Lesson From The Tax Court: Substantiating Gambling Losses On Per-Casino Basis

The old saying “you win some, you lose some” is not true for most recreational gamblers.  For them, the saying is more like “you win some, you lose more.”  But proving that proves a problem.  In Jacob Bright v. Commissioner, Docket No. 10095-22 (May 4, 2023), Judge Buch teaches us how taxpayers can use their player cards to substantiate their wagering losses.  There, Mr. Bright reported some $241,000 of wagering gains on his 2019 return, and an equal amount of losses.  However, he apparently did not follow best practices—as very nicely explained in this article—of keeping daily contemporaneous records.  When audited, the IRS accepted his self-reported income (natch!) but disallowed all the losses for lack of substantiation (double natch!).

In Tax Court, Judge Buch allowed Mr. Bright to introduce reports of his player card activity, from each of the three Casinos he gambled at in 2019.  That created a sufficient basis for the Court to use the Cohan rule, albeit differently for each Casino.  The Court used this method to estimate $191,000 of losses.  In taking this approach for calculating wagering losses, Judge Buch gives us a new idea of “per session” netting worth considering, not only for proving up wagering losses, but also for calculating wagering gains.  I would call it a “per establishment” approach.  It makes a good bit of sense.  Details below the fold.

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Lesson From The Tax Court: On Time Is Late

In law, even more than in comedy, timing can be critical.  In comedy you just lose a laugh.  In law, you lose a case.  In Roy A. Nutt and Bonnie W. Nutt v. Commissioner, 160 T.C. No. 10 (May 2, 2023) (Judge Buch), we learn why a petition seemingly submitted on time will be rejected as late.  There, the Nutts electronically submitted their Petition to the Tax Court on the last day they could file.  Now we all know you really don't want to ever do that.  But sometimes it just happens.  And the last day to file is just as timely as the first day to file.  The Nutts submitted their Petition at 11:05 p.m.  So they seemed to be on time.

The problem was that they were filing from Alabama (Central Time) and the Tax Court’s Clerk’s office is in Washington D.C. (Eastern Time).  Thus, even though they submitted on time, Judge Buch holds that their Petition was filed late, because 11:05 p.m. in Alabama was five minutes after midnight in Washington D.C.  Thus, sticking to its increasingly archaic view that the timing rules for filing a Petition are jurisdictional, the Tax Court dismissed the Petition.

Note this is another precedential opinion issued in a case with unrepresented taxpayers.  Here, the IRS moved to dismiss and briefed the issue, but there was no responding brief to counter the government’s view.  These pro-se taxpayers probably did not know about all the Tax Court precedent applying equitable principles to rescue seemingly late-filed petitions.  I give a close review of those cases in Bryan Camp, Equitable Doctrines and Jurisdictional Time Periods, Part 2, 159 Tax Notes 1581 (June 11, 2018).

To his great credit, Judge Buch has, in a similar case, asked for amicus briefs on the issue.  I hope the Tax Court there comes to a different conclusion.  It’s always a balancing act: weighing the need for taxpayer access to judicial review with the need to obey statutory limits. Perhaps the Tax Court might reconsider how that balance should work for electronically filed documents.  However, as Professor Book puts it in this post over at Procedurally Taxing, after this case taxpayers now have a steeper hill to climb. You will find the sad details below the fold, along with my modest thoughts on how to strike a better balance. 

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Lesson From The Tax Court: Allocating Between Excludable Child Support and Includable Interest

As inflation rises so does interest in interest.  Certainly when my 1-year CD matures next month I will be looking for a rate better than the 2% rate that seemed so great last year!  If I get a 4.5% I will be happy ... but who knows what my dollars will be worth next year?

And that’s how we typically think of interest: it’s all about inflation, the old idea that “dollars tomorrow will be worth less than dollars today.”  But the concept of “interest” is a bit more nuanced than just being compensation for the diminished value of dollars in the future.  It is also a compensation for risk: the risk that the money will not in fact be repaid—think junk bonds.  And interest also compensates for opportunity costs: a lender is giving up the ability to use (consume or invest) that money now.  In short, interest is compensation for multiple consequences of the use or forbearance of money, similar to how rent is compensation for several different sticks of property rights given up by the lessor.

It is for these reasons that interest has always been taxed as a separate item of income, separate and apart from the underlying loan or deferred payment.  We see that lesson again today in Susan D. Rodgers v. Commissioner, T.C. Memo. 2023-56 (May 9, 2023) (Judge Gale), where the taxpayer received periodic payments from the State of Alabama in 2015 that it had collected from her ex-spouse to satisfy a court judgment for child support arrearages, plus interest.  She treated all the payments as excludable child support despite receiving a 1099-INT from Alabama that treated all the payments as interest on the arrearages.

Thus this case also presents a lesson in allocation.  How should a taxpayer decide how much of a given payment represents taxable interest or non-taxable child support?  And on that issue, dear readers, I think the Tax Court may have been misled by the State of Alabama into ignoring federal law to find that all of each payment was interest.  Details below the fold.

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Lesson From The Tax Court: Exclusion Rules For Disability Payments

A tax break is just another way of saying “government subsidy.”  Most folks do not even think about that when they get a medical bill.  They are generally just upset about the size of the co-pay!  But Congress subsidizes medical care by allowing taxpayers to exclude from income everything the health insurance plans pay the medical providers above the co-pay.

The scope of that subsidy, however, depends on who pays for the insurance in the first place.  If the taxpayer pays for the insurance, the exclusion is governed by §104(a)(3).  That provision does not just exclude payments for actual medical services.  It excludes any and all amounts paid on account of physical injury or sickness.  In contrast, if the taxpayer’s employer pays for the insurance, then the exclusion is governed by §105(b) and that is a more restrictive exclusion.  The §105 exclusion is limited to actual reimbursements (or payments) for identified medical care.

The differences between the §104(a)(3) exclusion and the §105(b) exclusion are most apparent when a taxpayer receives disability payments, as we learn in Cynthia L. Hailstone and John Linford v. Commissioner, T.C. Summ. Op. 2023-17 (Apr. 24, 2023) (Judge Leyden).  There, the taxpayer received disability payments and attempted to exclude those from income.  That might have worked under §104(a)(3) if the taxpayers had paid for the insurance, but since the payments at issue came from an employer-paid plan, the exclusion was not permitted, per §105(b).  Details below the fold.

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Lesson From The Tax Court: Better Deals With Appeals

One recurring lesson I teach in Tax Practice and Procedure is that you generally serve your client better by resolving their issues at the lowest level.  That requires helping them be realistic in understanding the range of potential outcomes.  It requires an understanding that IRS offices, such as the Office of Appeals, generally have more discretion than does the Tax Court to resolve problems.  It also requires understanding that when the Tax Court reviews an IRS discretionary action, it will only change that action when it is convinced the IRS decision was bonkers or, in the dry technical terms of the law, the decision was an “abuse of discretion.”  And, no, the Tax Court will not make a taxpayer’s argument for them, as we recently learned in Lesson From The Tax Court: The Tax Court Is Not Your Advocate, TaxProf Blog (Feb. 6, 2023).

Today I present a case where pro se taxpayers learned that lesson the hard way.  In Ronald Powell and Cynthia Powell, T.C. Memo. 2023-48 (Apr. 17, 2023) (Judge Lauber), the taxpayers did not like the Installment Agreement offered them by Appeals.  They thought they could do better in Tax Court.  They thought wrong.  Details below the fold.

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Lesson From The Tax Court: Prepare Once, File Twice

Most of us don’t think about what it means to file our tax return.  We may rely on software or a hired return preparer to transmit our return to the IRS. The returns are either snail-mailed to the applicable Service Center, or they are e-filed to that amorphous “cloud.”  We know it is important to file our returns in order to trigger the 3-year limitation period for assessment in §6501(a).  But once we send them in, we’re done.

But most of us do not claim to live in the U.S. Virgin Islands (USVI).  Taxpayers who do may need to file twice, as we learn in David W. Tice v. Commissioner, 160 T.C. No. 8 (Apr. 10, 2023) (Judge Pugh). a reviewed Tax Court opinion.  In holding that the taxpayer was obligated to file his returns with both the USVI and the IRS, the opinion reverses the Court’s prior approach, which we learned about in Lesson From The Tax Court: Forms Follow Function In Return Filing, TaxProf Blog (Jan. 5, 2018).  Previously, the Court had focused on the passive voice of §6501(a) to decide that filing only once with USVI triggered the three year limitation period when the USVI sent a couple of pages of the return to the IRS.  Today’s opinion reads the active voice of §932(a)(2) as imposing a more robust obligation.  Intervening Treasury Regulations might comfort those who believe they only need file once.  However, more cautious advisors may still want to prepare once and file twice.  See what you think.  Details below the fold.

