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Everything you never thought you’d read about 📽️ Celeb Tax Cases, but here you are.
Martha Stewart’s Tax Troubles: When Good Things Go to Prison (And What We Can Learn)
📽️ Celeb Tax Cases
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November 20, 2025
TaxStache Team
Martha Stewart didn’t go to prison for insider trading or tax evasion. She went for lying to investigators about a stock sale. Her case is a reminder that trading patterns attract government scrutiny and that honest, accurate reporting is always your safest tax strategy.
Tigers, Tattoos, and Taxes: The Mike Tyson Story
📽️ Celeb Tax Cases
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November 20, 2025
TaxStache Team
For most of his career, Mike Tyson's earnings were astronomical. Until the IRS caught up with him and it became a tragic race to the bottom.
I’m Your Huckleberry … And I Owe the IRS: The Val Kilmer Story
📽️ Celeb Tax Cases
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November 20, 2025
TaxStache Team
Val Kilmer has been many things. But reality has a funny way of catching up to even the coolest people on the planet. And there is no institution on Earth more reliably, relentlessly real than the IRS.
Outwit, Outplay, Outlast … the IRS? Not So Much.
📽️ Celeb Tax Cases
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November 16, 2025
TaxStache Team
Richard Hatch played Survivor brilliantly and became the first winner of the show. Later on, he faced a new opponent, one that didn't care so much about reality TV: the Internal Revenue Service.
The IRS Over the Rainbow: How Judy Garland Lost Her Fortune
📽️ Celeb Tax Cases
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October 31, 2025
TaxStache Team
Judy Garland dazzled onstage, but offstage, the IRS had front-row seats to her financial unraveling.
The Queen of Mean Meets Mr. IRS: Leona Helmsley’s Very Expensive Home Makeover
📽️ Celeb Tax Cases
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October 20, 2025
TaxStache Team
Leona Helmsley didn't just flirt with creative accounting; she tried to marry it, which, as the IRS is fond of pointing out, is bigamy.
Abs of Steel, Receipts of Lies: The Situation vs. The IRS
📽️ Celeb Tax Cases
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September 26, 2025
TaxStache Team
Learn how Mike "The Situation" Sorrentino's multimillion-dollar "Jersey Shore" empire led to a conviction for tax evasion and an 8-month prison sentence.
National Treasure, International Tax Disaster: The IRS vs. Nicolas Cage
📽️ Celeb Tax Cases
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September 19, 2025
TaxStache Team
Once one of Hollywood's highest-paid actors, Nicolas Cage's eccentric spending spree led to a staggering $14 million IRS debt and a frantic career sprint to regain solvency.