The 7 Most Insane Ways People Legally Avoided Paying Taxes

#3. An Exotic Dancer Deducts Her Breast Implants


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.

How does she use seat belts?

Yes, she decided to bypass the pleasantly large boobs stage to the "Sweet holy crap, what monster cut you open and implanted you with basketballs!?" stage. Or maybe bowling balls are a better comparison -- each new boob weighed 10 pounds. After the life-changing event, she adopted a new identity and changed her stage name to the subtle "Chesty Love."

Naturally, she decided to deduct the implants as a business expense. The IRS, having said no to much more normal deductions, obviously said no to this one. They backed up their response by saying that business deductions only work for outlays that are "ordinary and necessary" in the business field and that the IRS code does not allow deductions that improve your appearance. Chesty pressed the point, saying that when she went back to work, her fees and tips doubled. Obviously, her boobs were improving her career.

None of the tips were voluntary -- the boobs just created their own money gravitational field.

So, Chesty sued the IRS for the deduction and did a hell of a job proving that her boobs were necessary in her profession. She argued that the implants should be in the category of a business uniform -- they were useless outside of the context of her job, and she intended to remove them immediately after she retired from exotic dancing. She also explained that the surgery did not improve her appearance, as she was constantly ridiculed on the streets and was ostracized by her family.

"When we hugged I just didn't feel very close to them."

Apparently convinced by Chesty's testimony, or at least mesmerized by the boobs in front of them, the tax court agreed to deduct her breast implants. They stated, on a federal court record, that her boobs were so horrendously large that they could've only been used for business purposes, so that made them deductible. We suppose there is a moral here, though we're not exactly sure what it is.

For some reason we were too busy typing "travel pillow" into Amazon.

#2. An NBA Player Deducts His Fines


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.

"$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."

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

Apparently Odom made sense, as the tax attorney he later hired stated that the IRS completely threw in the towel for his fines and fitness claims, and they settled for about 10 cents on the dollar. In the settlement, the IRS agreed to take only $7,827 plus $1,000 in interest. It wasn't a perfect victory for Odom, but against the IRS, it's the equivalent of winning six championship rings (suck it, Jordan). In the end, Odom received a large deduction that we're sure he used wisely.

Such as bribing E! executives to make a second season.

#1. A Drug Dealer Deducts His Drugs


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.

"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.

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.

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.

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.

Recommended For Your Pleasure

To turn on reply notifications, click here


The Cracked Podcast

Choosing to "Like" Cracked has no side effects, so what's the worst that could happen?

The Weekly Hit List

Sit back... Relax... We'll do all the work.
Get a weekly update on the best at Cracked. Subscribe now!