Loopholes

Dealing with deficiency and restitution in a tax evasion case is a minefield, but there's a good example of how it's done this month. There's architecture, both additional research credits for buildings and software in discovery. There are the fine points of the innocent spouse checklist, Rev. Proc. 2013-34. Two common deductions, home office and hobby losses, get reexamined. Cryptocurrency staking is taxed. A brilliant move earns a much-belated refund of an enhanced accuracy penalty. And the scoresheet in the Boechler jurisdiction-vs-claim-processing gets a new entry.

The Jeffrey Winick tax story is about one of the simplest methods of not paying taxes. That simple method of not paying is simply not paying. Winick is a very successful real estate broker specializing in retail leases. The company he founded, Winick Realty (now rebranded RTL), has in the past been listed as one the top five of retail brokers in New York City. As far as my friend Grok can discern, Winick managed all this with no formal education beyond high school. That makes it extra impressive. I identify with him just a bit. He grew up in Kew Gardens Hill, Queens, New York, and is 75 years old. I also grew up not far from Manhattan and am 74. I sometimes fantasize about living in Manhattan. He's living there, and apparently he was really living. His lifestyle was a major topic in the litigation.

I'm almost nostalgic for the days of 2021-2022, the COVID-induced tsunami of Tax Court filings and cases. This month we've seen only eight T. C. Memos, of which two were routine undocumented deduction cases (Section 6001 or Section 274), no Sum. Ops, and no T. C.s. It's been years since practitioners murmured the old, nearly-forgotten slogan as they booked their summer vacations: "File in May and go away," but it may be time again. Here's what happened.

It is painful when you finally realize that the money you expected to be repaid is never coming back. The tiny silver lining in that cloud might be the tax benefit of “writing off” the debt. Unfortunately, that silver lining may well be eclipsed by an even bigger cloud. Writing bad debt off is not that easy, and there’s probably no silver lining to that cloud. Ironically, you might find that the mistakes that caused you to be holding a bad debt might be what prevents you from getting a usable deduction.

Tax professionals are inundated with tax developments from all branches of the government and from all levels of government on a daily basis. Our technical tax knowledge expands weekly. Given the immensity of tax law changes in P.L. 119-21 (July 4, 2025), informally named the One Big Beautiful Bill Act (OBBBA), and the guidance we’ll continue to get over the next few years along with non-OBBBA updates, we might run out of time and bandwidth to step back and ask what additional relevance this guidance, as well as various reports issued by the government every day, mean for the well-being of our tax system. This article unpacks select tax law changes and government documents to offer four subtle messages within them. Generally, the messages don’t bode well for an effective tax and revenue system. The article ends with some suggestions on what can help improve our tax system.

The Fifth Circuit Court of Appeals opinion in Sirius Solutions L.L.L.P. v. Commissioner may change our views of entity choice. If the decision holds up, partnerships will be able to effectively make the portion of limited partner income subject to self-employment tax whatever they want, including zero. This contrasts with the IRS position upheld by the Tax Court in Soroban Capital that treated all of the income of limited partners who were active in the business as self-employment income.

April brings both anomalies and the same-old from Tax Court. Congressional enactments that misfire give opportunities to inventive practitioners, while self-represented petitioners continue to do the darndest things. All these are teaching moments that make "the small court" a continuing professional education course that never ends.

Think Outside the Tax Box is thrilled to bring you the 2026 Summer Education Series, sponsored by Sandy Bay! The fifth installment of this beloved annual series, we will be bringing our loyal subscribers monthly webinars featuring some of the brightest minds in tax all summer long. Each webinar will feature our usual blend of high-quality education and entertainment and include continuing education credits for those who qualify. All of this is included in your regular subscription! Continue reading to see what we have in store...