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Wanna Bet?

When Springsteen kicked into “Glory Days” during halftime of the Super Bowl, I groaned. I had lost a bet on The Boss’s set list and now was forced to join a Facebook group called “NEW JERSEY: We Pump Our Fists, Not Our Gas.” That was when Mrs. Closer suggested I had a gambling problem. “The problem,” she said, “is that you’re a lousy gambler.” I set out to prove her wrong. For one week, I went on a gambling binge, rigging wagers I knew I could win. No money was at stake; all I hoped to gain was betting confidence. And maybe some free stuff.



Citing a Pennsylvania weather report on Groundhog Day, my friend Nicole swore that the pampered rodent would not see his shadow. This was a sucker bet. The groundhog saw his shadow 93 of the past 109 years. Make that 94 out of 110. Net gain: A “nunchuck,” a gun that catapults plastic nuns.


I bet my colleague John, who is aptly named because I always see him in the bathroom, that I could go 12 hours without using the toilet. “You’re on,” he said. “But you can’t use one of those Stadium Pals.” I didn’t have to. Even after he e-mailed a video of Niagara Falls and trash-talked ruthlessly (“It’s a long ride home when your pants are frozen to your thighs”), my bladder was Olympian. NET GAIN: John’s crystal 2002 Chicago Tribune Team Award.


In these tough times, I theorized that someone would pick up a penny on the sidewalk in front of the Tribune Tower within ten minutes. My colleague Bill disagreed and promised to burn me all his Miles Davis discs if I won. If I lost, I had to burn all my Def Leppard. (Not for Bill. I had to literally set them on fire.) The coin lasted 19 minutes before an old lady snatched it. NET LOSS: 32 bad songs that remind me of high school. Plus the penny.


I am a master at state capitals, so I challenged my old J-school buddy Eric to see who could name more in 15 minutes. I blew only Nashville, Bismarck, and Dover, and forgot about Arkansas altogether. Not bad. Turns out I got hustled. “My kids have a CD with that Animaniacs capital song,” Eric said, after beating me, 47-46. “I’ve heard it at least 50 times.” NET LOSS:  See The Capital Song video.


Ever more desperate, I picked an easy target next. My softball teammate Alisha, a.k.a. “Piledriver,” drank half the booze in Ames during her five years at Iowa State, so I bet her I could stay sober longer than she could. First to imbibe buys the other’s choice of hooch. Forty-eight hours later, the bet completely slipped my mind and I had a glass of Chianti with dinner. NET LOSS: Bottle of Jägermeister.


Mrs. Closer needed a few things from the dollar store, where her spending sprees are legendary. I bet that she’d squander more than $18, and if she did, she could no longer make fun of my parallel parking. She not only won—$16—she broke the bettor’s covenant. “I would’ve made fun of your parallel parking either way,” she said. “You’re the worst.” NET LOSS:  All interest in betting. And last remaining shreds of self-esteem.


Figuring I couldn’t sink any lower, I e-mailed Tom Skilling on February 8th and made a prediction: “The sun’ll come out tomorrow. Bet your bottom dollar?” Skilling said it would be cloudy with some haze and fog, with patchy drizzle building to rain during the afternoon. “But I’ve been humbled by Mother Nature more than once in my career,” he said. Sport that he is, he bet anyway. NET GAIN: Uncle Tommy’s bottom dollar. Things are looking up.

Photography: (Skilling) Courtesy of WGN Television

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