Sixth Circuit Opines on Types of Deference after Loper Bright (4/28/25)

In United States v. Bricker, ___ F.4th ___ (6th Cir. 2/22/25), CA6 here and GS here the majority held that 18 U.S.C. § 3582(c)(1)(A) allowing a court to reduce a final prison sentence for “extraordinary and compelling reasons” was sufficiently plain in meaning that Congress did not delegate to the Sentencing Commission the authority to interpret the phrase to include consideration of a nonretroactive sentencing law change it as it had in U.S.S.G. § 1B1.13(b)(6). The majority reached that conclusion based on its holding of plain meaning or nonambiguity.

Query would the majority holding have been different if the Court found an express delegation of interpretive authority which still requires ambiguity but cannot be based on ambiguity alone? I get into that issue below.

The dissenting judge (Jane Stranch) argues that “extraordinary and compelling reasons” is ambiguous, without a plain meaning (at least with regard to the factor under consideration), and that Congress delegated the authority to the Commission to interpret “extraordinary and compelling reasons” within the bounds of its ambiguity. The dissent did not argue that ambiguity alone warranted the conclusion of congressional delegation of interpretive authority (that is prohibited by Loper Bright’s rejection of Chevron deference), but that the structure and context of the provision made it clear that Congress intended the Commission to interpret the ambiguous phrase. Under this argument, the delegation would pass muster under Loper Bright Enters. v. Raimondo, 603 U.S. 369 (2024).

The interesting part of Judge Stranch’s dissent is her conclusion that Congress delegated interpretive authority to the Commission. She argues that delegated interpretive authority (again based on factors other than ambiguity alone) is governed by the same deference as under Chevron—reasonable within the scope of ambiguity. (All iterations of deference have required statutory ambiguity; Chevron alone treated ambiguity as the basis for a fictional congressional delegation.) Of course, delegated interpretive authority requires some ambiguity, otherwise there is no interpretive authority to delegate or apply. But once there is ambiguity and a delegation of interpretive authority not based on ambiguity, the agency reasonable interpretation should control. And, the elements for Loper Bright qualified deference are present--congressional delegation and reasonable interpretation within the scope of the statutory ambiguity.

A key issue in the difference between the majority and the dissent was a Sixth Circuit precedent, United States v. McCall, 56 F.4th 1048 (6th Cir. 2022) (en banc). McCall’s en banc decision had treated the phrase “extraordinary and compelling reasons” before the Commission’s later guidance in question in Bricker to have a plain meaning not to include a nonretroactive factor such as a reduction in authorized sentences. Of course, under the Chevron regime, agency interpretations could overrule prior court precedents in some cases. Nat’l Cable & Telecomms. Ass’n v. Brand X Internet Servs., 545 U.S. 967 (2005). With the demise of Chevron via Loper Bright, Brand X was no longer controlling for agency interpretations given deference based on ambiguity alone. In Bricker, the majority held that McCall was controlling on the issue of whether the phrase “extraordinary and compelling reasons” was ambiguous; McCall held the phrase was not on the retroactive factor issue. The majority thought McCall’s holding of nonambiguity was binding precedent on the issue of consideration of a nonretroactive sentencing factor. 

Conflicting Statutes of Limitations for Regular Tax Assessments and Restitution-Based Assessments (4/27/25)

 In United States v. Brown (W.D. WA Case No. 24-cv-05021 Dkt. No. 38 Order dated 4/21/25), GS here and CL here, the Court upheld the validity of a restitution-based assessment (“RBA”) against Brown that was for the same tax that had been previously assessed against Brown. (For prior Blogs on RBAs on the Federal Tax Crimes Blog, see here, and on the Federal Tax Procedure Blog, here.) For clarity, I will differentiate the two assessments by calling the first-in-time assessment, the regular assessment and the second-in-time assessment the RBA. The reason that was even an issue was because Brown never fully paid the regular assessment and the 10-year statute of limitations to collect any balance on the regular assessment (by reducing to judgment) had expired. Brown claimed that, since the statute of limitations on the regular assessment had expired, thus preventing the IRS from claiming on that regular assessment, the IRS could not end-run the regular assessment statute of limitations based on the RBA assessment. At least that is how I understand Brown’s claim that the court rejected, thus permitting the government to reduce the RBA to judgment and use the RBA extended statute of limitations to collect (including further extending the statute of limitations).

