Loopholes

Tax Court concludes tax season this year with a webinar on Practical Perspectives on Discovery, chaired by Judge Greaves, on April 16, 11:00 a.m. Eastern. With all the discovery jousting accompanying conservation easements and other high-dollar litigation, this is a must for all practitioners, so I'm headlining it. Information and registration on the Tax Court website.

Baseball, apple pie, and finding creative ways to pay fewer taxes, is there anything more American? Judge Learned Hand famously said in 1934, “Any one may so arrange his affairs that his taxes shall be as low as possible; he is not bound to choose that pattern which will best pay the Treasury; there is not even a patriotic duty to increase one’s taxes.” Since the inception of the Federal Income Tax, taxpayers have looked for increasingly creative ways to avoid it. This exploration is no different: A taxpayer attempts to wash his hands of his tax liability all together.

February was Discovery Month at Tax Court. The high-deficiency, high-profile conservation easement cases coming from IRS crackdown put a premium on the old continuing legal education staple "win your case at discovery." But it doesn't go so well for shotgun demands, nor for broad-spectrum claims of privilege. Of course, more was resolved than just discovery disputes, but I'll get to those.

New year, new rules, the changing features of United States Tax Court practice and procedure confront the tax practitioner (even those who don't practice in Tax Court themselves), who must keep current among all the demands on our time, especially as the season opens. Let's jump in.

A case currently before the Supreme Court, Charles Moore, G. Moore et ux. v. United States , has the court looking at some of the fundamentals of the Constitution’s treatment of taxation. Advocates of various views are hoping for an earthshaking result. Also, many “tax protester” arguments base themselves on misreading of Supreme Court decisions from around the time of the 16th Amendment. Knowing a fuller version of what surrounds the snippets they feed you probably won’t help you bring them around if they have drunk deep of the tax protester Kool-Aid, but it will help you maintain your own sanity. Let’s start with what the Moore case is about.

The last month of 2023 featured more technical expositions than policy discussion. Practitioners will find insights worth their time. Generalists shouldn't overlook some nuggets here. As always, Tax Court sees and deals with more varieties of income taxation than any other court.

Despite the five days off for the two Federal holidays this month, there's plenty from Tax Court, for both specialists and general practitioners. No other Court gets as deep into the "wrinkled skin" of US tax law. As always, there's something for (almost) everyone.

Coming up on the end of the year, year end planning is kind of a ritual for me. I take my first pass in early November and will do it again no later than December. It is pretty boring. I thought it would be worthwhile to do a survey of a variety of year end tips articles. What is going on here is something like Ahab’s hunt for the great white whale. I am looking for something to help out HENRY. HENRY stands for High Earnings Not Rich Yet. I wrote about the quest in 2019. I found nothing much for HENRY then, and this year’s batch of advice articles really does not offer much. The articles do not all say exactly the same thing, but there is a lot of commonality. Due to the sophisticated nature of the readership of TOTTB, I will just allude to the tips, not explain them in detail, because I am going someplace else with this. There is nothing dramatic for HENRY coming from conventional advisers, which accounts for HENRY’s vulnerability to sketchy tax shelters. I will share a bit about what I have seen in that department and reflect a bit.