Today in Tax Court

By: Roger Ledbetter
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  • Summary

  • 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.
    Copyright 2023 All rights reserved.
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Economics
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Episodes
  • Episode 13 - Cantor Fitzgerald v. Commissioner

    Episode 13 - Cantor Fitzgerald v. Commissioner
    Mar 12 2025

    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 income.
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    31 mins
  • Episode 12 - Hubert Ent. v. Commissioner

    Episode 12 - Hubert Ent. v. Commissioner
    Feb 21 2025

    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!
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    33 mins
  • Episode 11 - Weston v. Commissioner

    Episode 11 - Weston v. Commissioner
    Feb 14 2025

    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 deductions as basis or losses in later years.

    A great episode on where and how business expenses can and should be deducted. Enjoy!
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    29 mins

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