I think the court properly gives a good textual reading of the applicable statutory provisions. I am concerned that the decision may not be consistent with the purpose or intent of the statute. (For a textualist, purpose or intent may not matter.) Although I have not filtered back through the legislative history, my understanding of the purpose of the RBA was to avoid requiring the IRS to jump through assessment hoops for tax ordered as restitution. In other words, it was to permit the IRS to make an immediate assessment where it had not assessed before. (Stated otherwise, it was not to give the IRS two independent assessments to collect. The Code provisions do not say that, but that is my understanding of the need for an RBA. If the tax later subject to restitution had already been assessed, there would be no need for an RBA. And the IRS could deal with an expiring statute of limitations on the regular assessment by simply reducing the regular assessment to judgment, thereby refreshing the statute of limitations.

It is true that § 6501 says that § 6501(c)(1) says: “In the case of a false or fraudulent return with the intent to evade tax, the tax may be assessed, or a proceeding in court for collection of such tax may be begun without assessment, at any time.” But, at a minimum, that would only apply where there was no regular assessment and presumably no RBA. Where there is a regular assessment, one might argue through inference that the regular assessment statute and its limitation period should apply.

Court Dismisses Bivens Claim Against IRS Agents for Asserting Accuracy-Related Penalties (4/21/25)

In Ray v. Priver, et al., 2025 U.S. Dist. LEXIS 71600, 2025 WL 1113406 (D. D.C. 4/15/25), CL here and GS here, The Court dismissed Ray’s Bivens actions against IRS agents that, he claimed, violated his constitutional rights in the IRS’s assertion of the accuracy-related penalty under § 6662(b)(1) and (2) and then in improperly influencing the Tax Court’s sustaining of the penalties in Ames v. Commissioner, T.C. Memo. 2019-36, GS here, aff’d in part and reversed in part with respect to a portion of the penalties, Ray v. Commissioner. 13 F.4th 467 (5th Cir. 2021), after remand motion to Reopen the Record denied in Tax Court (10/28/22), aff’d on appeal Ray v. Commissioner, 2023 U.S. App. LEXIS 21799, 2023 WL 5346067 (5th Cir. 8/18/23), GS here*, and petition for rehearing denied Ray v. Commissioner, 2023 U.S. App. LEXIS 27464 (5th Cir. 10/16/23). At the end of all that commotion from the main Tax Court case in 2019, Ray was liable for some of the accuracy-related penalty but not for a portion for which the Court of Appeals reversed the Tax Court on its denial of the “reasonable cause” defense.

I asked Gemini, Google’s AI Tool, to summarize the case. The following is the result which I have massaged somewhat (reminder these AI Tools, while good, need to be carefully reviewed and revised as appropriate).

Background:

• In 2014, the IRS audited Ray and issued a notice of deficiency, including a penalty under 26 U.S.C. § 6662(a) & (b)(1) (negligence or disregard) (b)(2) (substantial understatement).
• Ray claims this penalty was unwarranted, alleging that two other IRS agents found insufficient evidence for it. He asserts that Lawson and Priver knew this but still pursued the penalty and falsified evidence in his administrative file.
• Ray initially challenged the penalty in Tax Court, where he alleges Priver and Lawson repeatedly lied and falsified evidence. The Tax Court upheld the penalty, but the Fifth Circuit reversed finding Ray not liable for some of the penalty based on reasonable cause. On remand, the Tax Court entered decision sustaining the deficiency and the portion of the penalty approved by the Fifth Circuit.
• Ray later obtained files through a FOIA request, which he claims revealed that Priver and Lawson maliciously prosecuted the penalty claim and concealed exculpatory evidence.

Claims:

• Ray sued Priver and Lawson in their individual and official capacities, alleging what he called a Bivens action:
• Count I: Malicious prosecution in violation of the Fourth Amendment.
• Count II: Denial of a fair trial under the Fifth Amendment's Due Process Clause.

