Lesson From The Tax Court: Accounting For Attorney Malpractice Settlements

Sometimes, losing plaintiffs think their attorney messed up.  Sometimes, they are so sure that they sue their attorney for legal malpractice.  I think of those as lawsuits-within-lawsuits, kind of like the story-within-a-story literary device, perhaps most famously used by Shakespeare in Hamlet.  In a malpractice action, the original lawsuit becomes a lawsuit-within-a-lawsuit because the court decides the malpractice action in part by making a counterfactual inquiry on what could have been the outcome in the original lawsuit.

Sometimes, plaintiffs actually win the malpractice action.  More often they settle, accepting some amount of money from the attorney (or, more often, the attorney’s insurer) in exchange for promising to go away and never come back.

The extent to which an attorney malpractice settlement constitutes gross income is the ostensible lesson in two recent cases.  In Carol E. Holliday v. Commissioner, T.C. Memo. 2021-69 (June 7, 2021) (Judge Pugh), and in Debra Jean Blum v. Commissioner, T.C. Memo. 2021-18 (Feb. 18, 2021) (Judge Urda), the Tax Court rejected both taxpayers’ attempt to exclude settlements of their attorney malpractice claims from gross income, even though both taxpayers may well have been able to exclude settlements of the original action.  Using an “in lieu of” test, the Tax Court said that the settlement of the malpractice claim was different than settlement of the original claim.  The original claim had become merely a lawsuit-within-a-lawsuit, a play-within-a-play, and thus had an insufficient nexus with the actual payment to support exclusion.

The less obvious lesson in these cases is how the ostensible lesson creates a bargaining chip for malpractice attorneys sitting at the poker table of settlement negotiations.  Taxpayers might account for the tax treatment of malpractice settlements either by structuring the settlement to make the payments eligible for exclusion, or by grossing up the settlement to reflect taxes imposed that would not have been imposed on settlement of the original action.  Details below the fold.

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Lesson From The Tax Court: The Perils of Stipulations

Tax Court procedure marches to a different beat from other federal courts.  For example, when a taxpayer files a Petition contesting a Notice of Deficiency (NOD) the taxpayer cannot voluntarily dismiss the case the way litigants can do in federal district court.  See Lesson From The Tax Court: The Hotel California Rule, TaxProf Blog (Nov. 12, 2018).  And it is not just pro se litigants who get tripped up, which is to be expected despite the heroic guidance given by the Tax Court on its webpage.  Experienced practitioners sometimes goof this up as well.

The recent case of Donald Bailey and Sandra M. Bailey v. Commissioner, T.C. Memo. 2021-55 (May 10, 2021) (Judge Pugh), teaches an important lesson about the crucial role of stipulations in the Tax Court’s decisional process: litigants must have a firm grasp of their case very early, or risk stipulating themselves into defeat as the taxpayers did in this case.  Details below the fold.

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Lesson From The Tax Court: The Structure Of Substantiation Requirements

Say you have 20 boxes of 5 different sizes.  Each size comes in 2 different colors  You can organize them in two ways.  You could create 5 groups of sizes, subdivided into 2 colors each.  Or you could create 2 groups of color, subdivided into 5 sizes each.  Or you could, like many of our clients, smash the boxes, throw then in a closet, and hope you never need them again.

Organizing boxes of deductions involves similar choices. The Tax Court keeps telling us that taxpayers bear the burden to prove their entitlement to deductions.  Taxpayers repeatedly fail to learn the lesson. Viola Chancellor v. Commissioner, T.C. Memo. 2021-50 (May 4, 2021) (Judge Urda), teaches a nice lesson on how one might organize various deductions according to the applicable substantiation requirement.  Judge Urda’s opinion addresses deductions taken on Schedule C by dividing them into two groups depending on their substantiation requirements.  Organizing deductions by their substantiation requirements is useful because taxpayers can use the Cohan rule to fill some substantiation requirements, but not others.  Spotting when and how to use the Cohan rule can be useful for tax preparation and planning, especially when your client’s dog ate the receipts — an increasingly tenuous claim in light of electronic receipts.  So I think it’s a lesson worth learning.  Details below the fold.

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Lesson From The Tax Court: CDP Settlement Officer Must Work Previously Rejected OIC

Last week’s case of Katherine Mason, et. al, v. Commissioner, T.C. Memo. 2021-64 (May 20, 2021) (Judge Holmes), teaches that the IRS Office of Appeals must consider in a CDP hearing the merits of an Offer In Compromise (OIC) that a prior office found was submitted solely to delay collection.  I kid you not.  Agreeing with the taxpayer that “the CDP process is aimed very deliberately to give most taxpayers an opportunity to delay collection,” Op. at 21, Judge Holmes held that the CDP Settlement Officer abused her discretion when she refused to consider an OIC on its merits, even though she found it had been properly rejected for having been submitted precisely for purposes of delay.  Yes folks, welcome once again to the wacky world of Collection Delay Process.  I also see the case as teaching us both the value—and the limits on value—added by judicial review.  Finally, I think the taxpayer simply won the opportunity to lose again.  See if you agree.  Details below the fold. 

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Lesson From The Tax Court: A Timely Lesson For Filing Returns

This year, the tax filing deadline for most folks is today, Monday, May 17th (here in Texas we get until June 15th because of the winter freeze).  The May 17th date is thanks to this questionable national extension issued by the IRS.  I say questionable because it is not clear why §7508A or any other statute gives the IRS the authority to extend the statutory deadline nationwide this year.  But no one is complaining.

And the IRS needs the extension as much as taxpayers do.  TIGTA reported in March that the IRS had still not processed almost 12 million 2019 paper returns as of last December 20th.  That should not be a criticism of the IRS.  While perhaps not the “master class” tweeted by Ms. Yellen, the IRS has done remarkably well to keep the machinery of tax collection moving during this time of COVID and Congressional Simon-Says statutes requiring immediate distribution of multiple Economic Impact Payments.  It would be difficult to expect more of any agency.  In short, everyone needs a little more time this year.

So today is Tax Day!  It's a great time for the lesson I see in William J. Spain and Idovia A. Spain v. Commissioner, T.C. Memo. 2021-58 (May 11, 2021) (Judge Lauber): how to comply with filing requirements and how to substantiate that compliance.  Sure, it’s a CDP case, but the lesson is equally applicable to all those last-minute tax return filings that will happen today.  In today’s case, the taxpayer’s careless CPA used his office postage meter to mail the Tax Court petition, but put no date on the envelope.  He relied on the U.S. Post Office to pick up the mail and postmark it.  Bad move.  The USPS did not postmark the envelope.  That failure at least created an opportunity to rescue the situation, but the CPA failed there as well.  The sad details are below the fold.

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Lesson From The Tax Court: The Measure Of Intent For Gift Exclusions Under §102(a)

When my church stopped in-person worship services in 2020, we kept paying our part-time child-care workers.  We first paid them with PPP loan money (which we treated as wages).  When that ran out, we decided to continue payments.  Why did we do that?  First, they were part of our church family and we knew that losing those amounts would be a hardship for them.  Second, we wanted to retain goodwill so they would come back when we resumed in-person worship.  So we had dual intent, mixed motives.  Which dominated would determine whether those continued payments were taxable compensation or non-taxable gifts.  How is a Court supposed to figure that out?

