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😮 Wacky Tax Tales
April 6, 2026
The Taxman Doesn’t Judge: A Lesson From a Brothel Owner
If you ever find yourself with a free weekend and a high tolerance for tedium, try picking up the Internal Revenue Code. It is a
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😮 Wacky Tax Tales
March 30, 2026
The Drug Dealer Wrote Off His Scale, and Congress Got a Headache
It is a well-established fact that the Internal Revenue Service is not particularly sentimental about the source of your income. They taxed Al Capone for
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😮 Wacky Tax Tales
March 15, 2026
What Happens in Vegas, Gets Disallowed by the IRS: The Sanford Case
J.P. Sanford, a Texas attorney, went to Las Vegas in 1962 with a plan. He believed he had a system to turn the game of
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😮 Wacky Tax Tales
February 6, 2026
The Case of the Missing Signature: When “I Do” Also Means “You Owe.”
The Burton's went to Tax Court over a disagreement over federal tax law. Burton, finding himself in the unenviable position of having a completed tax
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😮 Wacky Tax Tales
January 24, 2026
Beefing with the IRS
A Wisconsin bodybuilder tried to deduct three pounds of buffalo meat a day as “business fuel.” The IRS said no. The Tax Court agreed. You
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😮 Wacky Tax Tales
January 19, 2026
Can You Deduct Cat Food as a Business Expense? A Strange, True Story
Samuel and Carol Seawright owned a 42-acre junkyard in South Carolina, a sprawling kingdom of scrap metal. However, their most significant business challenge wasn't rust,
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😮 Wacky Tax Tales
December 22, 2025
John Daly’s $57 Million Lesson: When Good Tax Records Meet Bad Decisions
John Daly was known as a colorful PGA golfer. What many might not realize is that he also was an avid gambler, and learned a
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😮 Wacky Tax Tales
November 19, 2025
How Bitcoin Jesus Tried to Ghost the IRS
Roger Ver had a really good run, until he ran straight into the IRS. Bitcoin Jesus forgot all about his "exit tax" when he tried
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😮 Wacky Tax Tales
November 8, 2025
The Case of the Ambitious Nurse and the IRS
Most of us have had that thought: "If I just got another degree, I could be better at my job." A nurse from Maryland, had
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