Tax Court Deploys Interpretive Tools to Resolve Complex Transaction/Scheme to Exploit Statutory Glitch (9/17/26)

In Sysco Corp. v. Commissioner, T.C. Memo. 2026-84, TC here at # 108 dtd 9/14/26 & GS here, the Court rejects Sysco’s attempts to avoid the result of prior T.C. decisions resolving the issue in Sysco. Varian Medical Systems, Inc. & Subs. v. Commissioner (Varian I), 163 T.C. 76 (2024) (reviewed), and Varian Medical Systems, Inc. & Subs. v. Commissioner (Varian II), No. 8435- 23, 166 T.C. (Apr. 8, 2026).

In this blog, I do not address the substantive issue that the parties fussed about. Rather, I address the tools of statutory interpretation the Court claimed to deploy in resolving the interpretive issue.

My basic theory of statutory interpretation is that it is in many ways similar to factfinding—it is lawfinding. In factfinding, relevant evidence generally should be considered for what it is worth. See FRE 401 and 402. So, too, in statutory interpretation relevant evidence as to the meaning of the statutory text should be considered for what it is worth. My main beef in the current statutory interpretation milieu is the notion that interpreters should categorically reject legislative history (other than statutory history). 

Let’s walk through how the court deploys the tools of statutory interpretation:

1. the Court “begin[s] with the [statutory] text.” (*7.) I fully agree with that and cannot imagine anyone who would disagree. Indeed, on this point, I agree with Justice Kagan’s famous statement that “We’re all textualists now.)

2. Immediately after stating the obvious starting point (#1), the Court jumps into quicksand: “when the statute does not define a term, “we ask what that term’s ‘ordinary, contemporary, common meaning’ was when Congress enacted” the relevant text. The court correctly cites cases that do stand for the proposition and, I suppose, the proposition is correct, provided that there is more nuance. How does one determine the statutory term’s “ordinary, contemporary, common meaning” relevant to its meaning in a complex tax statute?

Interesting Concurring Opinion on Canons (or Maxims) of Statutory Interpretation (5/29/26; 8/21/26)

In Flight Options LLC v. United States, 177 F.4th 709 (6th Cir. 2026), CA6 here and GS here, the Court reversed a district court holding that Flight Options, a fractional-share jet company, was liable for withholding tax in the amount of $39 million on fixed fees it charged to pay for the overhead and management of its clients' private jets. The tax involved was the

7.5% excise tax on the “amount paid for” domestic “transportation by air,” 26 U.S.C. §§4261(a), 4262(a)(1), what the statute called a “ticket tax” at all relevant times of this dispute, id. §4261(e)(1)(C), (e)(5) (2012).

Although I do not plan to deal with the substantive merits of the withholding tax in issue, basically a high-level overview is that the tax is easily calculated, collected, and paid over for the travel that most of us experience on commercial airlines where the price of the ticket is all in for cover all associated costs to the airline of providing the air transportation (included quite indirect costs of management and even paying lawyers). Private-jet companies operate differently, not including all costs in a single fare but separately calculating and charging for its costs and profit. So, Flight Options, calculated, collected, and paid over only that ticket tax related to “usage charges for each flight a client takes, not to fixed fees it charges its clients for overhead and management of its fractional jet business.” The latter charges are the types of charges that commercial airliners build into the ticket fare and thus are, for commercial travel, subject to the ticket tax. In effect, the IRS attempted to require private-jet providers to include some of those charges in the base to which the ticket tax, and thus withholding obligation, applied, thus making the ticket tax more comparable in impact between commercial providers and private-jet providers. (Added 4:50 pm: To put that another way, for a pro rata tax, private-jet flyers pay less than commercial-jet flyers. Think about that.)

The Court of Appeals (Judge Sutton for a unanimous panel) rejects the IRS position the district court sustained. Of course, the issue is to apply the ticket tax designed with the commercial-jet model where all-in costs are included in the ticket price subject to the tax. As noted above, the private-jet providers separately state their costs (with separately stated costs including profit). The effect of the Court’s holding is that private-jet providers get a competitive advantage relative to commercial-jet providers. The Court confers that competitive advantage by deploying the favorite interpretive tool of literalist textualists—Dictionaries. Using those vaunted tools, the Court’s parsing of the tax indicated to the Court that the text was uncertain as to the liability—ambiguous, if you will—and thus it is improper to hold a third-party withholder for a liability that is uncertain. In the process the Court deployed two canons, called “relevant taxpayer canons”: (i) the Pro-Taxpayer Canon, called a general canon, that interprets uncertainty in tax liability in favor of the taxpayer and against the IRS; and (ii) a related canon, called a "specific canon," that to hold a party charged with collecting the tax for the IRS must have “precise and not speculative” instructions in the statute (meaning in his telling that ambiguity is resolved in favor of the putative withholder).

Fifth Circuit Claims a Pro-Taxpayer Canon When the Court Should have Interpreted the Exemption in the Statute Fairly or Applied the Anti-Taxpayer Canon (1/27/26; 8/21/26))

I posted much of the information in this blog entry at the bottom of the immediately preceding blog: Fifth Circuit Knows a Limited Partner When Reads It (1/24/26; 1/27/26), here. I decided that the information should not be buried in the prior blog but should be lifted into it’s own blog entry. So here it is. For context, yesterday’s blog was about the Fifth Circuit’s opinions in Sirius Solutions, L.L.L.P v. Commissioner, ___ F.4th ___ (5th Cir. 2025), CA5 here and GS here, which held that the limited partner exception in § 1402(a)(13) does not apply to earnings allocated to a nominal limited partner even though providing services to a limited partnership. Please note that I bold-faced exception because that the majority and the dissenting opinions agree it is an exception to the general rule of taxation. (In view of this blog entry, I have eliminated the information from the bottom of the prior blog entry.)