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Lesson From The Tax Court: The Actual Payment Doctrine

Today is a lesson in timing.  When I teach timing I emphasize to my students that they must analyze income items separately from deduction items.  Today is an example of how the analysis applicable to inclusion can be different from the analysis applicable to deductions.

As to income, we all know about the constructive receipt doctrine.  Even if a taxpayer has not actually received some slug of money, they are deemed to have constructively received it if the money was made available to them in the year and there was no legal restriction on their accessing it.

Today’s lesson teaches that the deduction analysis is different.  To take a deduction the taxpayer must make an actual payment.  There is no such thing as constructive payment.  In Edwin L. Gage and Elain R. Gage v. Commissioner, T.C. Memo. 2023-47 (Apr. 12, 2023) (Judge Holmes), the taxpayers purchased a cashier’s check in December 2012 to settle a lawsuit and gave it to their attorney.  They took a 162 deduction for 2012, even though their attorney did not deliver the cashier's check to to the opposing party until March 2013.  In holding that they could not deduct that payment in 2012, Judge Holmes explains why their commitment to pay and their actual purchase of a cashier’s check did not amount to making an actual payment in 2012.  Details below the fold.

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Lesson From The Tax Court: It Takes More Than Putting In The Hours To Avoid §469 Restrictions

Tax Day approaches.  I know many folks are putting in the hours on preparing tax returns this week ... or else putting in the minutes filing Form 4868.  But we all know—especially when unhappy clients come to us to fix a return messed up by some whack-a-doodle preparer—just putting in hours in filing tax returns does not make one a tax professional.

In Robert L. Drocella and Pamela M. Drocella v. Commissioner, T.C. Summ. Op. 2023-12 (Apr. 3, 2023), Judge Leyden teaches us, and our clients, that simply putting in the hours working on one’s rentals does not make one a real estate professional for §469 purposes.  There the hard-working taxpayers were not allowed to escape §469’s prohibition on taking passive activity losses against active income even though they together put in over 1,500 hours in working their six rental properties.  We learn today there are two other tests to being a real estate professional and these taxpayers failed one of them:  they were unable to show the Court the how the hours they worked their rentals related to the hours they spent earning wages.  Details below the fold.

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Lesson From The Tax Court: Attend Carefully To Your Entity Baskets

Easter approaches.  On that day our church grounds will be overrun with children scampering to collect eggs into the various baskets, bags, and other containers they bring (or we give them if they need).  They do not have to worry about what kind of container they use to collect their eggs.  The candy will taste just as sweet.

You can think of business entities as being like Easter baskets.  They are containers taxpayers use to collect their income.  But unlike the happy children, taxpayers must take care in their choice of container.  That choice can affect the amount of income collected.  And it can leave a sour taste when the basket chosen is not the proper form.  In today’s Lesson, we learn how a taxpayer’s choice of business containers affects their ability to take deductions, and even affects their ability to litigate in Tax Court.

In Greatest Common Factor v. Commissioner, T.C. Memo. 2023-39 (Mar. 23, 2023) (Judge Kerrigan), the individual taxpayer chose to collect income through a C corporation and that choice affected the deductibility of the individual’s home office expenses.  In Techtron Holding, Inc. v. Commissioner, T.C. Memo 2023-29 (Mar. 9, 2023) (Judge Vasquez), the individual taxpayers collected income through ever-changing, multiple baskets of various kinds of business entities.  When the IRS audited and found deficiencies in one of the entities, the Tax Court decided it had no jurisdiction over that entity’s petition because the entity no longer existed at the time the petition was filed.  Details below the fold.

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Lesson From The Tax Court: The Whistleblower Who Blew Too Hard

Section 7623(b)(1) says that the IRS must reward whistleblowers when the information they provide causes the IRS to start “any administrative or judicial action” to collect unreported or unpaid taxes.  In such cases, whistleblowers can get an award of up to 30% of the proceeds actually collected from such actions.  Id.  So what happens if the whistleblower's information does not lead to an administrative or judicial action against the particular taxpayer fingered by the whistleblower, but instead prompts the IRS to create a general administrative program to target taxpayers like the one fingered by the whistleblower?

That was the claim in Thomas Shands v. Commissioner, 160 T.C. No. 5 (Mar. 8, 2023) (Judge Greaves).  There, the whistleblower claimed entitlement to 30% of some $1 billion collected from the IRS’s second Offshore Voluntary Disclosure Initiative (OVDI) in 2011.  His theory was that his blowing the whistle on one particularly influential tax evader prompted both the creation of the second OVDI and a rush by taxpayers to voluntarily disclose under the program.

The Tax Court ruled that Mr. Shands’ claim was overblown (pun totally intended).  Both the statute and implementing regulations make it clear that the relevant “administrative or judicial action” is one against particular identified taxpayers.  The creation of a general administrative program such as OVDI was not the kind of action that triggered a mandatory award.  Therefore, under the newly restricted reading of its authority to review whistleblower petitions, the Tax Court held that it lacked jurisdiction to review whether his information really did or did not contribute to OVDI.  The IRS simply had not started a requisite administrative or judicial action.  Details below the fold.

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Lesson From The Tax Court: Another Reason To Keep Good Records

Last week’s Lesson looked at the inherent unreliability of third-party information returns.  Taxpayers need to keep good records to refute those errors.  This week’s Lesson continues that theme: keeping good records can help avoid a bank deposits analysis.  When the IRS is forced to reconstruct income using the bank deposits method, it puts taxpayers in the hard place of having to prove why every bank deposit should not be counted as gross income for that year.

A pair of opinions issued by Judge Buch on the same day gives us a lesson on the unhappy consequences to taxpayers when their poor record-keeping leads the IRS to use a bank deposits method to reconstruct income.  In both Kevin B. Cheam and Julie Lim v. Commissioner, T.C. Memo. 2023-23 (Feb. 27, 2023), and Lundy Nath and Tanya Nath, T.C. Memo. 2023-22 (Feb. 27, 2023), the taxpayers’ failure to keep adequate books and records forced the IRS to conduct a bank deposits analysis, thus putting the burden on the taxpayers to show which bank deposits represented something other than gross income.  In neither case could the taxpayers show the Court nontaxable sources of income for the deposits the IRS asserted were unreported income.  And their record-keeping failures also hurt them in the usual way on the deduction side as well.  Details below the fold.

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Lesson From The Tax Court: The Inherent Unreliability Of Third-Party Reporting

Third-party reporting has long been crucial to tax administration.  Empirically, it helps taxpayers comply with their reporting duties.  Congress first starting requiring information returns in 1917 and keeps expanding the concept to reach new economic situations, such as the rise of the gig economy and on-line marketplaces.

But third-party information returns are inherently unreliable because they report payments, not income.  That is the lesson we learn in Tanisha Trice v. Commissioner, T.C. Memo. 2023-15 (Feb. 13, 2023) (Judge Gustafson).  In this case we learn the lesson with respect to Social Security Disability reporting.  There, the Form SSA-1099 reported payments to Ms. Trice of $15,365.  Judge Gustafson explains why that alone was not enough to support the Notice of Deficiency as to the payments that Ms. Trice denied receiving.  As to those, the IRS was required to produce additional evidence under §6201(d) because Ms. Trice had reasonably objected to that amount and had fully cooperated with the IRS.  Details below the fold.

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Lesson From The Tax Court: Fill Out The Damn Form

The fuss has focused on FBARs.  The FBAR requirements and penalty provisions have been hotly litigated.  Recently the Supreme Court issued an opinion in Bittner v. U.S., deciding that the penalties were not as harsh as the government thought they should be.

But forget FBAR.  Today’s lesson is about a different, yet equally important, foreign account reporting requirement: the one found in 26 U.S.C. §6048 that relates to foreign trusts.  The FBAR stuff is over in 31 U.S.C. §5314.  Completely different title.

