasonably expect to obtain a “fair return” on their investment. BCL 1104-a. This typically involves the valuation and buyout of the petitioners’ shares. However, the other shareholder(s) or the corporation may also elect to purchase the shares owned by the petitioners at fair value. BCL 1118. “Fair value” is not necessarily the same as “fair market value.” See Friedman v. Beway Realty Corp. 87 N.Y.2d 161 (1995).

[iii] Go figure. If the goal was to be bought out, congratulations. Why fight it? Or was Dad concerned that Daughter would render Corp unable to buy him out and, so, he wanted to pursue his own remedies?

[iv] Exempt from federal income tax under Sec. 501(a) of the Code, as an organization described in Sec. 501(c)(3) of the Code (educational, religious, scientific, and charitable purposes); a “private foundation” in that it did not receive financial support from the “general public.”

[v] Although a decedent should fund their revocable trust to the fullest extent possible prior to their demise, it is often the case that they forget to transfer – or that they intentionally retain direct ownership of – an asset, which thereby becomes part of their probate estate. In that case, the decedent’s last will and testament typically provides that the probate estate shall “pour over” into the now irrevocable trust – which acts as a “will substitute” – to be disposed of in accordance with the terms of the trust.

[vi] It should be noted that, effective for tax years beginning after December 31, 1997, certain tax-exempt organizations became eligible to own shares of stock in an S corporation; however, a qualifying organization’s share of S corporation income is treated as unrelated business income. IRC Sec. 1361(c)(6) and Sec. 512(e).

[vii] In general, “fair market value” as of the date of a decedent’s death is the value at which the property included in the decedent’s gross estate must be reported on their estate tax return. Reg. Sec. 20.2031-1(b).

[viii] The term “disqualified person” means, in part, with respect to a private foundation, a person who is:

(A) a “substantial contributor” to the foundation,

(B) a “foundation manager”,

(C) an owner of more than 20% of:

(i) the total combined voting power of a corporation,

(ii) the profits interest of a partnership, or

(iii) the beneficial interest of a trust or unincorporated enterprise, which is a substantial contributor to the foundation,

(D) a “member of the family” of any individual described in subparagraph (A), (B) or (C), or

(E) a corporation of which persons described in subparagraph (A), (B), (C), or (D) own more than 35% of the total combined voting power.

The term “members of the family” with respect to any person who is a disqualified person includes the individual’s spouse, ancestors, children, grandchildren, great grandchildren, and the spouses of children, grandchildren, and great grandchildren. IRC Sec. 4946.

[ix] The Code authorizes the imposition of certain excise taxes on a private foundation, on those who are disqualified persons with respect to such foundation, and on the foundation’s managers. These taxes are intended to modify the behavior of these parties – who are not otherwise dependent upon the public for financial support – by encouraging certain activities (e.g., expenditures for charitable purposes) and discouraging others (such as self-dealing).

[x] https://www.law.cornell.edu/uscode/text/26/4941

[xi] See EN iv, above.

[xii] See IRC Sec. 4947, which treats such a trust as a private foundation that is subject to all of the private foundation requirements.

A revocable trust that becomes irrevocable upon the death of the decedent-grantor, from which the trustee is required to distribute all of the net assets in trust for or free of trust to charitable beneficiaries, is not considered a charitable trust under section 4947(a)(1) for a reasonable period of settlement after becoming irrevocable. After that period, the trust is considered a charitable trust under section 4947(a)(1). The term “reasonable period of settlement” means that period reasonably required (or if shorter, actually required) by the trustee to perform the ordinary duties of administration necessary for the settlement of the trust. These duties include, for example, the collection of assets, the payment of debts, taxes, and distributions, and the determination of the rights of the subsequent beneficiaries.

[xiii] Reg. Sec. 53.4941(d)-1(b)(3); the so-called “probate exception.” https://www.law.cornell.edu/cfr/text/26/53.4941%28d%29-1 This exception had its genesis in the IRS’s recognition that a private foundation generally needs liquidity in order to carry out its charitable grant-making mission. With the appropriate safeguards (supervision by a probate court) to ensure that the foundation receives fair market value and attains the requisite liquidity, the act of self-dealing presented by the foundation’s sale of an interest in a closely held business may be forgiven.

[xiv] Interestingly, a substantial contributor’s status as such does not terminate upon their death; thus, a member of their family also remains a disqualified person.

[xv] See EN vii.

[xvi] A group of individuals to which the reader no longer belongs.

[xvii] For example, a charitable lead trust or a charitable remainder trust. IRC Sec. 2055(e). https://www.law.cornell.edu/uscode/text/26/2055.

[xviii] IRC Sec. 4943. https://www.law.cornell.edu/uscode/text/26/4943.

[xix] Taxable at 21% – as opposed to a 1% or 2% tax on investment income under IRC Sec. 4940 – and perhaps without a distribution from the corporation with which to pay the tax.

[xx] For example, corporate-owned life insurance to fund the buyout of the foundation’s interest, or the granting of options to family members to acquire the foundation’s interest.

I am excited to announce that my June 18, 2018 blog post “S Corps, CFCs & The Tax Cuts & Jobs Act” has been published as Chapter 6 in The Tax Cuts and Jobs Act: A Guide for Practitioners e-book. The chapter discusses the Tax Cuts & Jobs Act’s changes to the taxation of business income arising from the foreign activities of U.S. persons – and what that means for the increasing number of closely-held U.S. businesses who have established operations overseas.

The e-book was produced by the National Association of Enrolled Agents (NAEA). If you are interested in purchasing a copy, please click here.

Sibling Rivalry

Many of us encounter family-owned corporations in which the founder’s children are engaged in the business to varying degrees. They may even own shares in the corporation, typically having received them as gifts from their parents.[i] These situations may develop in such a way that they present difficult succession planning considerations for the business.

It may be that two or more siblings actively participate in the business. The more capable among them may aspire to lead the corporation after their parents have retired or passed away. At some point, their competing goals, personalities, or divergent management styles may generate enough friction between the siblings, and within the corporation, so as to jeopardize the continued well-being of the business.[ii]

Alternatively, the siblings may be interested in different parts of the corporation’s business. Each sibling may be responsible for a different line of business; for example, a different product, service, or geographic region. Their differing interests may lead to disagreements as to the allocation of resources and the prioritization of goals.

The dispute between the siblings will sometimes fester – and their relationship will deteriorate – to the point where litigation, along with its attendant costs and disruption of the business, are inevitable.[iii]

Dividing the Business?

In that case, it may still be possible to de-escalate the situation, and avoid further bloodshed[iv] – not to mention expense and loss of revenue – if it can be demonstrated to the feuding siblings that the business may be divided between them on a tax-efficient (i.e., economical) basis, especially where they have already incurred significant legal costs in trying to divorce themselves from one another.

Of course, it would be preferable (and less expensive) if the siblings could separate from one another without first resorting to litigation, although it is often the case that such litigation becomes the impetus for a more constructive approach toward the settlement of the parties’ disputes.

Indeed, if the parents could reasonably foresee the risk of serious disagreement among their successors in the business, they may decide to explore with their tax and corporate advisers whether the business can be divided among the kids while the parents are still alive and before the business suffers the adverse consequences that typically accompany such infighting.[v]

There are two basic forms of corporate division by which two or more shareholders may go their separate ways. In the “split-off” form of division, the parent corporation distributes all of its shares in a subsidiary corporation[vi] to one of more of its shareholders in a complete redemption of their shares in the parent corporation, leaving the parent corporation in the hands of its remaining shareholders. In the “split-up” form of division, the parent corporation distributes all its shares in at least two subsidiary corporations to at least two different sets of shareholders in a complete liquidation of the parent corporation.

There is also a third form of division – a “spin-off” – by which a parent corporation may distribute the stock of its subsidiary corporation to at least some of its shareholders by way of a “dividend,” thereby changing the form of the relationship to that of brother-sister corporations with some degree of common ownership.[vii]

“Tax-Free” Divisions

Whatever form of division is selected, there are numerous requirements that must be satisfied in order for the division to receive favorable tax treatment. In general,

    1. the distributing parent corporation must distribute to some or all of its shareholders all of the stock of a subsidiary corporation[viii] controlled by the parent,
    2. the distributing corporation and the subsidiary corporation must each be engaged in the “active conduct of a trade or business” immediately after the distribution,[ix]
    3. neither active trade or business was acquired in a taxable transaction during the five-year period preceding the distribution,
    4. there is a real and substantial business purpose for the distribution that cannot be accomplished by another nontaxable alternative which is neither impractical, nor unduly expensive,
    5. the transaction must not be used principally as a “device” for the distribution of the earnings and profits of either the distributing corporation or the subsidiary corporation,
    6. the distributee shareholders did not acquire their shares in the distributing parent corporation by “purchase” during the five-year period ending on the date of the distribution; and
    7. the distribution is not made pursuant to a plan by which at least 50% of parent or of the former subsidiary is acquired by third parties.[x]

In general, if these requirements are satisfied, (1) the shareholders will not recognize gain or loss upon the receipt of the subsidiary stock, (2) the distributing corporation will not recognize gain or loss upon the distribution of the subsidiary stock to the shareholders, (3) the aggregate basis of the subsidiary stock received by each shareholder immediately after the distribution will equal the shareholder’s aggregate basis in the distributing corporation stock surrendered in the distribution, and (4) the holding period of the subsidiary stock received by each shareholder will include the holding period of the stock in the distributing corporation with respect to which the distribution of the subsidiary stock is made.[xi]

If these criteria are not met, then the distributing corporation will be treated as having sold the distributed property for an amount equal to the property’s fair market value, it will have to recognize the gain realized on deemed sale of the property, and it will be taxed thereon. The shareholders will be taxed on their receipt of the property distributed by the corporation, either as a dividend of an amount equal to the fair market value of such property, or as a payment of the same amount in exchange for their shares of stock in the distributing corporation.

In order to avoid the adverse tax consequences described immediately above, it is imperative that each of the requirements for a “tax-free” division of the distributing corporation be satisfied.

Business Purpose

In the context of a family-owned corporation, the requirement that the distribution be carried out for a real and substantial corporate business purpose may present a unique challenge, at least where the ostensible business purpose for the division of the corporation is to enable competing siblings – who would otherwise succeed to the ownership and management of the corporation – to go their separate ways.

Specifically, it may be difficult in that case, depending upon the facts and circumstances, to distinguish between a corporate business purpose, on the one hand, and a personal non-business purpose of the shareholders, on the other.

That being said, it should be noted that one of the most commonly relied upon corporate business purposes for the distribution of a subsidiary as part of a corporate division is that it will enhance the success of each corporation’s business by enabling a significant shareholder or shareholder group to concentrate on a particular line of business, and to thereby resolve management or other problems that arise, or are exacerbated, by the operation of different businesses within a single corporation.[xii]

However, the IRS has long recognized the potential, in the context of a family-owned corporation, for such a distribution to also facilitate the personal planning (such as estate planning or gifts) of a shareholder.

In order to better understand how to prepare for an IRS challenge on such grounds,[xiii] the parties and their advisers will need to familiarize themselves, in the first instance, with the published guidance provided by the IRS itself, including the two rulings described below.[xiv]

Scenario One

The IRS once considered the case of a corporation (“Corp”) that operated an automobile dealership.[xv] Its franchise for the sale of automobiles was in Dad’s name; the franchise could not be held by the corporation, was renewable periodically, and was not transferable by inheritance or otherwise.

Dad managed Corp and owned a majority of its stock. He was elderly, and the Corp stock constituted the bulk of his estate. The balance of Corp’s stock was held equally by Dad’s five daughters, only three of whom were active in the business.

Corp’s wholly-owned subsidiary (“Sub”) was engaged in the business of renting automobiles.

The automobile manufacturer did not permit the granting or continuing of a franchise where there were inactive shareholders in the corporation unless an active majority shareholder held the franchise. Alternatively, the manufacturer permitted the granting or continuing of a franchise where there was no majority shareholder, provided the shareholders were few in number and all were active in the business.

The IRS noted that, upon Dad’s death or retirement, the present stock ownership of Corp, with proportionate bequests or gifts to Dad’s daughters, would preclude satisfaction of the active-shareholder criteria described above for the purpose of renewing the franchise.

In order to ensure that its remaining shareholders would be able to renew the franchise upon Dad’s death or retirement under the alternate conditions of the franchise policy – without chancing a potential interruption in the continuity of, or even the loss of, the franchise which might occur if nothing was done until after Dad’s departure – Corp distributed 75% of Sub’s stock to the two inactive-daughter shareholders in exchange for all of their stock in Corp. The remaining 25% of Sub’s stock was distributed to Dad in exchange for Corp shares of equal value.

Dad intended that, upon his death, the inactive-daughter shareholders would receive their inheritance in Sub stock (and assets other than Corp stock), while the active-daughter shareholders would receive his shares of Corp stock.