I ask readers to consider seriously footnote 8 of the majority Sirius majority opinion  spanning Slip Op. 23-24):

  n8 Even if the IRS and Tax Court’s arguments had persuasive authority, they would at most establish ambiguity. But that is not enough for the Government’s passive investor rule to prevail. It is a “longstanding canon of construction that if the words of a tax statute are doubtful, the doubt must be resolved against the government and in favor of the taxpayer.” United States v. Marshall, 798 F.3d 296, 318 (5th Cir. 2015) (quotation omitted).

First, Loper Bright claims (I think nonsensically) that courts can always interpret out ambiguity in the statute. See e.g., Chevron, Loper Bright, and Statutory Ambiguity (Federal Tax Procedure Blog 1/8/26; 1/9/26), here.  If there is genuine ambiguity where the court is unable to determine the best interpretation between two or more interpretations within the zone of ambiguity, the court will need a tie-breaker which artificially resolves the ambiguity to decide the case. Chevron offered such a tie-breaker, but Loper Bright rejected Chevron without substituting any other tie-breaker. Of course, the alleged "longstanding canon of construction the majority claims in footnote 8 could supply a tie-breaker in the majority's imagination. I address here the validity of the majority's claim of this "pro-taxpayer" canon of construction.

Canons of statutory construction  are “rules of thumb that help courts determine the meaning of legislation.”  They are said to “limit judicial discretion and render statutory meaning more predictable.”  E.g., Jonathan H. Choi, The Substantive Canons of Tax Law, 72 Stan. L. Rev. 195, 228-229 (2020), here. On the other hand, they are said to be “readily manipulable and [frustrate] the policy preferences of Congress.”  Karl Llewellyn famously observed that “there are two opposing canons on almost every point.”  

A variation on the theme is that maxims, which may function like canons, might be viewed as minims because they reveal so little and are "singularly unhelpful when it comes to deciding cases." United States v. Ingredient Technology Corp., 698 F.2d 88, 94 (2d Cir. 1983)

Professor Choi notes that the opposing canon  (called an anti-taxpayer canon) is to construe exemptions from tax against the taxpayer who cannot show that the statute requires the exemption. (See Choi, pp. 251-254.) Furthermore, Choi notes that the pro-taxpayer canon is not now in vogue. (See Choi, pp. 253-254, quoting Scalia and Garner arguing for applying the fair meaning of statutes; in any event, the anti--taxpayer rule for tax exemptions, "has been sufficiently widely validated and cited that, in my view, its place among the substantive canons is secure" and "the courts have widely embraced this canon." So, the mere fact that the majority felt the need, albeit in a footnote, to use the dubiously applicable pro-taxpayer canon instead of a fair meaning of the statutory exemption or the anti-taxpayer rule, is suspect.

Fifth Circuit Knows a Limited Partner When Reads It (1/24/26; 1/20/26)

Most readers of this blog will already have heard of or even read the opinions (majority and dissenting) in Sirius Solutions, L.L.L.P v. Commissioner, ___ F.4th ___ (5th Cir. 2025), CA5 here and GS here, Basically, the majority held that the limited partner exception in § 1402(a)(13) does not apply to earnings allocated to a nominal limited partner. Bottom-line that interpretation means that partners providing services to a partnership can escape the Social Security and Medicare tax on income they allocate to their limited partner interests even though that income is really the return on their personal services. The Tax Court held otherwise in the Tax Court phase of Sirius, based on Soroban Capital Partners LP v. Commissioner, 161 T.C. 310 (2023).

I do not plan to get deeply into the merits of the majority and dissenting opinions. Two reasonable articles are Jon Endean, Reflections on the Fifth Circuit’s Ruling on Limited Partner Exception (TaxProf Blog 1/21/26), here; and Maureen Leedy, Fifth Circuit Reverses Tax Court on Limited Partner Self-Employment Tax (ThomsonReuters 1/21/26), here.

On the merits, I do say that, it seems to me, the difference between the majority and the minority is that the majority is not practical in being a faithful agent to Congress and the minority, like the Tax Court, is more practical in being the faithful agent.

JAT Comments:

1. I think it relevant, at least at the margins, that the two judges in the majority are Trump appointees and the judge in the minority is an Obama appointee.

2. The differences in statutory interpretation driven by ideologies and, for the majority, simplisms is stark. A good example is the majority’s claim “legislative history is generally of dubious value in statutory interpretation” and the follow-through that “where, as here, textual arguments yield a clear answer, judges must stop.” (Slip Op. 19; cleaned up with internal quotations marks and citations omitted.) I think originalists have beat that horse beyond its ability to persuade; why is not Congress’ view of the legislation it enacted relevant to interpreting the legislation? If one takes the view, as I do, that interpreting the law is an exercise like fact-finding (see Chevron, Loper Bright, and Statutory Ambiguity (Federal Tax Procedure Blog 1/8/26; 1/9/26), here)), then why would not relevant evidence be considered for whatever persuasive value it might have?