And today’s lesson is not about penalties.  It’s about the assessment limitations period.  In Leigh C. Fairbank and Barbara J. Fairbank v. Commissioner, T.C. Memo. 2023-19 (Feb. 23, 2023) (Judge Weiler), we learn that a failure to comply with the §6048 reporting requirement by never filing the proper form---not even during audit---extends the time in which the IRS can assess really old tax deficiencies.  How old?  Try 15 years old.  Regardless of the outcome in Bittner, folks need to learn this lesson!  Details below the fold.

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Lesson From The Tax Court: The New Evidence Rule In Spousal Relief Cases

When a taxpayer requests spousal relief under §6015, the IRS must decide whether to grant it.  If the IRS denies relief, the taxpayer can petition the Tax Court. §6015(e).  In 2019 Congress created a modified administrative record rule for how the Tax Court is supposed to conduct that review.  Taxpayer First Act, 133 Stat. 981, 988.

It’s awkward.  Congress tells the Court to review the IRS decision de novo but, at the same time, tells the Court to do that using only a limited information set consisting of (a) “the administrative record established at the time of the determination” and (b) “any additional newly discovered or previously unavailable evidence.”  §6015(e)(7).

Sydney Ann Chaney Thomas v. Commissioner, 160 T.C. No. 4 (Feb. 13, 2023) (Judge Toro), is a reviewed opinion where a unanimous Tax Court interprets the phrase “newly discovered or previously unavailable evidence” broadly rather than narrowly, thus creating a new evidence rule (pun intended) that robustly protecting its ability to conduct the required de novo review.  Ironically, the decision worked against the taxpayer in this case because it was the IRS that here wanted to introduce new information (the taxpayer’s social media posts).  The taxpayer objected that those posts had been publicly available during the administrative proceeding; therefore they were not newly discovered or previously unavailable.  The Court rejected that argument and admitted the posts as evidence.

Today’s case is also an illustrative contrast to the T.C. opinion I discussed in last week’s post.  That was a case where the taxpayer was proceeding pro se.  And there the Court had no benefit of briefing from both sides.  I think the Court’s opinion showed it.  In today’s case, the taxpayer was (eventually) represented by one of the best tax attorneys I know, Megan Brackney.  Thus the Court had the benefit of a well-presented taxpayer argument.  The Court also had the benefit of a strong amicus brief submitted jointly by the Center for Taxpayer Rights, the Community Tax Law Project, the UC-SF LITC and the Villanova LITC.  That made the Tax Court’s opinion all the more robust, which is what it will need if and when its decision is reviewed in turn by a Court of Appeals.

Spoiler alert.  This post is a little longer than normal.  Sorry, Lew.

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Lesson From The Tax Court: The Limited Review Of Passport Revocation Certifications

Today’s lesson is about §7345, created by Congress in 2015.  The idea behind §7345 is simple.  If you owe taxes and the government threatens to take your passport, you are more likely to pay up.  But its operation is complex.  It requires the IRS to first certify to the State Department that a taxpayer has a “seriously delinquent tax debt.”  Then the State Department is authorized to take certain actions based on that certification.  Section 7345 permits taxpayers to seek Tax Court Review of IRS Certifications.

The Tax Court does not get many passport cases.  According to the Court’s FY 2024 Budget Request, of the 29,000 petitions filed in 2022, only 25 were §7345 petitions.  For those who are interested in learning more about the Court’s budget request, Keith Fogg posted this great review over on Procedurally Taxing.

So when the Tax Court gets a passport case, it often uses it to shape its §7345 jurisprudence by issuing precedential Tax Court opinions.  Today’s case is one of those. Blake M. Adams v. Commissioner, 160 T.C. No. 1 (Jan. 24, 2023) (Judge Toro), teaches two lessons.  First, the Court holds that it will not look behind the IRS certification to redetermine the merits of the tax liabilities that make up the certification.  Second, the Court also decides it lacks authority to determine whether the assessment underlying the Certification was procedurally defective.

Note that this is a case where the taxpayer was unrepresented.  While the Court’s desire to settle important §7345 issues is understandable, I question whether doing so in a pro-se case is desirable. Next week we will see a case where the Court wrote a much stronger opinion after first suggesting that the pro se taxpayer find counsel (who then filed briefed the issue) and also accepting an amicus brief. I offer my thoughts on this below the fold.

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Lesson From The Tax Court: The Tax Court Is Not Your Advocate

Today I present two lessons.  First, we learn why diabetes is not a per se disability sufficient to avoid penalties for early 401(k) distributions.  Second, we learn that pro se litigants cannot rely on the Tax Court to consider potential arguments they could have raised, but did not.

Diabetes is a well-known and widespread disease, afflicting some 37.3 million people in the U.S., according to the CDC’s 2022 National Diabetes Statistics Report.  That’s just over 11% of the US population.  Medical complications abound, as detailed in this report from the Diabetes Institute Research Foundation.

Managing diabetes and its attendant complications can be difficult and expensive.  In recognition of that, Canada gives this tax credit to Canadians who must manage the disease.  And in the U.S., many of the costs associated with diabetes qualify for the medical expense deduction under §213.  See e.g. IRS Publication 502 (2021) at p. 7 (explaining that cost of blood sugar test kit for diabetes is a qualifying medical expense).

In Robert B. Lucas v. Commissioner, T.C. Memo. 2023-9 (Jan. 17, 2023) (Judge Urda), the unemployed taxpayer took an early distribution from his 401(k) plan to help make ends meet, which included helping to manage his diabetes.  The issue was whether he had to pay the §72(t) 10% penalty for early distributions.  He could avoid the entire penalty if his diabetes qualified as a disability, and he could avoid some of it if the distribution was used for expenses allowable as a §213 deduction.  As to the first, Judge Urda teaches us why diabetes is not, in and of itself, a disability sufficient to escape the 10% penalty.  As to the second, Judge Urda notes the issue but, because the taxpayer did not raise it, “[w]e accordingly deem the issue forfeited.”  Op. at 4.  In doing that, Judge Urda teaches an important lesson on the role of the Tax Court.

Details below the fold.

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Lesson From The Tax Court: Corporations In The Bardo

Lincoln in The Bardo is not a book for everyone.  It’s main characters (none of whom are Lincoln) are caught in the bardo, an indeterminate space between death and final after-life, whatever one conceives that to be.  But they are slow to realize it, clinging to a belief in their continued existence as they were.  Filled with unreliable narrators and casually vacillating in time and space, the novel is not an easy read.  But it is well worth the effort, being a lovely meditation on the meaning of life and the meaning of death.

XC Foundation v. Commissioner, T.C. Memo. 2023-2 (Jan. 5, 2023) (Judge Lauber), is an easy read about a corporation in the bardo.  It teaches a practical lesson: always ensure that your corporate client is fully alive and well under state law before you try to file a petition.  There, a corporation attempted to file a petition to contest an IRS decision to revoke its 501(c)(3) status.  Well, actually, the corporation did not file the petition.  It couldn’t.  It was caught in a kind of bardo, an indeterminate space between corporate life and permanent corporate death.  California, the state that had given it life, had suspended its charter, killing its capacity to sue and be sued.  But like the characters in the novel, it ignored its own death and tried to convince the Tax Court to do so as well.  It turns out that taxpayers in the bardo cannot file petitions that the Tax Court can hear, just as Lincoln could not hear the pleas of the novel's characters.  They are the pleas of ghosts.  Details below the fold.

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A Year Of Lessons From The Tax Court (2022)

Here is a chronological listing of all the Lessons From The Tax Court I posted in 2022, with links to the Lesson, the primary case discussed, and its author.  I have also listed the primary Code sections mentioned or discussed in the Lesson.  At the end of the chronological listing, you will find a table listing the posts by which Tax Court Judge authored the Court's opinion.

January 18: The Tacit Consent Rule, Om P. Soni and Anjali Soni v. Commissioner, T.C. Memo. 2021-137 (Dec. 1, 2021) (Judge Copeland) — §6013, §223, §51(b), §301(d), §6061(b), §6651, §6662

February 7: The Innocence Requirement In § 6015(c) Proportional Relief, Tara K. Tobin (Petitioner) and Jeffrey Tobin (Intervenor) v. Commissioner, T.C. Summ. Op. 2021-36 (Nov. 16, 2021) (Judge Guy) — §6015(c) 

February 14: The Proper Baseline For Offers In Compromise, Edmund Gerald Flynn v. Commissioner, T.C. Memo. 2022-5 (Feb. 3, 2022) (Judge Urda) — §7122

February 22: The Tax Liabilities You Leave Behind, Estate of Anthony K. Washington v. Commissioner, T.C. Memo. 2022-4 (Feb. 2, 2022) (Judge Toro) — §6323

 

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Lesson From The Tax Court: Taxpayers Behaving Badly 2022

This will be my last new post until January. Next Monday, December 19, my annual Year Of Lessons From The Tax Court will appear in this space. It is a chronological listing of all the Lessons I posted in 2022, with links to each Lesson, the primary case discussed, and the judge who wrote the opinion. You can find last year's edition here.