Juan Pesante, Jr., and Maria A. Moreno-Pesante v. Commissioner, (Bench Opinion, May 6, 2021) (Judge Copeland) teaches how the Tax Court measures the intent of a payor to determine whether a taxpayer may exclude a payment as a gift under §102(a).  There, the payor had sent mixed messages on whether a $25,000 payment to Mr. Pesante was a gift.  The Tax Court agreed with the IRS that the payment was not a gift.  Judge Copeland’s reasoning gives a great road map for how taxpayers and their tax advisors should approach this messy life-in-all-its-fullness issue.  Details below the fold. 

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Michael Jackson's Estate Beats The IRS: Tax Court Sets FMV Of His Name And Likeness At $4 Million, Not $161 Million

Wall Street Journal, Michael Jackson Estate to Face Smaller Tax Bill After Court Ruling:

Michael Jackson’s estate prevailed over the Internal Revenue Service on several key issues in a closely watched court case, an outcome that will push the estate’s tax burden below the government’s initial assessment.

In a ruling issued Monday, U.S. Tax Court Judge Mark Holmes found that the singer’s name and likeness were worth $4 million when he died in 2009 at the age of 50, not the $161 million the government had claimed. The IRS won on some other points about the value of other Jackson assets, but will get far less than the hundreds of millions of dollars in taxes and penalties it had sought from the estate.

The government and the estate settled some issues, and the case came down to the question of how to value three main assets: Mr. Jackson’s name and likeness and two entities tied to the music business.

The estate initially started with some lower values, but by Monday’s decision, it had said those three assets were worth $5.3 million combined. The government had started with higher values and an estate tax bill topping $500 million, but eventually concluded those three assets were worth $481.9 million combined. Judge Holmes, in his ruling, said they were worth $111.5 million. The estate’s actual tax bill will be determined later. ...

A central question in the case was this: Was it foreseeable that the estate would—as it since has done—build a successful business around Mr. Jackson’s image? Or was that such a long shot that the estate could plausibly claim, as it initially did, that Mr. Jackson’s name and likeness was worth $2,105? As Judge Holmes put it, the estate was “valuing the image and likeness of one of the best known celebrities in the world—the King of Pop—at the price of a heavily used 20-year-old Honda Civic.” ...

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Lesson From The Tax Court: The Multiple Paths For Loss Deductions

Section 165 permits certain groups of taxpayers to deduct certain losses of capital under certain circumstances.  I emphasize to my students that §165 is, at bottom, a capital recovery provision.  There is no deduction for lost opportunities, lost profits, or lost pets.  It's only for losses of capital “sustained during the taxable year and not compensated for by insurance or otherwise.” §165(a).

Ronnie S. Baum and Teresa K. Baum v. Commissioner, T.C. Memo. 2021-46 (Apr. 27, 2021) (Judge Kerrigan) teaches a nice basic lesson on the multiple ways taxpayers can deduct the loss of money under §165.  There the taxpayers claimed to have lost money in a stock purchase deal gone bad.  They tried to claim a theft loss deduction of $300,000 for tax year 2015.  The Tax Court said no.  The lesson I see is not so much about the rules for theft losses.  Rather, the reasons why these taxpayers lost gives a nice lesson in the various options taxpayers have in deducting losses.  It's a woulda-coulda-shoulda lesson.  In fact, I think the Baums may still be able to get the deduction, for a different reason in a different year.  I may be wrong!  I invite your thoughts below the fold.

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Law Prof Stacy Leeds Challenges Oklahoma's Attempt To Tax Her Tribal Income After McGirt

Following up on Stacy Leeds (Arizona State; Google Scholar) & Lonnie Beard (Arkansas), A Wealth of Sovereign Choices: Tax Implications of McGirt v. Oklahoma and the Promise of Tribal Economic Development, 56 Tulsa L. Rev. __ (2021):  Stacy Leeds, the nation's first Native American female dean, has filed this 12-page individual income tax protest letter with the Oklahoma Tax Commission after they adjusted her 2019 return. She has given me permission to share the letter "in hopes that the treaty arguments and other legal authorities are 'out there' for educational purposes":

On March 4, 2021, I received your letter postmarked February 25, 2021 notifying me that you adjusted my Oklahoma 2019 income tax return. I hereby protest and object to all aspects of your adjustment. Under Oklahoma law, the laws of the United States and the laws of the Cherokee Nation, your adjustment is inappropriate and without legal authority. I respectfully request you reverse your course of action and take the additional steps outlined in my protest letter. ...

For your records, I have attached a copy of my Arkansas income tax returns. The Arkansas return confirms the amount paid to Arkansas matches the credit taken on my Oklahoma return. Under Oklahoma law, I am entitled to a tax credit for taxes paid to another state and my return was correct.

I have uploaded the following information into your online system proving my legal status as a Cherokee Nation citizen and my legal status as a Cherokee Nation resident. ...

Your letter incorrectly summarizes Oklahoma law with respect to Oklahoma income tax authority over resident tribal citizens. Your letter instructs me (and similarly situated persons who receive this form letter) that Oklahoma will “disallow or adjust” all income unless all three requirements are met: “be a tribal member, live and work on Indian land to which the member belongs.” (emphasis added)

This language is contrary law and very misleading. There is no requirement that a tribal citizen “live and work on Indian land.” A tribal citizen need only live within their Nation’s jurisdictional boundaries and derive their income from sources inside that same Nation.

Oklahoma lacks authority to tax the income of resident tribal citizens. A resident tribal citizen’s income does not simply qualify them to ask Oklahoma officials for an “exemption” every year on a required Oklahoma income tax filing. Oklahoma is without any governmental authority over that person, as it relates earnings derived inside Indian country.

At present, you require each resident tribal citizen to carry the burden and expense of annually filing an Oklahoma tax return and producing repetitive additional documentation in order to be considered for an exemption. This affords Oklahoma repeat decision-making authority over tribal citizens inside Indian country. Like McGirt v. Oklahoma, this is an Oklahoma overreach unsupported by legal authority.

Only those tribal citizens residing outside their tribe’s jurisdiction, or who derive Oklahoma income from outside their tribe’s jurisdiction, should bear the burden and expense of filing Oklahoma income tax returns and producing several unnecessary documents year after year. Should a material change in their tax circumstance occur that truly subjects them to Oklahoma authority, then they should have a duty to file.

To Oklahoma’s (substantial) financial benefit, OTC’s letters and instructions mislead tribal citizens to such a degree that tribal citizens are highly unlikely to seek an exemption or challenge Oklahoma’s inflated authority. This results in millions of dollars of overpayment by tribal citizens who are unlawfully subjected to Oklahoma income taxes. This over-taxation occurs, in large part, because Oklahoma knowingly misrepresents the law. The United States Supreme Court has repeatedly rejected Oklahoma’s extension of state jurisdiction over Indians inside Indian country.

I respectfully ask that you correct this language in future correspondences and be more transparent in your form letters and instructions to the public. You have a duty to truthfully communicate. You have a substantial interest in working together with tribal Nations, but instead you mislead and deceive tribal citizens under threat of penalty.

The default is not Oklahoma jurisdiction. The default is that Oklahoma lacks jurisdiction to tax the earnings of resident tribal citizens.

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Lesson From The Tax Court: Abatement Of Assessment Brings No Relief From Liability

Letters from the IRS are often confusing, both to clients and to practitioners.  So when the taxpayers in Robert Craig Colton and Alina Mazwin v Commissioner, T.C. Memo. 2021-44 (Apr. 21, 2021) (Judge Lauber) received a letter from the IRS saying “you do not owe us any money” for the very year they were disputing in Tax Court, you would not blame them for thinking that the IRS had conceded the case.  It hadn't.  The letter was only telling them that a premature assessment of the deficiency had been abated, not that the IRS's judgment about the underlying liability had changed.  The case teaches the important lesson that assessment and liability are different.  One must always be aware of the distinction between an assessment (or abatement) and the underlying liability.  Details below the fold.

