On Win-Loss Records on Appeal (with War Stories) (5/5/25; 5/6/25)

Note, some of my statistics reported below have been corrected on 5/6/25 11:00am.

I have sprinkled some of my blog entries with war stories from my time with DOJ Tax (1969-1977, with just over 4 years in Appellate and just over 3 years in a refund trial section, called Refund 2, which covered roughly Virginia through Texas. In the Refund 2 trial section, I handled cases in South Carolina, the Northern and Middle Districts of Georgia, Eastern District of North Carolina, and 2 life insurance company cases in Florida and Texas (I forget which districts, but I think Middle District of Florida and Northern District of Texas (because Vester Hughes was opposing counsel) although those cases were not resolved by the time I left DOJ Tax. Today, inspired by the article I quote below, I offer some more war stories through statistics.

The inspiration is a recent article, Stephen K. Cooper, DOJ Tax Chief Touts Winning Court Record On Appeals, 2025 Law360 16-164 (1/16/25) [free link unavailable]. The article covers a talk by Francesca Ugolini, the acting chief of the DOJ Tax Division—there has been no Presidentially appointed and Senate-approved Assistant Attorney General for some time. The article includes the following: 

          The U.S. Department of Justice's Tax Division won an overwhelming majority of appeals in tax cases last year by prioritizing strong legal arguments in disputes that had the potential to significantly affect federal tax administration, the head of the division said Thursday.

          Francesca Ugolini, chief of the DOJ's Tax Division, said in the last fiscal year, the government prevailed in 94% of appeals brought by taxpayers and had an unexpected success rate of 75% for its own appeals.

          "We usually do prevail in over 90% of the taxpayer appeals," Ugolini said at the D.C. Bar Tax Conference, held in Washington, D.C., and online. Regarding the government's appeals, "it's usually over 50%," she said.

          "It's not always as high as 75%, but we have some pretty, pretty good success in the appellate courts," she said.

          Ugolini attributed the higher-than-normal success rate to the division's thorough review process that was used to decide whether to appeal a case the government has lost at the trial level. This includes assessing the strength of the legal arguments, the potential impact on federal tax administration and whether the case presents the best vehicle to address the issue.

          "We don't like to lose on appeal, so we're looking at the strength of the case," she said. "That includes … the strength of our legal argument, what the standard of review is [and] what the precedent is in the circuit.

          "We're more likely to appeal cases that involve legal questions, because those are reviewed de novo on appeal, whereas adverse fact findings are reviewed for clear error, and they're really hard to reverse on appeal."

          The administrative implications of the case are also important to the DOJ in its decision-making process, Ugolini said.

          "We're also looking at what is the broader effect on the federal tax system," she said. "Is this issue important to the IRS administratively? What's the impact on federal tax administration? And then we're also looking at, is this the best case to present the issue?"

On Burden of Production and Related Concepts and an Appellate War Story on Scope of Review (5/12/24)

In a recent revision to my working draft of the Federal Tax Procedure Book (with the 2024 version due in early August 2024), I added to the discussion of the Burden of Production. (The 2023.2 version of the Practitioner edition, here, has the Burden of Production discussion starting on p. 617.) As I note there, the burden of production concept is usually discussed in a jury trial setting where the party bearing the burden of persuasion will lose on motion for directed verdict without getting to the jury if there is not enough evidence on a key fact to be submitted to the jury. That is a production burden or, as some call it, the risk of nonproduction. This burden is addressed to the function of the judge rather than the jury.

In a recent article, I noted that “The burden of production could also come into play on a motion for summary judgment, motion for j.n.o.v., or even on appeal when the trial judge or appellate judges determine that the evidence was of such quality that a reasonable juror could not make a determination.” John A. Townsend, Burden of Proof in Tax Cases: Valuation and Ranges—An Update, 73 Tax Lawyer 389, 402 n. 42 & 404 n. 49 (2020). I decided to add that thought to the Burden of Production discussion in the working draft of the Federal Tax Procedure Book so that it will appear in the 2024 edition.

As I now have it in the working draft, the added paragraph is (footnote omitted):

          The burden of production is discussed above in its traditional jury-trial setting where it would be invoked in a motion for directed verdict. There is an analog in motions for summary judgment, motion for judgment notwithstanding verdict (j.n.o.v.), and appeals. In each of those settings, a proponent may succeed if the record has unrebutted persuasive evidence that a reasonable jury could not find for the opponent. In other words, the opponent on a motion for summary judgment has a burden of production (or risk of nonproduction) equivalent to show evidence that a reasonable jury could find for the opponent.