I will be spending my days (except for Christmas Day) grading exams.  Grades are due Monday, January 2 and then I resume teaching on January 11, so you will not likely see my next Lesson From The Tax Court until January 23 (the week after the MLK holiday).

As is now customary, my last new 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), here (for 2019), here (for 2020), and here (for 2021).  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.

And again this year I am giving out a Norm Peterson Award.  You will find more explanation below the fold.

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Lesson From The Tax Court: It’s Not Income If You Pay It Back In Time

We all know that taxpayers do not have to report loans as income.  But it's not clear why.  It has something to do with the obligation to repay.  It might be the obligation to repay burdens other assets so the loan does not represent an actual increase in wealth.  Or it might be the obligation to repay creates an open transaction that crosses tax years and, for good administrative reasons, we simply presume the loan amount will be repaid in full.  For more details, see Lesson From The Tax Court: The Phantom Of The Tax Code—Discharge Of Indebtedness, TaxProf Blog (Feb. 19, 2018).

But what about when a taxpayer simply receives a payment that is not a loan, but appears to be a payment the taxpayer has a right to keep?  When it later turns out to be erroneous, and the taxpayer repays it, was it even income to start with?  Today we learn that if repayment of an erroneous distribution occurs in the same tax year as the distribution, there is no income to report.  That was good news for the taxpayers in Elijah Servance and Corliss Severance v. Commissioner, T.C. Summ. Op. 2022-23 (Nov. 21, 2022) (Judge Copeland), who received disability payments from Hartford Life Insurance Co. that they repaid in the same year.  The IRS said the payments were income.  The Tax Court held for the taxpayers.  Sure, the taxpayer lost the other, bigger, issue in the case—the one that got the Tax Analyst Headline of “Couple Could Not Exclude Retirement Benefits From Income.”  But this smaller issue about their disability insurance payments gives us two great lessons: one in tax law and one in tax procedure.  Details below the fold.

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Lesson From The Tax Court: An Object Lesson For Tax Professionals

It is not always easy to follow the advice you give others. A common question I get is "how long should I keep my tax records?" My somewhat snarky reply is “as long as you need to.” The response is not entirely snarky because even though each tax year stands alone, events that occur in one year might have tax repercussions many, many years later.

In Betty Amos v. Commissioner, T.C. Memo. 2022-109 (Nov. 10, 2022) (Judge Urda), the taxpayer failed to keep records as long as she needed to is.  It is an object lesson for all of us. Ms. Amos was a highly successful tax practitioner, a CPA, who had decades of high-level business experience.  On her 2014 and 2015 returns she reported about $100,000 of IRA income against which she claimed over $4 million of net operating losses (NOLs) that dated back to 1999. While she could produce her 1999 tax returns showing the NOLs, she could not produce the underlying records substantiating what she had then reported, causing Judge Urda to write “It beggars belief that she would be unaware...[of] her responsibility to demonstrate her entitlement to the deductions she claimed.” Op. at 11.  Details below the fold. 

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Lesson From The Tax Court: The Impact Of De Novo Review In Spousal Relief Cases

I don't just inflict misery on tax students.  I also teach a class in Civil Procedure to first year law students.  One recurring lesson there concerns the different standards courts of appeals use when reviewing trial court decisions.  I want my students to learn to that the applicable standard of review matters.  It not only makes a huge difference in the outcome of the current case, but it also can make a huge difference in the precedential effect of that case on later cases.

We learn today how the different standards of review affect both outcomes and precedential value of old spousal relief cases.  We also learn how the Tax Court might be induced to finesse the bastardized administrative record rule in §6015(e)(7).  In Pia O. Bacigalupi v. Commissioner, Docket No. 20480-21 (Order of Oct. 27, 2022) (Judge Holmes), the IRS Office of Appeals decided Ms. Baciglupi should be held to the joint liability she had agreed to bear when she signed the joint returns.  They were unmoved by her present circumstances and denied her request for §6015(f) equitable relief.  Despite the record review rule, Judge Holmes allowed her to testify, and on the basis of that testimony disagreed with the IRS about two crucial factors for spousal relief.  Under an abuse of discretion review, that disagreement would not have mattered but under the de novo review, it made all the difference.  The de novo review standard also allowed Judge Holmes to ignore certain precedents unfavorable to Ms. Baciglupi.  Notice, however, this is just an unpublished bench opinion, so don’t get too excited.  For more about that, I recommend Keith Fogg’s excellent post from last week on bench opinions in general and this case in particular.  Meanwhile, you will find today's lesson in more detail below the fold. 

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Lesson From The Tax Court: Fake It Till You Make It

Today’s lesson is how to win a valuation dispute with the IRS.  I don’t teach much about valuation in my basic tax course. When we work problems involving property, the problems generally tell students to assume a certain fair market value (FMV) for the property.  For example, when I teach the deductions allowed by §170 for contributions of property to a charity, what I want students to learn is the reduce-to-basis rule.  To work that particular rule, those problems just assert an FMV because I’m trying to get them to focus on what kind of property is being donated and to what kind of charity.  See e.g. last week’s lesson “The Reduce-To-Basis Rule For §170 Deductions,” TaxProf Blog (Oct. 17, 2022).

I tell students that in real life, valuation is often open to dispute.  That is because facts matter.  And facts may often be disputed.  Moreover, assumptions matter as well.  And assumptions may often be questioned.

This week, we learn a great lesson from the Tax Court on how to win a valuation dispute against the IRS: have a better expert.  While that is easy to say, the 43-page opinion in Champions Retreat Golf Founders LLC et al. v. Commissioner, T.C. Memo. 2022-106 (Oct. 17, 2022) (Judge Pugh), teaches how it is not always easy to do. Today’s case involves the valuation of a conservation easement.  The taxpayer’s expert was not the best, but the IRS’s expert was worse.  So the taxpayer won.  The lesson is kind of like the old joke that you don’t have to outrun the bear: a taxpayer’s valuation does not have to be the best possible; it just has to be better than the IRS’ valuation.  Details below the fold.

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Lesson From The Tax Court: The Reduce-To-Basis Rule For §170 Deductions

Basis is probably the most important concept I teach in my intro income tax course.  I like thinking of basis as the tax history of a piece of property.  It tracks what ought not to be taxed upon eventual sale or exchange of that property under the calculations required by §1001.  But a proper understanding and tracking of basis can also be important for other reasons, such as determining the amount of a §165 loss ... or calculating the amount of a §170 deduction for  charitable donations.

Donald Furrer and Rita Furrer  v. Commissioner, T.C. Memo. 2022-100 (Sept. 28, 2022) (Judge Lauber), teaches a lesson on the importance of basis in determining the amount of a §170 deduction for the donation of property to charity.  We also learn a cautionary lesson on the use and mis-use of Charitable Remainder Annuity Trusts (CRATs).  The taxpayers here were farmers who donated crops to a CRAT and then attempted to claim a §170 deduction based on the fair market value of the donated crops.  That ran afoul of the reduce-to-basis rule.  Details below the fold.

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Lesson From The Tax Court: Know Your TMP

In my now 22 years of teaching tax, I have assiduously avoided teaching partnership taxation.  With any luck, I’ll never have to.  Inside and outside basis still confuse the heck outta me.  But I do teach tax procedure, so I’ve been forced over the years to learn something about the rules governing audits of partnerships.

If there is one stand-out lesson I’ve learned, it’s the one Judge Buch teaches us in Trevor R. Pettennude v. Commissioner, T.C. Memo. 2022-79 (July 18, 2022): individual partners are often at the mercy of their Tax Matter Partner (TMP) when it comes to participating in partnership-level determinations.  The burden is on each partner to know their TMP, and to ensure they are in the loop on important partnership matters.  That may even more true post-TEFRA.  In today’s case, Mr. Pettennude was a tiny partner in a large coal tax credit shelter partnership.  The IRS caught on and audited the partnership.  No one told Mr. Pettennude about either the audit or its results (not happy ones) until the IRS told him he owed about $850,000 in additional taxes.  He tried to contest that in a CDP hearing.  It did not go well.  Details below the fold.

