Taxes Shmaxes

As you might imagine, my dating a Jewish IRS agent has its benefits. Rachel (I've changed her name to protect Hannah's identity) can ensure that I will not be audited, can figure out our restaurant tip in seconds, and, to my great delight, was willing to share with me a listing of the nerviest tax deductions attempted to be taken by Jewish taxpayers this year. Names have been changed to protect the privacy of the taxpayers. Other than that, though, these are the actual tax deductions, verbatim, taken from this year's 1040 Forms. They were all, as you might imagine, disallowed.

How did Rachel determine that these taxpayers were Jewish, since there is no place on the tax form to indicate religion? Simply by their names, which in many cases were obviously Jewish-sounding. Religious profiling? Perhaps. I mean, it's certainly possible that Shmuel Liebowitz is an Episcopalian, but Rachel and I took that leap of faith and tossed him -- as well as Heshie Blattburg and the others below -- into the Jewish Taxpayers file.

And now, a representative selection of the nervy, disallowed Jewish tax deductions that were taken this year, each with my own commentary, inspired by all the Jewish scholars' commentary on the Talmud, only not nearly as historical, uplifting or insightful...

Woman deducts personal property taxes paid while playing Monopoly. Roberta Schwartz states, "My husband is an attorney and said there is no law on the books forbidding people from deducting their Monopoly game's property taxes. He even did a Google search. Nothing." Schwartz adds that she's not worried about a potential worst-case scenario, "because I've got two Get Out of Jail Free cards." Schwartz is further charged with attempting to bribe a Michigan state official -- with Monopoly money. "Just my luck I get an honest civil servant. I even threw in two hotels, but he wouldn't budge. Nu? Some people, I swear."

Chicken soup is no different than going to a doctor. Just tastier.

Man deducts travel expenses to and from Hermie's Delicatessen. College-educated sports announcer Ben Leiber puts an extra 35 miles on his car's odometer each week travelling to and from his beloved Hermie's Delicatessen. "If you're a fan of perfection, Hermie's rye bread and corned beef will bring tears to your eyes," affirms Leiber. One day, Hermie noticed that Leiber was suffering from a cold. Leiber confided he just couldn't get rid of it. "Hermie told me, 'My schmaltz herring and chicken soup is better than any medicine in the market.' I realized he was right. That's when I decided to deduct my travel expenses and the cost of the food. It's no different than going to a doctor. Just tastier. The IRS has no sense of fairness. I should've insisted on a Jewish IRS agent; he would have understood."

Teacher deducts game show winnings as "retirement contribution." When 64 year old Israel Horowitz won $125,000 on "Jeopardy" last year, he was thrilled. "I was planning on retiring the following year and this money would be a substantial part of the retirement fund for myself and my wife, Shirley. We were qvelling in unison." That was the logic Horowitz gave the IRS when they asked him why he listed the money as a retirement contribution. After the IRS explained why Horowitz would not be allowed to do this, he took Shirley to Las Vegas, where they proceeded to lose the entire amount of money during a series of high-stakes poker games. "It's okay," said Horowitz. "I'm a teacher and I was teaching Shirley to play poker, so I'll just deduct it as a business loss. What? What're you looking at me that way for?"

DMV supervisor deducts entire worker's salary as "charitable contribution."

Supervisor Flo Rabinovitz can't understand why the IRS won't allow her to deduct the $47,000 salary she pays Department of Motor Vehicles clerk Wally Fink, as a "charitable contribution." She confides, "Look, Wally and I don't get along. Frankly, he's a waste of space. But if I fired him, his family of four would have no health insurance and I couldn't live with that guilt. So, really, my continuing to pay him is more of a charitable contribution than anything else." Rabinovitz already had a red flag on her IRS account dating from three years ago when she attempted to deduct the cost of fifteen bottles of tequila as a medical expense. "I have a signed note from a medical doctor saying that I am deficient in vitamins only available from the agave cactus plant."

Single woman claims child-care credit.

27 year old Miriam Goldstein deducted a $5,000 child-care credit. The IRS disallowed the credit on the grounds that Goldstein is childless. Goldstein's argument: "My husband,
Izzy, – God love him – is an extremely immature, irresponsible man. He doesn't cook, clean, pick up after himself, or do anything I ask him to do. It's like having a child around the house. A child I care for every day. So I requested a child-care credit. Seems fair to me. Excuse me; Izzy's playing Empty Beer Can Bowling again and something's going to be ruined. Izzy, enough!"

So, what can we learn from all of this? That Jews have chutzpah to spare? That the IRS is not easily fooled? That if you want to stay off the Feds' radar, it's probably best not to claim brisket and tzimmes as medical expenses? Yes, but I think the lessons herein go deeper, much deeper. And as soon as I figure out what they are, I'll get back to you. Now it's time to take Hannah, I mean Rachel, out for dinner and a movie. I'm using my tax refund check to treat her, and want to cash it right away in case the IRS decides they have some issue with my deducting everything I spent on my last girlfriend – as a gambling loss.