Defendants' Motion to Dismiss:

• Defendants moved to dismiss, arguing:
• Improper service (later moot due to government acceptance of service).
• Sovereign immunity bars official-capacity claims (conceded by Ray).
• Failure to state a claim against individual defendants under Bivens v. Six Unknown Named Agents of Federal Bureau of Narcotics.

Court's Ruling:

• The Court GRANTED the Defendants' motion to dismiss.
• The Court agreed that Ray's claims against Priver and Lawson in their official capacities are barred by sovereign immunity.
• Regarding the individual-capacity claims, the Court applied the two-step Bivens analysis:
• New Context: The Court found that Ray's claims arise in a "new context" because they involve IRS employees, a different statutory mandate (Internal Revenue Code), and do not align with the specific constitutional violations in the three previously recognized Bivens cases (Fourth Amendment unreasonable search and seizure, Fifth Amendment sex discrimination, and Eighth Amendment cruel and unusual punishment).
• Special Factors: The Court found "special factors" counseling against a new Bivens remedy, primarily the existence of a comprehensive alternative remedial scheme within the Internal Revenue Code. This scheme includes administrative review, the ability to sue for a refund, challenging assessments in Tax Court, and the Treasury Inspector General for Tax Administration (TIGTA) for investigating employee misconduct. The Court emphasized that even if these remedies don't provide complete relief (like monetary damages), their existence is sufficient to preclude a new Bivens action. 

• JAT Addition: The Court relied significantly on the Supreme Court’s admonition that expansions from past Bivens applications is “now a ‘disfavored’ judicial activity.” Hernandez v. Mesa, 589 U.S. 93, 102 (2020); and Ziglar v. Abbasi, 582 U.S. 120, 135 (2017) (citing Ashcroft v. Iqbal, 556 U. S. 662, 675 (2009)). 

Conclusion:

The Court concluded that Ray's case presents a new Bivens context, and the presence of an existing remedial scheme within the Internal Revenue Code constitutes a "special factor" that makes it inappropriate for the judiciary to imply a new damages remedy against individual IRS employees. Therefore, the Court dismissed Ray's amended complaint.

JAT Comments:

Political Thrashing Around Acting Commissioners and Commissioner of Internal Revenue (4/18/25; 4/19/25)

I thought I was through posting for the day and even for a few days. But this new item popped up. Jonathan Swan, Andrew Duehren, Alan Rappeport and Maggie Haberman, Head of I.R.S. Being Ousted Amid Treasury’s Power Struggle With Elon Musk (NYT 4/18/25), here. I think readers should be able to read the article, but if not a free article of some of the same content is Katherine Doyle, Trump is replacing the acting IRS commissioner, part of a dispute between treasury and Elon Musk (NBC News 4/18/25), here.

President Trump nominated a political actor, William Hollis Long II (“Billy”), Wikipedia here, but he has yet to have confirmation hearings. As the articles note, there has been some thrashing around in the “Acting” leadership in the IRS because of political meddling by Trump and his sycophants. I don’t propose to go into that.

The statute requires that the Commissioner have “demonstrated ability in management.”  § 7803(a)(1)(A), here. I would think that, by reasonable inference, Acting Commissioners should also meet that requirement. Hence, in the past Acting Commissioners were often drawn from high level Executive IRS officers who have demonstrated ability in management. Melanie Krause, Wikipedia here, former Acting who left a couple of days ago, had such demonstrated ability. She was replaced by Gary Shapley, one of the “whistleblowers” on the IRS investigation (conducted with the USAO Delaware) of Hunter Biden. It was never clear to me that Mr. Shapley had any such “demonstrated ability in management.” Nor, is it evident that Mr. Long, a former auctioneer and U.S. Representative, has such “demonstrated ability in management.”

Trump may have appointed Mr. Long to create further dysfunction in the IRS, so lack of management skills may be the whole point. Still, I would think that someone who is both smart and with management skills could do a better job of wrecking the IRS.