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Lesson From The Tax Court: Blind Reliance Is Not Reasonable Reliance

The Tax Code’s complexity is legend.  And logarithmic.  The more complex a taxpayer’s financial affairs become, the more difficult it becomes for even reasonable taxpayers to avoid errors.  In recognition of that, almost all of the major penalty statutes allow taxpayers to avoid penalties by showing that they had reasonable cause for errors found on audit.

When complexity hits a certain level, taxpayers turn to professionals for help.  Sometimes taxpayers think doing so absolves them of responsibility for any subsequent errors.  They think that relying on professional help is by itself reasonable.  Today’s case shows why that is not true.

Duane Pankratz v. Commissioner, T. C. Memo. 2021-26 (Mar. 3, 2021) (Judge Holmes), teaches that whether a taxpayer has reasonable cause to avoid penalties depends on much more than simply relying on a CPA to properly prepare the return or identify missing information.  There, the taxpayer engaged in a variety of business activities through 11 corporate entities.  After audit, the IRS proposed to assess over $10 million in deficiencies and penalties.  That’s a lot of error.  The taxpayer claimed to have a reasonable cause for the error: my tax professionals did not tell me.  Why that claim failed provides the main lesson.  Details below the fold. 

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Federal Judge Dismisses Santa Clara Law Students' COVID-19 Tuition Refund Class Action

Karen Sloan (Law.com), Santa Clara University Escapes Law Students' COVID Tuition Refund Class Action:

A federal judge in California has dismissed a class action brought by three Santa Clara University law students who sought a tuition refund after their classes moved online last spring due to COVID-19.

In her March 29 decision, U.S. District Judge Lucy Koh of the Northern District of California wrote that references to on-campus classes and activities on the university’s website, course catalogues and bulletins do not constitute a specific promise to students that classes would be held in-person—as the plaintiffs argued. Statements made in those documents are too general to “impose contractual obligations” on the university, Koh found. ...

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Lesson From The Tax Court: The Incoherence Of §6751(b)

Two recent Tax Court cases show us that while the §6751(b) supervisory approval requirement does apply to a tax penalty mechanically applied by a human employee it does not apply to the same penalty mechanically applied by a computer.  As a result, two similarly situated taxpayers get treated differently.  One gets penalized and the other does not.  It is an understandable result, but not a sensible one.  To me, it shows the incoherence of the statute.

In Andrew Mitchell Berry and Sara Berry v. Commissioner, T.C. Memo, 2021-42 (Apr. 7, 2021), Judge Marvell holds that a §6662(b)(2) understatement penalty is invalid without proper supervisory approval when proposed as a matter of routine in a 30-day letter issued by a Revenue Agent.  In contrast, Anna Elise Walton v. Commissioner, T.C. Memo. 2021-40 (Mar. 30, 2021) (Judge Urda) explains why supervisory approval is not required for the very same penalty if it is first proposed in a computer-generated CP2000 notice, issued without any human involvement.  Both the 30-day letter and the CP2000 notice serve the same function, to encourage the taxpayer to engage with the IRS to ensure the accuracy of their returns.  Yet the penalty proposed in one requires 2 humans to approve and the penalty proposed in the other requires no human approval.

These cases are straightforward applications of the statute.  They are unremarkable in their conclusions that human-proposed penalties need human review but computer-proposed penalties do not.  That is what the statute indeed says.  However, what makes them worth your time is that they demonstrate the strange interaction of penalty statutes and tax administration.  Here we have two equally culpable (or innocent, take your pick!) taxpayers, but only one gets hit with the same mechanically-computed penalty and that solely because of the difference in how the penalties are first proposed.  The difference is between what is routine and what is automatic.  It’s a difference created by how the IRS operates, the language of the statute, and the Tax Court’s interpretation of that statute.  And it’s a difference that makes little sense, at least to me.   I think there is a better distinction to be made.

If you are already a tax penalty jock and know how incoherent the system is, you do not need this lesson.  Otherwise, I invite you to dive into the details below the fold. 

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8th Circuit: University Of Iowa Administrators Are Personally Liable For Deregistering Christian Student Group After It Denied Leadership Role To Gay Student

Following up on my previous posts (links below):  Inside Higher Ed, Appeals Court Says Iowa Administrators Are Personally Liable in Lawsuit Brought by Christian Student Group:

A federal appeals court ruled Monday that University of Iowa administrators can be held personally liable and sued for damages due to their actions deregistering a Christian student group that denied a leadership position to a gay student. [Business Leaders in Christ v. University of Iowa, No. 19-1696 (8th Cir. Mar. 22, 2021)].

The case involves a student group called Business Leaders in Christ, whose members believe that same-sex relationships are “outside of God’s design.” After the group denied an executive leadership position to a gay student in 2017 on the stated grounds that the student “disagreed with, and would not agree to live by [BLinC’s] religious beliefs,” the university began a process that ultimately led to the revocation of the group’s status.

BLinC sued and, in a 2019 decision that alarmed advocates for LGBTQ+ students, a district court judge held that the university selectively enforced its Human Rights Policy and violated BLinC members’ constitutional rights to free speech, free association and free exercise of religion. The university did not appeal the judge's holding that it infringed on the BLinC members' First Amendment rights.

Rather, at issue in the appeal was whether the three individual Iowa administrators named as defendants could be personally liable and sued for damages, or whether they are shielded by qualified immunity, a legal doctrine that grants government officials immunity from civil lawsuits except in cases where their conduct violates “clearly established statutory or constitutional rights of which a reasonable person would have known.”

In a decision that hinged on an assessment of whether the rights at issue were “clearly established,” the U.S. Court of Appeals for the Eighth Circuit partially reversed the ruling of the district court, which had granted the administrators qualified immunity [Business Leaders in Christ v. University of Iowa, No. 19-1696 (8th Cir. Mar. 22, 2021)]. The appeals court held that the administrators can be held personally liable in relation to the students’ free expression and expressive association claims, but not in relation to claims related to free exercise of religion.

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Eleven Tax Profs File Amicus Briefs In Supreme Court Supporting Disclosure Of Donors To Nonprofits

Americans for Prosperity Foundation v. Rodriquez (No. 19-251), decision below:  903 F.3d 1000 (9th Cir. 2018)

Question Presented
Whether the exacting scrutiny this Court has long required of laws that abridge the freedoms of speech and association outside the election context—as called for by NAACP v. Alabama ex rel. Patterson, 357 U.S. 449 (1958), and its progeny—can be satisfied absent any showing that a blanket governmental demand for the individual identities and addresses of major donors to private nonprofit organizations is narrowly tailored to an asserted law-enforcement interest.

Brief of the California Association of Nonprofits as Amicus Curiae in Support of Respondent (Daniel Hemel (Chicago) & Anna-Rose Mathieson (California Appellate Law Group, San Francisco)):

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Lesson From The Tax Court: Passport Revocation Act Differs From Codification

Justice John Marshall is typically credited as creating the idea that the judicial branch has the power to declare Acts of Congress unconstitutional.  See Marbury v. Madison, 5 U.S. 137 (1803).  But courts exercise that power cautiously, refusing to confront allegations of unconstitutionality if they can plausibly dodge the issue. See generally, Gunnar P. Seaquist, The Constitutional Avoidance Canon of Statutory Construction, The Advocate 25 (Summer 2015).

