Adventures in AI and Federal Tax Procedure on § 7434 (10/3/26)

Today, I was reviewing a recent decision from the Seventh Circuit: Jacoby v. Idlewild Country Club, No. 25-1608 (7th Cir. Oct. 2, 2026) (nonprecedential disposition), CA7 here and TN here, and added it to a footnote in the § 7434 discussion in my working draft for the 2027 edition (to be published in early August 2027). Since I am trying to develop some skills in AI (even though I have not mastered my own intelligence, if any), I decided to use the § 7434 discussion with revisions to date to test what AI has to offer. I used ChatGPT Plus (a paid version). The results offered may be viewed here. I then took the version as ChatGPT rewrote it, pasted it into WordPerfect (my word processor of choice because I am an old lawyer who has not learned MS tricks), and then refined ChatGPT Plus’s offering. So, the files relevant to this exercise are:

1. The version submitted to ChatGPT Plus from the working draft for 2026. Here. This version has 4,750 words (per WP word count). The red font text indicate revisions in the working draft from the 2026 editions.
2. The version ChatGPT Plus offered (with the proposed footnotes as endnotes). Here. This version has 6,079 words (per WP word count).
3. My changes to the ChatGPT Plus that I have not decided whether to replace in the 2027 edition. Here. This version has 6,757 words (per WP word count).

I think each version has the same information as presented in the original from the 2027 working draft (¶ 1).

I would appreciate those having the interest to give me feedback as to which versions are better and more specifically if the two revised versions (¶ 2 and 3 above) are better in the sense of how they better convey the information in the original version (¶ 1) and are worth the additional words to convey the information.

Tax Court Issues a Precedential Opinion (T.C.) Holding that Form 872-T Does Not Revoke a Proper Form 872 Consent to Extend the Statute of Limitations; Well, Duh! (9/30/26; 10/4/26)

The Tax Court today issued a regular opinion in Fine v. Commissioner, 167 T.C. ___, No. 13 (2026) (T.C. # 24390-21 at #43 and GS here. The issue was, to use tax jargon, whether a taxpayer can use Form 872-T to terminate a Form 872 consent to extend the statute of limitations. OK, to be more precise, Form 872 is a Consent to Extend the Time to Assess Tax; Form 872-T is Notice of Termination of Special Consent to Extend the Time to Assess Tax. (Bold-face supplied by JAT.) On its face the name alone should tip one-off that it may not apply to Form 872, because Form 872 is not nominated a “Special” Consent. Reading Form 872-T, one can quickly determine that it applies to the Form 872-A, nominated Special Consent to Extend the Time to Assess Tax (bold-face supplied by JAT).

I dare say that only the most unaware tax practitioner would have known that a Form 872-T cannot revoke the date certain in a Form 872. But apparently such an unaware tax practitioner was the Fines' lawyer (both with respect to deploying / filing the Form 872-T (5 times) and making the argument in the Tax Court case (see Slip Op. 4 n. 5 identifying the person submitting the form as “individual is also counsel of record for petitioners in this case.”).

So, why would the Tax Court use a regular precedential opinion to state a truism known to all minimally competent tax lawyers? In my mind, this opinion should have been issued as an order and not even elevated to T.C. Memo. status. (But they are Tax Court Judges, and I am not.)

 For readers’ further consideration, I offer the following:

TFRP Cannot Exceed the Employer's Compromised Trust Fund Tax Liability On A Record That Does Not Explain the Compromise (9/28/26; 9/29/26)

In Amodio v. Commissioner, T.C. Memo. 2026-96, T.C. Dkt. 9959-22L at # 50 9/28/26 and GS here [to come], the Court held that, on the facts, the IRS cannot collect more on the Trust Fund Recovery Penalty  ("TFRP") in § 6672 than the employer and the IRS had compromised the underlying liability for. The Court reasoned that the TFRP is derivative of the employer’s liability, so that, absent some special consideration, the TFRP cannot exceed the employer's compromised liability.

On the facts presented in the opinion, that holding seems correct.

However, what is missing is why the employer’s liability was compromised. Generally, the IRS compromises tax liabilities based upon doubt as to liability and doubt as to collectibility. If the compromise had been based on doubt as to liability, Amodio seems right to me. If, however, the compromise had been based upon doubt as to collectibility, Amodio seems wrong to me. 

