Craziest Tax Write-Offs

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There have been a couple of completely ridiculous claims in this arena, like the man who tried to deduct money spent on his mistress as a business expense. There is another story about a man whose accountant asked him and his wife about the mortgage interest deduction on their condo in Utah. The deduction was legitimate, but his wife didn’t know about the condo—where he’d set up his mistress. It may have been the last time they filed a joint return.

I’ve got another one for you. The Academy Awards are coming up next week and one thing most movie stars have in common is that they aren’t hard to look at. A lot of aspiring actors and actresses are tempted to write off plastic surgery, but just because you incur an expense for business reasons doesn’t mean it qualifies as a deduction. Cosmetic surgery is generally not deductible because it’s for aesthetic reasons. To qualify as a medical deduction, the procedure must be medically necessary, meaning it was prescribed by a physician. So a nose job could qualify IF you are repairing a deviated septum. Remember, all your medical expenses, including any allowable plastic surgeries, must come to more than 7.5% of your adjusted gross income before you can claim them.

To qualify as a business expense, you have to prove the surgery is related to your job performance, and there is one infamous case of plastic surgery satisfying this requirement. Do you want to hear about it? It involves an exotic dancer with the stage name “Chesty Love.”

What’s the story?

She had her breasts augmented to a 56 FF and then a 56 N. After the IRS ruled that her surgeries were personal expenses, she appealed, citing her surge in income post surgery. Four years after she filed, a judge eventually ruled that the implants could be deducted, comparing them to work clothes and uniforms, which are allowable only if they satisfy a two-step test: (1) required as a condition of employment and (2) unsuitable for everyday use. Considering Chesty Love’s new assets weighed in at ten pounds apiece and she would have taken them “off” after work if possible, they were considered “props” that could, in fact, be deducted.

A young Amish man deducted his buggy. At first blush, this seems to be a completely legitimate write-off… It’s for business purposes. But the accountant looked closer and saw that the buggy had been outfitted with velvet interior, kick plates, dash lights, tinted windshield, speedometer, hydraulic brakes and dimmer switches! This Amish boy had completely pimped his buggy, spending over $3,500 instead of the average of about $2,700. Anyway, the accountant ended up allowing him to deduct a portion of the buggy.

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