ATL Article on Tax Structuring on Sale of MLB Team (2/8/24)

I picked this up today involving the type of planning that may keep well-paid tax controversy specialists busy in the future. Steven Chung, The Upcoming Baltimore Orioles Sale Is Structured To Avoid Capital Gains Taxes (Above the Law 2/7/24), here. The sale is described:

But it is not a straightforward sale. Rubenstein and his group will initially purchase 40% of the team. The remaining 60% will be sold, reportedly for tax reasons, after 94-year-old Angelos passes away. Angelos purchased the team in 1993 for $173 million. If the sale were to take place now, Angelos would face an estimated $250 million capital gains tax on the approximately $1.5 billion profit. But by waiting until after his passing, the basis step-up rule would increase his cost basis to current market value instead of his original purchase price. If the team is sold immediately thereafter, there will be little to no capital gains tax on the sale.

Rubenstein and his group [the buyers] would also enjoy some tax benefits as the new owners. According to Forbes, if the buyers are able to structure this as an asset sale, they will be able to take advantage of any losses incurred to offset other income. However, investors who do not materially participate in the team management can only use their losses to offset passive income such as real estate rental income.

 What is not clear is who will control the Orioles after Rubenstein’s initial 40% purchase. On one hand, the Angelos family could still control the team through its majority ownership. On the other hand, the Angelos family could allow Rubenstein to control the team after the initial purchase. If this happens, the IRS may try to reclassify the transaction as if 100% of the team was sold while Peter Angelos was still alive and thus trigger the capital gains tax. The IRS could argue that this two-step transaction was purely tax motivated, specifically to avoid the capital gains tax.

 The article goes on to discuss the tax issues familiar to and loved by all tax controversy afficionados-- “substance over form,” “codified economic substance doctrine,” and “step transaction doctrine.”  And the article notes:

Even if the sale avoids capital gains tax, Peter Angelos’s estate will be subject to federal estate taxes which is as high as 40% at the top bracket. Also, Maryland also has its own estate tax.

So, the IRS will certainly share in the success of this venture, with the only issue being how large its overall share will be.

Judge Halpern Synthesizes Taxpayer and IRS Burdens when Seeking a Tax Result Based on Substance Rather than Form (5/31/21)

In Complex Media Inc. v. Commissioner, T.C. Memo. 2021-14 (as revised 3/31/21), TN here and TC Dkt entry 87 here, in a 103 page opinion, Judge Halpern had some interesting discussion on issues important to tax procedure fans.  I won’t try to slice and dice the entire opinion but will just point out the discrete parts that caught my attention.

1. “This Court has never accepted the Danielson rule. And, because the cases before us are not appealable to the Third Circuit (or to any other appellate court that has accepted the Danielson rule), the Golsen doctrine does not require us to apply that rule here.”  (Slip Op. 53-54.)

2. More interesting is the Court’s discussion as to the different burdens when the IRS and the taxpayer seeks to avoid the form of the transaction.  The key excerpt is (Slip Op. 63-64):

In sum, as our caselaw has evolved, it has become more hospitable to taxpayers seeking to disavow the form of their transactions. While we no longer reject those arguments out of hand, as we did in Swiss Oil Corp., J.M. Turner & Co., and Television Indus., we have repeatedly indicated that taxpayers may face a higher burden than the Commissioner does in challenging transactional form. On occasion, as in Glacier State Elec. Supply, we have suggested that the taxpayer's higher burden might be an evidentiary one. But we have not identified specific factual questions that should be subject to a higher burden than that imposed by Rule 142(a) or articulated the quantum of evidence necessary to meet that burden. [*64] Nor have we offered a clear justification for imposing on the taxpayer a higher burden to prove facts relevant to the disavowal of form than the generally applicable preponderance of the evidence standard.

Therefore, we now conclude that the additional burden the taxpayer has to meet in disavowing transactional form relates not to the quantum of evidence but instead to its content--not how much evidence but what that evidence must show by the usual preponderance. The Commissioner can succeed in disregarding the form of a transaction by showing that the form in which the taxpayer cast the transaction does not reflect its economic substance. For the taxpayer to disavow the form it chose (or at least acquiesced to), it must make that showing and more. In particular, the taxpayer must establish that the form of the transaction was not chosen for the purpose of obtaining tax benefits (to either the taxpayer itself, as in Estate of Durkin, or to a counterparty, as in Coleman) that are inconsistent with those the taxpayer seeks through disregarding that form. When the form that the taxpayer seeks to disavow was chosen for reasons other than providing tax benefits inconsistent with those the taxpayer seeks, the policy concerns articulated in Danielson will not be present.

I have revised the relevant discussion in my Federal Tax Procedure book working draft to be published in August.  I link here a pdf of the discussion with the changes redlined.  Note that the page numbers and footnote numbers will be different in the final version published in August.

JAT comments:

Tax Procedure Book Errata - Tax Common Law Doctrines and Statutory Interpretation (1/2/17)

Book Outline Section	Nature of Update	Location for current editions
Ch. 2 ¶ 1.B., Statutes and their Meanings	Introduce common law doctrines of statutory interpretation - business purpose, form over substance and economic substance	Student Ed. P. 37 Practitioner Ed. p. 42 (immediately before C. Committees and Committee Reports)

Finally, tax statutory interpretation includes applying the text in the light of certain precepts that inhere in the scheme of taxation that Congress adopted.  Students of tax law will already have heard concepts, often called tax common law doctrines, such as the business purpose doctrine, form over substance, and economic substance, which inform the application of the statute even when the statutory text says nothing about those concepts. n. 33a

n. 33a In Santander Holdings United States v. United States, ___ F.3d ___, 2016 U.S. App. LEXIS 22400 (1st Cir. 2016), the Court said:

               The federal income tax is, and always has been, based on statute. The economic substance doctrine, like other common law tax doctrines, can thus perhaps best be thought of as a tool of statutory interpretation, n8 as then-Judge Breyer characterized it in his opinion for this court in Dewees v. Commissioner, 870 F.2d 21, 35-36 (1st Cir. 1989).

   n8 As one commentator says:

               A related . . . claim is that the legislature assumes that long-standing common law doctrines such as economic substance will be used to interpret the statutes it enacts. Under this claim, the doctrines have been implicitly adopted as part of the statute -- at least where the statute does not indicate otherwise.

               Joseph Bankman, The Economic Substance Doctrine, 74 S. Cal. L. Rev. 5, 11 (2000).

Caveat, the footnote numbers above are based on  the footnote numbers in the current Practitioner Edition.  The footnote numbers will not be the same in the next Edition scheduled for publication in August 2017.