The problem in Amodio was that nobody explained the basis for the compromise. The IRS just failed to put on the evidence uniquely within its control and thus Amodio is correct on the record as described in the opinion.

Added 9/29/26 9:00am:

I asked ChatGPT Plus to critique the portion of the Amodio opinion dealing with the issue discussed above. For those interested in ChatGPT Plus's critique, see here and here I gave ChatGPT Plus two prompts, the second following through on the first. ChatGPT Plus's responses are lengthy but seem to me to add nuance beyond the cryptic discussion in the opinion.

Article on Using Machine Learning for Predicting Tax Ownership (9/27/26)

I spent more time than I should have reading Young Ran (Christine) Kim and Dmitry Erokhin, Algorithmic Tax Ownership, 51 BYU L. Rev. 1437 (2026), here. Don’t get me wrong, I think the article’s discussion of its premises is quite good. What threw me off was the discussion of the “Algorithmic” part of the article. The authors deploy math and computer modeling to predict tax ownership by digesting a large dataset of cases that have dealt with tax ownership.

Of course, the authors mention prominently the iconic case from my time at DOJ Tax: Frank Lyon Co. v. United States, 435 U.S. 561, 582–83 (1978), GS here. I had an indirect role in Frank Lyon (which I’ll tell in the digression below).

Frank Lyon is the classic Supreme Court screw-up in tax law. For further discussions of the screw-up, see the citations in the article. (p. 1446 n. 22 and 1447 n. 32). One of my favorite articles is Charles I. Kingson, The Confusion over Tax Ownership, 93 TAX NOTES 409, 410 (2001), SSRN here (criticizing Frank Lyon as “nobody knows what it means”). Shortly after leaving DOJ Tax for private practice in 1997, I advised a bank wanting to do for a lead shareholder essentially the same deal as Worthen Bank did for Frank Lyon through his corporation. My advice was essentially that it’d be a crap shoot because nobody knew what Frank Lyon meant, but that we could clone the documents in Frank Lyon to recreate the exactly same structure and to be even more sure the bank should change the bank's name to Worthen Bank and his corporation's name to Frank Lyon Corp. Of course, that was hyperbole, but not much because the multi-factor test of tax ownership that Frank Lyon deployed is less than clear in their application in other cases.

Back to the article, it concludes as follows (p. 1494):

To refine tax ownership analysis, this Article applies machine learning, specifically focusing on repo transactions. It identifies economic benefits and burdens  Factor 1) as the most decisive factor in classifying transactions as either sales or loans, with 94.6% accuracy. Additional factors, while sometimes helpful, do not significantly impact classification outcomes.

Earlier (p. 1484):

Nevertheless, the proposed model undeniably reshapes the current tax ownership analysis by showing the decisive factor of the analysis is who bears the economic benefits and burdens of the underlying asset. The clarity this model brings to tax ownership analysis is applicable in a wide array of contexts including repo transactions, sales and leasebacks, litigation financing, and more.

ChatGPT Plus on Loper Bright's Superficial Claim of Court's Ability to Determine a Single Best Reading in State of Ambiguity (9/24/26; 9/25/26)

In my recent article, John A. Townsend, Loper Bright Flip Flops on Chevron Deference: A Tax Lawyer's Perspective, 79 Tax Law. 323 (2026), on SSRN here, I critiqued the Court’s opinion in Loper Bright Enterprises v. Raimondo, 603 U.S. 369 (2024) (C.J. Roberts), here [Preliminary Print]. One of the points I made was that the Court’s claim that “statutes, no matter how impenetrable, do— in fact, must—have a single, best meaning.” (603 U.S., at 400.) The Court also claimed that courts could and must discern that single best meaning without a default rule to decide the case—such as Chevron and, presumably, some substantive canons that require ambiguity. In Loper Bright’s sweeping claims, no room seemed to be left for statutory ambiguity. However, statutory ambiguity was a common phenomenon before Loper Bright; Loper Bright cannot by fiat eliminate statutory ambiguity.