I thought I would elaborate in this blog by reference to a recent tax opinion. In Meyer, Borgman & Johnson, Inc. v. Commissioner, 100 F.4th 986 (8th Cir. 5/6/24), CA8 here and GS here, the Court affirmed the Tax Court’s grant of summary judgment holding that the taxpayer did not qualify for § 41’s credit for qualified research expenses” because the expenses were “funded” by another party (rather than at taxpayer risk) within the meaning of § 41(d)(4)(H). I will not go further into the law; the opinion is very short, so I encourage those interested to read it.

Obviously, in granting summary judgment, the Tax Court had to make findings of fact and conclusions of law. Under my analysis above, the taxpayer bearing the burden of persuasion and thus the burden of production on summary judgment had to show that there were sufficient facts under the law to warrant the Court denying the summary judgment. In other words, in the face of an otherwise appropriate IRS motion for summary judgment, the taxpayer had to ensure that the facts on the motion for summary judgment were of sufficient quality to make the issue a triable issue. In the jury analog, the facts would have to be sufficient to get the issue to the jury if the facts were as presented in the motion for summary judgment.

I focus on the Court’s statement in Meyer, Borgman & Johnson, Inc. of the standard of review on appeal, because it seems to be less than precise about what it was doing in the context of reviewing the grant of a motion for summary judgment. I quote the relevant portion of the opinion (Slip Op. 2, cleaned up to strip out case citations and quotes to get to the reasoning and bold-face supplied by JAT):

On summary judgment, the Tax Court ruled that MBJ’s research was “funded” within the meaning of 26 U.S.C. § 41(d)(4)(H), meaning that MBJ did not qualify for the credits. This court reviews de novo a grant of summary judgment. Summary Judgment pursuant to Tax Court Rule 121 is derived from Rule 56 of the Federal Rules of Civil Procedure and is interpreted consistently with interpretations of Rule 56. Contract interpretation and the propriety of summary judgment are legal issues we review de novo.

This court reviews de novo the Tax Court’s legal conclusions; findings of fact are upheld unless clearly erroneous. An income tax deduction is a matter of legislative grace and* the burden of clearly showing the right to the claimed deduction is on the taxpayer.

Statistical Sampling for Large Dataset Issues in Tax Litigation (3/23/24)

In Kapur v. Commissioner, T.C. Memo. 2024-28, GS here,  the Court (Judge Pugh) set out the issue as follows (Slip Op. 2, two footnotes omitted):

    Before the Court is petitioners' Motion for Protective Order. The parties dispute whether discovery and trial should be limited to a sample of projects at this stage of litigation. We decline to order sampling for the reasons summarized below. n4
   n4 This appears to be a recurring issue. See, e.g., Phx. Design Grp., Inc. v. Commissioner, No. 4759-22 (T.C. Aug. 29, 2023) (order); Feller v. Commissioner, No. 11581-20 (T.C. Aug. 10, 2023) (order). Respondent referred us to these orders but of course they are not precedential.

The Court reviews (Slip Op. 5) sampling by agreement of the parties (whether encouraged by the Court or not). The Court then says (Slip. Op. 5-6, bold face supplied by JAT):

    Respondent also claims that we do not have discretion to order sampling at the request of petitioners if respondent objects. We disagree: We do have authority to limit discovery (including by ordering sampling) over the objection of a party. See Rule 70(c)(1). Nonetheless, we agree that exercising our discretion to limit the scope of discovery and trial in 6*6 accordance with petitioners' Motion for Protective Order is improper at this stage. The only issue in this case is whether petitioners are entitled to the research credits claimed for the years in issue. Evaluating compliance with section 41 necessarily involves consideration of the underlying business components. And petitioners agree that they have the burden of showing entitlement to the claimed research credits. See Feigh, 152 T.C. at 270. As we have said previously, "[a]bsent an agreement between the parties, project sampling improperly relieves the taxpayer of its burden of proving entitlement to the research credit claimed." Betz v. Commissioner, T.C. Memo. 2023-84, at *77 n.30 (citing Bayer, 850 F. Supp. 2d at 538, 545-46).

