Get Into the Game: Betting Like Buffett


By Kristy Barry

Photo by Aaron Friedman.

I bet on a lot of things, from Tetris to Oscar-nominated animated short films, to my brother Zack eating five pounds of gummy bears. Over a card game, I’ll bet a one-eyed man his remaining good eye.

With the credibility of a horoscope writer, I wager adamantly. “LeBron will not leave Cleveland,” I insist–privy to classified intel. “Cleveland is his kingdom, the fans have built him a throne, he won’t leave his childhood home and abandon the throne.”

During his announcement to leave Cleveland for Miami, I screamed at the TV and lost $50. As I also did when I bet my twin sister Katie that she couldn’t guess the year on a penny I had just picked off the sidewalk.

But Warren Buffett has outdone me, not the first time nor the last or in the most creative fashion, but he’s claiming to fork over $1 billion dollars to anyone who fills out a flawless NCAA men’s college tournament bracket online, which has never been done since ESPN began the e-bracket challenge in 1998.

President Obama, who fills out a bracket each year for a televised segment for ESPN, predicts a Michigan St. vs. Louisville final and jokes about what he’d do with his billion dollar prize. “I’m sure somebody would ask me to pay down more of the federal debt,” Obama tells ESPN. “Michelle might want a few shoes.”

After the first day of play, millions of Americans will be dismissing their dreams of owning private islands and riding a helicopter to work. After all, the odds of nailing a perfect bracket is 1:9,223,372,036,854,775,808. The somewhat consolation prize is that the 20 people with the most accurate brackets will be awarded $100,000.

I like petty betting better–these spunky, pesky invitations to play. Petty betting declares what’s important to you, what you desire to gain, what you could care less about losing. To show a vulnerability in revealing what you’re willing to sacrifice–be it money, dignity, time, or valuables.

Every year, this college basketball tournament is prime bet-staking ground.

Last year, over a quite inconsequential UNLV vs. California game, my friend Cameron bet me that California would win. Despite previous apathy for this particular game, he seemed dogged so I let him open negotiations.

“A cat,” he said. “Loser has to accept a cat from the other person.”

The score is tight in the second half, and he remembers he hates cats. So, he says, “I bet you a fish.” The winner will buy the loser a living fish to care for. A challenge piggybacking a challenge. Deal.

I struggle remembering to water bamboo plants, much less feed a swimming little thing. And “little,” I hoped, like a starfish (we rule out sharks, piranhas, and octopi). This fish will stay alive, I tell myself, because Cameron can’t have the satisfaction in knowing I can’t keep a fish alive. This thing will live in a bowl, residing on my nightstand, staring at me while I sleep like a love-stoned boyfriend, and live ten years longer than its expectancy.

Meanwhile, UNLV falls behind and while I’m praying for buzzer-beaters, he’s researching fish. I lose the bet and he tells me he finds a fish that lives for 40 years.

This year, I repeatedly ask where my fish is, unruffled by the loss/gain and he insists, “It’s on its way from Thailand.” I start to think it’s a sci-fi sea monster that can breathe fire underwater and eat me alive with jaws closely resembling a white picket fence.

Days later, Cameron bets against Ohio State, and in losing the bet, he has to dress like a woman for a night on the town with me. He hasn’t made good on this bet yet, but when he does, he may be dressed in a head-to-toe green fishnet suit from Fantasy World on 6th Ave. Then I’ll ask again about my fish, if he can catch one with his hole-ridden onesie.

I can also use the fishnet suit for a bet I made with a Michigan fan that if Ohio State won, I can dress him up to march in the Gay Pride Parade. His other wagering option is that he can buy us both tickets to the Boyz II Men reunion concert at the Barclays Center in Brooklyn. The trouble is he doesn’t want to sit through me wailing the lyrics to “On Bended Knee” with 18,000 other goons who once thought they were cool wearing slap bracelets, a pony tail off the side of their head, and socks over the pant leg of their Jordache jeans.

Best bet of all though, without a doubt, is that I bet a trash-talking Syracuse Orange fan that if Ohio State beats Syracuse, I could dress him up as the “Brutus the Buckeye” mascot complete with a paper mache head. He underestimated not only Ohio State’s basketball team, but my arts-and-crafts offense of sorts as well. He’s wearing a big tan helmet along with ared and grey striped sweater, and a smile literally painted on his face. To the others at this crowded Buckeye bar in Times Square, he’s the ULTIMATE BUCKEYE FAN.

This year, I predict Ohio State to win the whole tournament. The team can possibly play Syracuse in the second round of the tournament, a match-up so enticing to me that I rally friends, call off work, secure borrowing a car, and prepare to drive seven hours to Buffalo for the game.

Ohio State plays Dayton first and I generously mention beforehand that if I win Warren Buffett’s bracket challenge, I will buy my friends each personal masseuses that would serve as alarm clocks, waking them up every morning with a foot massage and a plate of sizzling bacon—to show my charitable side.

As it turns out, the Buckeyes cannot fend off the Dayton Flyers, and Ohio State loses by one point. Like at least 80 percent of America in that moment, I feel like I’ve lost a billion dollars.

Kristy feeling like she’s lost a billion dollars. Photo courtesy of Kristy Barry.

The Syracuse fan texts to chide me about losing the game, while I happen to be riding a rollercoaster by myself at Adventureland in Long Island. I’m jerking around each turn of the coaster, screaming and freezing and wind-whipped, but am happy I didn’t drive to Buffalo. I’m also secretly relieved that the anxiety of the tournament is passing, that perhaps this March Madness, I can sit back and enjoy the ride. I will not compulsively check my brackets, upend my schedule to watch games, or throw things at the TV.

I can still petty bet against my pesky friends who root for the University of North Carolina, Michigan, or Michigan State. Although there’s only so much trash-talking and wagering gusto you can muster when your favorite team loses to the Dayton Flyers, I can do it anyways. You can’t win if you don’t play. And I’m not giving up on those Boyz II Men concert tickets yet.

For more, check out Kristy in conversation on BTR Sports, every Sunday on BreakThru Radio.