Added 9/24/26 8:00pm: In my Federal Tax Procedure Book 2026 (Practitioner Ed. p. 91; Student Ed. p. 58) this issue is the first issue I raise about Loper Bright:

1. What does a court do when, after it applies Loper Bright’s exhortations to determine the “best” interpretation, the court still finds statutory ambiguity (interpretive equipoise)? Ambiguity (interpretive equipoise) existed before Loper Bright and exists after Loper Bright. Remember the lesson of lenity–ambiguity (interpretive equipoise) requires a default rule to resolve the case.

I decided to use ChatGPT Plus to further explore the phenomenon of statutory ambiguity. That AI tool gave surprisingly cogent answers and step by step reasoning that highlight the lapse in logic of Loper Bright. I wish I had the responses in preparing the article cited above. I offer below the last two prompts and response (after refining earlier prompts and responses). I have left the bold-face and italics as ChatGPT had them; also, ChatGPT sometimes refers to Loper Bright as Loper and does not italicize Loper or Chevron. I have not changed that. Remember these are the final prompts and responses after earlier prompts drilled down to these final two prompt. Those interested in seeing the entire discussion with ChatGPT Plus may do so here.

I am impressed with how ChatGPT responds in an analytically meaningful way to step through  the issues and reach its conclusions. To readers interested in this stuff, ENJOY!

Two points about the Responses: 

1. The first response below refers to my article above without citing the article or otherwise attributing it to me. See par. 4 below. I do not know if ChatGPT Plus recognized that the article that it cited was written by the person with whom it was "chatting." I infer that it did not recognize me as the author of the article.
2. The first response (par. 5) refers to the Flight Options case which it discussed in earlier responses and which I discuss in Interesting Concurring Opinion on Canons (or Maxims) of Statutory Interpretation (Federal Tax Procedure Blog 5/29/26; 8/21/26), here.

JAT Prompt #1: 

In the foregoing discussion, you used 50-50 as the state of interpretive equipoise. Can interpretive equipoise be encountered in a range--say of 45-50 or even 40-60. (These numbers are in percentages.)

ChatGPT Response to Prompt # 1:

Yes—but I would refine the terminology. Interpretive equipoise need not mean a mathematically exact 50–50 tie. It can sensibly describe a zone of interpretive uncertainty within which a court cannot determine, with sufficient confidence, that one interpretation is genuinely “better” than the other. There is, however, no judicially established numerical range such as 45–55 or 40–60.

That distinction becomes important under Loper Bright.

District Court Sustains IRS Summons at Treaty Partner's Request, Requesting Third-Party Contact Requirement (9/19/26)

In United States v. Yoon (N.D. Cal. No.26-cv-01423-VC  Order dtd 9/17/26 at # 34), CL here and GS here, the Court enforced an IRS summons issued in response to a request by a treaty partner, South Korea. The significant issues addressed are:

1. The Government need only satisfy the four-part Powell test. United States v. Powell, 379 U.S. 48, 57–58 (1964). (Slip Op. 3.)

2 In applying Powell, only the IRS’s good faith is in issue, not the treaty partner’s good faith. Id.

3 Relevance of the summons to a legitimate tax investigation of the treaty partner is not in issue. (Slip Op. 4-5.) South Korea’s request to the IRS “said that all that information was relevant, and it only sought records from the years that match its investigation;” the “request seems sensible on its face.” There is no requirement that the IRS go behind the treaty partner’s statement of relevance.

4. The Court rejected Yoon’s argument that § 7602(c) requires 45-day notice which was not given here. (Slip Op. 5-7.) The notice period, although stated without limitation in the statutory text, is properly read in context not to apply to a summons issued at a treaty partner’s request. The Court concluded (Slip Op. 7) that “there is no ambiguity” as to that reading of the statute.

