Diebold Foundation, Inc. v. Commissioner of Internal Revenue

736 F.3d 172, 2013 WL 6015660, 112 A.F.T.R.2d (RIA) 6901, 2013 U.S. App. LEXIS 22964
CourtCourt of Appeals for the Second Circuit
DecidedNovember 14, 2013
DocketDocket 12-3225-cv
StatusPublished
Cited by60 cases

This text of 736 F.3d 172 (Diebold Foundation, Inc. v. Commissioner of Internal Revenue) is published on Counsel Stack Legal Research, covering Court of Appeals for the Second Circuit primary law. Counsel Stack provides free access to over 12 million legal documents including statutes, case law, regulations, and constitutions.

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Diebold Foundation, Inc. v. Commissioner of Internal Revenue, 736 F.3d 172, 2013 WL 6015660, 112 A.F.T.R.2d (RIA) 6901, 2013 U.S. App. LEXIS 22964 (2d Cir. 2013).

Opinion

POOLER, Circuit Judge:

The Commissioner of Internal Revenue (“Commissioner”) appeals the decision of the United States Tax Court (Joseph Robert Goeke, J.) holding that the Diebold Foundation, Inc. (“Diebold”), could not be held liable as a transferee of a transferee under 26 U.S.C. § 6901. As an initial matter, we conclude that the standard of review for mixed questions of law and fact in a case on review from the Tax Court is the same as that for a case on review after a bench trial from the district court: de novo to the extent that the alleged error is in the misunderstanding of a legal standard and clear error to the extent the alleged error is in a factual determination. See 26 U.S.C. § 7482(a). On the merits, we hold that the two requirements of 26 U.S.C. § 6901 — transferee status and liability — are separate and independent inquiries, one procedural and governed by federal law, and the other substantive and governed by state law. We further hold that, under the New York Uniform Fraud *175 ulent Conveyance Act, the applicable state statute, the series of transactions at issue collapse based upon the constructive knowledge of the parties involved. The case is remanded to the Tax Court to determine in the first instance whether Diebold is a transferee of a transferee under § 6901 and whether the three-year statute of limitations of 26 U.S.C. § 6901(c)(2), which applies transferee of transferee liability, or the six-year statute of limitations of 26 U.S.C. § 6501(e)(1)(A), which applies to collection when substantial omissions are made from the report of gross income, governs. We thus vacate the decision of the Tax Court and remand the case for further proceedings consistent with this opinion.

BACKGROUND

I.

This case involves shareholders who owned stock in a C Corporation (“C Corp”), which in turn held appreciated property. Upon the disposition of appreciated property, taxpayers generally owe tax on the property’s built-in gain — that is, the difference between the amount realized from the disposition of the property and its adjusted basis. 26 U.S.C. §§ 1(h), 1001, 1221, 1222. A C Corp, a corporation governed by subchapter C of the Internal Revenue Code, Eisenberg v. Comm’r, 155 F.3d 50, 52 n. 3 (2d Cir.1998), is treated as a separate legal entity for tax purposes, 26 U.S.C. § 11. C Corps are also subject to tax on built-in gain. See 26 U.S.C. §§ 11, 1201.

When shareholders who own stock in a C Corp that in turn holds appreciated property wish to dispose of the C Corp, they can do so through one of two transactions: an asset sale or a stock sale. In an asset sale, the shareholders cause the C Corp to sell the appreciated property (triggering the built-in gain tax), and then distribute the remaining proceeds to the shareholders. 1 In a stock sale, the shareholders sell the C Corp stock to a third party. The C Corp continues to own the appreciated assets and the built-in gain tax is not triggered. In other words, in an asset sale, because C Corps are treated as separate legal entities for tax purposes, subject to corporate tax (independent of any capital gain taxes assessed against the earning shareholders), a C Corp’s sale of its assets imposes an additional tax liability. While the C Corp, and not the shareholders, pays this tax liability, such payment nonetheless reduces the amount of cash available for distribution to those shareholders.

In the case of a stock sale, the assets remain owned by the C Corp and the tax on the built-in gain is not triggered. Buyers would generally prefer to purchase the assets directly and receive a new basis equal to the purchase price, thus eliminating the built-in gain. Sellers generally disfavor the sale of assets because of the attendant tax liability and would prefer to sell the stock and move the tax liability on to the purchaser. However, the seller’s preferred transaction merely pushes the tax liability down the line; at any point when the shareholders of the C Corp— including new owners who purchased the shares in a stock sale — wish to sell the assets, the built-in gain tax will be triggered. Because of this accompanying tax liability, a stock sale will generally merit a lower sale price than an asset sale.

“Midco transactions” or “intermediary transactions” are structured to allow the parties to have it both ways: letting the seller engage in a stock sale and the buyer engage in an asset purchase. In such a *176 transaction, the selling shareholders sell their C Corp stock to an intermediary entity (or “Midco”) at a purchase price that does not discount for the built-in gain tax liability, as a stock sale to the ultimate purchaser would. The Midco then sells the assets of the C Corp to the buyer, who gets a purchase price basis in the assets. The Midco keeps the difference between the asset sale price and the stock purchase price as its fee. The Midco’s willingness to allow both buyer and seller to avoid the tax consequences inherent in holding appreciated assets in a C Corp is based on a claimed tax-exempt status or supposed tax attributes, such as losses, that allow it to absorb the built-in gain tax liability. See 1.R.S. Notice 2001-16, 2001-1 C.B. 730. If these tax attributes of the Midco prove to be artificial, then the tax liability created by the built-in gain on the sold assets still needs to be paid. In many instances, the Midco is a newly formed entity created for the sole purpose of facilitating such a transaction, without, other income or assets and thus likely to be judgment-proof. The IRS must then seek payment from the other parties involved in the transaction in order to satisfy the tax liability the transaction was created to avoid.

II.

Double . D Ranch, Inc., (“Double D”), a personal holding company, taxed as a C Corp, 26 U.S.C. § 542, had two shareholders: the Dorothy R. Diebold Marital Trust (“Marital Trust”) and The Diebold Foundation Inc. (“Diebold New York”) (together, the “Shareholders”). The trustees of the Marital Trust were the Bessemer Trust Company N.A. (“Bessemer”), operating primarily through its Senior Vice President, Austin J. Power, Jr., Dorothy Diebold (“Mrs. Diebold”), and Andrew W. Bisset, Mrs. Diebold’s attorney and personal advisor. The directors of Diebold New York were Mrs. Diebold, Bisset, and the three adult Diebold children.

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736 F.3d 172, 2013 WL 6015660, 112 A.F.T.R.2d (RIA) 6901, 2013 U.S. App. LEXIS 22964, Counsel Stack Legal Research, https://law.counselstack.com/opinion/diebold-foundation-inc-v-commissioner-of-internal-revenue-ca2-2013.