Today in Tax Court

Mar 28 2025 14 ep. 29 mins 6
Today in Tax Court Podcast artwork

Come for the stories, stay for the alpha. I read recent Tax Court cases and summarize them to share thoughts on: how the IRS thinks about taxes, relevant tax law, historical court cases you should know about.

  Business
RSS feed Share
Copy RSS


Subscribe on Podcast Addict


Episode 14 - Nwafor v. Commissioner

Mar 28 2025 23 mins  
Midwit meme meets Tax Court. How a taxpayer used one-sided journal entries to reduce income and inflate expenses to the tune of $200,000+. bUt ThE wOrK iS wOrTh sO MuCh mOrE! is a common reply when I tell people they can't write off X, Y, or Z as "donations" when they didn't pay tax on the income.

Episode 13 - Cantor Fitzgerald v. Commissioner

Mar 12 2025 30 mins  
After the 9/11 Terror Attacks, millions of dollars in business aid flowed from various government agencies. This case walks us through some of the more common arguments of what is taxable and not taxable income - even when it was in the form of disaster relief grants. We also work through some of the other common types of ways people receive cash but don't have to include it in inc

Episode 12 - Hubert Ent. v. Commissioner

Feb 21 2025 33 mins  
Did someone say HoldCo? What happens when your HoldCo crushes it and now you want money out of it? If it's a C-Corp it's tricky. Today's case walks through to common issues: - Getting money out without being double taxed - Shielding income via accelerated depreciation Have a listen and enjoy!

Episode 11 - Weston v. Commissioner

Feb 14 2025 28 mins  
The Tax Court refuses to subsidize "poor investment decisions" of the taxpayer. When Mr. Weston invested $2.1 million of his own life savings into real estate in Indiana that went belly-up, he takes a buckshot approach to try to deduct it. (1) Business Expense (2) Business Loss (Worthless) (3) Theft All fell on deaf ears of the Court and Mr. Weston got stuck having to delay the ded

Episode 10 - Langlois v. Commissioner

Feb 07 2025 18 mins  
2 for the price of 1 - Langlois v. Commissioner and Clark v. Commissioner Langlois was a power line worker who dabbled in landscaping and a hair salon side hustles. But the IRS disallowed like $100,000 in deductions for essentially bad recordkeeping. Clark was a movie memorabilia seller who tried to sneak one past the IRS by not paying self employment tax on his income. It didn't w

Episode 9 - Ogden v. Commissioner

Jan 31 2025 22 mins  
One of my favorite topics - Operating Agreement tax allocation language! Maybe one of the biggest things to get right when talking about partnership tax returns is the allocation of income and loss. It's not as straight forward as many think it is. In Ogden v. Commissioner (from 1985), the taxpayer had the majority of her loss taken away after the Court saw the operating agreement

Episode 8 - Franklin v. Commissioner

Jan 23 2025 19 mins  
A sheriff in Alabama gets caught "embezzling" from inmate food funds. But the argument is made that she only made a bad investment (she did) - and she avoids paying tax on the majority of the money taken. A wild story with few twists and turns - enjoy!

Episode 7 - Sehati v. Commissioner

Jan 17 2025 28 mins  
A desperate LinkedIn accounting job posting + a 40 year old treasure box + mall kiosks = a wild story. This case highlights how IRS auditors approach auditing small businesses, and what not to tell an IRS agent to get every entity in the org. chart audited. It winds up with a $3.8 million income hit to the taxpayers.

Episode 6 - Gregory v. Helvering

Jan 09 2025 24 mins  
Our first landmark court case to review: the Business Purpose Doctrine. Gregory set up a separate company and shifted assets just to avoid tax. This case is commonly referenced in tax court cases dealing with entity and transaction structuring. We also run through other types of "grey areas" like sale-leasebacks, contingent liability planning, and TICs.

Episode 5 - Hutcheson v. Commissioner

Jan 02 2025 21 mins  
A retirement plan fiduciary embezzles $5 million of other people's retirement assets. He wastes it on home renovations, cars, Costco trips, and trying to buy a golf course. He gets convicted of wire fraud and sentenced to jail - but now has a $3.7 million tax bill he is fighting. We cover the backstory and what kind of income is taxable and not.