5. With regard to this interpretation of the statute, the Court acknowledged the IRS’s long-time consistent interpretation to that effect in Regulation § 301.7602-2(c)(3)(C), noting that the interpretation might in a state of ambiguity be useful in statutory interpretation (absent here), this consideration (Slip Op. 7-8):

          For what it’s worth, another consideration works against Yoon here: the IRS’s own longstanding interpretation that section 7602(c) does not apply to foreign tax liabilities. 66 Fed. Reg. 77 (Jan. 2, 2001) (codified at 26 C.F.R. § 301.7602-2(c)(3)(C)). After considering the ordinary meaning of statutory language, a court may look to the interpretation of the agency responsible for implementing the statute. Leon-Vriviesca, 179 F.4th at 1191. Such agency interpretations receive “‘due respect,’ but not binding deference.” Lopez v. Garland, 116 F.4th 1032, 1039 (9th Cir. 2024) (quoting Loper Bright Enterprises v. Raimondo, 603 U.S. 369, 403 (2024)). The IRS’s regulation was issued in 2001, just a few years after the codification of section 7602(c) in 1998, and has remained consistent since then. Therefore, even if the statutory text were ambiguous, the IRS’s interpretation would be “especially useful in determining the statute’s meaning”—and that might cut against Yoon’s legislative purpose argument. Loper Bright, 603 U.S. at 394 (citing Skidmore v. Swift & Co., 323 U.S. 134, 140 (1944)).n5
   n5 The government makes an alternative argument that the general grant of rulemaking authority to the IRS in 26 U.S.C. § 7805(a) empowers the agency to “fill up details” in the statutory scheme; i.e., that section 7805(a) explicitly authorizes the agency to define the phrase “tax liability” in section 7602(c). But the best reading of the statutory text, informed by due respect to the IRS’s regulation, is that section 7602(c) does not apply to foreign tax liabilities. It is therefore not necessary to consider whether section 7805(a) can bear the weight that the government says it does.

JAT Comment:

District Court Sustains IRS Summons at Treaty Partner's Request, Requesting Third-Party Contact Requirement (9/19/26)

In United States v. Yoon (N.D. Cal. No.26-cv-01423-VC  Order dtd 9/17/26 at # 34), CL here and GS here [to come], the Court enforced an IRS summons issued in response to a request by a treaty partner, South Korea. The significant issues addressed are:

1. The Government need only satisfy the four-part Powell test. United States v. Powell, 379 U.S. 48, 57–58 (1964). (Slip Op. 3.)

2. In applying Powell, only the IRS’s good faith is in issue, not the treaty partner’s good faith. Id.

3. Relevance of the summons to a legitimate tax investigation of the treaty partner is not in issue. (Slip Op. 4-5.) South Korea’s request to the IRS “said that all that information was relevant, and it only sought records from the years that match its investigation;” the “request seems sensible on its face.” There is no requirement to test the treaty partner’s statement of relevance.

4. The Court rejected Yoon’s argument that § 7602(c) requires 45-day notice which was not given here. (Slip Op. 5-7.) The notice period, although stated without limitation in the statutory text, is properly read in context not to apply to a summons issued at a treaty partner’s request. The Court concluded (Slip Op. 7) that “there is no ambiguity” as to that reading of the statute.

5. With regard to this interpretation of the statute, the Court acknowledged the IRS’s long-time consistent interpretation to that effect in Regulation § 301.7602-2(c)(3)(C), noting that the interpretation might in a state of ambiguity be useful in statutory interpretation (absent here), this consideration (Slip Op. 7-8): 

          For what it’s worth, another consideration works against Yoon here: the IRS’s own longstanding interpretation that section 7602(c) does not apply to foreign tax liabilities. 66 Fed. Reg. 77 (Jan. 2, 2001) (codified at 26 C.F.R. § 301.7602-2(c)(3)(C)). After considering the ordinary meaning of statutory language, a court may look to the interpretation of the agency responsible for implementing the statute. Leon-Vriviesca, 179 F.4th at 1191. Such agency interpretations receive “‘due respect,’ but not binding deference.” Lopez v. Garland, 116 F.4th 1032, 1039 (9th Cir. 2024) (quoting Loper Bright Enterprises v. Raimondo, 603 U.S. 369, 403 (2024)). The IRS’s regulation was issued in 2001, just a few years after the codification of section 7602(c) in 1998, and has remained consistent since then. Therefore, even if the statutory text were ambiguous, the IRS’s interpretation would be “especially useful in determining the statute’s meaning”—and that might cut against Yoon’s legislative purpose argument. Loper Bright, 603 U.S. at 394 (citing Skidmore v. Swift & Co., 323 U.S. 134, 140 (1944)).n5
   n5 The government makes an alternative argument that the general grant of rulemaking authority to the IRS in 26 U.S.C. § 7805(a) empowers the agency to “fill up details” in the statutory scheme; i.e., that section 7805(a) explicitly authorizes the agency to define the phrase “tax liability” in section 7602(c). But the best reading of the statutory text, informed by due respect to the IRS’s regulation, is that section 7602(c) does not apply to foreign tax liabilities. It is therefore not necessary to consider whether section 7805(a) can bear the weight that the government says it does.

