Loopholes Archives - Page 9 of 19 - Think Outside the Tax Box
By Peter J Reilly CPA

When Debts Go Bad: The Challenges of Deducting Delinquent Debts

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.

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Maybe That Trust Really is Defective

There are times when I really would like to know the story behind the story. And that is the case with CCA 202352018. The only good thing about not knowing the story behind the story is that I get to make one up. The CCA is about one of the funniest oxymorons in the tax field. It concerns an intentionally defective grantor trust (IDGT). That is serious competition for my favorite tax oxymoron – passive activities. Let’s start out with some background on IDGT. This piece is mainly for the income tax preparers who have to deal with the implications of this fancy planning rather than the fancy planners.

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TAX COURT ROUNDUP – APRIL 2024

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.

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Crypto Gains and Tax Court Games: Exploring the “Unclean Hands” Defense

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.

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TAX COURT ROUNDUP – MARCH 2024

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.

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TAX COURT ROUNDUP – FEBRUARY 2024

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.

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The Constitution for Tax Pros

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.

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TAX COURT ROUNDUP – JANUARY 2024

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.

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TAX COURT ROUNDUP – DECEMBER 2023

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.

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