The IRS determined that distribution of the Sub stock to Dad furthered the objective of enabling Corp’s active-daughter shareholders to retain the franchise by increasing their percentage of ownership in Corp, and by providing Dad with Sub stock which he could bequeath or gift to the inactive-daughter shareholders, leaving his remaining Corp stock available for transfer to the active-daughter shareholders.

The IRS also found that Dad’s age presented an immediate problem, [xvi] and that the distribution of Sub’s stock was germane to the continuation of Corp’s business in the reasonably foreseeable future. Execution of the plan, therefore, was directly related to the retention of a franchise vital to Corp’s business and would forestall an impending disruption to such business by reason of the current active family group being unable to renew the corporation’s franchise upon Dad’s death or retirement.

Scenario Two

In another ruling[xvii] the IRS considered a corporation (“Corp”) the stock of which was owned equally by Parents, Son, and Daughter. Although Parents participated in some major management decisions, most of the management, and all of the operational activities, were performed by Son and Daughter.

Son and Daughter disagreed over the future direction of Corp’s business. Son wished to expand one line of business, but Daughter was opposed because this would require substantial borrowing by Corp. Daughter preferred to sell that line of business and concentrate on Corp’s other business. Despite the disagreement, the two siblings cooperated on the operation of the business in its historical manner without disruption. Nevertheless, it prevented each sibling from developing, as he or she saw fit, the business in which he or she was most interested.

Parents remained neutral on the disagreement between their children. However, because of the disagreement, Parents preferred to bequeath separate interests in the business to their children.

To enable Son and Daughter each to devote their undivided attention, and apply a consistent business strategy, to the line of business in which he or she was most interested, and to further Parents’ estate planning goals, Corp contributed one of its lines of business to a newly-formed and wholly-owned subsidiary corporation (“Sub”), and distributed 50% of Sub’s stock to Son in exchange for all of his stock in Corp. Corp then distributed the remaining Sub stock to Parents in exchange for half of their Corp stock.

Going forward, Daughter would manage and operate Corp and have no stock interest in Sub, and Son would manage and operate Sub and have no stock interest in Corp. Parents would also amend their wills to provide that Son and Daughter would inherit stock only in Sub and Corp, respectively. After the distribution, Parents would still own 50% of the outstanding stock of Corp and of Sub, and would continue to participate in certain management decisions related to the business of each corporation.

The IRS determined that the distribution would eliminate the disagreement between Son and Daughter over the future direction of Corp’s business, and would allow each sibling to devote their undivided attention to the line of business in which they were most interested, with the expectation that each business would benefit. Therefore, although the distribution was intended, in part, to further the personal estate planning of Parents and to promote family harmony, it was motivated in substantial part by a real and substantial non-tax purpose that was germane to the business of Corp. Thus, the business purpose requirement was satisfied.

Guideposts?

It is clear that the division of a family-owned corporation may be effectuated for the purpose of resolving or eliminating management disputes among siblings. It may also be undertaken for the purpose of staving off reasonably foreseeable or imminent harm to a business that is attributable to the composition of its shareholders.

Moreover, the division may be accomplished on a tax-efficient basis, provided the criteria set forth above are satisfied, including the requirement that the distribution by the family-owned corporation of the stock in its subsidiary be motivated in whole or in substantial part by a business purpose, as distinguished from a nonbusiness purpose. Specifically, can the parties to the transaction demonstrate that there is an immediate business reason for the distribution?

In each of the two scenarios described above, there were “clear and present” reasons for the divisive distribution; the failure to act would have resulted in significant harm to the business of either or both of the corporations. The difficulties anticipated were not remote, and the resulting harm to the business was not conjectural.

However, one can imagine a situation in which the immediacy of the stated business purpose may not be obvious to an outsider, or where the severity of the consequences to be avoided is not easily determinable. In the context of a family-owned corporation, the presence of these factors – a remote risk or an ill-defined harm – may call into question whether the distribution is motivated in substantial part by a bona fide business purpose; the failure to establish such a purpose may cause the corporation’s distribution of its subsidiary to be taxable.

For that reason, if a “divisive” transaction is to withstand IRS scrutiny, the closely held corporations and the shareholders that are parties to the transaction must be prepared to substantiate the corporate business purposes which they claim motivated the transaction in whole or substantial part. They must be ready to present documentation that provides complete factual support for the stated business purpose, that describes in detail the problems associated with the current corporate structure, and that demonstrates why the distribution will lessen or eliminate those problems. As always, this body of “evidence” should be compiled contemporaneously with the events that culminate in the division of the corporation – not after the IRS has selected the parties for audit.


[i] Or as partial gifts (as in the case of a bargain sale); rarely in exchange for capital contributions, or as compensation.

[ii] Regardless of the size of the social unit, be it a family, a business, or even a nation, the results can be severe. History gives us many examples. The Old Testament alone is full of references to the consequences of sibling rivalry: Cain and Abel, Isaac and Ismael, Esau and Jacob, then down to the sons of Solomon (ironic that the kingdom of the man who rendered the Judgment of Solomon – “suggesting” that a baby be split in half in order to ascertain its true mother – should be split in two after his death).

[iii] Forget about holidays and family gatherings – Thanksgiving is never the same.

[iv] Tax lawyers enjoy the figurative use of language because we are so rarely afforded the opportunity. Our exchanges (pun intended) with others are so often limited to words such as “gain, loss, deferral, recognition . . .” and, of course, “tax.”

[v] Too often, the parents don’t want to deal with the obviously gestating issues within their family. They tell themselves that the kids will learn to work together, or they will deny the problem altogether, leaving it for the kids to resolve it after the parents are gone. We know how that usually works out. Not the sort of legacy for which most folks yearn.

[vi] The subsidiary may be formed just prior to the distribution; for example, the parent corporation may contribute one line of business to a newly-formed subsidiary as a prelude to the distribution of the stock of the subsidiary, as described above; or it may be an existing entity that is engaged in a trade or business that is related to, or completely different from, the business conducted by the distributing corporation (or by its remaining subsidiary).

[vii] This is likely the form of division that parents would undertake in preparation for transferring different parts of their business to different children.

[viii] Often referred to as the “controlled corporation.”

[ix] I.e., a “trade or business” that has been “actively conducted” throughout the 5-year period ending on the date of the distribution. This requirement has spawned some litigation between taxpayers and the IRS.

[x] Underlying the divisive reorganization provisions of the Code is the principle that it would be inappropriate to tax a transaction as a result of which the participating taxpayers – the corporations and their shareholders – have not sufficiently changed the nature of their investment in the corporation’s assets or business, provided the transaction is motivated by a substantial non-tax business purpose.

[xi] IRC Sec. 355, IRC Sec. 368(a)(1)(D).

[xii] For example, in Example (2) of Reg. Sec. 1.355-2(b)(5), Corporation X is engaged in two businesses: the manufacture and sale of furniture and the sale of jewelry. The businesses are of equal value. The outstanding stock of X is owned equally by unrelated individuals A and B. A is more interested in the furniture business, while B is more interested in the jewelry business. A and B decide to split up the businesses and go their separate ways. A and B expect that the operations of each business will be enhanced by the separation because each shareholder will be able to devote his undivided attention to the business in which he is more interested and more proficient. Accordingly, X transfers the jewelry business to new corporation Y and distributes the stock of Y to B in exchange for all of B’s stock in X. The example concludes that the distribution is carried out for a corporate business purpose, notwithstanding that it is also carried out in part for shareholder purposes.

[xiii] An exercise that should be completed before the transaction is even undertaken.

[xiv] Although the IRS’s public pronouncements are generally limited to the application of the law to a specific set of facts, they nevertheless provide a useful glimpse into the IRS’s thinking on the issues examined therein.

[xv] Rev. Rul. 75-337.

[xvi] In contrast, the IRS described a decision where the court held, under a plan to avoid any remote possibility of interference in a business by future sons-in-law, that the spin-off had no immediate business reason, involved a personal motive, and had as its primary purpose a desire to make bequests in accordance with an estate plan. The difficulties anticipated were so remote that they might never come to pass. The daughters might never marry – thus eliminating completely any cause to worry about business interference by future sons-in-law. There was, at best, “only an envisaged possibility of future debilitating nepotism,” and the effect on the business was conjectural. Rafferty v. Commissioner, 452 F.2d 767 (1st Cir. 1971).

[xvii] Rev. Rul. 2003-52.

The Joy – and Tax Benefits – of Gifting

As we enter the “season of giving” and the end of yet another year, the thoughts of many tax advisers turn to . . . tax planning.(i) In keeping with the spirit of the season, an adviser may suggest that a client with a closely held business consider making a gift of equity in the business to the owner’s family or to a trust for their benefit.(ii)

Of course, annual exclusion gifts(iii) are standard fare and, over the course of several years, may result in the transfer of a not insignificant portion of the equity in a business.

However, the adviser may also recommend that the client consider making larger gifts, thereby utilizing a portion of their “unified” gift-and-estate tax exemption amount during their lifetime. Such a gift, the adviser will explain, may remove from the owner’s gross estate not only the current value of the transferred business interests, but also the future appreciation thereon.(iv)

The client and the adviser may then discuss the “size” of the gift and the valuation of the business interests to be gifted, including the application of discounts for lack of control and lack of marketability. At this point, the adviser may have to curb the client’s enthusiasm somewhat by reminding them that the IRS is still skeptical of certain valuation discounts, and that an adjustment in the valuation of a gifted business interest may result in a gift tax liability.

The key, the adviser will continue, is to remove as much value from the reach of the estate tax as reasonably possible, and without incurring a gift tax liability – by utilizing the client’s remaining exemption amount – while also leaving a portion of such exemption amount as a “cushion” in the event the IRS successfully challenges the client’s valuation.

“Ask and Ye Shall Receive”(v)

Enter the 2017 Tax Cuts and Jobs Act (the “Act”).(vi) Call it an early present for the 2018 gifting season.

One of the key features of the Act was the doubling of the federal estate and gift tax exemption for U.S. decedents dying, and for gifts made by U.S. individuals,(vii) after December 31, 2017, and before January 1, 2026.

This was accomplished by increasing the basic exemption amount (“BEA”) from $5 million to $10 million. Because the exemption amount is indexed for inflation (beginning with 2012), this provision resulted in an exemption amount of $11.18 million for 2018, and this amount will be increased to $11.4 million in 2019.(viii)

Exemption Amount in a Unified System

You will recall that the exemption amount is available with respect to taxable transfers made by an individual taxpayer either during their life (by gift) or at their death – in other words, the gift tax and the estate tax share a common exemption amount.(x)

The gift tax is imposed upon the taxable gifts made by an individual taxpayer during the taxable year (the “current taxable year”). The gift tax for the current taxable year is determined by: (1) computing a “total tentative tax” on the combined amount of all taxable gifts made by the taxpayer for the current and all prior years using the common gift tax and estate tax rate table; (2) computing a tentative tax only on all prior-year gifts; (3) subtracting the tentative tax on prior-year gifts from the tentative tax computed for all years to arrive at the portion of the total tentative tax attributable to current-year gifts; and, finally, (4) subtracting the amount of the taxpayer’s unified credit (derived from the unused exemption amount) not consumed by prior-year gifts.

Thus, taxable gift transfers(xi) that do not exceed a taxpayer’s exemption amount are not subject to gift tax. However, any part of the taxpayer’s exemption amount that is used during their life to offset taxable gifts reduces the amount of exemption that remains available at their death to offset the value of their taxable estate.(xii)

From a mechanical perspective, this “unified” relationship between the two taxes is expressed as follows:

• the deceased taxpayer’s taxable estate is combined with the value of any taxable gifts made by the taxpayer during their life;
• the estate tax rate is then applied to determine a “tentative” estate tax;
• the portion of this tentative estate tax that is attributable to lifetime gifts made by the deceased taxpayer is then subtracted from the tentative estate tax to determine the “gross estate tax” – i.e., the amount of estate tax before considering available credits, the most important of which is the so-called “unified credit”; and
• credits are subtracted to determine the estate tax liability.

This method of computation is designed to ensure that a taxpayer only gets one run up through the rate brackets for all lifetime gifts and transfers at death.(xiii)

What Happens After 2025?(xvi)

However, given the temporary nature of the increased exemption amount provided by the Act, many advisers questioned whether the cumulative nature of the gift and estate tax computations, as described above, would result in inconsistent tax treatment, or even double taxation, of certain transfers.

To its credit,(xv) Congress foresaw some of these issues and directed the IRS to prescribe regulations regarding the computation of the estate tax that would address any differences between the exemption amounts in effect: (i) at the time of a taxpayer’s death and (ii) at the time of any gifts made by the taxpayer.

Pending the issuance of this guidance – and pending the confirmation of what many advisers believed was an expression of Congressional intent not to punish individuals who make gifts using the increased exemption amount – many taxpayers decided not to take immediate advantage of the greatly increased exemption amount, lest they suffer any of the consequences referred to above.

Proposed Regulations

In response to Congress’s directive, however, the IRS proposed regulations last week that should allay the concerns of most taxpayers,(xvi) which in turn should smooth the way to increased gifting and other transfers that involve an initial or partial gift.