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Lesson From The Tax Court: Don’t Confuse Dummy Returns With Substitutes For Returns

The act of filing a return is central to tax administration. Section 6011 sets out the general requirement: “any person made liable for any tax imposed by this title” must file a return “according to the forms and regulations prescribed by the Secretary.”  Section 6012 gets more granular and gives more specific requirements and exemptions from filing.

When a taxpayer fails to file a return, even after being reminded to do so, the IRS can simply send the taxpayer a Notice of Deficiency (NOD), and let the taxpayer either agree to the proposed tax liability or petition Tax Court.  Or the IRS can follow the §6020 Substitute For Return (SFR) process whereby it creates a return for the taxpayer either with or without the taxpayer’s cooperation.

Regardless of how the IRS deals with the non-filer, an IRS employee first needs to create an account in the computer system for the relevant tax period.  They do that by inputting the proper Transaction Code and preparing what is called a “dummy return” to support it.  But there is one important difference between dummy returns used to set up the NOD process and dummy returns used to set up the SFR process: the §6651(a)(2) failure to pay penalties only apply to the failure to pay taxes shown on a “return.”  Thus, the penalties do not apply to bare NODs.  They do apply to SFRs.  That’s why today’s lesson is useful.

In William T. Ashford v. Commissioner, T.C. Memo. 2022-101 (Sept. 29, 2022) (Judge Vasquez), we learn what to look for in the IRS files to see whether a dummy return used by the IRS leads to a proper SFR or not.  We also learn why you cannot always trust the advice you see on the IRS website.  Details below the fold.

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Lesson From The Tax Court: Checks ... Still Matter

Who uses paper checks anymore?  Not my kids.  My daughter even prefers to incur a surcharge for using her debit card to pay her rent rather than walking a paper check to the rental office.  The practical reason, she says, is that when she uses her debit card she can immediately see the impact on her checking account balance by looking at her “available balance” number in her banking app.  If she wrote a check, she’d have to wait until the check cleared and she fears over-drawing her account.

That delay—between the time a person writes and check and the time it gets reflected in their checking account—is what gives us our lesson in Estate of William E. Demuth Jr. et al. v. Commissioner, T.C. Memo. 2022-72 (July 12, 2022 )(Judge Jones).  In that case the issue was the value of an investment account on the date of the decedent’s death.  On that date there were 10 checks totaling $436,000 that had been written on the account but had not cleared.  The Executor did not include that amount on the Form 706 because the recipients of the checks had deposited them before the decedent died.  Their accounts had been credited.  They had been paid.  Or so thought the Executor.  The IRS, however, thought that the checks had not been paid because they had not cleared the decedent’s bank.  So the money still belonged to the taxpayer and should have been included in the valuation of his Estate.

In (mostly) agreeing with the IRS, Judge Jones gives us a useful lesson on basic commercial law principles.  Maybe my kids won't care, but enough folks still use checks that it's a lesson worth remembering.  Details below the fold. 

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Lesson From The Tax Court: The Finality Of Closing Agreements

Section 7121 authorizes the IRS to enter into “an agreement in writing” with taxpayers “in respect of any internal revenue tax for any taxable period.”  Such agreements are called “Closing Agreements.”  As implied by that name, the big idea here is that such agreements are meant to “close” a particular tax issue or a particular tax year or years.  Accordingly, the general rule is that such agreements are final: they “close” the ability of either the IRS or the taxpayer to later assert a different position with respect to the matters covered in the Closing Agreement.

In Cory H. Smith v. Commissioner, 159 T.C. No. 3 (Aug. 25, 2022) (Judge Toro), the Tax Court teaches a lesson on that finality rule.  There, the taxpayer had signed a Closing Agreement for multiple years promising not to claim the §911 exclusion for foreign earned income.  He then reneged by filing amended returns (for some years) and original returns (for other years), breaking that promise.  Even though the opinion is a 43-page precedential opinion, the lesson is relatively simple: Closing Agreements are final; one must be very careful when signing one because final means final.

What is also interesting (at least to me) is why the Tax Court may have taken extra effort to hammer on the finality rule and issue this opinion as a T.C. opinion.  It seems Mr. Smith did not act alone.  He appears to have received some dubious advice from his tax return preparer, an Enrolled Agent (EA) who awkwardly styles himself as “Dr.” Castro.  Op. at 16, note 20.  That EA seems to have also given the same bum advice to a bunch of other taxpayers.  The Court notes that “at least 19 other cases pending in our Court involve the same issue as the one presented here.”  Op. at 11, note 14.  So making this first-out opinion a precedential opinion should help to efficiently dispose of all the rest.  The Court makes the effort to note that all 19 of the other cases involve this same EA.  This leads to some thoughts about potential §6694 penalties.

Details below the fold.

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Lesson From The Tax Court: The Law Of Unintended Consequences

To say the Internal Revenue Code is complex is like saying a virus is hard to see.  It understates the obvious. NSS.  Today the Tax Court teaches us one consequence of that complexity: the meaning and scope of one statute (§6103) can be altered by the later addition of another statute (§7623(b)).  The former is the statute that requires the IRS to keep taxpayer information confidential.  The latter is the statute that allows whistleblowers to obtain Tax Court review of a denial of a whistleblower award.

In Whistleblower 972-17W v. Commissioner, 159 T.C. No. 1 (July 13, 2022) (Judge Toro), the Court said the IRS had to give a whistleblower the unredacted returns and return information of three taxpayers that the whistleblower informed on.  Folks, this is a reviewed opinion and all 15 of the reviewing judges agreed with Judge Toro’s decision (one judge did not participate).  While the decision is rational, its conclusion is certainly not a slam dunk.  IMHO it misses the forest for the trees, resting on a curious presumption about the statutory text in 6103.  Whether or not readers agree with that, we can all agree this case illustrates how a later statute may give new meaning to the words in an older statute.  That is an inherent difficulty in interpreting statutory language that is part of such a wickedly complex Code.

Trigger warning: today’s post runs a bit longer than normal.  So the refresh rate will likely bother those who click through.  I am so sorry for that!  But this lesson is really just so cool that I hope you will persevere.

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Lesson From The Tax Court: Taxpayer Could Not Prove His Way Out Of §162(f)

The basic rule is simple: the taxpayer bears the burden of proof.  That is, all income is gross income unless the taxpayer proves a statutory entitlement to an exclusion; and no expenditure is deductible unless the taxpayer proves a statutory entitlement to a deduction.

Complexity comes in the statutes that allow exclusions and deductions.  But the basic burden does not change: it is ultimately the taxpayer who must persuade either the IRS or the Tax Court of their entitlement to the exclusion or deduction claimed.

Clement Ziroli and Dawn M. Ziroli v. Commissioner, T.C. Memo. 2022-75 (July 14, 2022) (Judge Nega), shows us how the burden of persuasion applies in the complexity of a deduction statute.  There, the taxpayer sought to deduct an expenditure that was allowed by §162(a) but might or might not be disallowed by the §162(f) prohibition of deductions for penalties.  The taxpayer was unable to persuade the Tax Court that the expenditure was not a penalty.  He could not prove the negative.  Hence, no deduction.

The lesson relates back to the idea we looked at last week: the ambiguity of penalties.  Here, that ambiguity worked against the taxpayer because of the burden of persuasion.  Details below the fold. 

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Lesson From The Tax Court: Non-Receipt of 1099 Does Not Get You Out of Penalties

When we think of penalties we naturally think of punishment.  I mean, to channel Steven Wright, if a penalty is not punishment when why does the word start with “penal”?  Both this week and next week’s lesson teach us how penalties serve other purposes as well.  Today, in Lionel E. Larochelle and Molly B. Larochelle v. Commissioner, T.C. Summ. Op. 2022-12 (July 12) (Judge Leyden), we learn why non-receipt of a Form 1099 does not constitute reasonable cause to escape the §6662(a) penalty for making a substantial understatement of tax.  Next week we will look at whether a court-ordered disgorgement of illegal gains is a penalty for purposes of a §162(f) prohibition on  deductions for governmental fines or penalties.  Today’s short lesson awaits below the fold. 

