5 Insane tax write-offs that prove the system is fucked

5 Insane tax write-offs that prove the system is fucked

PoliticsOctober 07, 2016 By Reilly Capps

In one fiscal year, Donald Trump lost nearly $1 billion. And now, his coven of TV slaves and political sybarites are spinning that as a “genius” tax avoidance strategy — because you don’t pay taxes when you don’t make money. Which is like someone saying that losing their underwear in a strip poker game is a genius way to avoid doing laundry.

But even at the lower end of the economic Slip n’ Slide, there are many incredible loopholes that have actually worked.

Boob jobs

Shoving plastic globes under your skin isn’t just a great way to get romantic attention from all the wrong kinds of people. It’s also a solid tax strategy. At least it was for Chesty Love, a stripper who got the IRS to treat her silicon bobbules as tax-deductible, work-related investments that will (and this is completely true) depreciate over time. Yes, the value of her breasts will literally decrease every year, and if that isn’t a cold sad analogy for the entire human sexual condition, we don’t know what is.

One cat, or 80 

Pet food and vet bills can be deductible as charitable expenses, because animals are all 501(c)3s, apparently. At least that was the ruling for one California woman who had roughly 70 to 80 “rescue” cats in her home and took care of them under the guise of volunteer work. She was awarded more than $12,000 in deductions from expenses relating to the care of strays she found and brought home.

Shopping organic

If you love heirloom tomatoes, fresh peaches and the smell of freshly rolled yoga mats, your taxes might love you back. In one case, the price difference between chemically-treated produce and the organic stuff was successfully written off as a medical expense. Kale smoothies never tasted so economically sound.

Itemizing illegal activities

If you’re cooking bath salts in your basement or pimping midgets out as sex slaves, the fact that the money came from a crime doesn’t matter: you still have to pay taxes on it. You can also deduct at least some of the costs of doing business, specifically your legal fees after getting caught. So you can maybe get off. Then sell more Krokodil from the basement. So Uncle Sam keeps getting his cut. See how this works?

Don’t pay your taxes. At all.

Just don’t. Don’t even file. There are gigabytes worth of justifications oozing out of the Internet’s cracks about why you shouldn’t, from the idea that the 16th Amendment wasn’t fully ratified to the popular notion that taxation is slavery .. and then there are timeless reasons from Henry David Thoreau. Back in the day, the government was fighting idiotic wars, and Thoreau hated helping fund the war machine. “Let your life be a counter-friction to stop the machine,” he wrote. Are the wars in the Middle East much better than the Spanish-American war? And what about the War on Drugs? You happy funding that one? 

As with all strategies, it's advised to consult an accountant. Thoreau wrote his words in the dim light of a jail cell. Then again, you might end up as the republican presidential nominee. We’ve only seen one year of Trump’s taxes, so we don’t know how else he’s gamed the system — shopping organic, becoming a crazy cat lady, or losing even bigger mountains of his daddy's dough. 

Regardless, there are many crazy ways to avoid Uncle Sam, and people everywhere have figured out how.