In describing the proposed regulations, the IRS identified and analyzed several situations that could have created unintended problems for a taxpayer, though it concluded that the existing methodology for determining the taxpayer’s gift and estate tax liabilities provided adequate protection against such problems:

Whether a taxpayer’s post-2017 increased exemption amount would be reduced by pre-2018 gifts on which gift tax was paid. If the taxpayer makes additional gifts during the post-2017 increased exemption period, would the gift tax computation apply the increased exemption to the pre-2018 gifts, thus reducing the exemption otherwise available to shelter gifts made during the post-2017 period, effectively allocating credit to a gift on which gift tax in fact was already paid, and denying the taxpayer the full benefit of the increased exemption amount for transfers made during the increased exemption period?

Whether the increased exemption amount available during the increased exemption period would be reduced by pre-2018 gifts on which gift tax was paid. If the taxpayer died during the increased exemption period, would the estate tax computation apply the increased exemption to the pre-2018 gifts, thus reducing the exemption otherwise available against the estate tax during the increased exemption period and, in effect, allocating credit to a gift on which gift tax was paid?

Whether the gift tax on a post-2025 transfer would be inflated by the theoretical gift tax on a gift made during the increased exemption period that was sheltered from gift tax when made. Would the gift tax determination on the post-2025 gift treat the gifts made during the increased exemption period as gifts that were not sheltered from gift tax given that the post-2025 gift tax determination is based on the exemption amount then in effect, rather than on the increased exemption amount, thereby increasing the gift on the later transfer and effectively subjecting the earlier gift to tax even though it was exempt from gift tax when made?

With respect to the first two situations described above, the IRS determined that the current methodology by which a taxpayer’s gift and estate tax liabilities are determined ensures that the increased exemption will not be reduced by a prior gift on which gift tax was paid. As to the third situation, the IRS concluded that the current methodology ensures that the tax on the current gift will not be improperly inflated.

New Regulations

However, there was one situation in which the IRS concluded that the methodology for computing the estate tax would, in effect, retroactively eliminate the benefit of the increased exemption that was available for gifts made during the increased exemption period.

Specifically, the IRS considered whether, for estate tax purposes, a gift made by a taxpayer during the increased exemption period, and that was sheltered from gift tax by the increased exemption available during such period, would inflate the taxpayer’s post-2025 estate tax liability.

The IRS determined that this result would follow if the estate tax computation failed to treat such gifts as sheltered from gift tax.

Under the current methodology, the estate tax computation treats the gifts made during the increased exemption period as taxable gifts not sheltered from gift tax by the increased exemption amount, given that the post-2025 estate tax computation is based on the exemption in effect at the decedent’s death rather than the exemption in effect on the date of the gifts.

For example, if a taxpayer made a gift of $11 million in 2018, (when the BEA is $10 million; a taxable gift of $1 million), then dies in 2026 with a taxable estate of $4 million (when the BEA is $5 million), the federal estate tax would be approximately $3,600,000: 40% estate tax on $9 million – specifically, the sum of the $4 million taxable estate plus $5 million of the 2018 gift that was sheltered from gift tax by the increased exemption. This, in effect, would impose estate tax on the portion of the 2018 gift that was sheltered from gift tax by the increased exemption allowable at that time.

Alternatively, what if the taxpayer dies in 2026 with no taxable estate? The taxpayer’s estate tax would be approximately $2 million, which is equal to a 40% tax on $5 million – the amount by which, after taking into account the $1 million portion of the 2018 gift on which gift tax was paid, the 2018 gift exceeded the BEA at death. This, in effect, would impose estate tax on the portion of the 2018 gift that was sheltered from the gift tax by the excess of the 2018 exemption over the 2026 exemption.

The IRS determined that this problem arises from the interplay between the differing exemption amounts that are taken into account in the computation of the estate tax.

Specifically, after first determining the tentative tax on the sum of a decedent’s taxable estate and their adjusted taxable gifts,(xvii)

i. the decedent’s estate must then determine the credit against gift taxes for all prior taxable gifts, using the exemption amount allowable on the dates of the gifts (the credit itself is determined using date of death tax rates);
ii. the gift tax payable is then subtracted from the tentative tax, the result being the net tentative estate tax; and
iii. the estate next determines a credit based on the exemption amount as in effect on the date of the decedent’s death, which is then applied to reduce the net tentative estate tax.

If this credit (based on the exemption amount at the date of death) is less than the credit allowable for the decedent’s taxable gifts (using the date of gift exemption amount), the effect is to increase the estate tax by the difference between the two credit amounts.

In this circumstance, the statutory requirements for computing the estate tax have the effect of imposing an estate tax on gifts made during the increased exemption period that were sheltered from gift tax by the increased exemption amount in effect when the gifts were made.

In order to address this unintended result, the proposed regulations would add a special computation rule in cases where (i) the portion of the credit as of the decedent’s date of death that is based on the exemption is less than (ii) the sum of the credits attributable to the exemption allowable in computing the gift tax payable. In that case, the portion of the credit against the net tentative estate tax that is attributable to the exemption amount would be based upon the greater of those two credit amounts.

Specifically, if the total amount allowable as a credit, to the extent based solely on the BEA, in computing the gift tax payable on the decedent’s post-1976 taxable gifts, exceeds the credit amount based solely on the BEA in effect at the date of death, the credit against the net tentative estate tax would be based on the larger BEA.

For example, if a decedent made cumulative taxable gifts of $9 million, all of which were sheltered from gift tax by a BEA of $10 million applicable on the dates of the gifts,(xviii) and if the decedent died after 2025 when the BEA was $5 million, the credit to be applied in computing the estate tax would be based upon the $9 million of exemption amount that was used to compute the gift tax payable.

Time to Act?

By addressing the unintended results presented in the situation described – a gift made the decedent during the increased exemption period, followed by the death of the decedent after the end of such period – the proposed regulations ensure that the decedent’s estate will not be inappropriately taxed with respect to the gift.

With this “certainty,” an individual business owner who has been thinking about gifting a substantial interest in their business may want to accelerate their gift planning. As an additional incentive, the owner need only look at the results of the mid-term elections, which do not bode well for the future of the increased exemption amount. In other words, it may behoove the owner to treat 2020 (rather than 2025) as the final year for which the increased exemption amount will be available, and to plan accordingly. Those owners who decide to take advantage of the increased exemption amount by making gifts should consider how they may best leverage it.

And as always, tax savings, estate planning, and gifting strategies have to be considered in light of what is best for the business and what the owner is comfortable giving up.

—————————————————————
(i) What? Did you really expect something else? Tax planning is not a seasonal exercise – it is something to be considered every day, similar to many other business decisions.
(ii) Of course, the interest to be gifted should be “disposable” in that the owner can comfortably afford to give up the interest. Even if that is the case, the owner may still want to consider the retention of certain “tax-favored” economic rights with respect to the interest so as to reduce the amount of the gift for tax purposes.
(iii) Usually into an irrevocable trust, and coupled with the granting of “Crummey powers” to the beneficiaries so as to support the gift as one of a “present interest” in property. A donor’s annual exclusion amount is set at $15,000 per donee for 2018 and $15,000 for 2019.
(iv) In other words, a dollar removed today will remove that dollar plus the appreciation on that dollar; a dollar at death shields only that dollar.
The removal of this value from the reach of the estate tax has to be weighed against the loss of the stepped-up basis that the beneficiaries of the decedent’s estate would otherwise enjoy if the gifted business interest were included in the decedent’s gross estate.
(v) Matthew 7:7-8. Actually, many folks asked for the repeal of the estate tax. “You Can’t Always Get What You Want,” The Rolling Stones.
(vi) P.L. 115-97.
(vii) For purposes of the estate tax, this includes a U.S. citizen or domiciliary. The distinction between a U.S. individual and non-resident-non-citizen is significant. In the absence of any estate and gift tax treaty between the U.S and the foreign individual’s country, the foreign individual is not granted any exclusion amount for purposes of determining their U.S. gift tax liability, and only a $60,000 exclusion amount for U.S. estate tax purposes.
(viii) https://www.irs.gov/pub/irs-drop/rp-18-57.pdf
(ix) Only individual transferors are subject to the gift tax. Thus, in the case of a transfer from a business entity that is treated as a gift, one or more of the owners of the business entity will be treated as having made the gift.
(x) They also share a common tax rate table.
(xi) As distinguished, for example, from the annual exclusion gift – set at $15,000 per donee for 2018 and for 2019 – which is not treated as a taxable gift (it is not counted against the exemption amount).
(xii) An election is available under which the federal exemption amount that was not used by a decedent during their life or at their death may be used by the decedent’s surviving spouse (“portability”) during such spouse’s life or death.
(xiii) A similar approach is followed in determining the gift tax, which is imposed on an individual’s transfers by gift during each calendar year.
(xiv) As indicated above, the increased exemption amount is scheduled to sunset after 2025, at which point the lower, pre-TCJA basic exclusion amount is reinstated, as adjusted for inflation through 2025. Of course, a change in Washington after 2020 could accelerate a reduction in the exemption amount.
(xv) I bet you don’t hear that much these days.
(xvi) https://www.federalregister.gov/documents/2018/11/23/2018-25538/estate-and-gift-taxes-difference-in-the-basic-exclusion-amount; the regulations are proposed to be effective on and after the date they are published as final regulations in the Federal Register.
(xvii) Defined as all taxable gifts made after 1976 other than those included in the gross estate.
(xviii) Post-TCJA and before 2026.

If there was one part of the Tax Cuts and Jobs Act (“TCJA”) that estate planners were especially pleased to see, it was the increase in the basic exclusion amount from $5.49 million, in 2017, to $11.18 million for gifts made, and decedents dying, in 2018.[i] However, many estate planners failed to appreciate the potential impact of an income tax provision that came late to the party and that was specifically intended to benefit the individual owners of pass-through entities (“PTEs”).

A Brief History

As it made its way through Congress, the TCJA was billed[ii] as a boon for corporate taxpayers, and indeed it was. The corporate tax rate was reduced from 35% to 21%. The corporate AMT was eliminated. The system for the taxation of foreign income was changed in a way that skews in favor of C corporations.

But what about the closely held business – the sole proprietorships, the S corps, the partnerships and LLCs that are owned primarily by individual taxpayers and that often represent the most significant asset in their estates?

These businesses are usually formed as PTEs for tax purposes, meaning that the net operating income generated by these entities is generally not subjected to an entity-level tax; rather, it flows through to the individual owners, who are taxed thereon as if they had realized it directly.

With the introduction of the TCJA, the owners of many PTEs began to wonder whether they should revoke their S corporation elections, or whether they should incorporate[iii] their sole proprietorships and partnerships.

In response to the anxiety felt by individual business owners, Congress enacted a special deduction for PTEs in the form of Sec. 199A.[iv] However, shortly after its enactment on December 22, 2017, tax advisers starting peppering the IRS with questions about the application of 199A.

The IRS eventually proposed regulations in August, for which hearings were held in mid-October.[v]

In September, House Republicans introduced plans for making Sec. 199A “permanent.” Then, during the first week of November, the Republicans lost control of the House.[vi]

Notwithstanding this state of affairs, the fact remains that 199A is the law for at least two more years,[vii] and estate planners will have to deal with it; after all, the income tax consequences arising from an individual’s transfer of an interest in a PTE in furtherance of their estate plan will either enhance or reduce the overall economic benefit generated by the transfer.

In order to better appreciate the application of 199A to such “estate planning transfers,” a quick refresher may be in order.

Sec. 199A Basics

Under Sec. 199A, a non-corporate taxpayer[viii] – meaning an individual, a trust, or an estate – who owns an interest in a PTE that is engaged in a qualified trade or business (“QTB”),[ix] may claim a deduction for a taxable year equal to 20% of their qualified business income (“QBI”)[x] for the taxable year.[xi]

This general rule, however, is subject to a limitation that, if triggered, may reduce the amount of the 199A deduction that may be claimed by the non-corporate taxpayer (the “limitation”).

What triggers the limitation? The amount of the taxpayer’s taxable income from all sources[xii] – not just the taxpayer’s share of the QTB’s taxable income. Moreover, if the taxpayer files a joint return with their spouse, the spouse’s taxable income is also taken into account.

Specifically, once the taxpayer’s taxable income exceeds a specified threshold amount, the limitation becomes applicable, though not fully; rather, it is phased in. In the case of a single individual, the limitation starts to apply at taxable income of $157,500 (the so-called “threshold amount”). The limitation is fully phased in when taxable income exceeds $207,500.[xiii]

This $157,500 threshold amount also applies to non-grantor trusts and to estates.

These thresholds are applied at the level of each non-corporate owner of the business – not at the level of the entity that actually conducts the business. Thus, some owners of a QTB who have higher taxable incomes may be subject to the limitations, while others with lower taxable incomes may not.

The Limitation

As stated earlier, the Sec. 199A deduction for an individual, a trust, or an estate for a particular tax year is generally equal to the 20% of the taxpayer’s QBI for the year.

