How many times have you said to a client, “Please don’t agree to any deal terms until we’ve had a chance to discuss your goals and plans, consider your options, and analyze the consequences.”

How many times has a client presented you with a fully executed “letter of intent” – one that you’ve never seen before – that almost (but, thankfully, not quite) constitutes an agreement to buy or sell?[1]

I’m being only partially facetious. Of course the client knows their business, well, “like nobody’s business,” and it may be that the advisor cannot add much to the business deal.

Too often, however, a taxpayer decides upon a series of steps without appreciating the tax – and, therefore, the “net” economic – consequences thereof. In some cases, the taxpayer should have known better – some truths are obvious; in others, the result is not necessarily intuitive, but it could have been anticipated and planned for had the taxpayer sought the assistance of a tax adviser.

I recently encountered this scenario in two different matters, each involving the same substantive tax issues – one obvious, the other less so (at least for a “non-tax person”) – and each requiring an analysis of how the interplay of the applicable tax rules may affect the economics of the transaction.

A Tax Truth

There are certain “tax truths” that are self-evident; for example, the gain realized by a taxpayer from the conversion into cash of property used in a business (a sale), or from the exchange of such property for other property differing materially in kind, is treated as income – the taxpayer has so changed the fundamental nature of their property interest that the Code requires the taxpayer to recognize the gain realized on the disposition and to be taxed thereon.

Amount Realized

The amount realized by a taxpayer from the disposition of their business property is the sum of any money, plus the fair market value of any other property, received by the taxpayer in exchange for their property. The taxpayer’s taxable gain from the disposition is determined by reducing the amount realized by the taxpayer’s adjusted basis for the property.

Cost Basis

In general, a taxpayer’s adjusted basis for a property used in their business represents the unreturned or unrecovered portion of the taxpayer’s investment in the property. When a taxpayer purchases property, the taxpayer is said to have a “cost basis” for the property – the amount of the taxpayer’s investment is equal to the amount paid to acquire the property.

Adjusted Basis

Depending upon the nature of the property – and depending upon the incentives provided by the Code for investing in such property – the taxpayer’s cost must be capitalized[2] and may be recovered (and its basis adjusted) over time through annual deductions for depreciation or amortization[3], or the taxpayer may elect to deduct (or “expense”) the cost in the year the property is placed into service[4] rather than by depreciating the cost over time.[5] These deductions enable the taxpayer to recover at least some of their investment in the property – prior to its disposition – by offsetting the ordinary income generated by the business. Significantly, a taxpayer’s basis for shares of stock in a corporation is not recoverable in this manner.

When the taxpayer sells the property, they recover their adjusted basis for the property – i.e., the remaining balance of their unrecovered investment – before recognizing any gain.[6]

Another Tax Truth

In contrast to the sale of property, or the disposition of such property in exchange for materially different property, no gain is recognized[7] when the taxpayer exchanges property (the “relinquished property”) that has been used in their trade or business solely for property of a “like kind” (the “replacement property”) that will also be used in the trade or business. The nature of the taxpayer’s relationship to the replacement property is not materially different from their relationship to the relinquished property; thus, the “like kind exchange” is not an appropriate occasion for the recognition of gain and the imposition of tax.

Tax Deferral

That is not to say that the gain realized on the like kind exchange is wiped away. Rather, the recognition of such gain is deferred until the taxpayer disposes of the replacement property in a taxable transaction. In order to preserve the gain inherent in the property at the time of the like kind exchange, the taxpayer is required to take the replacement property with the same basis that the taxpayer had in the relinquished property.[8]

These concepts, which are so often associated with the disposition of real property, have their counterparts in the Code’s corporate tax provisions. The Code excepts from the general recognition rule certain exchanges of property and of stock that are incident to specified readjustments of a corporate structure, that are undertaken for a bona fide business purpose, and that effect only a readjustment of a continuing interest in property under a modified corporate form.

Subsidiary Liquidation

Thus, when a corporation (the “parent”) owns shares of stock representing at least 80% of the total voting power and fair market value of another corporation (the “sub”), and causes the sub to liquidate into the parent – i.e., to transfer all of its assets, subject to all of its liabilities, to the parent, in exchange for, and in cancellation of, the sub’s outstanding stock – neither the sub nor the parent is required to recognize any of the gain realized in the exchange.[9]

As in the case of the like kind exchange, the gain inherent in the sub’s assets, which are distributed to the parent in connection with the liquidation of the sub, is preserved in the hands of the parent by requiring the parent to hold those assets with the same adjusted basis that they had in the hands of the sub.[10]

The same result follows when an S corporation elects to treat a wholly-owned sub as a qualified subchapter S subsidiary (“QSUB”), or when a parent causes a sub to merge into an LLC that is wholly-owned by the parent and that is disregarded as an entity separate from the parent for tax purposes. In both cases[11], the parent is treated as acquiring the assets of the sub in a tax-deferred liquidation of the sub, and the parent takes those assets with the same adjusted basis as the sub.

Truths Collide

The two “truths” described above coexist peacefully where the parent created and funded the sub (“organically” you might say). In that case, the parent’s basis for its shares of sub stock reflect its actual investment in the sub – the amount of cash contributed by the parent or the adjusted basis (unrecovered investment) of the assets contributed by the parent – and the sub’s basis for its assets reflects the sub’s adjusted cost basis or the parent’s basis for the assets contributed.

