Pimlico, LLC v. Commissioner of Internal Revenue

Whether the United States Court of Appeals for the Second Circuit erred in refusing to review the evidentiary error that infected the Tax Court’s opinion, issued nine years after trial, on the grounds that, although the appellant made extensive arguments regarding the error in the body of its brief, it waived its right to have the error considered under the plain error standard of review by citing to that standard of review in a footnote.

Whether the Internal Revenue Service’s antitextual anti-abuse rule, 26 C.F.R. § 1.701–2, which permits the Commissioner to “recast” a partnership transaction to achieve the Commissioner’s preferred tax result even if, as here, the transaction “fall[s] within the literal words of a particular statutory or regulatory provision,” is invalid under this Court’s decision in Loper Bright Enterprises v. Raimondo, 603 U.S. 369 (2024).