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Lesson From The Tax Court: Excise Tax On Messed Up IRA Rollover Different From Income Tax

The tax laws are conflicted.  They encourage retirement savings by permitting taxpayers to deduct contributions to their Individual Retirement Accounts (IRA’s).  But that encouragement is hedged by various restrictions and caps as well as a special excise tax imposed on contributions that exceed the applicable caps.  And Congress crosses its fingers if taxpayers take early distributions.  Those can result in penalties as well as inclusion in gross income.  However, Congress uncrosses those fingers if the early distributions are properly rolled into another IRA.

Given these various statutory hedges and crossed-fingers, it’s no wonder that navigating the tax rules for retirement accounts is tricky!  Particularly tricky are managing rollovers from one type of retirement plan to another.  Mistakes there can have both income tax consequences and excise tax consequences.  Thus, we must always keep straight the difference between different types of taxes, just like we saw in last week’s lesson.

This week, we learn how excise tax consequences are different than income tax consequences of a messed up IRA rollover.  In Clair R. Couturier, Jr. v. Commissioner, T.C. Memo. 2022-69 (July 6, 2022) (Judge Lauber), the taxpayer escaped a huge income tax liability for messing up some of the rollover rules because the limitation period for assessment had run, but got snagged for a $8.5 million excise tax for excess IRA contributions.  Yeah, we’re talking a lot of money here, putting enough at risk for the taxpayer to hire one of the best tax lawyers in the country to represent him.  Alas, even Lavar Taylor could not pull him out of the $8.5 million hole.  He tried to argue that the IRS was bound by the income tax characterization of the transaction.  The Court rejected that argument because...an excise tax is not an income tax.  Details below the fold. 

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Lesson From The Tax Court: No §6015 Equitable Relief For §6672 Penalties

The Internal Revenue Code is full of taxes and penalties.  Oh my, so many taxes and penalties!  You must always stay aware of which kinds of taxes or penalties are at issue in order to know what rules of law apply.  This week and next week will give us two lessons on the importance in keeping straight the different kinds of taxes and penalties.

In Angela M. Chavis, 158 T.C. No. 8 (June 15, 2022) (Judge Lauber), the taxpayer was seeking spousal relief under §6015(f) from Trust Fund Recovery Penalties assessed per §6672 against her and her then-husband.  The liability for §6672 penalties is joint and several.  And, if you squint, the text of §6015(f) appears to allow relief from any joint and several liability.  Today we learn not to squint. Section 6015(f) provides relief only from joint liability for income taxes.  Trust Fund Recovery Penalties are not income taxes.  So no spousal relief for §6672 penalties.  You will find a bit more (but not much) below the fold.  It’s a short lesson for a hot summer day.

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Lesson From The Tax Court: The Difference Between Rejecting An OIC And Reviewing A Rejection

Tax collection is a process, not an event.  The process can last ten years or more.  During that time many different events may occur.  Different events may bring with them different decision-makers within the IRS.  The secret sauce of representing clients is that when you hit an unfavorable decision-maker, try to find a new one.  An example of that is getting a CDP hearing.  CDP hearings allow taxpayers to pause collection while they ask for alternatives to full collection, such as Offers In Compromise (OICs).  The CDP hearing is conducted by a Settlement Officer (SO) in the IRS Independent Office of Appeals (Appeals).

Thus, the SO represents a new layer of decision-making.  But what do you get with this new decision-maker?  Today’s lesson teaches that you may not get what you think.

Michael D. Brown v. Commissioner, 158 T.C. No. 9 (June 23, 2022) (Judge Lauber), address what I think is a common misconception about CDP hearings: that Appeals makes decisions about collection alternatives.  It does not.  It reviews decisions made by the relevant IRS function.  At issue in Brown was whether the IRS waited more than two years to reject his OIC, which was proposed as part of a CDP hearing.  If so, then his low-ball OIC would be deemed accepted under §7122(f).  Although the IRS unit that evaluated his OIC rejected it after a few months, the formal Appeals decision in the CDP hearing came more than two years later.  Mr. Brown went to Tax Court, claiming the benefit of §7122(f).  The Tax Court said no.  Appeals did not reject the OIC; all it was doing was reviewing the rejection decision made by the IRS.

This was not a slam dunk win for the IRS.  I think it’s worth your time to see why.  Details below the fold.

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Lesson From The Tax Court: TP Did Not File Return By Giving Copy To IRS Employee

Figuring out when or whether a taxpayer has filed a return is important for many reasons.  On the one hand, proper filing limits the time for the IRS to assess.  Thus taxpayers generally want the courts to find they have filed.  On the other hand, filing a frivolous or fraudulent return can lead to penalties.  In those situations, taxpayers want the courts to find they have not filed! 

Sometimes a taxpayer will give an IRS employee a copy of a return they claim was previously filed.  Does that constitute the filing of a return?  Well, it depends. Just like last week, I think it useful to compare the Tax Court and Circuit Court cases.

In a logic-challenged opinion, the Ninth Circuit recently decided giving a copy did constitute filing a return ... for for statute of limitations purposes.  See Seaview Trading, LLC v. Commissioner, 447 F.3d 706 (9th Cir. 2022), rev’g T.C. Memo. 2019-122. While I agree with the dissenting judge that “the majority's analysis and conclusions are logically absurd and should not be the holding of this court,” there is no denying the decision was good news for taxpayers.

Now comes the Tax Court and in Chule Rain Walker v. Commissioner, T.C. Memo. 2022-63 (June 15, 2022), Judge Nega decides that giving an IRS employee a copy of a frivolous return does not constitute filing a return ... for frivolous penalty purposes!

Win-win for taxpayers?  As usual, the devil is in the details, which you can find below the fold. 

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Lesson From The Tax Court: A Reasonable Basis For Deducting Scrubs?

My students—especially those with accounting backgrounds—come to class expecting that tax law is all about bright line rules and lots of calculations.  They are either disappointed, frustrated, or relieved to find that tax law is like other law: it’s words, words that are generally complex, often opaque, and frequently mysterious.  That’s why taxpayers need competent tax practitioners to advise them!

Some tax practitioners are more aggressive and some are more cautious.  Today’s lesson is for the more aggressive ones.  In Raul Romana and Maria Corazon Romana v. Commissioner, T.C. Sum. Op. 2022-9 (June 16, 2022), Judge Carluzzo generously allowed a taxpayer to deduct the cost of a her “scrublike clothing.”

Those of us who are more cautious will disregard this decision.  It’s an outlier and, no, I certainly would not advise my client to start deducting the cost of this type of clothing!  At the same time, however, the opinion may well provide aggressive taxpayers and their advisors protections from penalties if and when they try this trick at home.  The substantive tax lesson is short and sweet.  The penalty lesson is more complex, opaque, and mysterious.

Details below the fold.

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Lesson From The Tax Court: Ask The Right Court

It’s sweet to beat the tax man.  It’s even sweeter when you can make the government pay your litigation costs and attorneys fees under §7430.  But the bitter lesson for today is that you must be careful to ask the right court.  Law is hierarchical.  You can appeal a lower court’s adverse decision to a higher court.  But you cannot appeal a higher court’s adverse decision to a lower court!

In Celia Mazzei v. Commissioner, T.C. Memo. 2022-43 (May 2, 2022) (Judge Thornton), the taxpayer asked the wrong court for attorneys fees and because of that had nowhere to go when the court denied fees.  Ms. Mazzei had fought the IRS for over 10 years, losing in Tax Court in a reviewed opinion in 2018.  Undaunted, she appealed to the Ninth Circuit.  She won!  Yay!  Her attorneys then filed a “protective” motion with the Ninth Circuit for both her appellate litigation costs (about $70,000) and her trial court litigation costs (some $330,000).  The government argued that its litigating position was substantially justified.

The Ninth Circuit’s response was disappointingly succinct: “denied.”  Undaunted, Ms. Mazzei’s attorneys then asked the Tax Court for the $330,000 in trial court litigation costs.  The government opposed the motion for the same reason it gave the Ninth Circuit.  Judge Thornton, however, rejected the §7430 request for a different reason.  He ruled that the  Ninth Circuit’s single word left the Tax Court powerless to act on the request.  Appeals go up the hierarchy, not down.  The taxpayer had asked the wrong court.  Details below the fold.

