6

A Cat Lady Deducts Her 70 Cats as a Charity

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Reclusive cat enthusiast Jan Van Dusen enjoys the felines. In fact, she would go out of her way to capture random feral cats on the street and care for them in her home, to the point that she was caring for 70-plus cats at one time. After treating them for any injuries they had sustained, sometimes she would release them back into the wild. Other times (70 other times, to be precise), she wouldn't.

As one would imagine, caring for a large pride of stray animals racked up some serious costs. For her 2004 tax return, Van Dusen tried to write off $12,068 for all her cat "rescue" items like cat food, vet bills, paper towels and other supplies.

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Pictured: Other supplies.

5

A Corrupt Businessman Deducts His Illegal Bribes

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4

Robert Mayo Writes Off Gambling Losses

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If there are two things we've learned from watching gambling movies like Casino, it's never play in a casino when Pesci or DeNiro runs it, and that the house always wins. Gambling never ends well for the vast majority of people who do it, and when they keep giving you free drinks, you should take that as a sign that they just want to take advantage of you. As a result, you would think that no one at any level of government would feel sorry for you for blowing your paycheck down at the track.

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Although they use similar methods as casinos when you owe them money.

But in 2001, gambler Robert Mayo bet $131,760 on horse racing and collected $120,463 on his wagers. So he wound up in the hole. Naturally, on his tax returns for the year he listed $10,968 in expenses for travel to the racetracks, research and "handicapping information."

It seems like a ballsy move to challenge the IRS after you lost in Vegas, because the odds of beating the IRS are bigger than even Vegas would touch. However, a decade later, the court ruled with Mayo, saying that these were not gambling losses, but business expenses. This was a very important case, as it deemed on a federal level that being a professional gambler is an actual job.

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That's the sound of a thousand people quitting their real jobs and quickly becoming professional homeless people.

3

An Exotic Dancer Deducts Her Breast Implants

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People who say it's what's on the inside that counts probably don't work as strippers. Just look at the case of Cynthia Hess, better known by her stage name, "Tonda Marie." While she made money as an exotic dancer, she made less than other dancers due to her "hereditary deficiency," which was her way of saying she had average-sized boobs. In the competitive environment of taking your shirt off in front of horny guys, average doesn't cut it. So Tonda decided to get breast implants to make a better living. What does she go for? A good handful of C cups? Double D's? Try 56 FF.

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How does she use seat belts?

2

An NBA Player Deducts His Fines

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Depending on what type of person you are, you know Lamar Odom either as a forward for the Dallas Mavericks or as Mr. Khloe Kardashian. Fewer people know Lamar Odom as something he recently became: an amateur tax lawyer.

In 2010, the IRS sent him an $87,000-plus interest bill concerning his 2007 taxes, as well as a letter saying he was not allowed to deduct $172,000 in "fitness fees" and, even stupider, $12,000 in NBA fines from his 2007 tax return. In 2007, he was a modest man living on a modest salary of $9.3 million, so Odom challenged the IRS' ruling and sued them. Odom was a college dropout and made his living using every muscle other than his brain, but this didn't stop him from filing the suit and representing himself.

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"$5,000? No thanks, I'll fix my own torn knee ligament."

When asked about his $172,000 deduction for fitness fees, he stated that, as a pro athlete, he is obligated to stay fit and healthy, and therefore all his regimens could be deducted as business expenses. That is a logical response, but considering he has a workout that could be easily performed at any gym or any prison, the large fees account for either a holodecklike virtual reality facility he has in his backyard or a robotic personal trainer. Or maybe he just hates taxes as much as the next guy who doesn't have a multimillion dollar salary.

Regarding the $12,000 deduction for his NBA fines, otherwise known as the cost of doing things he shouldn't have been doing, he creatively stated that they "are commonly assessed on professional athletes and are work related. Therefore the fines incurred are ordinary and necessary employee business expense."

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"Basketball is my hobby. Fouls and verbal abuse are full time jobs."

1

A Drug Dealer Deducts His Drugs

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Criminals follow the law pretty leniently, but even they need to stay on top of their taxes; just ask Al Capone. Back in 1975, Jeffrey Edmondson was a drug dealer who was busted and charged with drug trafficking. The IRS, in the mood to add crippling financial debt to a prison sentence, audited Jeffrey for $17,000 in back taxes he needed to pay for failing to declare his income made from drug dealing.

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"Sign here, here and here under confessi -- I mean conCESSions."

While awaiting trial, instead of trying to prove the innocence he didn't have, Edmondson filed a tax return that listed his taxable net income and a good list of business deductions, and left his occupation blank. That is because if any of the cops who arrested him found out he was a drug dealer, he would get into so much trouble. The act of putting only one's net income and amount of taxes due on a return is apparently a common practice for drug dealers. It's called the "Fifth Amendment" tax return and also goes by a lesser-known title, the "I'm a drug dealer, and I'll pay your stupid money if you agree not to tell anyone what I do" tax return.

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Yay freedom!

Predictably, the IRS looked at his business deductions, then probably correctly assumed he was high on LSD and ignored them. Edmondson was serious, though, and his tax deduction would go on to the Tax Court. Despite having no receipts to back up his claims, which would've instantly cost him his chance for a deduction today, Edmondson apparently made a lot of sense. He claimed that he established a business in his home, which would've qualified him for a home office deduction, and he named several purchases -- including his drugs -- as necessary business expenses.

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There's also the little known "bitches getting up in my grill" assessment.

Judge William Goffe was apparently very impressed with Edmondson's "honesty" concerning his illegal dealings, as well as his logic, so he agreed to deduct his expenses. Some of the things that were successfully deducted were a $50 scale, the cost of 29,000 miles on his car that were used to drive to pick up drugs, 100 pounds of weed and 1 million amphetamine tablets. If you think that was an absurd amount of drugs, you obviously didn't live in the '70s.

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And if you don't ... can we please have your autograph, Mr. Richards?

After reading about this, it was easy for drug dealers to get excited at a new chance to save a lot of money that they could spend on hired muscle and flamboyant outfits. Also after reading this, it was easy for U.S. senators to get really pissed off at the ruling. Sen. William Armstrong, R-Colo., was displeased and made it a goal to prevent future drug dealers from having a nice tax loophole. He succeeded. In 1982, the senator managed to get a new tax rule added that disallowed any deduction earned in a business that dealt with the trafficking of illegal substances. So you'll need to go with the huge fake boobs instead.

For more people who walked around perpetually flipping the bird, check out 6 Comic Book Easter Eggs That Stuck It to The Man. Or discover the 9 Insane Cases that Prove the U.S. Legal System Is Screwed.