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The Five Greatest Tax Write-Offs of All Time

tax write off

The annual day of financial reckoning has arrived: it’s tax day.

And in honor of this yearly government-sanctioned fleecing, we’d like to applaud those intrepid few who’ve stuck it to the man—and wound up with a free swimming pool out of the deal, or recouped a $50,000 night of making it rain—by rehashing some of history’s most ingenious write-offs and how they turned out. So without further ado, we present to you:

The five greatest tax write-offs of all time.

pool tax write off The Deduction: A $4,000 swimming pool. The Reasoning: Ken Cherry’s doctors advised him to take up swimming to improve his health. So he built an indoor pool. The Verdict: It was found that his health did improve drastically and that the pool was used almost strictly for treating his ailments, so this healthcare write-off was approved.

Drake-Making-It-Rain-02 The Deduction: A $50,000 trip to the strip club. The Reasoning: We all know and love the rapper Drake. One night, he made a very public appearance at a strip club with 50 grand in cash and proceeded to “make it rain.” For all intents and purposes, it was an “advertising and publicity” expense. The Verdict: Because of Drake’s celebrity status, he can actually claim this on his taxes. (And we can assume he did.)

Medical_Marijuana The Deduction: 100 pounds of marijuana. The Reasoning: After getting the Al Capone treatment from his criminal dealings as a drug trafficker, Jeffrey Edmondson was facing prison and $17,000 in unreported wages. Until he reported them—with deductions for a home office, travel expenses and purchasing products (drugs) to sell. The Verdict: He’d been found guilty of the drug dealing, but it ended up clearing his name on the tax front. Sadly, this loophole has since been closed.

implants The Deduction: Breast implants. The Reasoning: Cynthia Hess, better known as “Chesty Love” on stage, claimed that her 56FF breasts were not enlarged for cosmetic purposes (she cited their outrageous size as a source of ridicule), but solely practical within the scope of her work. The Verdict: She triumphantly revealed her successful write-off on The Jerry Springer Show.

fullscreen_pc The Deduction: $10,000 in gambling losses. The Reasoning: Robert Mayo claimed that he spent so much time and money gambling, it could be legitimately considered his part-time profession. The Verdict: The courts agreed that he could claim “gambler” as a profession—and allowed him to write off the losses (as long as he didn't splash the pot).


  • Najib Benouar