Robert Rowen v. Commissioner, 156 T.C. No. 8 (Mar. 30, 2021) (Judge Toro), shows us the caution of the Tax Court.  There, the taxpayer invited the Court to declare the passport revocation process, created by Congress in the FAST Act of 2015, unconstitutional.  The Court unanimously dodged the invitation, based on the taxpayer’s failure to distinguish between an Act of Congress and the codification of an Act.  The Tax Court viewed the only part of the FAST Act at issue to be the part codified in the Internal Revenue Code in §7345.  It held that since §7345 does not, on its own, trigger any deprivation of property or liberty, this was not the proper case for the Court to rule on the constitutionality of the entire passport revocation process.  I invite readers to form their own conclusions about the plausibility of the Court’s dodge.  Details below the fold.

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Lesson From The Tax Court: Failing Business No Reason To Stop Collection In CDP Hearing

Collection Due Process (CDP) is designed to protect taxpayers from abusive collection actions by the IRS.  American Limousines, Inc. v. Commissioner, T.C. Memo. 2121-36 (Mar. 25, 2021) (Judge Halpern), teaches that CDP does not require the IRS to stop trying to collect from a business just because the business was failing.  There the taxpayer owed over $1.1 million in employment taxes.  The Office of Appeals rejected both the taxpayer’s installment payment offer of $2,000 per month, and its alternative proposal to be placed in CNC.  The taxpayer said that the Office of Appeals should have put it into CNC to allow its business to improve.  The Tax Court upheld the Appeals determination, finding that Appeals satisfactorily balanced the need for collection against the difficulties enforced collection would create for the taxpayer.  Details below the fold.

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Lesson From The Tax Court: S Corp Payments To Sole Shareholder Were Wages

I think of corporations as a type of vessel that sails the seas of commerce.  Like real ships, corporations are commanded by officers.  All crew, including officers, are compensated for their services.  At the end of the commercial voyage, however, an end marked either by time or transaction, profits earned are distributed to the owners of the ship.  When the officers are also the owners it becomes difficult to distinguish payments that represent wages for their services in commanding the ship from payments that represent distribution of profits.  Yet for both employment and income tax reasons, such distinction must be made.

In Lateesa Ward and Ward & Ward Company v. Commissioner, T.C. Memo. 2021-32 (Mar. 15, 2021) (Judge Holmes), we learn why payments from the taxpayer’s S corporation to the taxpayer were wages and not distributions of profit.  The case teaches a basic employment tax lesson for S Corps and a basic income tax lesson for sole shareholders.  Details below the fold.

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D.C. Circuit: Law Prof May Be Entitled To Attorney's Fees Due To Her 'Serious Scholarly Interest' After Beating IRS In FOIA Litigation

Kwoka v. IRS, No. 19-5310 (D.C. Cir. Mar. 9, 2021):

This case presents a recurring question in our court: under what circumstances is a prevailing plaintiff in a Freedom of Information Act (FOIA) case—here a law professor [Margaret Kwoka (Denver)] seeking information from the Internal Revenue Service—entitled to an award of attorney’s fees? The district court denied the professor’s request for fees. For the reasons set forth below, we vacate and remand for further proceedings consistent with this opinion. ...

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Lesson From The Tax Court: The Presumption Of Regularity For NODs

Tax protestors are the cowbirds of the tax ecosystem, forcing the employment of resources that could be put to more productive use.  Nonetheless, tax protestors sometimes provide a service: they help us revisit basic lessons about tax and tax administration.  Today’s lesson is one such basic lesson: about the presumption of regularity.

The presumption of regularity is a broad doctrine that courts use when faced with disputes about the legitimacy of federal agency actions. In Brian E. Harriss v. Commissioner, T.C. Memo. 2021-31 (Mar. 11, 2021) (Judge Thornton), the taxpayer argued that a Notice of Deficiency (NOD) issued to him was invalid because the IRS employee who signed it was not authorized to sign it.  In rejecting the argument, Judge Thornton teaches a useful basic lesson in how the presumption of regularity applies to NODs.  Details below the fold.

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WSJ: He Got $300,000 From Credit-Card Rewards. The IRS Said It Was Taxable Income.

Wall Street Journal, He Got $300,000 From Credit-Card Rewards. The IRS Said It Was Taxable Income.:

Konstantin Anikeev, an experimental physicist, assembled everything he needed for an inquiry far outside his field.

His materials included American Express cards, the government’s view that credit-card rewards aren’t income, and his own willingness to spend time buying gift cards and money orders. He pulled the concept from personal-finance websites: Exploit the difference between unlimited 5% rewards and lower fees on gift cards and money orders. ...

It (mostly) worked.

Mr. Anikeev’s financial-optimization plan in 2013 and 2014—including $6.4 million in credit-card charges—led to an Internal Revenue Service audit and a finding that he and his wife had more than $310,000 in income that should have been taxed.

Judge Robert Goeke’s decision last month largely affirmed longstanding Internal Revenue Service practice, which says credit-card rewards are usually nontaxable rebates [Anikeev v. Commissioner, T.C. Memo. 2021-23 (Feb. 23, 2021)]. In other words, buying a pair of shoes for $100 and getting a 5% reward is really a $95 purchase, not $5 of income. But the judge also offered the IRS avenues for tougher enforcement. ...

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Lesson From The Tax Court: New 'Consequential Moment' Rule For §6751 Supervisory Approval

Section 6751(b)(1) causes no end of interpretive trouble for the Tax Court, no end of administrative difficulties for the IRS, and no end of windfalls for those lucky taxpayers who get to avoid penalties because the Tax Court later decides the IRS committed procedural errors.

In Brian D. Beland and Denae A. Beland v. Commissioner, 156 T.C. No. 5 (Mar. 1, 2021) (Judge Greaves), the Court has once again changed how it interprets §6751(b)(1).  It now says written supervisory approval must be made before an ill-defined “consequential moment.”  Here, that moment came when the Revenue Agent (RA) and her immediate supervisor met in person with the taxpayers to discuss a proposed Revenue Agent Report (RAR).  Contained in the RAR was a proposed fraud penalty.  But the supervisor—sitting next to the RA—had not given written approval for the fraud penalty before the meeting.  Too late!  The lucky taxpayer was thus able to avoid contesting the merits of a fraud penalty.  There is also a lesson here about administrative summonses, but may be more a lesson for the Tax Court than from the Tax Court because this opinion appears to rest, in part, on a misunderstanding of summons law.  Details below the fold.

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Lesson From The Tax Court: No Second Bite In CDP For Rejected OIC

One overarching theme of my Tax Procedure course is that tax collection is a process, not an event.  Many events occur during the time between assessment of a liability and the collection of that liability, and it is easy to fixate on them in isolation, forgetting their place in the process.  One important event can be a Collection Due Process hearing and subsequent appeal to Tax Court.  Since I started writing these posts (back in September 2017) we’ve learned a lot of lessons from the Tax Court about the shape and scope of CDP.  In Craig L. Galloway v. Commissioner, T.C. Memo. 2021-24 (Feb. 24, 2021) (Judge Urda), we learn that what a taxpayer can do in a CDP hearing may be limited by earlier events in the collection process.  Details below the fold.

