Statutory Interpretation as a Continuum and Equipoise in the Continuum (12/20/25)

Continuing on my exploration of AI (I am still a novice), I asked several AI tools about ambiguity and continuum of confidence in statutory interpretation as a way to think about when ambiguity does not permit a court to determine the best interpretation to the required confidence level (in percentages say 51%, 60%, 67%, etc.). I offer here the best of the AI outcomes (from MS CoPilot) with both text and footnotes indented and then make a few comments.

Below is a polished, law‑review‑style Part II that builds naturally on your Part I. It is structured, argumentative, and footnoted in proper Bluebook form. If you want, I can later add subparts (A, B, C), case studies, or integrate it into a full article.

II. The Ambiguity Continuum in Judicial Practice

Courts frequently describe statutory text as either “clear” or “ambiguous,” but this binary framing masks the far more nuanced reality of interpretive practice. In actual adjudication, judges encounter not a dichotomy but a continuum of ambiguity, ranging from provisions whose meaning is overwhelmingly apparent to those whose linguistic indeterminacy leaves multiple interpretations equally plausible.¹ Judicial methodology—whether textualist, purposivist, or something else—does not eliminate this continuum; rather, it structures how judges navigate it. Understanding this spectrum is essential to explaining why interpretive disputes persist even when judges purport to apply the same tools.

A. The Myth of Binary Clarity

The conventional judicial rhetoric of “plain meaning” suggests that statutory clarity is a threshold condition: either the text speaks for itself or it does not.² Yet linguistic theory and empirical studies of judicial behavior demonstrate that clarity is rarely self‑evident.³ Even seemingly straightforward provisions often contain latent ambiguities that become visible only when applied to specific factual contexts.⁴ As Justice Kagan has observed, “we’re all textualists now,” but textualism itself requires judges to make fine‑grained judgments about how much clarity is enough.⁵

These judgments are not mechanical. They depend on context, background assumptions, and the judge’s own interpretive priors.⁶ A provision may appear clear to one judge because she reads it against a particular linguistic or structural backdrop, while another judge—equally committed to textual fidelity—may find the same provision ambiguous.⁷ The very act of declaring a statute “clear” is thus an interpretive conclusion, not an objective fact.

B. Degrees of Ambiguity and the Use of Interpretive Tools

As ambiguity increases along the continuum, courts predictably rely more heavily on interpretive tools to resolve uncertainty. Textual canons, for example, function as probability‑adjusting heuristics: they shift the likelihood of one interpretation over another by appealing to linguistic conventions, structural coherence, or background norms.⁸ Legislative history, when used, serves a similar function by providing additional evidence about how Congress likely understood the statutory language.⁹ Substantive canons—such as the rule of lenity, the presumption against retroactivity, or federalism clear‑statement rules—operate at the far end of the continuum, where ambiguity is so deep that ordinary interpretive tools fail to produce a dominant reading.¹⁰

Conservation Easement Case Set for Trial Only on Valuation (and No Other Issue) with No Post-Trial Briefs (12/29/25)

I note that today, among the orders released, the following Order was issued setting a trial of the valuation issue (and no other issue) in a conservation easement case. (I copy and paste the full order below, but readers may access the original order for case # 8669-20, here, at docket entry 86.)

Since gross overvaluation is the common flaw of many bullshit tax shelters, Judge Lauber is cutting to the chase. Any other flaws in the legal structure of the shelter may not matter after this limited trial.

The wording of the order to reject post-trial briefs suggests that Judge Lauber will issue a bench opinion. See Tax Court Rejects a Bullshit Tax Shelter False Valuation Claim with Warning of Sanctions for Taxpayers, their Counsel, and Expert Witness Proffering the Bullshit (7/16/25; 9/10/25), here. As suggested in that prior blog, one issue that may arise is whether the petitioner’s submission of a bullshit valuation may draw sanctions.

United States Tax Court
Washington, DC 20217

MORGAN RUN PARTNERS, LLC,
OVERFLOW MARKETING, LLC, TAX
MATTERS PARTNER,

Petitioner

v.

COMMISSIONER OF INTERNAL
REVENUE,

Respondent

Docket No. 8669-20.

Brockman Civil Case with Civil Fraud Penalties Settled (12/26/25)

 I have written before on the Brockman multi-year tax evasion scheme. See here. Brockman was indicted but, before he could be tried, he died, thereby resolving the criminal case without a verdict of guilty or not guilty.

The civil case was settled with entry of the Tax Court decision in Brockman Estate v. Commissioner (T.C. Case No. 764-22 Dkt. # 33 Order Dtd. 12/23/25), here. The decision document addresses the deficiencies and civil fraud penalties under § 6663. As is the nature of decision documents, the decision document does not address the interest on the tax and the penalties. The principal amounts of deficiencies and penalty are major, aggregating $750 MM; the interest which I roughly calculate to 12/24/25 at $782MM brings the total due to over $1.5 billion. I prepared a spreadsheet which I offer for review and download here. (Note that the interest calculations are rough and ready but should be in the ballpark.)