Target Sub

But what if the parent (the “buyer”) purchased the stock of the sub (the “target”) from an unrelated third party[12] in exchange for an amount of cash equal to the fair market value of the sub? Obviously, the parent would acquire the stock with a cost basis. Without more, the sub’s basis for its assets would not be affected by the purchase of its stock.

If the parent later sold the sub stock, it would recover its stock basis before realizing any gain.

Alternatively, if the sub sold its assets, it would recognize and be taxed on the gain realized.

Suppose the parent decided, for good business reasons, to liquidate the newly-acquired sub? According to the IRS, the two transactions – i.e., the acquisition of target-sub’s stock and the subsequent liquidation of target-sub into parent-buyer – will be respected as two separate transactions, even if they were undertaken as part of a single plan.[13]

Disappearing Basis

Consequently, notwithstanding that the parent had a fair market value cost basis for its target-sub stock immediately after the acquisition of sub’s stock and before the sub’s liquidation, the parent would take the sub’s assets with the same basis that the sub had for the assets. In effect, the parent’s cost basis for the sub’s stock ceases to have any role in the tax lives of the parent and of the assets formerly held by the sub – it simply disappears.

The same result would follow if parent-buyer were an S corporation and it elected to treat its newly-acquired target-sub as a QSUB.[14]

Thus, on the parent’s subsequent sale of the sub’s assets, the parent would recognize gain of an amount determined by reference to the sub’s adjusted basis in such assets.

At first blush, this may seem like an unfair result. After all, the parent has just paid fair market value consideration for the sub stock, yet it is burdened with a tax liability without necessarily experiencing any accretion in value.

This conclusion, however, overlooks the fact that the parent was able to acquire the sub’s assets on a tax-deferred basis – i.e., without causing the sub to incur any corporate-level income tax liability – by virtue of the liquidation.

It also overlooks the fact that the parent-buyer may have been able to negotiate with the target-sub’s selling shareholders to require that the parties elect to treat the acquisition of the sub’s stock as a purchase of its assets; in that case, the parent would have acquired such assets with a cost basis following the actual or deemed liquidation of the sub.[15]

Forewarned . . .

In the end, it is important that the parent-buyer be aware of the foregoing considerations prior to negotiating its purchase of the target-sub stock, including the consideration therefor.

Assuming the parent-buyer must acquire the target-sub’s stock – because there is some business or legal imperative that prevents it from acquiring the sub’s assets – the parent-buyer should be prepared to increase its purchase price for the stock if it wants to convince the target-sub’s shareholders to treat the stock sale as a sale of target-sub’s assets for tax purposes.

If the “deemed asset sale” election is not available, then the parent-buyer should consider offering a purchase price for the sub stock that reflects its inability to recover its cost basis for the stock through depreciation or amortization, and that reflects the tax liability inherent in the sub’s assets (their “built-in gain”), regardless of any plans to liquidate the sub. By adjusting the purchase price for the increased economic cost of the stock deal, the buyer may be able to partially offset the cost of the disappearing basis.

Of course, the buyer’s goals for acquiring a target business, including the anticipated economic benefits, may outweigh these tax considerations, or the relative bargaining power of the two sides may be such that the buyer cannot obtain the economic concessions described above without risking the loss of the deal.

In any event, the buyer must be made aware of the tax consequences in order to make an educated decision.[16]

[1] What’s your favorite antacid?

[2] It becomes or is added to its basis.

[3] Over the “useful life” of the property.

[4] Subject to certain limitations.

[5] The Tax Cuts and Jobs Act extended the ability to expense the cost of certain tangible property.

[6] It is important to note that regardless of how much the property may change in value, the taxpayer’s adjusted basis continues to represent their actual, unrecovered investment in the property. It is also important to note that a taxpayer’s stock basis may only be recovered upon the sale or liquidation of the stock.

[7] Included in income.

[8] This is consistent with the taxpayer’s deemed continuing investment in the “same” property.

[9] Without this rule, the sub would recognize gain equal to the excess of the fair market value of the assets distributed in liquidation to the parent over the sub’s adjusted basis in such assets, and the parent would recognize gain equal to the excess of the net fair market value of the assets received in liquidation of its sub stock over the parent’s adjusted basis for such stock.

[10] Thus, if the parent later sells those assets, its gain will be determined by reference to the sub’s basis in the assets.

[11] Provided the sub is solvent and the parent is not “exempt” from tax.

[12] Whether by way of a straight sale or a reverse subsidiary merger. Most buyers would certainly prefer to purchase assets from the target corporation, rather than purchase stock from the target’s shareholders.

[13] This was not always the case. Before the enactment of IRC 338, the IRS collapsed the two steps to treat parent as having purchased sub’s assets, and taking a cost basis in the assets, under the so-called “Kimbell-Diamond doctrine.”

[14] As indicated earlier, if an S corporation parent makes a valid QSUB election with respect to a subsidiary, the subsidiary is deemed to have liquidated into the S corporation, and all of the assets, liabilities, and items of income, deduction, and credit of the QSUB are treated as belonging to the S corporation.

[15] Assuming they qualified to make such an election. Whether under IRC Sec. 338(h)(10) or IRC Sec, 336(e), the cooperation of the selling shareholder(s) is required for the election, and a knowledgeable seller may use this leverage to extract a higher purchase price.

[16] As Sy Syms used to say: “An educated consumer is our best customer.”