As I understand the Court said it can order sampling for discovery purposes but cannot order sampling over IRS objection for resolution of the merits on issues as to which the taxpayer bears the burden of persuasion.

It is not clear to me that the final conclusion is consistent with the Court’s earlier rejection of the IRS claim that Court does not have authority to order sampling when the IRS does not agree. Another way of reading the paragraph is that the Court will not order sampling based on the stage of pretrial development right now in Kapur.

This raises some issues for me, but let me start with my understanding of good sampling that permits reasonable inferences about the universe of data that is sampled. Those reasonable inferences can be stated in possibilities or margins of error for the inferences, which generally can be slimmed down by increasing the sample size.

War Story-Appellate: My Early Brush (1969) with Administrative Law Meaning of Legislative Regulations (3/16/24)

I am starting a new series of procedure-related appellate war stories, mostly from my time with DOJ Tax Appellate Section (1969-1974). The purpose of the series is to tell the war story because it is interesting to me but to do so only when the telling of the story offers some opportunity for students (including for this purpose, practitioners) to learn from the story. I have previously posted some such war stories; all such stories will be under the label “War Story-Appellate", here (the link can be clicked at any time to show all postings).

Today’s War Story-Appellate relates to one of the first cases I handled with DOJ Tax, Davis v. Commissioner, 422 F.2d 401 (6th Cir. 1970), here. I wrote the brief in late 1969; the case was decided in 1970. The substantive issue was whether the taxpayer had proved entitlement to more expenses than allowed by the Tax Court. That is not a tough issue to address and is factual with no precedential importance. The Sixth Circuit addressed it in a one-line per curiam opinion:

On consideration of the files and records in this case, the judgement of the Tax Court is affirmed for the reasons set forth in the Memorandum Opinion of the Tax Court, Tax Ct. Memo 1969-74.

As I have said before in War Story-Appellate, the DOJ Tax Appellate Section did not assign tough cases to relatively new attorneys. I had joined DOJ Tax Appellate in June 1969. I had not yet proved my self capable of handling more difficult cases.

My Davis assignment had a more significant threshold procedural issue that is not addressed in the Sixth Circuit’s one-line per curiam opinion. The issue was (presented in our brief as filed, here, p. 1):

1. Whether this Court has jurisdiction over the merits of this appeal when taxpayer failed to file a notice of appeal until ninety-two days after entry of the Tax Court decision.

Actually, that question was written by my reviewer, Tom Stapleton. In my draft (here), I stated the question as follows:

1, Whether the taxpayer's untimely filing of the notice of appeal from the Tax Court's decision denies this Court from deciding the merits of the appeal.

Tom’s version was better, but still not optimal. How would I improve the question today? Here is my current shot at the best statement of the issue.

1. Whether FRAP 13(a)'s requirement to file notice of appeal within 90 days from the Tax Court decision override the previously enacted statute's (§ 7483) three-month requirement.

Garland v. Cargill-Comments on Briefs and Oral Argument (2/29/24)

Yesterday, the Supreme Court held oral argument in Garland v. Cargill (No. 22-976 docket here, oral argument audio here, and transcript of oral argument here). The ultimate issue is whether “bump stock” devices are within the definition of “machinegun” in the National Firearms Act of 1934, as amended, and the Gun Control Act of 1968. Bump stocks were not devised when the statute was enacted and there is no definitive interpretation of the statutory term “machinegun” that includes or excludes bump stocks. Hence, the job of the regulator or the court in interpreting or applying the term is to determine whether, within the fair bounds of interpretation, the term includes or excludes bump stocks.

At first glance, this issue might call for the application of Chevron deference. Recall that Chevron deference requires two steps—

• Step One where the Court determines whether, on the text alone using proper tools of statutory interpretation, the text resolves the issue. If the text does, the interpreted text applies and there is no deference. If the text does not resolve the interpretive issue and the text is said to be ambiguous.
• Step Two, reached only if Step One does not resolve the interpretive issue, where the court determines whether the agency interpretation is reasonable (also called permissible). If so, the agency interpretation will prevail. Note that I said “prevail” rather than that the agency interpretation receives deference which is the standard Chevron Step Two formulation. Deference is only meaningful when the agency interpretation is not the best interpretation. If, within the zone of ambiguity in the statutory text, the agency interpretation is the better interpretation or even in equipoise as to the best interpretation, applying the agency interpretation is not deference.  See e.g., What is the Best Interpretation for Purposes of Determining a Not Best Interpretation for Chevron Deference? (Federal Tax Procedure Blog 10/21/22; 11/8/22), here.