One small error in the Tax Court decision document is that the 2006 civil fraud penalty (§ 6663) is stated as $35,00,000.00 which I infer to be $35,000,000.00.

Obviously, given the numbers in the spreadsheet there is a facial anomaly because for the years 2006 and 2015 the civil fraud penalty amount exceeds 75% of the deficiency. I suppose there can be an explanation. There was a jeopardy assessment which may have applied some of the tax, but more likely there may have been an advance payment(s) that reduced the deficiency amounts (but not the civil fraud penalty amount). I just have not dug into that issue.

This blog entry is cross-posted on my Federal Tax Crimes Blog here.

IRS Seeks Comments on Proposed Revisions to Voluntary Disclosure Procedure (12/23/25)

 On December 22, 2025, the IRS opened a 90-day public comment period, ending March 22, 2026, for proposed updates to its Voluntary Disclosure Practice. See IRS seeks public comment on Voluntary Disclosure Practice proposal (12/22/25), here. The indicated updates are short, so I will not summarize them here.

I mention the items that drew my particular interest with some comments as appropriate:

1. Pay all applicable taxes, penalties, and interest in full within 3 months of conditional approval. Previously, as I understood it, the VDP permitted the taxpayer to undergo IRS processes for installment payments or perhaps even compromise. The update requires full payment.

2. As before “The disclosure period will generally cover the most recent six years for delinquent and amended returns (the “Disclosure Period”).”

3. Taxpayers must start the process by submitting “Form 14457, Voluntary Disclosure Practice Preclearance Request and Application” where they "identify all years of noncompliance and provide a full and accurate description of the taxpayer’s willful noncompliance.” Note that, as stated, the disclosure of all years is not limited to the “Disclosure Period” as defined. The Form 14457 is now required, so this is not a change. I mention it because the Form itself seems to tie the disclosures to the Disclosure Period. See e.g., Instructions for “Line 3. Tentative years for which you are making the disclosure. See infra regarding determination of disclosure period.” Is the IRS really going to require all periods of willful noncompliance, even if prior the noncompliance in the Disclosure Period and even outside the normal criminal statute of limitations of six-years. Maybe.

Tax Court on Default Rules in Statutory Interpretation-Herein Also of Chevron, Loper Bright and APA § 706(2(A) (11/14/25)

In Apache Corp. v. Commissioner, 165 T.C. ___ No. 11 (11/1325), reviewed opinion, the Court addressed the momentous (to some) issue of whether a taxpayer electing not to carryback some categories of net operating losses (NOLs) can reserve in the election to carryback other categories of NOLs. The opinions in Appache may be viewed on the Tax Court Docket Sheet for Case # 25984-22, here, at #56, on my Google Drive here, on GS here, and on TN here.  I must say that I have neither worried nor lost sleep over that issue, either before or after this opinion. As respects the issue actually decided in Apache, I am agnostic which may be an admission that I have not really dug deeply into the issue. So, I don’t propose here to deal with the merits of the issue decided.

I want to address the methodology in reaching the majority opinion and Judge Buch’s concurring opinion.

Judge Buch’s concurring opinion (Slip Op. 22-23) is very short. If I may summarize a very short opinion:

(i)          the statutory text is inconclusive on the competing interpretations which are equally plausible, phenomenon I describe as statutory ambiguity where a best interpretation cannot be made; and

(ii)        where the statute is ambiguous, courts are “inclined to rely on the traditional canon that construes revenue-raising laws against their drafter.”

The majority determines that the statutory text is not ambiguous but then says (Slip Op. 18-19) that the default rule Judge Buch relies on should carry the day even if the text were ambiguous (calling it a “tiebreaking principle"). As stated, this supposed principle, sometimes stated as a canon or maxim of interpretation, operates like the rule of lenity that construes criminal statutes in favor of a defendant, which is a default rule in cases of ambiguity. See e.g., Ryan D. Doerfler, The "Ambiguity" Fallacy, 88 Geo. Wash. L. Rev. 1110, 1116 (2020) (referring to Chevron and lenity as default rules); Intisar A. Rabb, The Appellate Rule of Lenity: Responding to Abbe R. Gluck & Richard A. Posner, Statutory Interpretation on the Bench: A Survey of Forty-Two Judges on the Federal Courts of Appeals, 131 Harv. L. Rev. 179, 194 N. 77 (2018) (Same re lenity).

That interpretive methodology in ambiguity is a default rule similar to the Chevron default rule prior to Chevron’s demise in Loper Bright. As readers of this blog and observers in general know, Loper Bright overruled Chevron and thus the Chevron default rule does not apply in a state of ambiguity as between two or more interpretations, one of which is an agency interpretation qualifying for Chevron deference (generally notice and comment interpretive regulations).