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Lesson From The Tax Court: The Fearsome Scope Of Evil §280E

When Congress creates a tax benefit, it often qualifies that benefit.  Many time Congress does that in the very provision granting the benefit.  For example, the exclusion for employee fringe benefits in §132 contains many qualifiers, such as a non-discrimination requirement for several of the benefits. Other times, however, Congress writes a completely different statute to qualify a benefit.  You find many of these statutes gathered in Chapter 1 (“Normal Taxes), Subchapter B (“Computation of Taxable Income”), Part IX (“Items Not Deductible”), starting with §261.  Just when a taxpayer gets all happy by being allowed a deduction by some statute, one of these swoops in to deny or qualify the deduction.  So I call these the “evil 200’s.”

Section 280E creates a draconian qualification for businesses engaged in the trafficking of substances that are illegal under federal law.  Because marijuana is still illegal under federal law, that has caused no end of tax headaches for businesses that are perfectly legal under state law.  Those businesses keep attacking the scope of §280E, with decidedly mixed results.

In San Jose Wellness v. Commissioner, 156 T.C. No. 4 (Feb. 17, 2021) (Judge Toro) the Tax Court interpreted §280E broadly to prohibit deductions for depreciation and for charitable contributions.  While one might read the opinion as saying that §280E prohibits deductions for all expenditures made by a marijuana business, regardless of that expenditure’s relationship to the operation of the business, I do not think it actually goes that far.  At least I hope not.  Details below the fold.

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Lesson From The Tax Court: The §104(a)(2) Causality Rule

Two years ago on Valentine’s Day I was rear-ended.  The accident was, literally, a pain in the neck but the injury was relatively minor.  The insurance company fixed my car and also sent me a $2,800 settlement check.  Section 104(a)(2) permits me to exclude all of that $2,800 because of what I call the causality rule: taxpayers can exclude from income any amounts received “on account of” a personal physical injury.

We learn a good lesson about the causality rule in Timothy Stassi and Cindi Stassi v. Commissioner, T.C. Summ. Op. 2021-5 (Feb. 7, 2021) (Judge Kerrigan).  There, Ms. Stassi had sued her former employer.  They settled.  Part of the settlement check was to compensate her for having suffered through an unpleasant work environment, which (generously interpreted) caused a painful outbreak of shingles.  Both the IRS and the Tax Court said the payments were not “on account of” her physical injuries within the meaning of §104(a)(2).  Thus, Ms. Stassi could not exclude any part of the settlement check.

In this post I also want to draw readers’ attention to certain language in Judge Kerrigan’s opinion.  Yes, it is just a summary opinion and so carries no precedential weight, but if the opinion truly reflects Judge Kerrigan’s view of how the §104(a)(2) exclusion works, then it may signal a change in the law. Detail below the fold. 

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Lesson From The Tax Court: When A Hotel Becomes A Tax Home

The concept of “tax home” is central to the §162 deduction for business travel.  Akeem Adebayo Soboyede v. Commissioner, T.C. Summ. Op. 2021-3 (Jan. 26, 2021) (Judge Greaves) teaches us that a tax home is not where a taxpayer actually has a home, but is rather where the taxpayer ought to have a home.  In this case, the taxpayer performed legal services in Minnesota and in the Washington D.C. area.  The taxpayer’s principal residence was in Minnesota.  When in D.C., he mostly stayed in a suburban hotel.  The IRS and Tax Court decided that the taxpayer ought to have lived in the D.C. area because that is where he made most of his money and spent most of his work time.  It was thus his tax home for §162 purposes.  Part of this lesson is thus learning how to work deductions for business travel when a taxpayer’s primary residence is in their secondary work location.  Details below the fold. 

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Lesson From The Tax Court: No Product? No §162 Deduction!

Section 162 has simple language.  It permits deduction for all “the ordinary and necessary expenses paid or incurred in carrying on a trade or business.”  The simplicity is deceptive.  All the terms need further interpretation.  In William Bruce Costello and Martiza Legarcie v. Commissioner, T.C. Memo. 2021-9 (Jan. 25, 2021) Judge Halpern teaches us one interpretation of “carrying on a trade or business”: you need a product.  In this case the taxpayers owned land on which they sequentially tried raising chickens, crops, and beef.  None of the efforts resulted in salable product.  The Tax Court agreed with the IRS that these activities did not amount to carrying on a discernible business because the taxpayers never sold anything.  The Court thus denied deductions for the costs associated with the activities.

The need for product is key.  Other Tax Court cases teach us that a taxpayer does not actually have to sell product to be carrying on a business, but still needs to have product.  No product, no §162 deduction.  No kidding.  Details below the fold.

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Lesson From The Tax Court: No Deduction For Disguised Dividends

A lesson that comes up often in my tax class is how economic substance trumps transactional form.  One common example is when a corporate taxpayer seeks to deduct payments that seem to be compensation payments.  Sometimes, however, not all is what it seems and the corporation is really distributing corporate profits rather than incurring a corporate expense.

In last week’s case of Aspro, Inc. v. Commissioner, T.C. Memo. 2021-8 (Jan. 21, 2021), Judge Pugh’s clear and crisp opinion teaches us how the Court decides whether compensation payments are really disguised dividends, a lesson we can use to help clients avoid the mess that this taxpayer got into.

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Lesson From The Tax Court: The CDP Silver Linings Playbook

Tax practitioners tend not to know much about bankruptcy.  Today’s lesson is for them.  In Wiley Ramey v. Commissioner, 156 T.C. No. 1 (Jan. 14, 2021), Judge Toro held that a CDP notice properly sent to a taxpayer’s last known address triggers the time period for the taxpayer to request a CDP hearing, even if the CDP notice is actually delivered to a different person who shares that address.  That is the tax lesson most folks will see in this case, and it’s a good one.

I see an additional lesson, a bankruptcy lesson.  While the taxpayer’s failure to timely request a CDP hearing meant no he received no Tax Court review of the administrative hearing, the news is not all bad.  The lesson for today is about silver linings:  the taxpayer’s equivalent hearing still got the delay benefits of CDP, and that delay did not count against Mr. Ramey should he file bankruptcy and seek a discharge of the tax liabilities at issue.  Practitioners would not be crazy to put this lesson in a Playbook, a CDP Silver Linings Playbook.  Yeah, it was a good movie, too.  More below the fold.

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Lesson From The Tax Court: Too Much Control Over IRA Distribution Makes It Income

Note: The Tax Court has migrated to a different operational internet platform.  As of last Friday, any opinions (if any) issued by  the Court since it closed its old platform in late November, are not accessible.  Further, older opinions are also not accessible, unless another website (such as leagle.com or casetext.com) captured a copy before the old platform closed.  That is why I am unable to provide a link to this week's case.  If any reader has public link to the opinion I would be grateful.

A fundamental concept I teach my tax students is the idea of control.  Taxpayers who engage in schemes where they ostensibly never touch a payment but in reality control its disposition often cannot escape taxation.  In Brett John Ball v. Commissioner, T.C. Memo. 2020-152 (Nov. 10, 2020) (Judge Halpern), the taxpayer caused his self-directed IRA to distribute money to a wholly owned LLC, then caused the LLC to issue short-term loans to real estate entities.  When the loans were repaid, Mr. Ball re-deposited the money into the IRA.  The taxpayer had some decent arguments on why he should not have to report the IRA distributions as income.  Judge Halpern rejected those arguments, teaching us a lesson about how much control is too much control.

