The perennial nature of tax time does nothing to assuage the overall stress, anxiety, frustration, procrastination and general loathing associated with the chore of preparing your income taxes. For those who prepare their own taxes, the strain can seem particularly acute, yet even ensuring you’ve provided all the necessary documentation to a paid tax preparer can be stressful.
This year, countless Americans will labor over mountains of paperwork, hunt for rogue receipts, itemize ad nauseum, and search for every possible deduction to ensure they don’t overpay even a single dime to Uncle Sam’s outstretched hand. And when it comes to deductions, you might be surprised at the creativity — or plain stupidity — of your fellow taxpayers. So, as the dark cloud of the April 15th deadline looms, I thought I’d attempt a little humor by relaying a few anecdotes of ridiculous and outlandish deductions desperate taxpayers have attempted to declare that shockingly, didn’t pass the proverbial IRS muster.
Fur to Foster Conversation
One businessman thought he could get away with deducting the mink coat in which he draped his wife when entertaining or speaking to clients. His rationale? This cunning guy claimed that his wife’s lavish coat served as a delightful icebreaker and conversation piece. Too bad he got skunked by the IRS.
Drug and Prostitution Expenses
Shocking though it may be, it turns out that you cannot deduct expenses for careers that are, well, illegal. For those who declare “prostitution” as their profession, the IRS won’t be footing the bill for the fancy lingerie or condoms the job requires. The same is true of marijuana growers and dealers, some of whom have tried writing off the cost of everything from potting soil to the plastic baggies in which they package their “product.”
The Doctor’s System
Sure, doctors require all sorts of high-tech and serious-sounding tools and gadgets to practice medicine, but what exactly is a “time monitoring system”? When one CPA reviewed the taxes of a physician who was being audited came across this rather large deduction, he had the same question. When he asked the doc to explain this mysterious “time monitoring system,” he was treated to a display of the doctor’s blinged out Rolex.
Watch for the Fallout
During the height of the Cold War, one patriot followed the cue of other frightened Americans and constructed a nuclear fallout shelter on his property. Granted, those things aren’t cheap, but none of his other fallout-fearing peers tried to take it as a tax deduction. So just how did he list his new shelter? As “preventative medicine,” of course!
All for Education
One creative Spanish teacher ordered the Spanish-language subscription from his cable provider and, of course, purchased a new television on which to watch his favorite Spanish-language shows. Since he was an educator — and an educator specializing in Spanish, no less — he thought it only appropriate that the IRS reimburse him for these “teaching expenses.” How do you say “Nice try” in Spanish?
Up in Smoke
This one has to be my personal favorite. A failing and frustrated furniture store owner decided the best way to get out of business was to hire someone to burn it down. And as it turns out, this man was very diligent when listing the expenses he incurred in this calamity. Not only did he accurately report the loss of his building, as well as his payout of $500,000 in insurance money, he also listed a $10,000 deduction as a “consulting fee.” As it turns out, no matter how much you consult with an arsonist, the whole thing is illegal. Imagine that. Both business owner and arsonist/consultant ended up in prison.