In the facts of Cargill, the agency interpretation of “machinegun” to include bump stocks was made in the Trump administration in a notice and comment regulation adopting an “interpretive” rule. (I will address the interpretive characterization for the regulation below.) In adopting the regulation, the agency relied on Chevron. In the litigation culminating in Cargill in the Supreme Court, the agency did not rely on Chevron but rather asserted that the interpretation was the best interpretation. (Conceptually, the best interpretation can be determined at Step One or at Step Two (if the agency interpretation is the best in the zone of ambiguity); so it is unclear which Step the government’s reliance on the best interpretation applies.)

At oral argument, apparently because the government was not relying on deference or perhaps the uncertain future of Chevron deference, Chevron or deference was not mentioned. The argument simply addressed whether the text “machinegun” resolved the issue.

Justice Thomas and Tax -- The Plot Sickens (10/29/23; 10/7/24)

Introduction: Today's topic is off-topic to tax procedure, although it does relate to trial of a tax case in problematic circumstances.

Justice Thomas’ most recently revealed conduct raising considerable controversy in ethics, legality (tax), and prudence is the alleged forgiveness in whole or part of a loan made to Justice Thomas by an alleged acquaintance (perhaps hanger-on) to acquire a luxury RV. Some alleged that, if the allegation is true, Justice Thomas had taxable income (lawyers call it cancellation of indebtedness (“COI”) income) or a nontaxable gift. Either characterization can create potential problems for Justice Thomas–if COI income, Justice Thomas might have tax reporting and paying obligations; if a gift, the “donor” would have tax reporting obligations.  I suggest in this post that the allegation it is both more subtle and potentially sinister than those claims.

From my days at DOJ Tax handling two cases, I believe that there is nuance that is missed in the claims discussed in the above paragraph. The two cases are Spartan Petroleum Company v. United States, 437 F. Supp. 733 (D.S.C. 1977) and Cooper v. United States, 1975 U.S. Dist. LEXIS 11633 (S.D. ALA 1975).

Together, those cases held correctly that 

(i) a cancellation of indebtedness is not treated as COI income if the cancellation is a medium to make a transfer with another tax character (in Spartan Petroleum, the cancellation of indebtedness was additional consideration for transfer of property; btw there was a Tax Management portfolio that wrongly recommended that shuffle); and 

(ii) following through on the Spartan Petroleum holding, a cancellation of indebtedness can be a means to benefit the debtor having some tax character other than COI income. Thus, the COI can represent a gift which is not taxable income to the donee (Thomas potentially) but is a reportable gift potentially subject to gift tax to the donor.  Gift tax status requires that the motive for the gift (here, if applicable, by COI) be detached and disinterested generosity which is the debtor’s (Thomas' burden to prove). If it is not detached and disinterested generosity, the teaching of Cooper is that it is taxable income, because the motive is likely expecting some benefit or advantage the debtor could provide. Cooper was a prominent Alabama politician in the Wallace governing circle and in a good position to benefit the Bank of Pineapple and its principals, one of whom by the way at the time had the highest grades ever recorded at University of Alabama and, at a very young age, had been General Stillwell’s top aide in China; and his bank held a large amount of interest free state deposits.)  I took the bank President's deposition in the Eglin Air Force prison (a country club prison); he delivered the goods. In other words, in that case the COI was income for influence–a bribe with an expected or hoped for benefit.

War Story – Judge Henry J. Friendly (8/31/23)

I am writing an article that, for reasons not relevant to this blog entry, I have to address Judge Henry J. Friendly’s lament about two inconsistent lines of authority for deference in Pittston Stevedoring Corp. v. Dellaventura, 544 F.2d 35, 49 (2d Cir. 1976), here, aff’d sub nom. Northeast Marine Terminal Co. v. Caputo, 432 U.S. 249 (1977). As many, particularly older practitioners, will know, Judge Friendly was a giant among appellate judges, said to be the best of his generation. See, e.g., Pierre Laval (a 2d Circuit Judge), Remarks on Henry Friendly, 15 Green Bag 2d 257 (2012), here (highly recommended for practitioners who are not very familiar with Judge Friendly).