Trump’s First Term Commissioner was Charles P. (“Chuck”) Rettig, Wikipedia here. I know Chuck and like him a lot. I was not aware of his demonstrated ability in management, but I did know him to be a very smart, competent, and experienced tax attorney with great people skills. From what I can determine, he did a great job as Commissioner. By contrast, I have no reason to believe that Billy Long brings those characteristics, much less management skills, to the job for which he has been appointed. Maybe with his auctioneer skills, he can sell off the outsourcing of the IRS to the highest bidder (perhaps Musk).

Update on 4/19/25 @ 3:45pm: The President has named Michael Faulkender, Deputy Secretary of Treasurer, as the Acting Commissioner of Internal Revenue to act until the Presidential nominee (currently Billly Long, the auctioneer) is approved by the Senate. Faulkener's Wikipedia page is here. It is not apparent from the Wikipedia description that Faulkender has “demonstrated ability in management,” although he certainly appears to be a smart and capable person and likely can meet the demands of the office. 

In terms of credentials and apparent mental firepower, Faulkender stands head and shoulders over the immediately preceding Acting Commission, Gary Shapley, Wikipedia here, who lasted just a few days in office and whose only claim to prominence was that, as an IRS Criminal Investigation Special Agent, he blew the whistle on claimed mismanagement of the Delaware U.S. Attorney’s investigation of Hunter Biden. Having blown the whistle on matters that implicate Joe Biden, Shapley became the darling of the conservatives and particularly Donald J. Trump, who hates Joe Biden with a passion. It was not clear to me how Shapley remotely qualified for the position of Acting Commissioner of Internal Revenue. Of course, as I noted above, it is not clear to me how the nominee for Commissioner, Billy Long, the auctioneer, remotely qualifies.

The Section 7217 Crime of Executive Office, including President, Requesting or Directing IRS to Examine or Audit (4/18/25)

I have been thinking about President Trump’s public scrap with Harvard University, In doing so, I have reviewed § 7217, titled " Prohibition on executive branch influence over taxpayer audits and other investigations," here, which makes it a felony crime (5 years) for any “applicable person”—including the President—"to request, directly or indirectly, any officer or employee of the Internal Revenue Service to conduct or terminate an audit or other investigation of any particular taxpayer with respect to the tax liability of such taxpayer.” I won’t go through the “applicable person” list because the President is clearly one of them. And the crime is to "directly or indirectly" make the request.

I discuss § 7217 in my Federal Tax Procedure Book, 2023 Practitioner Edition p. 420 and Student Edition p. 291. In reviewing that discussion to see whether I should change anything in the Working Draft for the 2024 Editions, I have made minimal changes to the text but have added a footnote with respect to the exclusion of the Attorney General from the prohibition. As revised in the Working Draft for the 2024 Editions, the second sentence (with footnote for the Practitioner Edition) says:

The executive branch personnel within the scope of this prohibition are: (i) the President and Vice President and their respective executive offices; and (ii) persons at level 1 of 5 U.S.C. § 5312 (generally department heads other than the Attorney General).n1828a*
   n1818a I have not researched legislative history of this section to determine whether it explains why the Attorney General was excluded from the prohibition on Executive level actors. One reason might be that DOJ Tax, acting on behalf of the AG, must interact with the IRS often to carry out its duties and probably could and should be able to request the IRS to examine or audit. Another reason could be that the prohibition, enacted in 1998, was at a time when the norm had been established to avoid such White House or Executive Office direction of the AG and DOJ generally.
          The exclusion of the AG from the prohibition takes on great significance in the Trump Second Administration (2024-2028) where (i) Trump acts contrary to the norm, publicly claiming that the DOJ acts under his control and (ii) Trump installed a compliant AG, Pamela Bondi, willing to do his bidding or his wishes as she perceives them. Could Trump skirt the prohibition by asking or directing the AG to request an IRS examination? For example, it is widely reported that, in his attempt to make Harvard University bend the knee to him, Trump has publicly proclaimed that the IRS should revoke Harvard’s tax exempt status. E.g., Aimee Picchi, Can Trump or the IRS strip Harvard of its tax-exempt status? Here's what to know (CBS News 4/17/25). By publicly attacking Harvard’s tax exempt status, is that enough to indirectly direct the AG to make the request to the IRS or even for the IRS, “sua sponte,” to act to examine Harvard? The statute does prohibit requests “directly or indirectly.” A comparison might be made to Henry II who in a moment of pique at Thomas Becket, Archbishop of Canterbury, is  alleged to have said "Will no one rid me of this turbulent priest?” (or some variant) which some of his sycophants took as a direction or request and murdered Becket in 1170. See Wikipedia “Thomas Becket,” here (last edited 4/9/25 and viewed 4/17/25) (noting that “Regardless of what Henry said, it was interpreted as a royal command.”). Can the President avoid § 7217 in that manner? Or, to extend the thought, could the IRS begin examinations of persons with whom the President expresses displeasure? Or at least the principal actors drawing the President’s angst? Readers might also consider Trump’s Executive Order among many on the first day of office supposedly to end the weaponization of Government. See Executive Order titled “Ending the Weaponization of the Federal Government” # 14147 (1/20/25), here. I think the record to date shows at least the possibility that Trump has weaponized the Federal Government despite his own Executive Order. Of course, violating his own Executive Order merely shows that the President is a hypocrite, and, so far as I am aware, hypocrisy is not a crime, nor is violating an Executive Order.

