Philip Caprio v. New York State Department of Taxation and Finance

37 N.E.3d 707, 25 N.Y.3d 744, 16 N.Y.S.3d 204
CourtNew York Court of Appeals
DecidedJuly 1, 2015
Docket116
StatusPublished
Cited by6 cases

This text of 37 N.E.3d 707 (Philip Caprio v. New York State Department of Taxation and Finance) is published on Counsel Stack Legal Research, covering New York Court of Appeals primary law. Counsel Stack provides free access to over 12 million legal documents including statutes, case law, regulations, and constitutions.

Bluebook
Philip Caprio v. New York State Department of Taxation and Finance, 37 N.E.3d 707, 25 N.Y.3d 744, 16 N.Y.S.3d 204 (N.Y. 2015).

Opinion

OPINION OF THE COURT

Stein, J.

On this appeal, we are asked to decide whether the 3 1 /2-year retroactive application of the 2010 amendments to Tax Law § 632 (a) (2) (L 2010, ch 57, § 1, part C) is unconstitutional, as applied to plaintiffs, under the Due Process Clauses of the United States and New York State Constitutions. The amendments, as applied here, involve the intersection of two federal tax statutes, 26 USC §§ 338 (h) (10) and 453 (h) (1) (A), which address “deemed asset sales” and use of the installment method of accounting, respectively. Plaintiffs challenge the amendments insofar as they retroactively imposed a tax on the 2007 sale of the stock of their subchapter S corporation in a deemed asset sale, for which they utilized the installment method for federal tax purposes. Applying the balancing of the equities test set forth in James Sq. Assoc. LP v Mullen (21 NY3d 233, 246 [2013]) and Matter of Replan Dev. v Department of Hous. Preserv. & Dev. of City of N.Y. (70 NY2d 451, 456 [1987], appeal dismissed 485 US 950 [1988]), we conclude that retroactive application of the 2010 amendments did not violate plaintiffs’ due process rights.

I

Plaintiffs are Florida residents who owned the capital stock of Tri-Maintenance & Contractors, Inc. doing business as TMC Services, Inc., a New Jersey corporation that provided janitorial services. TMC had elected to be taxed as a subchapter S corporation for state and federal tax purposes (see Internal Revenue Code [26 USC] §§ 1361-1379; Tax Law § 660). An S corporation is permitted to avoid paying corporate income taxes by passing through income to its shareholders, who are then responsible for reporting the income on their personal tax returns. The character of the income remains the same and is treated as though the shareholder realized it directly from the S corporation’s source, or incurred it in the same manner that the corporation did (see 26 USC § 1366 [a], [b]; Tax Law § 617 [b]).

*747 Resident New York shareholders pay state income tax on all pass-through S corporation income (see Tax Law § 617 [a], [b]), but nonresidents are assessed proportional New York State income taxes based on the percentage of the S corporation’s total gains that are derived from or connected with New York sources of corporate income (see Tax Law §§ 631 [a] [1] [B]; 632 [a] [2]). To ensure parallel state and federal treatment, each item of pass-through gain retains the same character for state and federal income tax purposes (see Tax Law §§617 [b]; 632 [e] [2]). TMC earned nearly 50% of its total income in New York.

In 2007, plaintiffs sold all of their shares in TMC to Sanitors Services, Inc., for approximately $20 million. Plaintiffs and Sanitors jointly made an election under Internal Revenue Code (26 USC) § 338 (h) (10) to treat the transaction as a “deemed asset sale,” pursuant to which the corporation that is being sold is treated, for tax purposes, as if it sold all of its assets to the buyer and then distributed the sale proceeds to its shareholders in a complete liquidation. A deemed asset sale is generally made at the request of the purchaser, which receives the beneficial tax consequences of an asset sale, such as a stepped up basis for the target (i.e., selling) corporation’s assets, that it could not obtain from a straight stock purchase. For federal tax purposes, the gains realized by the target corporation are treated as corporate asset sale gains and, in the case of an S corporation, usually passed through to shareholders as taxable asset sale income, rather than as capital gains on stocks, which would be subject to a more favorable tax rate (see 26 CFR 1.338[h][10]-l [d] [3] — [5]; see also Byron F. Egan, Asset Acquisitions: Assuming and Avoiding Li abilities, 116 Penn St L Rev 913, 928 [2012]). 1

Further, the sale here was structured in such a way that the purchase price was to be paid in installments pursuant to promissory notes, rather than with cash up-front. 2 When the installment method is used, taxpayers recognize gains or *748 income in the taxable years in which the payments are actually received, rather than the year the notes representing the installment obligation are received (see 26 USC § 453 [h] [1] [A]). We note that, in their submissions before Supreme Court, plaintiffs limited their challenge to the retroactive application of the amendments pertaining to the tax treatment of installment obligations under 26 USC § 453 (h) (1) (A), and expressly acknowledged that they “d[id] not challenge those portions of the 2010 Amendments related to 26 USC § 338 (h) (10), which have no bearing on [plaintiffs’] claims and [were] not even identified in the Verified Complaint.” That acknowledgment— along with the use of the installment method, and the fact that plaintiffs limited their challenge to retroactive application of the statute and conceded that prospective application cannot be contested (37 Misc 3d 964, 975 [Sup Ct, NY County 2012])— distinguishes this case from Burton v New York State Dept. of Taxation & Fin. (25 NY3d 732 [2015] [decided herewith]), in which the plaintiffs challenge the prospective application of the amendments to transactions in which an election has been made under section 338 (h) (10).

On its 2007 tax returns, TMC reported the deemed asset sale in the same manner as if it had actually sold its assets to Sanitors and received, in consideration, the installment obligations. It used the installment method of accounting to report its gain arising from the sale — i.e., TMC did not report any gain because it had not received any cash payments as of the date of its deemed liquidation; nor did it recognize any gain from the distribution of the installment obligations to plaintiffs in the deemed liquidation. Plaintiffs, however, reported a gain on their 2007 federal income tax returns of approximately $18 million (resulting from the payments received that year under the first installment obligation) and reported a gain of approximately $1 million on their 2008 federal income tax returns in connection with additional payments received that year.

In contrast, with respect to their New York income taxes, plaintiffs reported no income or gain derived from the sale of TMC, arguing that, pursuant to various federal tax statutes and regulations, the payments they received from the sale were treated as the proceeds of a sale of stock — an intangible asset — the gain from which is not taxable to them by the State under Tax Law § 631 (b) (2). Specifically, plaintiffs relied upon 26 USC § 453 (h) (1) (A), which states that

“[i]f, in a liquidation to which [26 USC §] 331 applies, the shareholder receives (in exchange for the *749 shareholder’s stock) an installment obligation acquired in respect of a sale or exchange by the corporation . . .

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37 N.E.3d 707, 25 N.Y.3d 744, 16 N.Y.S.3d 204, Counsel Stack Legal Research, https://law.counselstack.com/opinion/philip-caprio-v-new-york-state-department-of-taxation-and-finance-ny-2015.