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A Year Of Lessons From The Tax Court (2020)

• Jan. 6:  Taxpayer Who Got $1.6m Assessment Reduced To $170k Not Entitled To Costs (Klopfenstein v. Commissioner, T.C. Memo. 2019-156 (Dec. 9, 2019) (Judge Lauber) — § 7430)
• Jan. 13:  A Practical Interpretation Of The Penalty Approval Statute § 6751 (Belair Woods LLC v. Commissioner, 154 T.C. No. 1 (Jan. 6, 2020) (Judge Lauber); Tribune Media Co. v. Commissioner, T.C. Memo. 2020-2 (Jan. 6, 2020) (Judge Buch) — § 6751)
• Jan. 20:  Employee Cannot Deduct Expense That Could Have Been Reimbursed (Near v. Commissioner, T.C. Memo. 2020-10 (Jan. 14, 2020) (Judge Kerrigan) — § 162)
• Jan. 27: §6672 Trust Fund Recovery Penalty Is Really A Penalty ... Sort Of (Chadwick v. Commissioner, 154 T.C. No 5 (Jan. 21, 2020) (Judge Lauber) — § 6672)

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Lesson From The Tax Court: Taxpayers Behaving Badly (2020)

This will be my last post until January.  I will be spending my days (except for Christmas Day) grading exams.  Grades are due Monday, January 4th so you will likely see my next Lesson From The Tax Court on January 11th.

My last blog of the year is a list of some of the cases I read during the year where something in the facts made me just shake my head (SMH in texting parlance).  You can find the previous lists here (for 2018) and here (for 2019).  This year I have five to share with you.  I present them in chronological order.  I invite you to consider which of them may be examples of just an empty head and which are examples of something worse.

New this year is a feature I am calling the Norm Peterson Award.  You will find more explanation below the fold.

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Lesson From The Tax Court: The Right Way To Do Conservation Easements

Over 40 years ago, Congress modified §170 to permit deductions for donations of partial interests in land when such donations advanced an important public purpose such as protecting environmentally or historically important land from development.  Starting in the early 2000’s, however, developers and tax shelter promoters began exploiting conservation easements to provide huge tax deductions for donations that provided little or no conservation benefit.  The problem reached the point that the IRS issued Notice 2017-10 which described certain syndicated conservation easement arrangements and listed them as tax shelter transactions. This informative Senate Finance Committee Report from August 2020 details the abuses.

But not all conservation easements are tax shelters.  Kumar Rajagopalan and Susamma Kumar v. Commissioner, T.C. Memo. 2020-159 (Nov. 19, 2020) (Judge Holmes) shows how taxpayers can properly deduct the donation of a conservation easement if they have good planning, good representation, and good luck.  Details below the fold.

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Lesson From The Tax Court: International Pilot’s Tax Home Argument Does Not Fly

Douglas H. Cutting v. Commissioner, T.C. Memo. 2020-158 (Nov. 19, 2020) (Judge Pugh), teaches a useful lesson about that puzzling concept called “tax home” as it relates to the §911 foreign earned income exclusion.  Taxpayers can claim the §911 exclusion if their tax home is in a foreign country.  Mr. Cutting's wasn’t, even though his personal home — the place he returned to when not flying — was Thailand, where he lived with his wife and step-daughter.  A tax home, however, is not where the heart is.  Details below the fold.

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Lesson From The Tax Court: Taxpayer Wins CDP Case But Cannot Recover Costs

The Tax Code contains a variety of statutes designed to protect taxpayers from unreasonable and arbitrary decisions by the IRS.  I think of them as quality control measures: they require supervisory approval of certain decisions, such as the decision to impose a penalty (§6751) or the decision to open a second examination (§7605(b)).  One can also think of quality control as any procedure that allows a different decision-maker to enter the picture, not just a supervisor.  That was the lesson last week, when the Office of Chief Counsel entered the picture and fixed a problem.

But no matter what quality controls the IRS uses, or what training it gives its employees, final decisions about either the assessment or collection of taxes are sometimes simply not defensible.  Getting such decisions corrected in court costs taxpayer both time and money.  Section 7430 permits such taxpayers to recover the costs they incurred to fix an unreasonable decision.  In that sense, it is another quality control measure.

In Tung Dang and Hieu Pham Dang v. Commissioner, T.C. Memo. 2020-150 (Nov. 9, 2020) Judge Marvel teaches a lesson on the limits a taxpayer’s ability to recover costs under §7430.  There, the Office of Appeals made an indefensible decision about the collection of the Dangs’ unpaid taxes and the IRS conceded the case in Tax Court.  Nonetheless, the Dangs were not eligible to recover the costs they incurred in fixing that unreasonable CDP decision.  Details below the fold.

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Lesson From The Tax Court: How To Beat The Bureaucracy

My friends joke that my time as an attorney in the IRS Office of Chief Counsel was spent in the belly of the Beast.  I’m not a fan of that analogy because it implies the IRS is a single entity.  As regular readers of this blog (if any exist) know, I regularly argue against that view.  The best way to think of the IRS---both in theory and practice---is that it is a collection of different offices (or functions) each of which has certain defined authorities.  Folks, it’s a bureaucracy, not a beast.

Today’s case, Colleen Michelle Leith, Petitioner, and Oraine J. Leith, Intervenor v. Commissioner, T.C. Memo. 2020-149 (Nov. 4, 2020) (Judge Vasquez), teaches a great lesson on how getting to a different bureaucratic decision-maker can turn defeat into victory.  There, the taxpayer sought spousal relief and lost in the IRS.  Although the Tax Court decision is in her favor, she really won the case in the Office of Chief Counsel.  Details below the fold. 

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Lesson From The Tax Court: To Get Administrative Grace You Must Follow Administrative Rules

Today’s lesson is about timing, and the concept of administrative grace. Section 165 permits taxpayers to deduct losses from theft and §165(e) provides the timing rule: the loss “shall be treated as sustained during the taxable year in which the taxpayer discovers such loss.”

Rev. Proc. 2009-20 gives taxpayers who seek to deduct losses from certain Ponzi-type schemes some very generous safe harbors that relieve them of difficult substantiation requirements. But taxpayers seeking such shelter must navigate the specific procedural rules outlined in the Rev. Proc. One procedural rule is a bright-line timing rule about the year in which taxpayers could take the loss deduction. Taxpayers who do not use the Rev. Proc. are subject to the normal burdens of proving up the amount and timing of their theft losses.

In a consolidated case, Michael C. Giambrone et al v. Commissioner, T.C. Memo. 2020-145 (Oct. 19, 2020) (Judge Lauber), the taxpayers did not follow the Rev. Proc. 2009-20’s timing rule, but argued they should still get the relief given by the Rev. Proc. because their timing was consistent with the statutory timing requirement. Judge Lauber said no. Details below the fold.

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Lesson From The Tax Court: Losing Gambler Gets Twice Lucky In Tax Court

Taxpayers rarely walk away from casinos richer than when they entered.  The odds are not in their favor.  If a slot machine pays out $1,200 or more, however, the casino will still report that win on a W-2G, even if the taxpayer loses all of it before leaving the casino.  The theory is that $1,200 is income to the taxpayer and the taxpayer’s choice to use it for more gambling is no different than the taxpayer’s choice to use that $1,200 for other consumption.

The IRS recognizes that the reality is different from theory and so it permits taxpayers to net their gambling gains and gambling losses for each visit to---or session at---a casino.  In the unlikely event they leave the casino a net winner, those wagering gains are gross income which must be reported.  If they leave a net loser, they may be able to deduct those wagering losses against wagering gains up to the amount of wagering gains.  Tax Court precedents uphold this per-session method of accounting for gambling gains and losses.  In addition, plenty of precedent requires taxpayers to substantiate their wagering losses for each session.

