Loopholes Archives - Think Outside the Tax Box


By Peter J Reilly CPA

Poor Tax Judgement Turns Junk Call Gold into Lead

Everything becomes a tax story eventually. That is what provides me with a lot of "I was today years old" experiences as tax stories are the one thing that I follow religiously. So I first learned about the field of Telephone Consumer Protection Act (TCPA) litigation from reading the proposed findings and recommended dispositions in the case of Ruben Escano v. Innovative Financial Partners LLC and Josh Benson. Innovative Financial Partners is a subsidiary of Humana.



What one Judge called "the wrinkled skin of tax law" is on display in US Tax Court again. This month was a technician's bento box, a variety.

Read More

2024 Summer Education Series Event Calendar

We are so excited to announce the 2024 Summer Education Series! All summer long we will be bringing our loyal subscribers monthly webinars featuring some of the brightest minds in tax. 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...

Read More

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.

Read More


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.

Read More

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.

Read More


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.

Read More


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.

Read More

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.

Read More
1 2 3 9


  • Scroll to Top

    Thank you for subscribing to Tax Law Pro

    You are granted a non-exclusive, non-transferable, revocable license to access and use Tax Law Pro by Think Outside the Tax Box, Inc., strictly according to these terms of use.