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4 bizarre ways people avoided paying taxes

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January 14, 2020 By Stacey Bumpus

One way or another, most Americans are expected to pay taxes. Tax avoidance might be legal, but tax evasion constitutes a serious crime. Do it, and you’ll likely end up paying a tax penalty.

So, how to not pay taxes legally? It turns out that you can avoid paying taxes if you understand some of the ins and outs of the tax code. And in many cases, some Americans have turned not paying taxes into something of an art form, securing deductions for things that would normally seem entirely off-limits. So, here are some pretty novel ideas for how not to pay taxes:

1. Drunken driver turns DUI into tax deduction

Some people have all the luck — or incredible persistence. Justin Rohrs managed to slide his truck off an embankment in 2005, only to be slapped with a DUI for driving intoxicated. Despite the circumstance under which his car was damaged, he decided to file an insurance claim for his truck for $33,629. After his insurer denied his claim, he attempted to claim his vehicle loss as a tax deduction.

At first, the IRS wasn’t having any of it. Rohrs took the matter to the U.S. Tax Court, claiming that he deserved a casualty loss deduction for his damaged truck. Shockingly, the judge agreed and allowed him to take the deduction.

2. Cats can be worth big money

Jan Van Dusen, a cat lover with more than 70 felines in her home, spent much of her time caring for strays she found in the wild. In some instances, after caring for the cats, she’d release them back into the wild. But more often than not, she fostered her furry friends and tried to find good homes for them.

The cost of caring for the cats began to mount for Van Dusen, so when she filed her 2004 tax return, she tried to write off $12,068 for cat-rescue items like food, vet bills, paper towels and more. After the IRS informed her that those expenses counted as personal ones and she couldn’t deduct them, she sued the IRS. Following a long battle, Van Dusen proved her cat care was charity, resulting in the IRS finally granting deductions for most of her claims.

3. Exotic dancer’s breast implants pay for themselves

Cynthia Hess, also known by her stage name Tonda Marie, was an exotic dancer who wanted to improve her business. In other words, she wanted bigger breasts. After getting a breast-enlargement procedure done, her business grew — along with the jump in her bra size to a 56FF.

Hess, now known as Chesty Love, decided to deduct her implants as a business expense. The IRS turned down her request, stating that business deductions work only in circumstances that are ordinary and necessary.

Hess sued the IRS, arguing that her new breasts should be considered a business uniform. She went on to say that she planned to have them removed immediately after retiring from exotic dancing. After much convincing, the tax court agreed that she would have added breasts that large only for business purposes — they were 10 pounds each — and decided to grant the deduction.

4. Even drug dealers get tax deductions

Drug dealer Jeffrey Edmondson could teach classes on how to avoid paying taxes legally. He got himself in trouble with the law after being busted and charged with drug trafficking. Eager to get even more out of the dealer, the IRS audited him for $17,000 in back taxes after he failed to declare his income from drug dealing.

Edmondson decided the government wouldn’t have the last laugh. Leading up to his trial, he filed a tax return that listed his taxable net income along with a list of business deductions. He left his occupation blank, of course. After looking at his return, the IRS turned down his deductions. But Edmondson was not ready to give up.

He took the matter to Tax Court, where he claimed he’d established a home business and wanted to claim home-office deductions — including drugs. Surprisingly, the judge agreed to allow him to deduct his expenses, which included a $50 scale, more than 19,000 miles in business mileage on his car and 100 pounds of marijuana.


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