Tax Court Dawson Access to Simultaneous Opening Briefs in Syndicated Conservation Easement (1/12/26)

Readers of this blog may know that the Tax Court’s Dawson tool shows the docket entries for cases but has historically included for public view by link only documents prepared and filed by the Court. Dawson is now showing some documents prepared and filed by the parties. For an example, I point to the Simultaneous Opening Briefs in Capitol Places II Owner, LLC v. Commissioner (T.C. No. 16536-23 here at ## 264-265) involving a syndicated conservation easement. (Simultaneous Opening Briefs are acronymed or initialized to SIOB in the system and I use that convention here.) Readers might particularly be interested in the Petitioner’s SIOB, at #265 (note that the Dawson system does not have permanent links, so those wanting to see or download the documents must do so from the docket entries which I link above). Added 1/12/26 @ 10:00pm: I have been reminded that, on 5/5/23, the Tax Court entered Administrative Order No. 2023-02, here, that PostTrial Briefs and Amicus Briefs would be available on Dawson to view and download.

Petitioner’s SIOB is 372 pages; the IRS’s is 221 pages. I have made no attempt to read either of those briefs, but I have paged through the table of contents of both briefs and some of the briefs (as discussed below). The Petitioner's table of contents is 12 pages long and indicates that the body of the brief is 339 pages long.

Judging from Petitioner's table of contents, Petitioner offers a generous smorgasbord of all imaginable claims, many of which appear to be Hail Mary arguments.  Gemini AI says a Hail Mary argument in a legal brief is an argument “highly unlikely to succeed but is included as a last resort, in the desperate hope that a court might accept it.” I am not opining that some of the arguments are weak on merits but merely offering my gut reaction. Of course, ultimately the fatal weakness in these shelters are the bullshit valuations that often accompany the syndications to justify the return reporting positions.

Some points I noted:

 1. IRS statement (p. 11):

 55. The 2014 Form 1065 claimed a noncash charitable contribution deduction in the amount of $23,909,000 for the façade easement contribution. Ex. 32-J.

 2. IRS ultimate findings of fact (pp 92-93):

ULTIMATE FINDINGS OF FACT

1. The FMV of the Subject Property prior to the donation of the easement was $2,770,000. Entire record.

2. The FMV of the Subject Property after the donation of the easement was $2,710,000. Entire record.

3. The FMV of the easement donation was $60,000. Entire record. 4. CP II Owner is not entitled to deduct (1) the $10,000 paid for the Clark Appraisal, (2) the $70,333 paid for the LDS, or (3) the $800,000 paid to GBX for “Tax Consulting” as rental real estate expenses, and those expenses were  properly reclassified as Other Deductions at Schedule K, Line 13d in the FPAA. Entire record.

5. The FPAA was issued timely and the assessment statute expiration date has not passed. Entire record.

6. The accuracy-related penalties asserted with respect to CP II Owner received timely  supervisory approval pursuant to I.R.C. § 6751(b). Entire record.

7. Penalties under I.R.C. § 6662 for gross valuation misstatement, substantial valuation misstatement, negligence,3 and substantial understatement of income tax apply; reasonable cause defenses do not apply. Entire record.

Fn 3 As discussed in respondent’s pre-trial memorandum filed on April 11, 2025, respondent is no longer asserting the negligence or disregard of rules or regulations penalty with respect to the noncash charitable contribution deduction adjustment.

Chevron, Loper Bright, and Statutory Ambiguity (1/8/26; 1/9/26)

Added 1/9/26 9:00pm: I would really appreciate readers notifying me of any case(s) they have read where the court said that it determined the best interpretation and nevertheless deferred under Chevron to a not best agency interpretation. Please respond either by comment or by email to me at jack@tjtaxlaw.com.

I start with two opposing statements:

“Chevron requires a federal court to accept the agency's construction of the statute, even if the agency's reading differs from what the court believes is the best statutory interpretation.” National Cable & Telecommunications Assn. v. Brand X Internet Services, 545 U.S. 967, 980 (2005) (Thomas, J. for the Court).

ChatGPT’s response to the following question: “Can you find me a United States case where the court determined the best interpretation of a statute but nevertheless applied Chevron to defer to a not best agency interpretation?”:

No United States case is identified in the provided search results where a court explicitly determined the best interpretation of a statute but nevertheless applied Chevron deference to a non-best agency interpretation. * * * * The results highlight Chevron's requirement for courts to defer to reasonable agency views of ambiguous statutes but provide no instance where a court labeled its own view "best" yet deferred anyway, likely because such language would contradict Step One's mandate to enforce unambiguous meanings.”

[JAT Note in support of ChatGPT’s response: I have read many Chevron cases and do not recall that a court ever said it had determined than interpretation other than the agency's was best but deferred to the agency interpretation. At an anecdotal level, I read cases identified by other scholars as Chevron cases and found that not one of the cases said the court determined the best interpretation was other than the agency interpretation and nevertheless deferred to the agency interpretation. See Is Chevron on Life Support; Does It Matter? (Federal Tax Procedure Blog 4/2/22; 4/3/22), here (focus on Category 5); and  Chevron Step Two Reasonableness and Agency Best Interpretations in Courts of Appeals (Federal Tax Procedure Blog 2/9/23), here (again focus on category 5). In not of those cases did a court state or fairly imply that it had determined a best interpretation and was deferring to the agency interpretation instead. Not one.]

I propose that (i) Chevron deference, properly applied, was a tie-breaker rule when a court found statutory text ambiguous as required to get past Step One (meaning that the court could not determine the best interpretation) and (ii) that Loper Bright’s rejection of Chevron deference leaves courts without guidance to resolve ambiguous statutory text. Of course, the phenomenon of statutory interpretive ambiguity is not unique to agency interpretations of statutes they administer, but at least Chevron offered a consistent and, in a sense, principled way to resolve ambiguity to reach a decision in the case at hand.

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.