However, when the above-referenced limitation becomes fully applicable, the taxpayer’s 199A deduction for the year is equal to the lesser of:

  • 20% of their QBI from a QTB, and
  • The greater of:
      • 50% of the W-2 Wages w/r/t such QTB, or
      • 25% of the W-2 Wages w/r/t such QTB plus 2.5% of the “unadjusted basis” of the “qualified property” in such QTB.

In considering the application of this limitation, the IRS recognized that there are bona fide non-tax, legal or business reasons for holding certain properties – such as real estate – separate from the operating business, and renting it to such business. For that reason, the proposed regulations allow the owners of a QTB to consider the unadjusted basis of such rental property in determining the limitations described above – even if the rental activity itself is not a QTB – provided the same taxpayers control both the QTB and the property.[xiv]

Thus, assuming the presence of at least one QTB,[xv] much of the planning for 199A will likely involve the taxpayer’s “management” of (i) their taxable income (including their wages and their share of QBI) and, thereby, their threshold amount for a particular year, (ii) the W-2 Wages paid by the business, (iii) the unadjusted basis of the qualified property[xvi] used in the business, and (iv) the aggregation of QTBs.

Of the foregoing items, the management of the unadjusted basis of qualified property may be especially fruitful in the context of estate planning, as may the management of the threshold amount.

Unadjusted Basis

Generally speaking, the unadjusted basis of qualified property is its original basis in the hands of the QTB as of the date it was placed into service by the business.

Where the business purchased the property, its cost basis would be its unadjusted basis – without regard to any adjustments for depreciation or expensing subsequently claimed with respect to the property – and this amount would be utilized in determining the limitation on an owner’s 199A deduction.

However, where the property was contributed to a PTE in a tax-free exchange for stock or a partnership interest, the PTE’s unadjusted basis would be the adjusted basis of the property in the hands of the contributor at the time of the contribution – i.e., it will reflect any cost recovery claimed by such person.

In the case of an individual who acquires property from a decedent before placing it into service in a QTB, the stepped-up basis becomes the unadjusted basis or purposes of 199A.

However, if the qualified property is held in a partnership, no Section 754 adjustment made at the death of a partner will be taken into account in determining the unadjusted basis for the transferee of the decedent’s interest for purposes of 199A.[xvii]

Based on the foregoing, and depending upon the business,[xviii] a taxpayer who can maximize the unadjusted basis of the QTB’s qualified property will increase the likelihood of supporting a larger 199A deduction in the face of the limitation.

Toward achieving this end, there may be circumstances in which qualified property should be owned directly by the owners of the PTE (say, as tenants-in-common[xix]), rather than by the PTE itself, and then leased by the owners to the business.

For example, if a sole proprietor is thinking about incorporating a business, or converting it into a partnership by bringing in a partner, and the business has qualified property with a relatively low unadjusted basis (say, the original cost basis), the sole proprietor may want to retain ownership of the depreciable property and lease it (rather than contribute it) to the business entity, so as (i) to preserve their original unadjusted cost basis and avoid a lower unadjusted cost basis in the hands of the entity (based on the owner’s adjusted basis for the property) to which it would otherwise have been contributed, and (ii) to afford their successors in the business and to the property an opportunity to increase their unadjusted basis in the property, assuming it has appreciated – basically, real estate – after the owner’s death.

Trusts – the Threshold Amount

A non-grantor trust is generally treated as a form of pass-through entity to the extent it distributes (or is required to distribute) its DNI (“distributable net income;” basically, taxable income with certain adjustments) to its beneficiaries, for which the trust claims a corresponding distribution deduction. In that case, the income tax liability for the income that is treated as having been distributed by the trust shifts to the beneficiaries to whom the distribution was made.

To the extent the trust retains its DNI – i.e., does not make (and is not required to make) a distribution to its beneficiaries – the trust itself is subject to income tax.

In the case of a non-grantor trust, at least in the first instance, the 199A deduction is applied at the trust level. Because the trust is generally treated as an individual for purposes of the income tax, the threshold amount for purposes of triggering the application of the limitation is set at $157,500 (with a $50,000 phase-in range).

Distribution

However, if the trust has made distributions during the tax year that carry out DNI to its beneficiaries, the trust’s share of the QBI, W-2 Wages, and Unadjusted Basis of the QTB in which it owns an interest are allocated between the trust and each beneficiary-distributee.

This allocation is based on the relative proportion of the DNI of the trust that is distributed, or that is required to be distributed, to each beneficiary, or that is retained by the trust. In other words, each beneficiary’s share of the trust’s 199A-related items is determined based on the proportion of the trust’s DNI that is deemed distributed to the beneficiary.

The individual beneficiary treats these items as though they had been allocated to them directly from the PTE that is engaged in the QTB.

Following this allocation, the trust uses its own taxable income for purposes of determining its own 199A deduction, and the beneficiaries use their own taxable incomes.

Based on the foregoing, a trustee may decide to make a distribution in a particular tax year if the trust beneficiaries to whom the distribution is made are in a better position to enjoy the 199A deduction than are the trust and the other beneficiaries.[xx]

In any case, the beneficiaries to whom a distribution is not made may object to the trustee’s decision notwithstanding the tax-based rationale.

Of course, where the trustee does not consider the tax attributes of an individual beneficiary, and makes a distribution to such individual which pushes them beyond the threshold amount, or disqualifies their SSTB from a 199A deduction, the beneficiary may very well assert that the trustee did not act prudently.

Limitations Applied to Non-grantor Trusts

The 199A threshold and phase-in amounts are applied at the level of the non-grantor trust.[xxi]

Because of this, the IRS is concerned that taxpayers will try to circumvent the threshold amount by dividing assets among multiple non-grantor trusts, each with its own threshold amount.

In order to prevent this from happening, the IRS has proposed regulations that introduce certain anti-abuse rules.[xxii]

Specifically, if multiple trusts are formed with a “significant purpose” – not necessarily the primary purpose – of receiving a deduction under 199A, the proposed regulations provide that the trusts will not be “respected” for purposes of 199A.[xxiii] Unfortunately, it is not entirely clear what this means: will the trusts not qualify at all, or will they be treated as a single trust for purposes of the deduction?

In addition, two or more trusts will be aggregated by the IRS, and treated as a single trust for purposes of 199A, if:

  • The trusts have substantially the same grantor(s),
  • Substantially the same “primary” beneficiary(ies), and
  • “A” principal purpose for establishing the trusts is the avoidance of federal income tax.

For purposes of applying this rule, spouses are treated as one person. In other words, if a spouse creates one trust and the other spouse creates a second trust, the grantors will be treated as the same for purposes of the applying this anti-abuse test, even if the trusts are created and funded independently by the two spouses.[xxiv]

If the creation of multiple trusts results in a “significant income tax benefit,” a principal purpose of avoiding tax will be presumed.

This presumption may be overcome, however, if there is a significant non-tax (or “non-income tax”) purpose that could not have been achieved without the creation of separate trusts; for example, if the dispositive terms of the trusts differ from one another.

Grantor Trust

The application of 199A to a grantor trust is much simpler because the individual grantor is treated as the owner of the trust property and income, and the trust is ignored, for purposes of the income tax.[xxv] Thus, any QTB interests held by the trust are treated as owned by the grantor for purposes of applying 199A.

In other words, the rules described above with respect to any individual owner of a QTB will apply to the grantor-owner of the trust; for example, the QBI, W-2 Wages, and Unadjusted Basis of the QTB operated by the PTE in which the trust holds an interest will pass through to the grantor.

Planning?

As we know, many irrevocable trusts to which completed gifts have been made are nevertheless taxed as grantor trusts for income tax purposes. The grantor has intentionally drafted the trust so that the income tax liability attributable to the trust will be taxed to the grantor, thereby enabling the trust to grow without reduction for income taxes, while at the same time reducing the grantor’s gross estate for purposes of the estate tax.

This may prove to be an expensive proposition for some grantors, which they may remedy by renouncing the retained rights or authorizing the trustee to toggle them on or off, or by being reimbursed from the trust (which defeats the purpose of grantor trust status).

The availability of the 199A deduction may reduce the need for avoiding or turning off grantor trust status, thus preserving the transfer tax benefits described above. In particular, where the business income would otherwise be taxed at a 37% federal rate,[xxvi] the full benefit of 199A would yield a less burdensome effective federal rate of 29.6%.

In addition to more “traditional” grantor trusts – which are treated as such because the grantor has retained certain rights with respect to the property contributed to the trust – there are other trusts to which the grantor trust rules may apply and which may, thereby, lend themselves to some 199A planning.

For example, a trust that holds S corporation stock may qualify as a subchapter S trust for which the sole current beneficiary of the trust may elect under Sec. 1361(d) (a “QSST” election) to be treated as the owner of such stock under Sec. 678 of the Code.[xxvii] Or a trust with separate shares for different beneficiaries, each of which is treated as a separate trust for which a beneficiary may elect treatment as a QSST.

Another possibility may be a trust that authorizes the trustee to grant a general power of appointment to a beneficiary as to only part of the trust – for example, as to a portion of one of the PTE interests held by the trust – thereby converting that portion of the trust into a grantor trust under Sec. 678.[xxviii]

What’s Next?

It remains to be seen what the final 199A regulations will look like.[xxix] That being said, estate planners should have enough guidance, based upon what has been published thus far, to advise taxpayers on how to avoid the anti-abuse rules for non-grantor trusts, how to take advantage of the grantor trust rules, and how to maximize the unadjusted basis for qualified property.

Hopefully, the final regulations will provide examples that illustrate the foregoing. Absent such examples, advisers will have to await the development of some Sec. 199A jurisprudence. Of course, this presupposes that 199A will survive through the 117th Congress.[xxx]


[i] The exclusion amount increases to $11.4 million in 2019. It is scheduled to return to “pre-TCJA” levels after 2025. See the recently proposed regulations at REG-106706-18.

[ii] Pun intended. P.L. 115-97.

[iii] Or “check the box” under Reg. Sec. 301.7701-3.

[iv] This provision covers tax years beginning after 12/31/2017, but it expires for tax years beginning after 12/31/2025.

[v] More recently, the IRS announced its 2018-2019 priority guidance project, which indicated that it planned to finalize some of the regulations already proposed, but that more regulations would be forthcoming; it also announced that a Revenue Procedure would be issued that would address some of the computational issues presented by the provision.

[vi] Thus, we find ourselves at the end of November 2018 with a provision that expires after December 31, 2025, for which the issued guidance is still in proposed form.

[vii] Through the next presidential election.

[viii] The deduction is not determined at the level of the PTE – it is determined at the level of each individual owner of the PTE, based upon each owner’s share of qualified business income.

[ix] In general, a QTB includes any trade or business other than a specified service trade or business (“SSTB”) and the provision of services as an employee.

If an individual taxpayer does not exceed the applicable taxable income threshold (described below), their QBI from their SSTB will be included in determining their 199A deduction. If the taxpayer exceeds the applicable threshold and phase-in amounts, none of the income and deduction items from the SSTB will be included in determining their 199A deduction.

[x] Basically, the owner’s pro rata share of the QTB’s taxable income.

[xi] This deduction amount is capped at 20% of the excess of (i) the owner’s taxable income for the year over (ii) their net capital gain for the year.

[xii] Business and investment, domestic and foreign.

[xiii] In the case of a joint return between spouses, the threshold amount is $315,000, and the limitation becomes fully applicable when taxable income exceeds $415,000.

[xiv] Consistent with this line of thinking, and recognizing that it is common for taxpayers to separate into different entities, parts of a business that are commonly thought of as a single business, the IRS will also allow individual owners – not the business entities themselves – to elect to aggregate (to treat as one business) different QTBs if they satisfy certain requirements, including, for example, that the same person or group of persons control each of the QTBs to be aggregated.

It should be noted that owners in the same PTEs do not have to aggregate in the same manner. Even minority owners are allowed to aggregate. In addition, a sole proprietor may aggregate their business with their share of a QTB being conducted through a PTE.

[xv] Whether a QTB exists or not is determined at the level of the PTE. An owner’s level of involvement in the business is irrelevant in determining their ability to claim a 199A deduction. A passive investor and an active investor are both entitled to claim the deduction, provided it is otherwise available.

[xvi] Basically, depreciable tangible property that is used in the QTB for the production of QBI, and for which the “depreciation period” has not yet expired.

[xvii] The Section 754 adjustment is not treated as a new asset that is placed into service for these purposes. Compare Reg. Sec. 1.743-1(j)(4).

[xviii] For example, is it labor- or capital-intensive?

[xix] Of course, this presents its own set of issues.

[xx] Of course, this assumes that the trustee has the relevant beneficiary information on the basis of which to make this decision, which may not be feasible.

[xxi] For purposes of determining whether the trust’s taxable income exceeds these amounts, the proposed regulations provide that the trust’s taxable income is determined before taking into account any distribution deduction. Query whether this represents a form of double counting? The distributed DNI is applied in determining the trust’s threshold, and it is applied again in determining the distributee’s.