I have a personal Judge Friendly anecdote from an appearance for DOJ Tax Division Appellate Section in my first brief and oral argument. Fishman v. Commissioner, 420 F. 2d 491 (2d Cir. 1970) (Per Curiam with authorship not attributed), here. I was assigned the case on the first day in the Appellate Section in June 1969. The Chief of Appellate, the great and wonderful Lee Jackson, did not assign a difficult case to newbies but he did say that if I lost the case (involving the timely-mailing timely filing, § 7502 regulations), a large part of the edifice of tax administration would fall. (He was trying to infuse importance into a case that would be hard to lose.) He also told me that my opposing counsel was Morton Ginsburg of New York but, since I heard that orally, I could only think of Marty Ginsburg who I had as a Professor of tax law (yes, that Marty Ginsburg, see Wikipedia here) and once testified was the smartest tax lawyer in the universe. (Some hyperbole there, but not much.) After I got over the shock of thinking it was Marty, I settled down to write the brief.

Being my first, the Appellate Section gave me a practice oral argument before three seasoned appellate lawyers, as best I recall Mickey Rothwacks, Bill Friedlander, and Grant Wiprud. At the conclusion, they pronounced that I would be a better oral advocate than brief writer. (I got much better at brief writing but started very low; which surprises me because one of the best lawyers in Section, Tom Stapleton, reviewed the brief and always in my experience brought the brief up to high standards on review.)

At oral argument before the 2d Circuit before Judges Friendly, Smith, and Anderson, though, I had 30 minutes for argument and planned to use no more than 15 minutes unless some of the judges’ questions prompted me to go longer. About 3 minutes into the argument, I concluded that each panel member was reading something other than paying attention to my oral argument (I inferred each was reading either the briefs or clerks’ briefing memoranda for the next case). So, I quickly and succinctly summarized my argument and closed in 5 or 6 minutes total. After I concluded, Judge Friendly thanked me and allowed opposing counsel to rebut. I don’t know whether Judge Friendly’s thanks was courtesy for a fresh but unpolished lawyer, a comment on the quality of the argument (I doubt), or that I quickly brought it to a close in 5 or 6 minutes rather than 15 or 30 minutes wasting everybody's time (I suspect).

Timely-Mailing, Timely-Filing - Tax Court Case Reminder of Requirements (9/11/12)

In my Tax Procedure class last Thursday, we covered return filings.  A key component of the discussion was the timely mailing, timely filing rule in Section 7502, here.  The Tax Court yesterday decided Scaggs v. Commissioner, T.C. Memo. 2012-258, here.  Scaggs offers an object lesson in how not to qualify for the timely mailing, timely filing rule.  So I will review the rules and then the decision in Scaggs.

I cut and paste my discussion from my Federal Tax Procedure book (no footnotes):

Section 7502 provides a “timely-mailing, timely-filing” rule, which treats the mailing date as the filing date for returns (and other documents) received by the IRS after the due date (either the original due date where there is no extension or the extended due date if there is an extension) but mailed on or before that due date.  The timely-mailing, timely-filing rules (and risks) may be summarized as follows:

1.   The document filed must be a “return, claim, statement, or other document required to be filed.”  I focus here on the “required to be filed” element.  Original tax returns are the quintessential type of document that is required to be file and thus clearly meets this element of the statute.  Tax Court petitions are also required to be filed by the Code in order to meet the jurisdictional requirements for the Tax Court and, in that sense, are required to be filed and thus meet this element of the statute.  What about amended returns?  The standard conceptualization of the amended return is that the Code itself does not require amended returns to be filed.  So, do amended returns qualify?  The answer is that some clearly do and some may not.  Since, as we shall see later, the Code requires claims for refunds to be filed within a statute of limitations period, amended returns making refund claims qualify as returns required to be filed thus permitting the taxpayer to meet this element of the timely mailing, timely filing rule.  But, that analysis does not apply to amended returns reporting additional liability.  The IRS has ruled that amended returns reporting additional liability are not “required” and thus any tax reported on such returns actually filed after the assessment limitations period but otherwise mailed within the assessment period, do not qualify under § 7502.  What this means is that the IRS may not assess and must return any payment remitted with the amended return reporting a liability.