Tax Court in Unanimous Reviewed Opinion Interprets and Applies the Accuracy-Related Economic Substance Penalty (11/12/25)

In Patel v. Commissioner, 165 T.C. ___, No. 10 (11/12/25) (unanimous reviewed opinion), the Tax Court (Judge Jones) applied the interpreted the requirements of the accuracy-related penalty for transactions that lack economic substance, § 6662(b)(6), which applies the economic substance doctrine as codified under I.R.C. § 7701(o). The Opinion (for which there is yet no Tax Court permalink, may be reviewed in the Tax Court docket entries for the lead case, here at # 421, dated 11/12/25, on my Google Drive here, on TN here, and on GS here. The transaction at issue was yet another captive insurance case, but addressed for the first time the economic substance accuracy-related penalty.

The Tax Court earlier had shot down the particular captive insurance on the substantive tax merits in Patel v. Commissioner (Patel I), T.C. Memo. 2020-133, here, and Patel v. Commissioner (Patel II), T.C. Memo. 2024-34, here. The new Patel opinion addresses penalty issues not resolved in the prior opinions.

The new Patel opinion offers a relatively straightforward application of the statutory text to a transaction that, in my opinion from the prior Patel opinions, lacked economic substance and was the type of transaction to which the penalty should apply. Indeed, I think the Court’s application of the principles of statutory interpretation, although I think wooden, are what the current judicial environment requires (including a bow to legislative history “For those who consider legislative history relevant.” (Slip Op. 18-19); as phrased, it is not clear whether Judge Jones for the Court felt legislative history was relevant).

Readers of this blog entry are directed to the opinion for the Court’s reasoning and steps.

JAT Comments/Musings:

I offer just the following comments that caught my specific attention as I wandered through the Opinion (in order as they arise in the opinion and not necessarily in order of importance):

1. A host of amici briefs were filed; they are identified at Slip Op. 2 n. 2. The Opinion identifies the amici briefs in the footnote but otherwise does not refer to them. The footnote does add: 

At respondent’s request, we ordered the parties to file briefs in response to the amicus briefs. At the parties’ request, we held oral argument on the issues raised by the briefs.

I have not seen the amici briefs but, since the Court does not refer otherwise to them, I am not going to speculate what effect amici briefs had to the outcome. I will say that I have known the Patels’ lead counsel for some time, he is a very good tax litigator, and assume that he covered the bases in the briefs on which his name appears.

2. The Opinion says (Slip Op. 3 n. 5): “We understand the interaction of section 6662(a) and (b)(6) to impose a single penalty. Because the Commissioner determined that penalty for multiple years (each of the tax years at issue), we will refer to it in the plural (penalties).” Think about that unexplained comment.

Tax Court Yet Again Finds Bullshit Conservation Easement Grossly Overvalued (11/4/25; 11/16/25)

In Paul Adams Quarrry Trust v. Commissioner, T.C. Memo. 2025-112, GS here and TN here, the Tax Court (Judge Toro) shot down another bullshit conservation easement gambit (this time not a syndicated one, but following the same game plan). As common in such cases, the Court found that the claimed value of the easement was grossly excessive, resulting in denial of most of the amount claimed and imposition of the gross valuation misstatement penalty under I.R.C. § 6662(a) and (h).

Worthy of note is the Court’s opening paragraph:

This case concerns the contribution of a conservation easement by Paul-Adams Quarry Trust, LLC (PaulAdams), in 2017. Petitioner is Francis L. (Rusty) Adams, Paul-Adams’s tax matters partner.1 Petitioner’s heightened rhetoric aside, this is not a difficult case. The principal question before the Court is the value of the easement Paul-Adams granted to the Oconee River Land Trust (Oconee Trust) in December 2017 over approximately 207 acres in Elberton, Georgia (Paul-Adams property). The easement restricted what Paul-Adams [*7] could do in the future with those 207 acres. Paul-Adams claimed in its return that the restriction reduced the value of the Paul-Adams property by $10,234,108. This claim has no basis in reality, and we therefore reject it.

The Court repeats this theme throughout the 100+ pages of the opinion.

Tax Court Warns Counsel in Advance of Trial in Syndicated Conservation Easement Case (10/31/25)

In Cottonpatch Timber Company, LLC v. Commissioner (T.C. No. 26103-22, here, at #54 Order dtd 10/29/25), TN here, Judge Gustafson sent warnings to counsel in a syndicated conservation easement case in advance of the trial setting currently for December 15, 2025. Specifically, he cautioned:

As to valuation, the Tax Court has criticized overvaluation of conservation easements in Mill Road, at *48-53, and in a number of recent opinions in other cases. Petitioner’s counsel should be able, in due course, to explain why its position this case is materially different from the strongly criticized positions in those cases, since a position that ignores those opinions and reflects the gross fallacies in those previous positions might be frivolous, see sec. 6673(a)(2), and trial time spent in disregard of those opinions would likely be a waste.