[xxii] Under both IRC Sec. 199A and Sec. 643(f).

[xxiii] Prop. Reg. Sec. 1.199A-6(d)(3).

[xxiv] Prop. Reg. Sec. 1.643(f)-1.

[xxv] IRC Sec. 671 through 679.

[xxvi] The new maximum federal rate for individuals after the TCJA.

[xxvii] See Reg. Sec. 1.1361-1(j).

[xxviii] A so-called “Mallinckrodt trust.”

[xxix] The proposed regulations also address the treatment of ESBTs under Sec. 199A. According to the proposed regulations, an ESBT is entitled to the deduction. Specifically, the “S portion” of the ESBT takes into account its share of the QBI and other items from any S corp owned by the ESBT.

The grantor trust portion of the trust, if any, passes its share to the grantor-owner.

The non-S/non-grantor trust portion of the trust takes into account the QBI, etc., of any other PTEs owned by the trust. Does that mean that the ESBT is treated as two separate trusts for purposes of the 199A rules? It is not yet clear.

[xxx] January 2021 to January 2023.

“I Didn’t See That Coming”

Over the years, I have seen many business owners blanche when they learn how much income tax they will have to pay upon the sale of their business.[i] I have heard their disappointment at realizing that they may not be retaining a greater portion of the proceeds from the sale toward which they have worked for so long.

Of course, if this information is imparted to the owner well before they have even identified a buyer for their business – as it should be[ii] – they may choose not to sell the business at all,[iii] or they may conclude that the business is not yet ready to be sold.[iv] Alternatively, and having been forewarned, the owner may negotiate for a tax-friendlier – and economically more efficient – deal structure.

Then there are those owners who sold their business for what they believed was a great price, but who never consulted with a tax adviser prior to the sale, and who only learned after their returns had been prepared[v] that they were going to owe a significant sum to the government. These are the ones for which an adviser must watch out.

You Can’t Make this Up

For example, many years ago, I was brought into a Federal income tax audit that was not going well. The examiner was properly focused on the gains and losses reported on the taxpayer’s income tax return.[vi] The taxpayer’s S corporation had sold its business for a healthy sum, but his personal return also included a large capital loss that offset part of the gain from the sale. There was no information on the return from which to determine the source of the loss. When asked, the taxpayer was unable to provide any details;[vii] rather, he directed me to the accountant. The latter hemmed and hawed, and promised to provide the necessary back-up – and all the while I tried to hold the IRS examiner at bay. Finally, the accountant confessed that there was no such loss. He explained that his office had switched accounting software while the return was being prepared,[viii] and there had been a glitch in a program that added a few zeros to the loss reported on the return. Talk about creative accounting.[ix]

Lightning Strikes Again?

I wish I could say that cases like the one described immediately above are rare, but then I came across this decision just last week.

Taxpayer owned five restaurants, each of which was held in a separate and wholly-owned S corporation. Taxpayer began selling his restaurants in Tax Year, realizing a long-term capital gain in excess of $3.5 million,[x] which he reported on his IRS Form 1040, U.S. Individual Income Tax Return, for Tax Year.

Taxpayer offset this gain with a long-term capital loss of almost $3.0 million, which he claimed was attributable to an asset that was described on his return as an “overseas investment.” Taxpayer reported that he had acquired this investment approximately six years earlier, and had disposed of it at the end of Tax Year for no consideration.[xi]

Something Stinks

The IRS examined Taxpayer’s return. Neither Taxpayer nor his accountant offered a plausible explanation as to how the loss was determined; specifically, they could not substantiate the claimed cost basis of almost $3.0 million.[xii] In addition, neither of them was able to identify the “acquisition date” for the alleged investment; in fact, the accountant stated that he had arbitrarily chosen a date so as to indicate that the loss “was long term.” The accountant also stated that he had come up with the term “overseas investment,” and had listed the year-end as the date of disposition, on the basis of a conversation with Taxpayer.

The IRS concluded that Taxpayer had not substantiated (i) that he had made an investment, (ii) what his basis in that alleged investment was, or (iii) that the investment had become worthless during Tax Year. The IRS mailed Taxpayer a notice of deficiency,[xiii] and Taxpayer timely petitioned the U.S. Tax Court.

At trial, Taxpayer explained that an acquaintance had pitched an investment concept to him. Unbelievably, Taxpayer testified that he had no idea what this investment involved, but he believed it had something to do with “low interest rates” and an “opportunity *** to basically leverage *** bank funds.”

Taxpayer submitted into evidence some promotional materials which he claimed to have reviewed before investing. Notwithstanding his decades of business experience, however, Taxpayer did not seek advice about this investment from his long-time accountant, who was also a wealth manager, or from anyone else.

Despite having little understanding of the investment, Taxpayer testified that he agreed to invest $2.5 million. He submitted into evidence a copy of a purported “Investment Agreement” according to which Taxpayer would receive a 50% membership interest in a limited liability company by investing $2.5 million, which would be deposited into the escrow account of a specified law firm.

Apart from Taxpayer’s testimony,[xiv] there was no evidence that Taxpayer ever made the $2.5 million investment. He testified that the source of funds for the investment was a loan that his restaurants secured. The restaurants did appear to have secured such a loan, and the loan proceeds were allocated among them as shown in their QuickBooks entries. But there was no evidence that the S corporations disbursed any of these funds to the law firm’s escrow account or to Taxpayer; and there was no evidence, in the form of bank statements, wire transfer cover sheets, receipts, or any other document, to show that Taxpayer transferred $2.5 million (or any other sum) to the law firm.

Taxpayer also testified that he had subsequently contributed another $500,000 to this “overseas investment.” He submitted into evidence documents showing a couple of wire transfers, a cashier’s check, and a “transaction journal,” none of which established the fact of his investment.

Taxpayer also claimed to have invested in a second, previously undisclosed, investment, although he produced no evidence to establish the fact of his ownership or the amount of his investment. Taxpayer also claimed to have purchased from others their interests in this investment during the same period that he professed the investment had become worthless. However, there was no documentary evidence to establish that any of these purchases were made.

Although Taxpayer was supposed to have received regular payouts from his investments, he testified that he had never received any kind of payment. Yet Taxpayer took no action of any kind to recover his alleged investment, and did not even investigate the possibility of doing so. Instead, as his accountant explained, Taxpayer drew an inference that the investment was not doing well from the fact that his “correspondence with [the promoter] was less regular and they weren’t as upbeat.”

The Court Smells It Too

The Court began by noting that the IRS’s determination in the notice of deficiency was presumed correct, and that Taxpayer had the burden of proving it erroneous.

The Court then observed that, on his return for Tax Year, Taxpayer reported a capital loss from the disposition of a single “overseas investment.” At trial, however, Taxpayer testified that this loss was actually attributable to investments in two separate entities. In any case, Taxpayer contended that this loss was deductible as a loss from “worthless securities.”

The Court explained that, “[i]f any security which is a capital asset becomes worthless during the taxable year, the loss resulting therefrom shall * * * be treated as a loss from the sale or exchange, on the last day of the taxable year, of a capital asset.” For purposes of this rule, the Court continued, the term “security” means “a share of stock in a corporation,” the “right to subscribe for, or to receive, a share of stock in a corporation,” or a bond or other evidence of indebtedness issued by a corporation or governmental entity.

According to the Court, in order for Taxpayer to be entitled to deduct the purported loss under this rule, he had to establish three distinct facts:

  • First, that he owned a “security,” as defined in the Code;
  • Second, his “adjusted basis” in that security; and
  • Third, that the security “bec[ame] worthless during the taxable year” for which the deduction is claimed.

“Worthlessness is a factual question,” the Court stated, “and [Taxpayer] has the burden of proof to overcome [the IRS’s] determination” that the security did not become worthless during the year in question.

The Court found that Taxpayer had substantiated none of these facts.

First, Taxpayer did not show that he owned a “security.” He did not contend that the “overseas investments” took the form of a bond or other evidence of indebtedness. And he did not establish that either investment actually existed, that either was a corporation, or that he made any investment that took the form of “share[s] of stock in a corporation.”

Second, Taxpayer did not establish his basis (if any) in the investments. There was no credible evidence, documentary or otherwise, to show that he, or his S corporations, made an initial investment of $2.5 million to acquire shares of stock in any business or investment entity. In no case did any such entity furnish Taxpayer with an acknowledgment that it had received funds from him for investment, or that his ownership interest in the entity had changed. There was simply no credible evidence that any payments were made to acquire shares of corporate stock.

Third, Taxpayer did not carry his burden of proving that his alleged investments became worthless during Tax Year. To establish worthlessness in a particular year, the Court explained, a taxpayer must generally point to a “fixed and identifiable event” that caused the security to lose all value. Such an event may include a corporate dissolution or similar occurrence that “clearly evidences destruction of both the potential and liquidating values of the stock.” To establish that he has abandoned a security, the taxpayer “must permanently surrender and relinquish all rights in the security and receive no consideration in exchange.” This determination is made on the basis of “all the facts and circumstances.”

“Assuming arguendo,” the Court stated, “that [Taxpayer] made an investment in ***, he has pointed to no identifiable event evidencing that his investment became worthless during” Tax Year. He allegedly based his inference to that effect on the pessimistic tone of his communications with the promoter. But these emails did not refer to any investment that Taxpayer may have made.

In any event, Taxpayer provided at trial no reason to believe that his alleged investment had become worthless during Tax Year rather than during one of the previous six or seven years. On the other hand, he testified that he continued to make supposed investments, allegedly to buy out the interests of other investors. “These transfers sit uncomfortably with [Taxpayer’s] assertion that he viewed his investment as worthless” during that time.

The Court remarked that, by the end of the trial, “the circumstances surrounding [Taxpayer’s] alleged ‘overseas investment’ were as mysterious as they had appeared on his tax return.” Even assuming that he had made some sort of investment, the Court determined that Taxpayer did not carry his burden of proving that he had purchased a “security,” what his basis was in that security, or that the security had become worthless during Tax Year.

Thus, the Court found that Taxpayer had claimed “a fictitious loss deduction” of almost $3.0 million for Tax Year because he wished to offset the $3.5 million gain that he was required to report upon his sale of the restaurants.

“Do’s and Don’ts”

Yes, there are rogue advisers out there, and there are rogue taxpayers – somehow, they manage to find each other. Stay clear of them.[xv]

The tax-efficient disposition of a business is a process that begins at the inception of the business. There are no shortcuts. Different strategies and structures may be economically “more appropriate” at different stages in the life of the business. Some are more flexible than others. They are all aimed at growing the business and, ultimately, at maximizing the economic return on the owner’s investment.

At times, however, the owner may be presented with a choice under circumstances that are not ideal – they don’t adhere to the “plan.” For example, an offer to purchase the business from the owner may be premature from the owner’s perspective. The owner may reject the offer and rue the decision years later. Or the owner may accept the offer and rue the decision years later. Or the owner may try to change the terms of the offer, whether through an earn-out, a rollover of some of their equity, a joint venture, or some other means by which they can participate in the continued growth of the business in a tax efficient manner.

Every situation, every business, and every owner is different. The point is to consider with one’s advisers those scenarios that are likely to arise, to understand their consequences,[xvi] and to plan for them as best as reasonably possible. Avoid surprises that may trigger irrational acts.[xvii] When surprises occur, as they often do notwithstanding one’s preparation and planning, seek out those advisers before taking any action in response.[xviii]


[i] These will include Federal, state, and sometimes city, income taxes; the taxes may be imposed at the level of both the business entity and its owners. The sale may also trigger sales tax and real estate transfer tax, depending upon the form of the transaction and the nature of the assets being sold.

[ii] It may be a worthwhile exercise for the owner to informally appraise their business every few years. You never know when “that” offer is going to come and, although most owners have a ballpark idea of what their business is worth, it helps to have a more objective perspective.

[iii] That being said, there may be exigent circumstances that compel the sale.

[iv] For example, it may be that the business still has “room to grow.”

[v] In the year following the year of the sale.

[vi] Among other items, there were questions about the adjusted basis of some of the assets.

[vii] “I didn’t really review the return,” he said. “I just signed where I was told.”

[viii] “The dog ate my homework.” I guess that doesn’t resonate much in an age when kids do their homework on a computer.

[ix] The exam ended well, under the circumstances. I spoke very frankly with the examiner and their manager, fired the accountant, and restored a measure of credibility that facilitated a settlement.

[x] Meaning that the amount received by Taxpayer in exchange for the restaurants exceeded Taxpayer’s unrecovered investment (“adjusted basis”) in the restaurants by over $3.5 million.

[xi] In other words, he wrote it off as worthless.

[xii] After all, you can’t lose more than your unrecovered investment.

[xiii] The so-called “90-day letter,” which refers to the ninety days within which the taxpayer must file a petition with the Tax Court to contest the deficiency asserted in the letter. If the taxpayer fails to respond timely, the IRS is free to assess the tax, demand payment, and then seek to collect it.

[xiv] Which the Court did not find credible.