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Lesson From The Tax Court: Taxpayer Held To His Word(s) Regarding Alimony

Congress eliminated the deduction for alimony in the December 2017 Reconciliation Act (informally called the Tax Cuts and Jobs Act, or TCJA).  The concept is still important, however.  First, the legislation grandfathered in alimony payments made pursuant to divorce or separation instruments executed on or before December 31, 2018.  So the question of whether a payment qualifies as alimony will thus still be important for many taxpayers for years to come.  Second, the definition continues to play an important role in analyzing the support requirements for dependents.  See §152(d)(5).

Determining whether payments constitute alimony is not always easy and errors can lead to §6662 penalties for careless taxpayers and their advisors.  Jihad Y. Ibrahim v. Commissioner, T.C. Summ. Op. 2022-7 (May 16, 2022) (Judge Weiler), teaches us the importance of the words used in divorce instruments. There, Dr. Ibrahim sought to deduct $50,000 in payments to his ex-wife.  He called them as alimony on his return.  But the marital separation agreement and the divorce decree did not call them that.  The IRS disallowed the deduction as contrary to the plain language in the divorce decree.  Despite Dr. Ibrahim’s ingenious arguments, the Tax Court agreed with the IRS and held the taxpayer to his word(s).  Details below the fold.

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Lesson From The Tax Court: The Sharp Corners Of The §170 Substantiation Requirements

The sainted Justice Holmes once wrote:  “Men must turn square corners when they deal with the Government.”  It is no accident that Justice Holmes wrote that in a tax case.  Rock Island R.R. v. United States, 254 U.S. 141, 143 (1920).  Of all the corners in all the laws governing citizen interaction with government, tax laws contain some of the squarest.  This is a lesson we’ve seen before.  See Lesson From The Tax Court: The Structure Of Substantiation Requirements of §170, TaxProf Blog (Sept. 24, 2018).  But I think it’s a lesson worth repeating: the substantiation rules in §170 contain some very sharp corners.  The lesson is important for high-end donations such as the one in today’s case.  And it is not just a lesson for taxpayers, but also for charities.

In Martha L. Albrecht v. Commissioner, T.C. Memo. 2022-53 (May 25, 2022) (Judge Greaves), the taxpayer made a very large donation to a museum and claimed a §170 charitable donation deduction on her return.  The IRS said that the 5-page document memorializing the gift did not meet the statutory substantiation requirements for such a gift.  The Tax Court agreed.  Thus, no §170 deduction.  Details below the fold.

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Lesson From The Tax Court: Counting The Days

Most people know that the IRS generally has three years to audit a return. Calculating the proper three-year period, however, requires close attention to both the start date and the end date.  You need to count those days properly.  I tried to drill into my students the practice of always consulting a calendar when attempting to calculate the proper dates.  Christian Renee Evert v. Commissioner, T.C. Memo. 2022-48 (May 9, 2022) (Judge Marshall), reinforces that teaching: to calculate the period in which the IRS can assess a tax, you need to properly count the days in the three year period.

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Lesson From The Tax Court: Avoiding The 2-Year Lookback Period In Bankruptcy

Today’s lesson is about how to maximize the discharge of tax liabilities through bankruptcy.  It's a lesson on timing.  Last year I blogged two cases showing how a bankruptcy tolls both the collection and assessment limitation periods in the Tax Code.  See Lesson From The Tax Court: For Whom The Bankruptcy Tolls, TaxProf Blog (July 19, 2021).  Today’s lesson is the flip side: we learn how taxpayers who want to discharge old tax liabilities through bankruptcy need to be careful about how the two-year lookback exception to discharge may be tolled by provisions in the Tax Code.

I offer today’s lesson in honor of Bob Pope, who died on April 29th.  Bob was one of those remarkable attorneys who could navigate the complex interplay of bankruptcy and tax law.  He was one of the founders of the Tax Collections, Bankruptcy and Workouts Committee in the ABA Section of Taxation, along with Paul Asofsky, Fran Sheehy, Ken Weil, and Mark Wallace.  He will be missed.

Bob would appreciate today’s lesson.  In Robert J. Norberg and Debra L. Norberg v. Commissioner, T. C. Memo 2022-30 (Apr. 5, 2022) (Judge Lauber), the taxpayers filed their 2016 return in February 2019 without paying the tax they reported due.  When the IRS started collection, the Norbergs asked for a CDP hearing.  When they got to Tax Court in September 2020 they filed a bankruptcy petition, hoping to wipe out the liability.  They failed because they mis-timed their bankruptcy petition.  An irony is that these taxpayers could have likely gotten their desired discharge if they had ignored the siren song of CDP.  Bob could have taught them that.  And, if you click below the fold, you too can learn this lesson on how to maximize the discharge of tax liabilities in bankruptcy.

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Lesson From The Tax Court: Distinguishing Employees From Independent Contractors

Pro Publica has proudly proclaimed that “If You’re Getting a W-2, You’re a Sucker.”  I know lots of workers who would strongly disagree.  For them, being a W-2 worker (a/k/a “employee”) is far more beneficial than their realistic alternative, which is being a 1099 worker (a/k/a “independent contractor”).  The Pro-Publica story was channeling this Brookings Institution study which noted how business owners can often hide their income but workers cannot because their employers rat them out with W-2s.

But most workers have no realistic choice.  Just ask your next Uber or Lyft driver.  For them, as for many others in various industries—from child-care to health-care to landscaping and construction—the choice is not whether or not to hide income.  Their choice is only whether their income gets reported to the IRS on a Form W-2 or a Form 1099.  The upside of being an employee is lower employment taxes and eligibility for unemployment benefits.  The potential downside is no §199A and no ability to deduct unreimbursed job expenses, given the current nastiness codified in §67(g).

And the choice of status is often on the employer.  Employers must decide whether and when to treat their workers as employees or as independent contractors.  Today’s lesson shows how they might be on the hook if they make the wrong classification.  Pediatric Impressions Home Health, Inc. v. Commissioner, T.C. Memo. 2022-35 (Apr. 12, 2022) (Judge Greaves), teaches us how Tax Court distinguishes employees from independent contracts.  It also shows us a potential safe harbor that employers can use to escape the unpaid obligations if it turns out they erroneously classified employees as independent contractors.  Details below the fold.

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Lesson From The Tax Court: What’s Excluded From The §132 Exclusion?

Tax Day is here! And what better way to observe the day than a lesson on §132, a lesson that evokes the ghost of Dan Rostenkowski, whose curmudgeonly visage appears to the right.  For those who don’t know, Rostenkowski was the chairman of the House Ways and Means Committee from 1981 until 1994 when, in the great tradition of Illinois politicians, he was indicted on various counts of fraud, eventually pleading guilty to mail fraud.  Yes, political corruption in Illinois actually has its own Wikipedia entry.

During his time as head of the House tax writing committee, Rostenkowski oversaw multiple major legislative changes. Perhaps his crowning glory was his role in the 1986 Tax Reform Act, which has long been viewed as a triumph (however short-lived) of sound tax reform.

Today’s lesson has its genesis in the earlier Deficit Reduction Act of 1984, PL 98-369, 98 Stat. 494.  There, Congress wrote a new §132 to exclude from gross income a long list of traditional employee fringe benefits.  In Douglas Mihalik and Wendy J. Mihalik v. Commissioner, T.C. Memo. 2022-36 (Apr. 13, 2022) (Judge Gustafson), Mr. Mihalik received free airline tickets for himself and members of his family. He sought the exclusionary shelter of §132.  While §132 is very broadly written to cover various family members of an employee, Judge Gustafson teaches us how some family members are excluded from the exclusion.  Details below the fold.

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Lesson From The Tax Court: 50 Ways To Lose Your Interest Abatement Request

Obtaining an abatement of interest reminds me of Paul Simon’s song 50 Ways to Leave Your Lover.  Sure, the “50 ways” in the song title is misleading.  By my count, Simon gives us only four.  And some are singularly unhelpful for real life advice.  I mean, “make a new plan, Stan”?  Really?  But the hyperbole does it’s job: it draws attention to idea there are the multiple ways to break off a relationship.

My Lesson title is also hyperbolic, but serves the same purpose.  When a taxpayer wants the IRS to abate interest charges, there are lots of ways to lose.  Jeremy Edwin Porter v. Commissioner, T.C. Memo 2022-23 (March 28, 2022)(Judge Greaves) gives us a nice review of some of them.  There, the hapless taxpayer was trying to get interest abated for, among other periods, a 34 month period where the Tax Court did not rule on pending discovery motions.  The Court sustained the IRS rejection of the abatement request because, even if the delay was unreasonable, and even if it was not attributable to Mr. Porter, it was caused by the Tax Court, not the IRS.  Ouch.

