What do you mean I can’t deduct that?

This weekend I made my annual pilgrimage to see Rocco, my trusted tax preparer since 1990. I’m convinced that he is a real-life version of Dorian Gray, as he, at least in my eyes, has aged almost imperceptibly over the past 27 years. Although he claims that the new tax law changes enacted under the Trump Administration has increased his number of gray hairs exponentially.

After ranting for a half-hour on the byzantine guidelines he now has to follow as a result, he assured me that my return won’t be any more complicated than in years past, as I didn’t have any unusual deductions.

So as I do every year at this time I did some research on some of last year’s most outrageous attempts at tax deductions and subsequent rejections by Uncle Sam. Here’s but a few of my admitted favorites.

1. Whiskey. Somebody thought that giving their clients a case or two of fine whiskey would make a nice gift. Too bad it violated their particular state laws.
2. Hiring a professional arsonist. Incredibly, a man with a failing business tied to collect on his $500K insurance policy by paying a firebug $10K to burn down his store. I wonder what deduction category that attempt fell under? Surely not business or homeowner improvement.
3. A trip to the Super Bowl. Some generous chap decided to take several of his clients and their spouses to the big game, but sadly was unable to validate it in any way that it was related to business. Here’s hoping it was at least an exciting contest.
4. Dance lessons for medicinal purposes. No you can’t  take dancing as a deduction for medical expenses, and the following reasons are outlawed – dancing to relive varicose veins, dancing to cure arthritis and finally, dancing to alleviate nerve disorders. I assume they were soon two-stepping straight to the tax courts.
5. Buying a racehorse. Sorry, it doesn’t matter if it’s Secretariat, Seabiscuit or a mare that’s one step from the glue factory. You can’t buy a racehorse, take clients out to see it run and then try and deduct it as a business expense. According to the IRS it falls into the personal expense category. Not a winning ticket by any means.