[xv] Some telltale signs: they intentionally draft ambiguity into a document; they say things like “this return is so convoluted, the IRS will never pick up the issue,” or “we control the preparation of the return, we can do whatever we want”; they ignore the legal separation among related entities; they bury questionable items in entries like “other expenses” and actually believe that no one will look.

[xvi] Which has to include running the numbers.

[xvii] One of my physics teachers was fond of saying, “Eschew obfuscation.”

[xviii] I know, I sound like your mother.

Dr. Wallace Wrightwood: “You’ve seen hundreds, thousands of pigeons, right?”
George Henderson: “Of course.”
Dr. Wallace Wrightwood: “Have you ever seen a baby pigeon? Well neither have I. I got a hunch they exist.”[i]

When was the last time you pored over a judge’s analysis of the bona fides of a family limited partnership (“FLP”), or pondered a court’s Solomon-like judgement regarding the fair market value of an interest in a FLP? [ii]

It used to be that such decisions were de rigeur in the world of estate and gift tax planning for family-owned business and investment entities, and planners would wait breathlessly for the outcome of the next learned opinion and the direction it would provide.

Then the federal transfer tax exemption began its seemingly inexorable climb, which spawned an interest in how to best leverage the increased exemption amount and remove still more of a family’s wealth from the transfer tax system.

Of course, there was a bump in 2016, with the issuance of proposed regulations that many believed would, if finalized, mark the end of the valuation discounts that made the use of FLPs, and the transfer of interests in family-owned businesses generally, so attractive as a gift planning tool. [iii]

The presidential election results ended the IRS’s regulatory efforts to clamp down on the abuse of FLPs, and the “temporary” mega-increase of the federal exemption, beginning with 2018, gave many taxpayers a comfortable “margin of error” for any valuation missteps. [iv]

Notwithstanding the relatively “favorable” environment for gift and estate tax planning in which we find ourselves, it will still behoove taxpayers and their advisers to remain attuned to the factors on which the IRS and the courts have historically focused in their analyses of FLPs and the transfer of interests in family-owned businesses, some of which were highlighted in a recent Tax Court decision. https://www.ustaxcourt.gov/ustcinop/OpinionViewer.aspx?ID=11800 [v]

“I’ll Take Care of Everything, Dad”

Decedent, acting through his attorney-in-fact [vi] (his daughter, “Daughter”), formed FLP as a limited partnership. The partnership agreement (the “Agreement”) stated that FLP’s purpose was to “provide a means for [D]ecedent’s family to manage and preserve family assets.” Decedent funded FLP primarily with marketable securities, municipal bonds, mutual funds, and cash. Its portfolio was managed by professional money managers. FLP never held any meetings.

F-LLC was FLP’s sole general partner (“GP”). Daughter was manager of F-LLC. The Agreement provided that the GP “shall perform or cause to be performed * * * the trade or business of the Partnership,” subject only to limitations set forth expressly in the Agreement.

Decedent and his children were FLP’s original limited partners (“LPs”) under the Agreement. The LPs, other than Decedent, received their LP interests as gifts. Decedent reported these gifts on a federal gift tax return (IRS Form 709).

Agreement
The Agreement provided that FLP would terminate in 2075, unless terminated sooner; for example, upon the removal of the GP. The LPs could remove the GP by written agreement of the LPs owning 75% or more of the partnership interests held by all LPs. If the partnership terminated by reason of the GP’s removal, then 75% of the LPs could reconstitute the partnership and elect a successor GP. LPs owning at least 75% of the ownership percentage in FLP could approve the admission of additional LPs to the partnership.

The Agreement provided that an LP could not sell or assign an interest in FLP without obtaining the written approval of the GP, which the Agreement provided would not be unreasonably withheld. Any partner who assigned their interest remained liable to the partnership for promised contributions or excessive distributions unless and until the assignee was admitted as a substituted LP. The GP could elect to treat an assignee as a substituted LP in the place of the assignor. An assignor was deemed to continue to hold the assigned interest for the purposes of any vote taken by LPs under the Agreement until the assignee was admitted as a substituted LP.

All transfers of interests in FLP were subject to limitations. Partners were allowed to make only permitted transfers of their interests. “Permitted transfers” were transfers (1) to any member of the transferor’s family, (2) to the transferor’s executor, trustee, or personal representative to whom his or her interest would pass at death or by operation of law, or (3) to any purchaser, but subject to the right of first refusal held by the certain partners.

Any partner who received an outside purchase offer for their interest was required, before accepting the offer, to provide each of the “priority family”, the partnership, and the general partner an opportunity to acquire the interest. Whether FLP exercised its right of first refusal to purchase a partner’s interest was subject to the approval of the GP and the LPs owning at least 50% of FLP’s interests held by all LPs (with the exception of the seller if they were an LP).

The Agreement referred to persons who acquired interests in FLP, but who were not admitted as substituted LPs, as “assignees”. Such “assignees” were entitled only to allocations and distributions in respect of their acquired interests. “Assignees” had no right to any information or accounting of the affairs of FLP, were not entitled to inspect its books or records, and did not have any of the rights of a partner under state law.

The Agreement provided that a transferee of an interest in FLP could become a substituted LP upon satisfying the following conditions: (1) the GP consented; (2) the transferee was a permitted transferee; and (3) the transferee became a party to the Agreement as an LP. The Agreement provided that an interest holder who was admitted to FLP as a substituted LP would be treated the same as an original LP under the terms of the Agreement.

On the same day that Decedent formed FLP, he established a revocable trust (the “Trust”), and also transferred his 88.99% LP interest in FLP to Trust. Decedent held the power during his life to amend, alter, revoke, or terminate Trust. He was its sole beneficiary, and Daughter was the trustee. Decedent was entitled to receive distributions of trust income and could receive distributions of trust principal upon his request.

Decedent, through Daughter, executed an agreement (the “Assignment”), which designated Decedent as “assignor” and the Trust as “assignee”. The Assignment provided that Decedent assigned all of his LP interests in FLP, and that the Trust, “by signing this [Assignment], hereby agrees to abide by all the terms and provisions in that certain [Agreement] of [FLP].”

Decedent’s transfer of his interest was a permitted transfer under the Agreement. Daughter signed the Assignment in her capacities as Decedent’s attorney-in-fact, as trustee of the Trust, and as managing member of F-LLC.

Estate Tax Return
Following Decedent’s death, [vii] his estate (the “Estate”) filed a federal estate tax return (IRS Form 706). The Estate reported on the estate tax return that Decedent had made revocable transfers during his lifetime. It identified on the estate tax return the transfers of Decedent’s LP interests to the Trust. [viii]

The Estate described the property transferred to the Trust as an “assignee interest” in an 88.99% LP interest. The Estate reported the value of the transferred interest on the tax return; in a supplemental statement, the Estate indicated that it claimed discounts for “lack of marketability, lack of control, and lack of liquidity.”

The IRS issued a notice of deficiency asserting an estate tax deficiency. The attached Forms 886-A set forth the IRS’s determination that the corrected value of decedent’s interest in FLP was greater than that reported by the Estate.

The Estate petitioned the Tax Court.

The Court’s Approach
The Court distinguished between the nature of the property interest transferred to the Trust (a legal issue) and the fair market value (“FMV”) of such interest (a question of fact). The parties, the Court stated, disagreed as to the type of interest that had to be valued in Decedent’s gross estate.

The Estate claimed that the Assignment created an assignee interest in Decedent’s LP interest under the Agreement. It valued Decedent’s interest in the Trust as an assignee interest.

The IRS asserted that the Assignment did not create an assignee interest held by the Trust. The IRS argued that Decedent transferred his 88.99% LP interest to the Trust and the value to be included in the gross estate should be that of an LP interest.

Thus, the Court had to determine whether the interest Decedent transferred to the Trust was an LP interest or an assignee interest.

Generally, state law determines the nature of the property interest that has been transferred for federal estate tax purposes. [x] The Court explained that, under applicable state law, a partnership interest was assignable unless the partnership agreement provided otherwise. An assignee of a partnership interest was entitled to receive allocations of income, gain, loss, deduction, credit, or similar items, and to receive distributions to which the assignor was entitled, but was not entitled “to exercise rights or powers of a partner”. The assignee may become a partner, with all rights and powers of a partner under a partnership agreement, if admitted in the manner that the agreement provided.

The Court emphasized, however, that the federal tax effect of a particular transaction was governed by the substance of the transaction rather than its form. “The doctrine that the substance of a transaction will prevail over its form,” the Court stated, “indicates a willingness to look beyond the formalities of intra-family partnership transfers to determine what, in substance, was transferred.”

With that, the Court considered both the form and the substance of Decedent’s transfer to the Trust to determine whether the property interest transferred was an assignee interest or an LP interest.

The Court’s Analysis
The Agreement allowed the transfer of LP interests, and for the admission of a transferee as a substituted LP, provided certain conditions were met. [xi]

The Estate contended that these conditions were never met with respect to the interest that Decedent transferred to the Trust and that, upon the execution of the Assignment, the Trust received only an assignee interest in Decedent’s 88.99% LP interest.

The Court observed that, although the transfer was labeled an “assignment,” the Assignment stated that the Trust was entitled to all rights associated with the ownership of Decedent’s 88.99% LP interest, not just those of an assignee. All “rights and appurtenances” belonging to Decedent’s interest, the Court continued, included the right to vote as an LP and exercise certain powers as provided in the Agreement. The Assignment also required that Decedent was bound to provide any documentation necessary “to provide * * * [the Trust] all the rights * * * [Decedent] may have had” in the LP interest.

The Assignment, the Court added, satisfied all the conditions for the transfer of Decedent’s LP interest and the admission of the Trust as a substituted LP. In order for a transferee to be admitted as a substituted LP in respect of a transferred interest in FLP, (1) the GP had to consent to the transferee’s admission, (2) the transfer had to be a permitted transfer, and (3) the transferee had to agree to be bound by the terms of the Agreement. Daughter signed the Assignment as manager of FLP’s GP and consented to its terms, which provided for the transfer of all of Decedent’s rights in his LP interest to the Trust. The transfer was a permitted transfer. Lastly, the Assignment provided that the Trust agreed to abide by all terms and provisions of the Agreement, and Daughter executed the Agreement on behalf of the Trust.

The Court concluded that the form of the Assignment established that Decedent transferred to the Trust an LP interest and not an assignee interest.

What’s the Difference Anyway?
The economic realities underlying the transfer of Decedent’s interest, the Court stated, supported the conclusion that the transferred interest should be treated as an LP interest for federal estate tax purposes; regardless of whether an assignee or an LP interest had been transferred, there would have been no substantial difference before and after the transfer to the Trust.

Pursuant to the Agreement, only the GP had the right to direct the FLP; neither LPs nor assignees had managerial rights. The Agreement provided that assignees had no rights to any information regarding FLP’s business or to inspection of its books or records.

However, according to the Court, this distinction made no difference in the present case because Daughter was both a partner who was entitled to information regarding FLP (i.e., the manager of the GP) and the trustee of the Trust.

The Agreement also provided that an “assignee” did not have the right to vote as an LP. However, this difference was not significant – whether the Trust held the voting rights associated with an LP interest was of no practical significance, the Court stated.

There were no votes by LPs following the execution of the Assignment. Additionally, during his life, Decedent held the power to revoke the transfer to the Trust. If he had revoked the transfer, he would have held all the rights of an LP in FLP, including the right to vote on partnership matters. Also, F-LLC, as the GP, could have treated the holder of an assignee interest as a substitute LP.

Therefore, under the facts and circumstances of this case, the Court determined there was no difference in substance between the transfer of an LP interest in FLP and the transfer of an assignee interest in that LP interest. Accordingly, as a matter of both form and substance, the interest to be valued for estate tax purposes was an 88.99% LP interest in FLP, rather than an assignee interest. [xii]

Takeaway
Bad facts, etc., but some may see a silver lining in the result of this case.

A taxpayer who cannot act on his own; his attorney-in-fact/Daughter creates the partnership and funds it with marketable securities and cash on his behalf; she appoints herself as the manager of the GP; she creates and funds the Trust with most of the LP interests on his behalf, and appoints herself as trustee of the Trust. Sounds perfect.

Notwithstanding the foregoing, the Court respected the partnership; [xiii] in fact, it appears that the IRS did not even challenge the partnership’s bona fides.

Query what business purpose the FLP had where it held only marketable securities and cash (all provided by Decedent), where its securities were managed by a professional money manager, and where it never held any meetings. This was just a valuation play.

