Income Tax Issues
Full Tax Court Opinions

Leyh v. Commissioner (157 T.C. No. 7)

On October 4, 2021, the Tax Court issued its opinion in Leyh v. Commissioner, 157 T.C. No. 7. The primary issue presented in Leyh was whether the petitioner was entitled to deduct, as alimony, an amount equal to the premiums paid to provide health insurance coverage for his then spouse Held:  Yes, sir. Background to Leyh v. Commissioner In 2012, the petitioner in Leyh v. Commissioner, Mr. Leyh, filed for divorce from his then wife, Ms.

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Procedural Issues
Full Tax Court Opinions

Rogers v. Commissioner (157 T.C. No. 3)

On August 2, 2021, the Tax Court issued its opinion in Rogers v. Commissioner, 157 T.C. No. 3. The primary issue presented in Rogers was whether the IRS Whistleblower Office abused its discretion when it rejected/denied the petitioner’s claim. Held: Oh yeah. Side Note One of the attorneys for the IRS is named Bartholomew Cirenza.  There’s a fair to middling chance that he has been given more swirlies, wedgies, and other sundry childhood punishments than

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Procedural Issues
Full Tax Court Opinions

Stein v. Commissioner (156 T.C. No. 11)

On June 17, 2021, the Tax Court issued its opinion in Stein v. Commissioner, 156 T.C. No. 11. The primary issue presented in Stein was whether the Tax Court has discretion to grant the petitioners’ motion to dismiss a stand-alone petition for recovery of administrative costs when the petition did not invoke the Tax Court’s jurisdiction to redetermine a deficiency under IRC § 6213(a). Factual Background The petitioners filed an application for the award of

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Business Related Issues

Mylan Inc. v. Commissioner (156 T.C. No. 10)

On April 27, 2021, the Tax Court issued its opinion in Mylan, Inc. v. Commissioner, 156 T.C. No. 10. The underlying issues presented in Mylan, Inc. were (1) whether the legal expenses incurred in preparing notice letters to brand name drug companies of petitioner’s intent to make generic versions of its drugs as part of the FDA approval process to do the same were capital or ordinary expenses; and (2) whether the legal expenses incurred

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Business Related Issues

De Los Santos v. Commissioner (156 T.C. No. 9)

On April 12, 2021, the Tax Court issued its opinion in De Los Santos v. Commissioner, 156 T.C. No. 9. The underlying issue presented in De Los Santos was whether the benefits (a split-dollar life insurance arrangement) received by the petitioners were received in their capacity as employees or shareholders, and, in turn, whether such economic benefits or taxable to the petitioner’s as ordinary compensation income or as a distribution under IRC § 301. The

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Procedural Issues
Full Tax Court Opinions

Rowen v. Commissioner (156 T.C. No. 8)

On March 30, 2021, the Tax Court issued its opinion in Rowen v. Commissioner, 156 T.C. No. 8. The underlying issue presented in Rowen was whether the IRS’s certification of the petitioner’s tax debt as “seriously delinquent” violated the Fifth Amendment and his basic human rights, because it infringed on his right to international travel. Background For more than two decades the petitioner avoided paying his taxes.  The opinion notes that the petitioner “failed” to

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Procedural Issues
Full Tax Court Opinions

Mainstay Business Solutions v. Commissioner (156 T.C. No. 7)

On March 4, 2021, the Tax Court issued its opinion in Mainstay Business Solutions v. Commissioner, 156 T.C. No. 7. The underlying issue presented in Mainstay Business Solutions was whether the Tax Court has the discretion to allow a petitioner to withdraw a petition when the petitioner did not invoke the Tax Court’s jurisdiction to redetermine a deficiency. Context I am a bit delinquent in my summaries. Mea culpa. Nonetheless, at the time of writing

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McCrory v. Commissioner (T.C. Memo. 2021-116)

On October 4, 2021, the Tax Court issued a Memorandum Opinion in the case of McCrory v. Commissioner (T.C. Memo. 2021-116). The primary issue presented in McCrory was whether the IRS Whistleblower Office’s rejections of the petitioner’s claims were unsupported by the administrative record and were arbitrary, capricious, an abuse

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Gregory v. Commissioner (T.C. Memo. 2021-115)

On September 29, 2021, the Tax Court issued a Memorandum Opinion in the case of Gregory v. Commissioner (T.C. Memo. 2021-115). The primary issue presented in Gregory was whether the claimed deductions permitted under IRC § 183(b) for activities not engaged in for profit are not subject to the 2%

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A Primer on Employment Tax Withholding

When the IRS is involved, monetary transactions are never as simple as they appear on the surface. The late, great comedian Mitch Hedberg once told a story about being given a receipt after buying a doughnut. I bought a doughnut, and they gave me a receipt for the doughnut. I

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Clark v. Commissioner (T.C. Memo. 2021-114)

On September 28, 2021, the Tax Court issued a Memorandum Opinion in the case of Clark v. Commissioner (T.C. Memo. 2021-114). The primary issue presented in Clark was whether the petitioner fraudulently underreported his income. Held:  Oh, dear God.  The fraud! The Tax Court’s Summary of the Issue in Clark

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Whistleblower 14377-16W v. Commissioner (T.C. Memo. 2021-113)

On September 27, 2021, the Tax Court issued a Memorandum Opinion in the case of Whistleblower 14377-16W v. Commissioner (T.C. Memo. 2021-113). The primary issues presented in Whistleblower 14377-16W were whether the whistleblower could proceed anonymously, and whether the WBO abused its discretion in denying the whistleblower-petitioner an award. Held:

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Brown v. Commissioner (T.C. Memo. 2021-112)

On September 23, 2021, the Tax Court issued a Memorandum Opinion in the case of Brown v. Commissioner (T.C. Memo. 2021-112). The sole issue presented in Brown was whether the Tax Court has jurisdiction to order the refund of a TIPRA payment. What is a TIPRA Payment? The Tax Increase

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