In John M. Coleman v. Commissioner, T.C. Memo. 2020-146 (Oct. 22, 2020), Judge Lauber bucked both sets of precedents to allow the taxpayer a gambling loss deduction equal to over $350,000 of gambling wins reported on various W-2Gs.  There are good reasons for why Judge Lauber did this, but the bottom line is that this taxpayer got twice lucky.  It helped that he was represented pro bono by two high-powered tax attorneys from Morgan Lewis.  Let's look at what we can learn from them and from this case.  Details below the fold.

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Lesson From The Tax Court: §6662 Penalties Treated As One For Supervisory Approval Requirement

Last week, the Tax Court issued an important opinion on the §6751(b)(1) supervisory review requirements.  In Jesus R. Oropeza v. Commissioner, 155 T.C. No. 9 (Oct. 13, 2020) (Judge Lauber), held that the 20% penalty under §6662(b)(6) is the same as the 40% penalty under §6662(i) and therefore the failure to secure proper approval for assertion of the former in an RAR precludes assertion of the latter in a later NOD.  The latter subsection simply “enhances” the amount of §6662(b)(6) penalty and does not impose a separate penalty.

The path of the law is not linear. Doctrinal development sometimes involves two steps forward, one step backwards, and maybe even a step or two sideways.  In Oropeza the Tax Court took what some may view as a step sideways, and what the government will likely view as a step backwards.  The decision seems in tension with prior Tax Court opinions that treat §6662 as containing multiple penalties for supervisory approval purposes, including an opinion by the same judge about the same taxpayer!  The upshot of today’s opinion is that practitioners need to read NODs very carefully. Details below the fold.

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Lesson From The Tax Court: The Slippery Slope Of Tax Court Review

Today’s post is about how the Tax Court reviews decisions of the IRS Whistleblower Office (WBO).  If you want to report a tax cheat, you have a variety of choices, detailed in this IRS webpage.  Typically, you write a letter or submit a Form 3439-A.  But if you want to also claim an award for blowing the whistle, you must submit a Form 211 with the IRS Whistleblower Office (WBO).  That is because the WBO is the office in the IRS that decides whether the information you gave resulted in additional collections of tax.  If it did, you get a cut.  If you don’t like the amount of the award, you can ask the Tax Court to review the WBO’s decision on the amount.

When the WBO decides that you are entitled to no award, however, it could be for a variety of reasons, only some of which are reviewable by the Tax Court.  In John Worthington v. Commissioner, T.C. Memo 2020-141 (Oct. 8, 2020) Judge Gustafson teaches the difference between those decisions the Tax Court will review and those it will not; it turns on the difference between the words “rejection” and “denial.”  To me, this case represents a wobbly first step onto a slippery slope towards reviewing IRS audit decisions.  That is not what WBO review used to cover but times, they may be a-changing!  Details below the fold.

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2d Circuit: Manhattan DA Can Obtain Trump's Tax Returns

New York Times, The Manhattan D.A. Can Obtain Trump’s Tax Returns, an Appeals Panel Rules:

The Manhattan district attorney can enforce a subpoena seeking President Trump’s personal and corporate tax returns, a federal appeals panel ruled on Wednesday, dealing yet another blow to the president’s yearlong battle to deny prosecutors his financial records Trump v. Vance, No. 20-2766 (2d Cir. Oct. 7, 2020)

The unanimous ruling by a three-judge panel in New York rejected the president’s arguments that the subpoena should be blocked because it was too broad and amounted to political harassment from the Manhattan district attorney, Cyrus R. Vance Jr., a Democrat. ...

Mr. Trump is expected to try to appeal the decision in the United States Supreme Court.

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Lesson From The Tax Court: Why Vacation Home Losses Are Difficult To Deduct

Tax shelters come in many forms.  Some shelters are activities that have no genuine economic purpose; they exist simply to generate tax benefits.  Some micro-captive insurance arrangements are a great example, as you can learn from this wonderful brief by former tax officials filed recently in a Supreme Court case (I blogged about the case here).  Other shelters are activities that allow taxpayers to deduct otherwise non-deductible personal expenses.

Today’s case involves that second kind of tax shelter.  Taxpayers who own vacation properties can generate deductions for maintenance, utilities, and depreciation by renting out the properties even while also using the properties for personal pleasure.  Thus, the rental activity can help ameliorate the personal costs of ownership by turning otherwise personal costs into rental costs.  And if the rental costs exceed the rental income, why then taxpayers have a loss and many taxpayers will try to use that loss to shelter non-rental income.

In Ronald J. Lucero and Mary L. Lucero v. Commissioner, T.C. Memo. 2020-136 (Sept. 29, 2020) Judge Pugh teaches a great lesson about the limits of using beach houses as tax shelters.  The taxpayers owned a beach house in Sea Ranch, California and rented it out.  They had net losses.  The Court did not allow them to deduct those losses to shelter non-rental income, even though their personal use was only about one week each year.  It’s a nice lesson on how the restrictions on deductions in §280A and §469 work.  Details below the fold.

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The Supreme Court’s 2019 Term In Tax

Jasper L. Cummings, Jr. (Alston & Bird, Raleigh, NC), The Supreme Court’s 2019 Term in Tax, 168 Tax Notes Fed. 2175 (Sept. 21, 2020):

In this ninth annual review of Supreme Court opinions involving tax matters, Cummings notes that the Court has mostly abandoned standard legal decisions to focus on political themes, which he identifies in several decisions. ...

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Lesson From The Tax Court: State Law Matters

My wife has spent her COVID time organizing efforts to celebrate Earth Day next April in our fair city of Lubbock, Texas.  Her efforts are paying off.  She and her colleagues are now to the point where they need to operate through a tax-exempt entity.  Well-meaning friends tell her “oh, it’s easy, just go fill out some forms and submit them to the IRS.”  Those friends think that forming a nonprofit entity is a one-step process, done at the federal level.  They do not realize that it is a two-step process: one must first form the entity under state law and then ask for tax-exemption from the IRS.  Today we learn that the choice of entity formation will affect the federal tax treatment of that entity.

In Clinton Deckard v. Commissioner, 155 T.C. No. 8 (Sept. 17, 2020) (Judge Thornton), the effect of state law was to preclude the taxpayer from electing S Corporation status.  There Mr. Deckard formed a nonprofit corporation under Kentucky law but soon started operating it for profit.  After a couple of years of losses, he tried to elect S Corporation status for the entity so he could pass through and deduct those losses.  Judge Thornton held he was bound to the corporate form he had created under Kentucky law.  State law matters.  Details below the fold. 

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Lesson From The Tax Court: Receipts Are Not Enough

In Anna M. Armstrong v. Commissioner, T.C. Sum. Op. 2020-26 (Sept. 17, 2020), Judge Panuthos teaches that substantiation does not just mean showing the amount of an expense; it means showing entitlement to deduct that expense.  It's an exemplary lesson in substantiation, including a review of the Cohan doctrine, and of the home office deduction.  Along the way, we learn just how tax practitioners can give value to their clients: teach them that receipts are not enough.

At first glance, this case might seem unimportant because it concerns below-the-line miscellaneous itemized deductions for unreimbursed employee expenses.  Section 67(g) totally disallows those types of deductions for tax years 2018-2025.

But I think this opinion is worth your time.

First, COVID.  Congress might actually re-authorize the deduction of unreimbursed employee expenses for tax year 2020 as part of the next COVID relief bill.  I do not have any inside knowledge on this, but some in Congress might view reviving unreimbursed employee expense deductions as a benefit to taxpayers forced to work from home during COVID shutdowns.  Others might believe that Congress gave enough relief in the Economic Impact Payments.  And this tax benefit is one that invites conflict and, hence, litigation.  Regardless of what Congress does, those taxpayers who are independent contractors continue to qualify for a home office deduction and this opinion teaches how to substantiate that use.  I give a couple of COVID thoughts at the end of the post.