Silver lining? Nope. Dodged one? Yep. A map to follow? Please don’t.
———————————————————————————–
i From “Harry and the Hendersons.” C’mon, don’t pretend you haven’t seen it.
ii Usually with a beverage for inspiration.
iii https://www.taxlawforchb.com/2016/09/the-irs-takes-the-offensive-on-valuation-discounts-part-one/ ; https://www.taxlawforchb.com/2016/09/the-irs-takes-the-offensive-on-valuation-discounts-part-two/ ; https://www.taxlawforchb.com/2016/09/the-irs-takes-the-offensive-on-valuation-discounts-part-three/ .
iv The exemption amount had been set to increase from $5.49 MM in 2017 to $5.62 MM in 2018. The Tax Cuts and Jobs Act doubled the exemption to $11.2 MM for 2018, adjusted for inflation beginning in 2019, with a return to the pre-2018 levels after 2025. P.L. 115-97.
v T.C. Memo. 2018-178.
vi Anyone remember Strangi?
vii The 706 was filed August 2012. If this filing was timely, then the DOD was in November 2011. The FLP and Trust were created in October 2008, three years earlier.
viii IRC Sec. 2038; Schedule G to the Form 706. Because the transfers were revocable by the Decedent – specifically, by his attorney-in-fact in this case – the property transferred was included in his gross estate for tax purposes.
ix You can’t make this up.
x See Commissioner v. Estate of Bosch, 387 U.S. 456 (1967).
xi See above.
xii The Court then turned to the FMV of the Trust’s interest in FLP. Based on its finding that the interest transferred was an 88.99% LP interest, the Court concluded that the interest did not lack control. Accordingly, no discount for lack of control was allowed. The Court agreed with the Estate that there should be a discount for lack of marketability. However, because the Court concluded that the interest Decedent transferred was an LP interest, not an assignee interest, it found the Estate’s discount was too generous and accepted the lower discounted applied by the IRS.
xiii Yet it did, and also allowed a lack of marketability discount in determining the FMV of the interest held by the Trust. Go figure.

How Does It Work?

Many employers struggle to hire and retain key employees. In addressing this challenge, employers will sometimes add unique benefits to the compensation package offered to such individuals. In fact, it is not unusual for the employer and the key employee to jointly structure the terms of such a benefit, often in response to a particular need of the employee.[i]

One of the more common benefits that a key employee may request to be included in such a compensation package is the provision of a “permanent” life insurance policy on the life of the employee; i.e., a policy that does not expire within a specified number of years, and which includes an investment component in addition to a death benefit.[ii] Of course, permanent insurance is more expensive than term life insurance, and may be too costly for the employee to acquire and carry alone.

Enter the split-dollar arrangement.

In general, a “split-dollar life insurance arrangement” entered into in connection with the performance of services is one between an employer (the “owner” of the policy) and a key employee (the “non-owner)”[iii] that satisfies the following criteria:

  • The employer pays the premiums on the policy, and
  • The employer is entitled to recover all, or a portion, of such premiums, and such recovery is to be made from, or is secured by, the life insurance proceeds.

The employee in this arrangement will typically designate the beneficiary of the death benefit,[iv] and may also have an interest in the cash value of the policy.

This arrangement is said to be compensatory, and certain economic benefits are treated as being provided by the employer-owner to the employee-non-owner.

Specifically, in determining gross income, the employee must take into account as compensation the value of the economic benefits provided to the employee under the arrangement.[v]

In general, the value of such benefits equals the cost of the current life insurance protection provided to the employee, plus the amount of the policy cash value to which the employee has “current access.”[vi]

But it’s Not Just for Employees

Although most split-dollar arrangements employed[vii] in the context of a business are compensatory in nature, it is possible for an arrangement to be entered into between a corporation and an individual in their capacity as a shareholder in the corporation.

In that case, the corporation would still pay all or a portion of the premiums, and the individual shareholder would designate the beneficiary of the death benefit, and may have an interest in the policy cash value.

However, the economic benefits provided by the corporation to the insured shareholder would constitute a distribution with respect to the shareholder’s stock in the corporation, which may represent a dividend to the shareholder,[viii] depending upon the corporation’s C corporation earnings and profits. In that case, the shareholder would be taxed at a much lower federal rate (23.8%), as compared to the rate applicable to compensation income (37%). If the corporation is an S corporation, it is possible that the distribution may not be taxable to the shareholder at all.[ix]

Thus, it is important, in determining the proper tax treatment of a split-dollar arrangement, that the parties thereto understand the capacity in which the benefit is being provided to the individual insured; i.e., as an employee or as a shareholder.

A recent decision by the Sixth Circuit Court of Appeals addressed this very issue.

Taxpayer as Employee or Shareholder?

Taxpayer was the sole shareholder of Corp, which was an S corporation. Taxpayer was also an employee of Corp.

Corp adopted a benefit plan in order to provide certain benefits to its employees. Pursuant to the plan, Corp provided Taxpayer a life insurance policy and paid a $100,000 annual premium in Tax Year. Because Corp was an S corporation, all of its income and deductions were “passed through” to Taxpayer for tax purposes.[x] On its Form 1120S return for Tax Year, Corp deducted the $100,000 premium as a business expense; thus, that amount of Corp’s income was not included in Taxpayer’s individual income as a pass-through item.[xi] However, Taxpayer also did not include as wages the economic benefits flowing from the life insurance policy.

The IRS challenged Taxpayer’s treatment of the split-dollar arrangement and issued a notice of deficiency, in response to which Taxpayer petitioned the Tax Court.

Tax Court

The Tax Court determined that Corp was not entitled to deduct the $100,000 premium payment.[xii] Because the $100,000 premium payment was not deductible, Corp underreported its income for that year and, due to its pass-through nature as an S corporation, the increased income was passed through to Taxpayer, who was then required to pay income tax on that amount. Taxpayer conceded that he had to report an amount equal to the premium payment as pass-through income.

The dispute before the Tax Court concerned whether Taxpayer was required to report as taxable wage income – in addition to the pass-through amount – the economic benefits flowing from the increase in the cash value of the life insurance policy caused by the payment of the premium.

The Tax Court ruled against Taxpayer, and found that he was required to account for the economic benefits in his individual income as wages:

[Corp’s] deduction, when disallowed . . . increased the S corporation’s gross income, which additional income was then passed on to [Taxpayer] as the shareholder of [Corp]. However, [Taxpayer], in addition to being a shareholder of the corporation, was also one of its employees. . . . , when the previously unreported and untaxed portion of the accumulation value of his policy was determined, the value of the $100,000 contribution by [Corp], was properly attributed to [Taxpayer] as an employee of the S corporation and a non-owner of the life insurance contract. While this result may seem aberrational in view of the pass-through treatment generally afforded to S corporations, it is a result mandated by the split-dollar life insurance regulations . . . . In instances other than those governed by the split-dollar life insurance regulations, the general rule of the non-taxability of previously taxed S corporation income is unperturbed. [Emph. added]

The Tax Court found that Taxpayer’s life insurance policy qualified as a compensatory arrangement. Moreover, the parties conceded that Taxpayer’s life insurance policy was not a shareholder arrangement.

Relying on the compensatory nature of the arrangement, the Tax Court rejected Taxpayer’s argument that the economic benefits (the “build-up” in cash value) should be treated as a shareholder distribution; instead, the Tax Court ruled that Taxpayer had to include as income the economic benefits resulting from Corp’s payment of a premium on Taxpayer’s life insurance policy.

Sixth Circuit

Taxpayer appealed the Tax Court’s decision to the Sixth Circuit, which considered the interplay of the split-dollar life insurance regulations and Subchapter S.

The Court explained that the split-dollar life insurance regulations apply “to any split-dollar life insurance arrangement,” whether the arrangement is a compensatory or a shareholder arrangement. When an arrangement is governed by the split-dollar life insurance regulations, the Court continued, the non-owner of the policy “must take into account the full value of all economic benefits” provided to them. “Depending on the relationship between the owner and the non-owner,” the Court stated, “the economic benefits may constitute a payment of compensation, a distribution in respect of stock, or a transfer having a different tax character.”

However, the Court also pointed out that another regulation (the “Regulation”) governs the tax treatment of the economic benefits flowing from a split-dollar arrangement to an individual insured who is a shareholder of the corporation paying the premiums. In particular, the Regulation states that “the provision by a corporation to its shareholder pursuant to a split-dollar life insurance arrangement . . . of economic benefits . . . is treated as a distribution of property.” The Court noted that, by its terms, the Regulation applies to both compensatory and shareholder arrangements.[xiii]

The Court then observed that the split-dollar regulations make no specific reference to S corporations. It added that there was minimal case law concerning the interplay of Subchapter S and the split-dollar regulations, and that it was not aware of any case dealing with the application of the Regulation to the economic benefits provided to shareholder-employees pursuant to a compensatory arrangement.

Taxpayer’s Position

The thrust of Taxpayer’s argument was that the economic benefits provided under the split-dollar arrangement should be treated as a distribution of property by an S corporation to its shareholder, notwithstanding that they flowed from a compensatory arrangement.[xiv]

Taxpayer relied on the statement in the Regulation that the provision of economic benefits “by a corporation to its shareholder pursuant to a split-dollar life insurance arrangement . . . is treated as a distribution of property.” Thus, Taxpayer argued, the economic benefits should be treated as a “distribution of property” from Corp to Taxpayer.[xv]

Taxpayer also relied on the statutory provisions governing the tax treatment of S corporations,[xvi] arguing that they “prevent double taxation otherwise imposed pursuant to an interpretative regulation addressing split dollar life insurance premiums that have been paid by S corporations.”

An S corporation’s income and deductions, Taxpayer asserted, are passed through to its shareholders, each shareholder is taxed on their allocable share thereof, and each shareholder’s stock basis is adjusted upward accordingly. In this case, $100,000 of Corp’s income – an amount equal to the nondeductible premium payment – was taxed to Taxpayer. How, then, Taxpayer argued, could he be taxed “again” as to the increase in the cash value of the policy attributable to premium?

IRS’s Position

The IRS argued[xvii] that the economic benefits should be treated as wage income – rather than as a shareholder distribution – because Taxpayer received the life insurance coverage as part of a compensatory split-dollar arrangement. The IRS noted that such treatment would be uncontroversial if the recipient of the economic benefits were an ordinary employee, rather than an S corporation’s shareholder-employee. The distinction between Taxpayer’s different roles – employee and shareholder – was, therefore, key to the IRS’s position.

The IRS pointed only to the distinction between compensatory and shareholder arrangements. The IRS recognized that the Regulation applies to both compensatory and shareholder arrangements but concluded that it “does not mean that in any situation where a compensatory arrangement covers a shareholder, the taxpayer’s status as a shareholder trumps his status as an employee, causing the economic benefit to be treated as a distribution to a shareholder,” because “[s]uch an interpretation of the regulation would make no sense, as it would defeat the reason for distinguishing between a compensatory arrangement and a shareholder arrangement.”

The Regulation is Dispositive

The Court rejected the IRS’s argument.

According to the Court, it was not clear that treating all economic benefits to shareholders as distributions – even to those who were also employed by the corporation –would undermine the purpose of the split-dollar regulations.

The Court noted that the Tax Court had not addressed the Regulation. However, the Court also added that if the economic benefits to Taxpayer were properly treated as a distribution of property to a shareholder – rather than as compensation to an employee – then the Tax Court had erred.

The Court decided that the Regulation was dispositive, and thereby rendered irrelevant whether Taxpayer received the economic benefits through a compensatory or shareholder split-dollar arrangement. The Regulation treats economic benefits provided to a shareholder pursuant to any split-dollar arrangement as a distribution of property with respect to the shareholder’s stock. The Court stated that the inclusion in the Regulation of all arrangements described in the split-dollar rules, which include compensatory arrangements – made clear that when a shareholder-employee receives economic benefits pursuant to a compensatory split-dollar arrangement, those benefits are treated as a distribution of property, and are thus deemed to have been paid to the shareholder in their capacity as a shareholder.

The Court stated that its interpretation was further supported by the fact that the split-dollar rules state that the tax treatment of the economic benefits depends on the “relationship between the owner and the non-owner.” The IRS argued that this language showed that the tax treatment depended on the nature of the split-dollar arrangement—compensatory or shareholder—but the Court pointed out that if this were the controlling factor, the Regulation could have said so (it does not).

Thus, the Court found that the Tax Court had erred by relying on the compensatory nature of Taxpayer’s split-dollar arrangement to conclude that the economic benefits were not distributions of property to a shareholder. Where a shareholder receives economic benefits from a split-dollar arrangement, the Regulation requires that those benefits be treated as a distribution of property to a shareholder.

The Court reversed the Tax Court’s decision with respect to the tax treatment of the economic benefits flowing to Taxpayer from Corp’s payment of the $100,000 premium on Taxpayer’s life insurance policy and held, pursuant to the Regulation, that those economic benefits had to be treated as distributions of property by Corp to its shareholder. Because Corp was an S corporation, that meant that the deemed distribution would be at least partially exempt from tax.[xviii]

Thoughts

Are you kidding? Compensation is compensation, isn’t it? It is paid for services rendered or to be rendered by the recipient to the payor. Except, at least according to the Sixth Circuit, when it is paid as part of a split-dollar life insurance arrangement to a shareholder of the payor who is also employed by the payor?