The Mill Road opinion is here.

In addition, Judge Gustafson closed with this cautionary advice:

          The judge stated to counsel that he is considering the possibility of issuing, at the conclusion of the trial in this case, a bench opinion pursuant to Rule 152. The parties should keep that possibility in mind as they prepare their pretrial memoranda, since in that event there would be no post-trial briefing.

These cautions to counsel echo Judge Buch’s Order with attached extensive bench opinion in a conservation easement shelter. Tax Court Rejects a Bullshit Tax Shelter False Valuation Claim with Warning of Sanctions for Taxpayers, their Counsel, and Expert Witness Proffering the Bullshit (Federal Tax Procedure Blog 7/16/25; 9/10/25), here. I think Tax Court judges are getting less tolerant, rightfully so, considering the massive waste of time for trials to claim grossly inflated valuations for conservation easements.

Tax Court in Reviewed Opinion Holds TEFRA Litigation Time Limits Jurisdictional (10/25/25)

I am late to post on North Wall Holdings, LLC v. Commissioner, 165 T.C. ___, No. 9 (10/21/25) (reviewed opinion, T.C. Case No. 27773-21, here, at # 50 and  GS here). North Wall is the latest on the tax saga starting with Boechler, P.C. v. Commissioner, 596 U.S. 199 (2022), holding that the time limit for instituting CDP Tax Court proceedings is not jurisdictional, meaning that equitable tolling for late filing may apply. In recent Supreme Court jurisprudence, many time limits have been held to be not jurisdictional. The key tax exception is United States v. Brockamp, 519 U.S. 347 (1997), holding that the refund time limits are jurisdictional.

Notwithstanding the general trend, the Tax Court has held § 6213(a)'s time limits for petitions for redeterminations of deficiencies are jurisdictional. Hallmark Research Collective v. Commissioner, 159 T.C. 126 (2022) (unanimous reviewed opinion). Three Courts of Appeals have now held the § 6213(a) time limits are not jurisdictional, thus permitting equitable tolling. See 6th Circuit Joins 2nd and 3rd Circuits in Holding § 6213(a)’s 90--day Petition-Filing Deadline is Not Jurisdictional (8/25/25; 9/8/25), here.

In North Wall, the opinion for the Court finds the TEFRA time limits jurisdictional. The opinion’s detailed discussion of the TEFRA interrelated time frames is quite excellent. I highly recommend. For purposes of this blog entry, the headnotes are sufficient:

          R mailed a Notice of Final Partnership Administrative Adjustment (FPAA) to the tax matters partner (TMP) of PS, a limited liability company treated as a partnership for federal income tax purposes and subject to the TEFRA unified audit and litigation procedures. P, a notice partner, filed a Petition for readjustment of partnership items 168 days after R mailed the FPAA to the TMP. R moved to dismiss P’s Petition for lack of jurisdiction. P objects.

          A TMP may file a petition for readjustment within 90 days of R’s mailing of an FPAA to the TMP. I.R.C. § 6226(a). A partner or group of partners entitled to notice may file a petition within 60 days after the close of the 90- day TMP petition period. I.R.C. § 6226(b)(1); see also I.R.C. § 6231(a)(8) (defining “notice partner”), (11) (defining “5-percent group”).

          The text, context, and relevant historical treatment of the TEFRA petition period establish that the period within which to file a petition is a jurisdictional limit. The text places the petition period within the jurisdictional grant. I.R.C. § 6226(b)(1), (f). In the context of the broader TEFRA provisions, allowing equitable tolling would render [*2] the TEFRA statutory scheme unworkable. Historically, courts have treated the TEFRA petition deadlines as jurisdictional, and Congress has amended TEFRA to specifically account for the effect of the petition deadlines’ being jurisdictional.

          Even setting aside the jurisdictional question, the complex TEFRA statutory scheme indicates that Congress did not intend for the equitable tolling doctrine to apply to untimely TEFRA petitions.

          Held: P’s Petition was untimely.

          Held, further, equitable tolling does not apply to hold open the prescribed periods set forth in I.R.C. § 6226(a) or (b) for filing a TEFRA petition.

Interest in DOJ Tax Reunion/Wake for DOJ Tax Alumni (10/17/25)

I am trying to assess interest among DOJ Tax Alumni for a Reunion/Wake for the Tax Division. Since some DOJ Tax Alumni read this blog, I offer this link to the blog post on the DOJ Tax Alumni Blog I maintain: Fillable On-Line Form to Assess Interest in DOJ Tax Alumni Reunion/Wake (10/7/25), here.