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69 F.4th 762
11th Cir.
2023
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Background

  • Carl and Leila Gregory owned a yacht (Lady Leila) through CLC Ventures, a disregarded Cayman Islands entity, and chartered it in 2014–2015.
  • CLC’s chartering activity lacked a profit motive under I.R.C. § 183, but generated income and significant expenses reported on the Gregorys’ Schedule C.
  • The IRS reclassified CLC’s income as “other income” and its expenses as itemized deductions (miscellaneous) on Schedule A, making them deductible only to the extent they exceeded 2% of AGI under I.R.C. § 67(a).
  • The IRS disallowed nearly all hobby-related deductions and assessed deficiencies; the Tax Court granted summary judgment for the Commissioner and upheld the deficiencies.
  • The Eleventh Circuit affirmed, holding that deductions allowed by § 183(b)(2) are below-the-line miscellaneous itemized deductions subject to the § 67(a) 2% floor.

Issues

Issue Plaintiff's Argument (Gregorys) Defendant's Argument (Commissioner) Held
Whether § 183(b)(2) deductions are above-the-line (reduce gross income) or below-the-line (itemized deductions) § 183(b)(2) creates an above-the-line deduction analogous to business expenses (§ 162) and thus should appear in § 62(a) adjustments § 183 does not specify placement; § 62’s exhaustive list omits § 183, so § 183(b)(2) deductions are not § 62(a) adjustments and must be itemized Held: § 183(b)(2) deductions are below-the-line itemized deductions (miscellaneous)
Whether § 183(b)(2)’s use of “amount” and reference to “gross income derived from such activity” implies above-the-line treatment The cap tied to the hobby’s gross income shows Congress intended the deduction to reduce gross income The statutory phrase sets only a cap (hobby income) on the allowed amount; it does not change deduction category Held: Court rejects plaintiff’s textual inference; the “gross income” reference is a cap benchmark only
Whether statutes are ambiguous and canons/legislative intent favor taxpayers Ambiguity exists; apply tax-canons (construe for taxpayer), absurdity and implied repeal arguments support the Gregorys The statutory scheme (I.R.C. §§ 62, 63, 67) plainly resolves placement; no genuine ambiguity; canon and absurd-result claims fail Held: No ambiguity after reading the Code as a whole; canons and repeal arguments unpersuasive; § 183(b)(2) deductions are miscellaneous itemized deductions subject to § 67(a)

Key Cases Cited

  • New Colonial Ice Co. v. Helvering, 292 U.S. 435 (U.S. 1934) (deductions depend on congressional grace)
  • Conn. Nat’l Bank v. Germain, 503 U.S. 249 (U.S. 1992) (statute presumed to mean what it says)
  • K Mart Corp. v. Cartier, Inc., 486 U.S. 281 (U.S. 1988) (interpretation must consider statutory language and design)
  • Brannen v. Commissioner, 722 F.2d 695 (11th Cir. 1984) (discusses § 162/§ 183 relationship re profit-motive and § 183(b)(2) cap)
  • Roberts v. Commissioner, 329 F.3d 1224 (11th Cir. 2003) (standard of review for Tax Court summary judgment)
  • Peterson v. Commissioner, 827 F.3d 968 (11th Cir. 2016) (de novo review of statutory questions)
  • Chevron U.S.A., Inc. v. Nat. Res. Def. Council, Inc., 467 U.S. 837 (U.S. 1984) (deference and giving effect to congressional intent principles cited)
  • Packard v. Commissioner, 746 F.3d 1219 (11th Cir. 2014) (narrow application of the absurdity doctrine)
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Case Details

Case Name: Carl L. Gregory v. Commissioner of Internal Revenue
Court Name: Court of Appeals for the Eleventh Circuit
Date Published: May 30, 2023
Citations: 69 F.4th 762; 22-10707
Docket Number: 22-10707
Court Abbreviation: 11th Cir.
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    Carl L. Gregory v. Commissioner of Internal Revenue, 69 F.4th 762