It is a basic principle of taxation that the capacity in which an owner of a business entity deals with the entity determines the appropriate tax treatment of the transaction. Salary paid by a corporation to a shareholder-employee for services actually rendered to the corporation is taxed as compensation.[xix] Where the amount paid is excessive for the services provided, the excess may be treated as a distribution to the shareholder in respect of their stock in the corporation (a dividend), the premise being that no one would pay more for the services than they were actually worth. Case closed, right?

What if the compensation paid to the shareholder-employee had been below market? Would the benefits provided under what was conceded to be a compensatory split-dollar arrangement still be treated as a distribution rather than as additional compensation?

What about the IRS’s historical concern over S corporations that pay less than reasonable compensation to their shareholder-employees in order to reduce their employment tax liability?

In holding as it did, has the Court created a second class of stock issue where none would otherwise have existed? The constructive distribution to a shareholder-employee of an S corporation sets that individual apart from other shareholders of the employer-corporation who are not employed in the business. Might it be easier to find that “a principal purpose” of the split-dollar arrangement (a “commercial contractual agreement”) is to circumvent the one class of stock requirement?[xx]

The Court should have upheld the Tax Court’s decision. It should have recognized that the literal wording of the Regulation needs to be revised to comport with the intention and language of the split-dollar rules.


[i] Actual equity, restricted equity, phantom equity, equity appreciation, change-in-control, and other equity-flavored or profits-based incentive bonus arrangements are also not uncommon.

[ii] For example, a whole life policy. A permanent policy will generally include an investment or savings component, reflected as the so-called “cash value” of the policy, against which the owner of the policy may borrow, or which may be withdrawn, during the life of the insured. Compare this to term insurance, which promises only a death benefit if the insured dies within a specified number of years.

[iii] The person named as the policy owner is generally treated as the “owner” of the policy for purposes of these rules. Thus, if the insured is named as the owner, they will be treated as the owner for purposes of these rules. However, if the only benefit accorded the insured is current life insurance protection (the death proceeds; they have no access to the cash value of the policy), then the non-owner is treated as the owner.

[iv] Often a trust for the benefit of the employee’s family.

[v] The employer will not be entitled to a deduction where it is a beneficiary of the policy.

[vi] To the extent it was not taken into account in a prior year. In general, the cash value builds up tax-free within the policy when the premium exceeds the cost of the insurance.

[vii] Yes, pun intended.

[viii] As in the case of compensatory split-dollar, the premium would not be deductible by the corporation.

[ix] Depending upon the shareholder’s stock basis and the corporation’s AAA; the deemed distribution would be treated as a return of already-taxed income or as a return of capital.

[x] IRC Sec. 1366.

[xi] The deduction claimed on the corporate return reduced, dollar-for-dollar, the amount of profit allocated to the shareholder on their Sch. K-1.

[xii] The corporation was a beneficiary of the policy (IRC Sec. 264); moreover, under Sec. 83, the employee had not included the premium in income.

[xiii] Reg. Sec. 1.301-1(q)(1)(i).

[xiv] Yep. You heard right.

[xv] Reg. Sec. 1.301-1(q)(1)(i).

[xvi] IRC Sec. 1366 (pass-through of corporate income), 1367 (upward basis adjustment for pass-through of income and downward for distribution thereof), and 1368 (treatment of S corporation distribution that would otherwise be treated as a dividend – return of already-taxed income and basis).

[xvii] And the Tax Court concluded.

[xviii] See IRC Sec. 1368.

[xix] And may be deducted to the extent it was reasonable.

[xx] Reg. Sec. 1.1361-1(l).

 

Ode to a Dividend

It sounds relatively simple:

A distribution of property made by a regular “C” corporation to an individual shareholder with respect to the corporation’s stock[i] (a) will be treated as a dividend[ii] to the extent it does not exceed the corporation’s earnings and profits; (b) any remaining portion of the distribution will be applied against, and will reduce, the shareholder’s adjusted basis for the stock, to the extent thereof – i.e., a tax-free return of the shareholder’s investment in the stock; and (c) any remaining portion of the distribution will be treated as capital gain from the sale or exchange of the stock.[iii]

Unfortunately for many taxpayers, establishing the proper tax treatment for a “dividend” distribution may be anything but simple,[iv] which may lead to adverse economic consequences. In most cases, the difficulty stems from the shareholder’s inability to establish the following elements:

  • the amount distributed by the corporation where the distribution is made in-kind rather than in cash – in other words, determining the “fair market value” of the property distributed;[v]
  • the “earnings and profits” of the corporation – basically, a running account that the corporation must maintain from its inception through the present, which indicates the net earnings of the corporation that are available for distribution to its shareholders; and
  • the shareholder’s holding period and adjusted basis for their shares of stock in the distributing corporation.[vi]

Stock Basis

The final item identified above – the shareholder’s basis for their stock – is generally not an issue for the shareholders of a closely held C corporation. In most cases, an individual made a contribution of cash to the capital of the corporation in exchange for stock in the corporation; in some cases, the individual purchased shares of stock from another shareholder. Unless the shareholder subsequently makes an additional capital contribution to the corporation (for example, pursuant to a capital call under a shareholders’ agreement),[vii] or unless the shareholder receives a distribution from the corporation that exceeds the shareholder’s share of the corporation’s earnings and profits, or unless the corporation redeems a significant portion of the shareholder’s stock (such that the shareholder experiences a substantial reduction in their equity interest relative to the other shareholders),[viii] the shareholder’s stock basis will be equal to the amount paid by them to acquire the stock, and will remain constant during the period they own the stock.[ix]

However, what if the shareholder’s capital contribution was made in-kind; for example, a contribution of real property or equipment, or of a contract or other intangible right? The amount of such contribution would be equal to the fair market value of the property; however, unless the transfer of the property was a taxable event to the contributing shareholder,[x] the shareholder’s basis for their stock in the corporation would be equal to their adjusted basis – i.e., their unrecovered investment – in the contributed property immediately before such contribution.[xi]

Alternatively, what if the shareholder made a transfer of cash to the corporation that was recorded by the corporation as a loan? What if the corporation never issued a promissory note to the shareholder or otherwise memorialized the terms of the loan (maturity, interest rate, collateral)? What if it never paid or accrued interest on the loan? Can the shareholder argue against the form of their “loan,” treating it, instead, as a capital contribution that would increase their stock basis?[xii]

The Taxpayer’s Burden

The taxpayer has the responsibility to substantiate the entries, deductions, and statements made on their tax returns. Thus, in the case of a “dividend” distribution by a closely-held corporation to an individual shareholder, the latter has the burden of proving the elements of the distribution,[xiii] described above, including that portion of the distribution that represents a nontaxable return of capital; in other words, the shareholder must be able to establish their adjusted basis for the stock on which the distribution is made.

In order to carry this burden, it is imperative that the taxpayer maintain accurate records to track the amount of their equity investment in the corporation. Where the stock was issued by the corporation in exchange for a contribution of cash, it would be very helpful to have a canceled check plus an executed capital contribution agreement, or corporate minutes accepting the contribution and authorizing the issuance of the stock. If the stock was received in exchange for an in-kind contribution of property in a non-taxable transaction, evidence of the taxpayer’s adjusted basis in the property is required; for example, the original receipt evidencing the taxpayer’s acquisition of the property, plus records of any subsequent adjustments, which may depend upon the nature of the property.[xiv] If the stock was purchased from another shareholder, the executed purchase and sale agreement, along with canceled checks or proof of satisfaction of any promissory note issued to the seller would be helpful.

Where a shareholder is unable to establish their basis for the stock – i.e., where the shareholder has failed to carry their burden of proof – the IRS will treat the shareholder as having a zero basis in such stock; consequently, the entire amount of the dividend distribution to the shareholder will be taxable,[xv] as one Taxpayer – who was already having a pretty bad day[xvi] – found to his detriment.

“Return-of-Capital” Defense

The Court of Appeals for the Ninth Circuit determined that a federal district court did not abuse its discretion in precluding Taxpayer’s “return-of-capital” defense. https://cdn.ca9.uscourts.gov/datastore/memoranda/2018/09/24/17-50091.pdf.

The Taxpayer was charged with tax evasion. As part of his defense, he tried to establish that there was no tax deficiency because the money removed from his corporation represented a return of capital, or stock basis.

The Court ruled that the district court “may preclude a defense theory where ‘the evidence, as described in the defendant’s offer of proof, is insufficient as a matter of law to support the proffered defense.’”

To establish a factual foundation for a “return-of-capital” theory, the Court stated, a taxpayer must show: “(1) a corporate distribution with respect to a corporation’s stock, (2) the absence of corporate earnings or profits, and (3) stock basis in excess of the value of the distribution.”

Taxpayer, the Court continued, failed to establish that his stock basis exceeded the value of the distributions. Taxpayer presented checks that purported to demonstrate the amount he paid to purchase the stock of Corp. He also provided a declaration stating that he transferred a deed of valuable property to Corp; despite being given the opportunity to do so, however, Taxpayer provided no evidence of the property’s value aside from his own estimate.

The government presented the declaration of a CPA involved in Corp’s bankruptcy proceedings who stated that “according to escrow documents,” the property Taxpayer transferred was assigned a value below that claimed by Taxpayer. It also presented a declaration that Taxpayer submitted in his divorce proceedings, in which Corp’s CPA stated the amount for which Corp had redeemed stock from Taxpayer, thereby reducing his basis. The government submitted the bank records for such payment.

The Court explained that Taxpayer had the burden to establish factual support for a finding that his stock basis exceeded the value of the distributions. Taxpayer’s testimony was insufficient to carry his burden. He did not provide evidentiary support for his valuation, nor evidence to rebut the documents establishing how much Corp paid Taxpayer for the redemption of stock.

Because the evidence did not establish that Taxpayer had a stock basis in Corp in excess of the value of the distributions, the Court decided that the district court did not abuse its discretion in finding that Taxpayer failed to establish a factual basis for a return-of-capital defense.

It Pays to Be Prepared[xvii]

A corporation’s distribution of a large dividend, or a shareholder’s sale of their stock for a price they “couldn’t refuse,” should represent a moment of affirmation of the shareholder’s investment or business decision-making.

Of course, the imposition of income taxes, and perhaps surtaxes, with respect to the amount received by the shareholder will tend to dampen the shareholder’s celebratory mood, but every shareholder/taxpayer expects to share some of their economic gains with the government in the form of taxes. Those who are well-advised will have accounted for this tax liability in planning for the welcomed economic event.

That being said, no taxpayer would willingly remit to the government more than what was properly owed. It is the taxpayer’s burden, however, to establish this amount by, among other things, establishing their basis in the stock that was sold or on which a corporate distribution was made.

Imagine a shareholder’s having to pay tax on dollars that actually represent a return of their capital investment – which should have been returned to them free of tax – simply because the shareholder was not prepared and unable to substantiate their basis in the stock. Talk about low-hanging fruit.

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[i] In others words, it is made to the individual in their capacity as a shareholder.

[ii] Taxable at a federal rate of 20%, though the 3.8% surtax on net investment income may also apply.

[iii] Taxable at a federal rate of 23.8% if long-term capital gain. See EN ii.

[iv] In the case of a closely held corporation, shareholders must also be attuned to the risk of constructive dividends distributions.

[v] This is also key for the corporation, which will be treated as having sold the property distributed if the fair market value of the property exceeds its adjusted basis in the hands of the corporation.

[vi] Which will be important if the amount of the distribution exceeds the earnings and profits and the stock’s adjusted basis; will the resulting gain be long-term or short-term capital gain?

[vii] In the case of a closely held corporation, most “capital contributions” made after the initial funding of the corporation take the form of loans from the shareholders, especially when made disproportionately among the shareholders.

[viii] An “exchange” under IRC Sec. 302.

[ix] Compare to the stock basis of a shareholder of an S corporation; their basis is adjusted every year to reflect their allocable share of the corporation’s income, gain, deduction, and loss, as well as the amount of any distribution made to them. IRC Sec. 1367.

[x] IRC Sec. 1001. In which case, they would take the stock with a cost (i.e., fair market value) basis. IRC Sec. 1012.

[xi] IRC Sec 351 and Sec. 358. In this way, the shareholder’s deferred gain is preserved.

[xii] The short answer: No; which is not to say that taxpayers have not tried that argument.

[xiii] The corporation will have to issue a Form 1099-DIV but, in the case of a close corporation, the controlling shareholder may be hard-pressed to rely upon such information return without more.

[xiv]  For example, depreciation schedules.  If the stock was inherited, the fair market of the stock on the date of the decedent’s death will be necessary. Start with a copy of the estate tax return filed by the decedent’s estate, on IRS Form 706. The appraisal obtained in connection with the estate tax return, or a copy of the shareholders’ agreement that fixed the price for the buyout of the stock upon the death of a shareholder, would be helpful.

[xv] Albeit, presumably, at the rate applicable to capital gain.

[xvi] Crime shouldn’t pay.

[xvii] No, I am not thinking about the song from the “Lion King” movie made famous by Jeremy Irons in the role of Scar. I am thinking of the Boy Scout motto. Taxpayers and their advisers would do well to adopt this motto.