* Note that the footnote number is consistent with the 2023 text but that footnote number will be different in 2024 final Professional Edition and the content of the footnote may even be revised before publication of the Edition.

Another Bullshit Tax Shelter Goes Down; On Frank Lyon (4/17/25)

Judge Lauber nails another bullshit tax shelter in GWA, LLC v. Commissioner, T.C. Memo. 2025-34, TC here at Dkt # 357, GS here [to come] and TN here. Suffice it to say that Judge Lauber was not confused by the smoke and mirrors the taxpayer threw up on the proverbial wall. The key issue is whether the financial contract was an option contract or an ownership contract. For the tax benefits, the taxpayer wanted to treat it as an option contract, the form in which it appeared; the taxpayer argued it was an option contract that permitted deferral and ultimate favorable tax treatment; the IRS asserted it was an ownership contract not allowing such treatment. Other issues were (i) whether the treatment as an ownership contract was, under the facts, a change of accounting requiring a § 481 adjustment (it did) and (ii) whether the taxpayer was subject to penalties (it is).

I write to discuss the role of Frank Lyon Co. v. United States, 435 U.S. 561, 573 (1978) in the opinion. Frank Lyon was a disaster of an opinion, and my principal poster child as to why tax cases are too important to have the Supreme Court decide them. (That is hyperbole, of course, but not much.) In Frank Lyon, the Court, while nominally honoring the venerable tax concept of substance over form, entered a fact-intensive multi-element inquiry to bless the form of a sale-leaseback transaction with tax ownership benefits (depreciation) going to the nominal lessor (Frank Lyon). I think that most careful observers of Frank Lyon believe that Frank Lyon was incorrectly decided. E.g., Charles I. Kingson, How Tax Thinks, 27 Suffolk U. L. Rev. 1031, 1034-35 (2004). “few [tax] shelters are shoddier than those approved by the Court in Lyon and Brown [Commissioner v. Clay B. Brown, 380 U.S. 563 (1965)]”; and Bernard Wolfman, The Supreme Court in the Lyon's Den: A Failure of Judicial Process, 66 Cornell L. Rev. 1075, 1098 (1981). Still, perhaps saving the day, courts generally find enough in Frank Lyon to reject bullshit tax shelters, as Judge Lauber did in GWA, LLC v. Commissioner.

I won’t get into a back story on Frank Lyon in which I was peripherally involved at DOJ Tax. Perhaps I will write on it sometime, in order to explain why, in my judgment, the Court imprudently granted the petition for certiorari in the first place and then wrote the opinion the way it did (in my view imprudently, rather than DIG the case). Nevertheless, that should not detract from the opinion on its four corners. Since Frank Lyon, most of the bullshit tax shelter legal opinions cite and claim to rely on Frank Lyon. Most judicial opinions cite Frank Lyon in shooting down bullshit tax shelters.