1962. It was the only year in which JFK was president for the whole entire year. World events impinged on my family. My older brother served onboard an aircraft carrier chasing Soviet submarines and when not recovering Mercury astronauts, had his four-year enlistment extended to five. Somehow the bright fourth grader that I was, I missed the story of the dramatic raid by the Philippines National Bureau of Investigation on March 3, 1962. According to reporter, Amando Doronila, who covered the raid, 200 agents seized 35 truckloads of documents from 27 offices and corporations controlled by American expatriate Harry Stonehill.

Why should we care? Believe it or not, the implications of that March 3, 1962, raid are still being litigated in the United States. Read on to learn more!

The story of Scott M. Hoensheid’s charitable planning gone awry as related by Judge Joseph W. Nega of the United States Tax Court is an interesting one.

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There was a recent IRS memo from an associate chief counsel that should be shocking but actually isn’t. Promoters have for many years been hawking a “copyrighted non-grantor irrevocable complex discretionary spendthrift trust,” which purported to avoid capital gains tax. You could learn about it on TikTok. It “worked” by citing Section 643(a)(3), which excludes capital gains allocable to corpus from distributable net income. You and I both know that DNI is not taxable income, but not everybody who learns the tax law from TikTok has caught onto that subtle point yet.

Although I have never encountered anything as egregious as the “copyrighted, etc, etc, trust” I have seen a lot of problems with trusts over the years (and partnerships and SALT – don’t get me started). Much of it has to do with working under a lot of pressure. Often, the things that are wrong end up not mattering all that much, but I get a little frightened, because maybe one of these days the IRS is going to start getting its act back together. If it does, I think things may be a little shocking to practitioners who have grown up in an environment where enforcement has been progressively gutted.

Judge Mark Holmes of the United States Tax Court expressed admiration for the achievements of Joseph G. Bucci Sr. whose American Rock Salt provides the salt to keep many of the streets in the Northeast passable in the winter. You can learn a bit about that from an interview in New York by Adriane Quinlan . The positive remarks were no help in the ultimate result. Judge Holmes agreed with the IRS that Bucci’s three side hustles — a real estate enterprise, a farm, and some racing horses — were “Activities not engaged in for profit” making losses unallowable. The total tab including accuracy penalties for 2016 and 2017 was $711,980. Judge Holmes explained the result in a bench opinion, which is less formal than a memo decision. The trial began in Buffalo on June 14, 2023.

Section 183, which limits or entirely eliminates deductions attributable to activities not entered into for profit, may be coming in for more attention from an invigorated IRS. Section 183 is commonly referred to, not without reason, as the hobby loss rule. Based on my extensive study of the case law, I believe that practitioners widely misunderstand 183. I have noted cases where taxpayers had not gotten a heads up from their adviser. More commonly there is a misunderstanding of 183(d), a presumption in favor of taxpayers that is rarely relevant at all, but which the agency can never use against them. Most important is the failure to appreciate that it is the objective of making a profit not the expectation that is necessary. With that in mind here are the most recent developments…

In the last few months, I have been getting “seems like old times” feeling as interest rates rise. They remain laughably low by the standards of my early days in the business. I can remember prime being 20%. And then there are all these issues with office rentals thanks to the aftermath of the plague.

One of the nice things about a career in accounting is that while you are affected by business cycles the need for our work is somewhat continuous. I’m thinking that now might be a good time to get ahead of the curve a little and study up on a Code Section that may be coming up a lot more – Code Section 108 – Income from discharge of indebtedness. Fortunately, a recent Tax Court opinion in the case of Michael G. and Julie A. Parker can provide us with a lesson in some of the important principles in this area.

If you build a mini business empire and it subsequently fails, a small consolation prize might be a net operating loss carryover that will shelter some or all of your more modest income for many years. Of course NOLs are only one among many carryovers that need tracking. In my experience the tracking often leaves much to be desired. Changes in tax preparers or even software can result in the loss of valuable carryovers. But that is not the worst of it…

If you were to ask most taxpayers what they worry about when it comes to their tax returns, they might say an unexpectedly high tax liability or even a late penalty. Next to none will worry they are at risk for criminal prosecution. There is a sound reason for this. In the fiscal year ending September 30, 2021, taxpayers filed over 261,000,000 tax returns. During that same period, IRS Criminal Investigation (CI) initiated only 2,581 investigations—a paltry 0.00098% of all tax returns filed. While CI entanglements are not a common experience, there are still lessons to be learned from looking at how things can go awry.

So what types of scenarios have resulted in criminal investigations by the IRS, and what can this teach the everyday taxpayer? First of all, working with an expert, such as a Certified Tax Planner, will help you better understand what is permissible by the IRS and reassure you that your returns are fraud-free. For a few tips on what not to do, read the cases below and review our key takeaways for each one.

The laws of tax planning that I developed over my writing career that will be expounded in the upcoming Reilly’s Laws of Tax Planning, published by Think Outside the Tax Box, lean a little on the conservative side, as tax planners use the term – conservative versus aggressive, not conservative versus liberal. This results, in large part, from their primary source being court decisions.
The 18th law stands out from the others in this regard. “Honest objective trumps realistic expectation” encourages practitioners to be somewhat more aggressive in claiming losses from activities that seem a little dubious . I still hold that view, even though there have been no encouraging developments in 2023. Here is a roundup on the action last year through December 2, 2023.

The story of James J. Maggard has some interesting and possibly valuable lessons. The one that strikes me as particularly important is that it makes it crystal clear that disproportionate distributions contrary to a corporation’s governing documents will not blow its S election. That does not mean that disproportionate distributions are just fine and that you don’t need to address them. There is a practical lesson about being careful who you take on as fellow shareholders. And there is another slightly odd lesson, that almost makes me want to create a new law of tax planning: Don’t deliberately involve the IRS in your business disputes. Their job is not to help you.