 JAT Comments:

D.C. District Court Rejects Tax Analyst's FOIA Request For Background File on TAM That Might Identify Taxpayer Among the Taxpayers that Littlejohn Disclosed (9/18/26)

In Tax Analysts v. IRS (D.D.C. No. 1:24-cv-03257 at # 32 Memo Opinion & Order dtd 9/9/26) CL here, Tax Analysts sought disclosure of the background file for Technical Advice Memorandum TAM 201929019, TN here, on basis shifting strategy. In its order, the Court did not identify the TAM, but the TAM is identified in the Complaint here, Answer here, and Government  Motion for Summary Judgment here. The Court’s order is short, so I just quote it:

          The parties have agreed that this case can easily be resolved once the identity of the subject taxpayer is known. See Pl. Resp. at 1; Reply at 1. Plaintiff does not have this information and, for reasons to be explained, the IRS refuses to make it available to the plaintiff. Instead, the parties agree that the case could move forward if this Court reviewed the disputed material in camera. See Pl. Resp. at 2; Reply at 1-2. At the Court's request, the IRS delivered the relevant materials to the Court on September 4, 2026, and the Court has now reviewed them.

          The parties agree that former IRS contractor Charles Littlejohn publicly disclosed tax return information of "some prominent Americans," including Donald Trump, Warren Buffett, Bill Gates, Rupert Murdoch, Mark Zuckerberg, Jeff Bezos, Elon Musk, and others. The parties now also agree that if the taxpayer here is a person of such prominence, he or she could easily be identified with the Littlejohn disclosure and related news reporting. See Pl. Resp. at 2; Reply at 1-2.Any member of the public would be able to identify the subject taxpayer. If that is the case, the parties agree, the Court necessarily would conclude that the withheld documents are exempt from disclosure. See id. (citing 26 U.S.C. §6110(c)(1) and (c)(5)). The Court, having now reviewed the documents in camera, concludes that the subject is a person of such prominence that disclosure would be tantamount to identifying the taxpayer. Therefore, the records may be withheld. Accordingly, it is hereby

          ORDERED that on or before September 23,2026, the parties shall meet and confer and file a joint status report suggesting appropriate next steps in this case.

As presented, the Memo and Order raises the question as to which taxpayer the TAM relates to—"Donald Trump, Warren Buffett, Bill Gates, Rupert Murdoch, Mark Zuckerberg, Jeff Bezos, Elon Musk, and others.”

Second Circuit Affirms the Tax Court in Holding Limited Partners Must Really Be Limited Partners (9/17/26)

In Soroban Capital Partners LP v. Commissioner, ___ F.4th ___ (2d Cir. 9/17/26), CA2 here, CL here, and GS here, the Panel (Judges Calebresi, Chin , and Merriam, with opinion by Chin) affirmed the Tax Court’s decision holding that persons nominated as limited partners who exercised managerial control did not qualify for the limited partner exception to the Medicare tax. Specifically, the opinion states its holding (Slip Op. 30):

We hold that "limited partner," as used in § 1402(a)(13), means a partner who, in addition to having limited liability, does not run, manage, or control the partnership's business.10 We arrive at this conclusion based on three sources that provide guidance as to the meaning of the term as used here: (1) the text of the statute and its ordinary meaning in 1977, when § 1402(a)(13) was enacted; (2) the statute's surrounding text and structure; and (3) the statute's legislative history and historical context.

This is a major opinion simply because the scam it shoots down was so egregious. I don’t feel that I can add anything meaningful to the substantive opinion. To the extent readers may be interested in my opinion, I think it is correct. I will make some comments that, like many of my blogs, will address picky issues in the opinion.

JAT Comments:

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?