This gives us a good excuse to review the many ways the IRS can reject an interest abatement request.  And perhaps learn how to be a diligent litigant so as to keep your client’s case moving along during Tax Court litigation.  I hope today’s lesson is more helpful than Simon’s song.  At least it won't be an earworm.  Details below the fold. 

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Lesson From The Tax Court: Penalty Approval In Conservation Easement Cases

The §6751(b) supervisory approval requirement for penalties has been a thorn in the side of both the IRS and the Tax Court.  Today’s lesson shows us how the IRS penalty approval process in conservation easement audits has forced taxpayers to reach for wilder and less credible attacks in their attempts to avoid penalties by finding IRS procedural foot-faults.

First, in Pickens Decorative Stone LLC v. Commissioner, T.C. Memo. 2022-22 (Mar. 17) (Judge Lauber), the taxpayer argued that when the IRS had publicly committed in a general Notice to seeking penalties against the types of syndicated conservation easement scheme it had engaged in, the IRS was disabled from complying with §6751(b) because the supervisor in the audit had not signed off on that public Notice.  Yeah, pull your eyebrows down; the argument lost.

Second, in Oxbow Bend, LLC v. Commissioner, T.C. Memo. 2022-23 (Mar. 21, 2022) (also Judge Lauber), the taxpayer similarly argued the IRS failed to comply with §6751(b) when the Revenue Agent (RA) had failed to secure supervisory approval before telling the taxpayer during a status conference that penalties were “under consideration” when in fact the RA was completing an internal document recommending penalties that very day.  That was a loser as well.  Details below the fold.

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Lesson From The Tax Court: Take The Administrative Appeal

Taxpayers famously focus on trying to get their “day in court” against the evil IRS.  The Independent Office of Appeals (Appeals) is no court.  It is not surprising, then, that taxpayers’ myopia often leads them down the dangerously wrong path of ignoring their opportunity to go to Appeals.  Today’s lesson teaches us one reason that is a mistake.

In Mahammad A. Kazmi v. Commissioner, T.C. Memo. 2022-13 (Mar. 1, 2022) (Judge Paris), the IRS was seeking to collect a §6672 Trust Fund Recovery Penalty (TFRP) assessed against the taxpayer.  In a Collection Due Process (CDP) hearing, Mr. Kazmi attempted to explain why the assessment was improper against him.  He relied on the rule that a taxpayer can challenge a liability in a CDP hearing if the taxpayer had not had a prior opportunity to do so.  While Mr. Kazmi had been given the opportunity to take an administrative appeal during the prior §6672 assessment process, he said that should not count because it did not give him a day in court.  While that argument might have traction in other situations, it failed in this one.  Details below the fold.

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Lesson From The Tax Court: What Constitutes A CDP 'Hearing'?

Before the IRS can start collecting unpaid tax liabilities by levy, §6330(b)(1) requires it to give taxpayers an opportunity for a Collection Due Process (CDP) hearing with the IRS Independent Office of Appeals.

Many taxpayers do not fully understand how CDP hearings work. First, they erroneously expect that a CDP hearing is a discrete and physical event where they (finally!) confront the evil IRS.  Second, they erroneously expect that the point of the hearing is for the evil IRS to justify collection, including proving the correctness of the assessment.  Finally, they expect that they can go to Tax Court and get a do-over if they don't like the result they get from the CDP hearing.  Taxpayer with those expectations are doomed to disappointment.

Today’s lesson is for them. In Brian K. Bunton and Karen A. Bunton v. Commissioner, T.C. Memo. 2022-20 (Mar. 10, 2022), Judge Morrison gives a nice short lesson on what constitutes a CDP hearings.  The taxpayers complained that their CDP hearing was defective because (1) the Settlement Officer (SO) had not given them an in-person hearing, and (2) the IRS did not show the assessment was correct.  The Court rejected those complaints and in so doing, shows us what constitutes a CDP hearing. Details below the fold.

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Lesson From The Tax Court: The Finality Rule For §7430 Qualified Offers

When you litigate against the IRS you may win but not prevail.  That is, even though §7430(a) promises that a “prevailing party” can recover costs and attorneys fees, it’s hard to be a "prevailing party" within the meaning of the statute.  If the government's ultimately losing position was substantially justified at the relevant time, the winning taxpayer won't be a prevailing party.  Sometimes that leads to a seemingly strange result that even if the Office of Appeals badly messes up, the taxpayer will not be a prevailing party if Chief Counsel catches the error and promptly concedes.  Keith Fogg blogged a good example of this over at Procedurally Taxing last week.

The Qualified Offer process is a substitute for being a prevailing party.  Making a properly qualified offer to settle a case removes the government's "substantially justified" defense.  Thus, if you make the offer during the administrative process, you can set up a recovery even if Chief Counsel concedes.

But making a effective Qualified Offer has its own difficulties.  Today’s lesson looks at one of the key rules for making a qualified offer: the finality rule.  In Gina C. Lewis v. Commissioner, 158 T.C. No. 3 (Mar. 3, 2022) (Judge Pugh), the taxpayer offered to settle an audit of her joint return by agreeing to 100% of a proposed deficiency.  But on a closer examination, she really just crossed her fingers, reserving the right to contest that liability through the §6015 spousal relief provisions at some unspecified later date.  So it was not really an offer to settle.  It was an offer to kick the can down the road.  Indeed, many years later, in Tax Court, the IRS agreed she was entitled to full relief under §6015(c).  Ms. Lewis then asked for costs and fees under §7430 on the grounds that the IRS had ended up worse off than if it had accepted her offer.  The Tax Court said no, for reasons discussed below the fold.

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Lesson From The Tax Court: The Tax Liabilities You Leave Behind

We all know you can’t take it with you.  But what happens to the “it” after you die?  Ideally, you will have paid all your debts, and your Estate will distribute your “it” to the objects of your affection. The IRS will probably not be one of the objects of your affection.

However, few of us do everything ideally.  If you leave behind unpaid tax obligations, Congress has ensured that the federal government gets priority over the objects of your affection.  And tax claims also take priority over most other creditors.  But most is not all.  Some creditors get paid before the Tax Dude.  Thus, if your unpaid tax obligations exceed the assets in your Estate, then the objects of your affection will take bupkis ... unless they also happen to be one of the few types of creditors that get priority over the unpaid taxes.

That is what we learn from Estate of Anthony K. Washington v. Commissioner, T.C. Memo. 2022-4 (Feb. 2, 2022) (Judge Toro).  There, the decedent died with unpaid federal tax liabilities that exceeded the assets in his Estate.  The decedent’s ex-wife tried to convince the Tax Court that her claim against the Estate took priority over the tax claim.  Alternatively, she argued that the IRS erred when it did not account for her claim in evaluating the Estate’s Offer In Compromise (OIC), because ignoring her claim simply was not fair because paying the tax claim would leave the Estate with nothing.

Both arguments failed.  The case teaches us a lesson about the federal tax lien and about the difficulty Estates face in obtaining OICs.  Details in the usual space, below the fold.

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Lesson From The Tax Court: The Proper Baseline For Offers In Compromise

Paying taxes can be painful.  When money is tight and other needs are pressing, sending money to the federal government understandably sinks on the taxpayer’s priority list.  But not the government’s!  Congress wants to make sure that paying taxes remains at the top of every taxpayer’s priority list.  That is why it gives the IRS really awesome collection powers.  If that duty to pay taxes is not uniformly enforced, the thinking goes, then voluntary compliance goes out the window and soon that window will be smashed by rocks thrown by rioting mobs.  Don’t want that.

At the same time, Congress recognizes that, sometimes, circumstances  should permit payment of less than the full amount.  The Offer In Compromise (OIC) process is designed to address those situations. The ability to secure an OIC, however, must always be evaluated against a default of full payment, not against a default of no payment.  That is what we learn from Edmund Gerald Flynn v. Commissioner, T.C. Memo. 2022-5 (Feb. 3, 2022) (Judge Urda).  There, the Court held that the taxpayer was not entitled to an OIC just because the full-pay obligation would be financially painful.  Details below the fold.

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