Second, Judge Panuthos gives a wonderfully compact, lucid explanation of what taxpayers and their representatives need to know about substantiation.  I repeatedly tell my students that when you want to understand the law, find a good trial court opinion that explains it.  This is one of those opinions.  It’s a great teaching case.

Finally, some readers might find current utility from these lessons because 2017 and possibly 2016 are still open years.  Besides, taxpayers frequently stumble over the substantiation rules, especially for establishing a home office, whether or not they are taking deductions above or below the line.  For all those reasons I invite you to continue reading....

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Tax Profs On Both Sides In Case Pending in Supreme Court: CIC Services v. IRS

Currently before the Supreme Court is a case called CIC Services v. IRS. It involves the question of whether §7421 — Commonly called the Anti-Injunction Act (“AIA”) — prevents CIC from suing the IRS over the propriety of Notice 2016-66. That Notice declares certain micro-captive insurance arrangements as “transactions of interest.” It triggers certain reporting requirements for both CIC (as a material advisor) and CIC clients who have engaged in the arrangements described in the Notice. CIC asserts the Notice was illegally issued.

CIC (and another entity who has since dropped out) sued in federal district court, asking the court to (1) declare Notice 2016-66 invalid and (2) permanently enjoin the Service from enforcing the Notice. The district court dismissed the suit as barred by both the AIA and the Declaratory Judgment Act (DJA), 28 U.S.C. §2201(a). The AIA says that “no suit for the purpose of restraining the assessment or collection of any tax shall be maintained in any court by any person, whether or not such person is the person against whom such tax was assessed.” The DJA permits suits for declaratory judgements except for suits “with respect to Federal taxes....”

A split Sixth Circuit panel affirmed. A closely divided Sixth Circuit then denied CIC’s petition for rehearing en banc. How closely divided? Six judges thought the rehearing petition should be denied. Six dissenting judges thought it should be granted. One judge said he thought the dissenters had the better of the argument but he was going to vote to deny because of circuit precedent. He expressed the hope that the Supreme Court would take the case. And, guess what? The Supreme Court took the case.

A summary of the Parties' argument and the Tax Prof briefs comes below the fold

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Lesson From The Tax Court: Rejected e-Filed Return Starts The SOL On Assessment

Perspective is important.  As we regularly see in politics and protests, different groups have different points of view.  In tax law, disputes between taxpayers and the IRS quite often stem from different perspectives on the law.  Courts are called upon to adopt one or the other perspective in resolving the dispute.

In Robin J. Fowler v. Commissioner, 155 T.C. No. 7 (Sept. 9, 2020), Judge Greaves adopts a strongly taxpayer perspective of the law.  He holds that even though the IRS rejected an e-filed return the return still triggered the 3-year limitation period on assessment.  This elevates the taxpayer perspective on the importance of the limitation period over the IRS perspective on the importance of being able to process a return.

The decision may be a consequential one, both for taxpayers and the IRS.  And not just because it's a fully reviewed opinion — a "we really mean it" opinion.  It may be consequential because of its ripple effects.  For example, will taxpayers whose e-filed returns are rejected now escape a late filing penalty if they either fail to resubmit or resubmit much later?  Further, both the IRS and taxpayers will now need to figure out whether the Court’s opinion applies to all e-file rejections or just certain ones and, if so, which ones.  Hello litigation.

If the IRS appeals the decision, a reviewing court may well take the IRS perspective.  After all, the Supreme Court has said, more than once, that “limitations statutes barring the collection of taxes otherwise due and unpaid are strictly construed in favor of the Government.” Bufferd v. Commissioner, 506 U.S. 523, 528 (1993).  That perspective, however, raises its own set of problems.  More on that below the fold.

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Lesson From The Tax Court: Form Over Substance Gives Taxpayers A Double Tax Benefit

Today’s lesson is about form and substance.  Tax practitioners are often called upon to decide what transactional form best accomplishes a client’s substantive purpose.  The power to choose the form of transactions sometimes creates a tension with the underlying economic substance when taxpayers and their advisors use form to disguise substance in the never-ending quest to gain tax benefits.  Courts and the IRS regularly police transactions using various doctrines to decide when form must yield to substance (e.g. step transaction doctrine, economic benefit doctrine).   When form is too much in tension with substance, substance wins.  Congress has attempted to codify this idea in §7701(o).

Today's lesson illustrates where tax law permits form to triumph over substance.  In Jon Dickinson and Helen Dickinson v. Commissioner, T.C. Memo. 2020-128 (Sept. 3, 2020)(Judge Greaves) the taxpayers were able to obtain the double tax benefit of donating appreciated shares of stock to charity by being very careful with the form of the donation.  Congress explicitly permits the form of a transaction to govern the tax result in charitable stock donation.  The tricky part of this case was that the taxpayers were donating shares of a closely held corporation.  And that implicates the assignment of income doctrine, one of those substance-over-form doctrines that courts use.  To see how Judge Greaves resolves the tension in favor of the taxpayer, see below the fold.

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Lesson From The Tax Court: Audit Reconsideration Is Not CDP

I cannot say it often enough: the IRS is not an entity.  It’s a collection of functions that, taken together, administer the internal revenue laws written by Congress.  So when someone says “the IRS did this” or “the IRS did that” they really mean that an action was taken by a discrete function, office, or employee within the organization we call the IRS.

Today we learn why taxpayers (and their representatives) need to understand how IRS functions relate to one another.   The taxpayer in Duy Duc Nguyen v. Commissioner, T.C. Memo. 2020-97 (June 30, 2020) (Judge Pugh) thought he was dealing with “the IRS” but he was really dealing with two separate functions: Exam and Appeals.  Because the information he supplied to Exam was not also supplied to Appeals, he was unable to contest the merits of an assessment in his CDP hearing.  Details below the fold.

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Arizona Supreme Court Agrees With Tax Prof Amicus Brief: Invest in Education's Ballot Initiative Summary Is Accurate

Lily Batchelder (NYU), Jeremy Bearer-Friend (George Washington), John R. Brooks (Georgetown), Paul Caron (Dean, Pepperdine), Adam Chodorow (Arizona State), Steven Dean (Brooklyn), David Gamage (Indiana), Jacob Goldin (Stanford), Hayes Holderness (Richmond), Ariel Jurow Kleiman (San Diego),  Richard Pomp (Connecticut), Erin Scharff (Arizona State), Darien Shanske (UC-Davis), Daniel Shaviro (NYU), Jay Soled (Rutgers), Kathleen DeLaney Thomas (North Carolina) & Vanessa Williamson (Brookings Institution), Amicus Brief of Tax Scholars in Support of Appellants:

It is hard to describe tax law succinctly. The federal Internal Revenue Code is over 6,000 pages and contains over 4 million words. As scholars who write about taxation, we are well aware of this challenge. Nevertheless, the 100-word summary that appeared on Invest in Education’s petitions accurately describes its proposed change to Arizona tax law.

Arizona's Invest in Education initiative would establish a new, separate surcharge of 3.5% on taxable income above certain threshold amounts. This new surcharge shall be imposed “[i]n addition to any other tax imposed by this chapter” and, it will be “collected regardless of whether the income tax rate brackets in this chapter are changed, replaced or eliminated by an act of the legislature.”

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