How Craig Gilmore picked the winning March Madness tournament bracket
This story appears in ESPN The Magazine's March 3 Analytics Issue. Subscribe today!
IN THE MINUTES after Warren Buffett announced his billion-dollar bounty for a perfect NCAA basketball bracket, Craig Gilmore's phone started to buzz. Last year Gilmore topped more than 9 million of his fellow contestants in the ESPN Tournament Challenge. He wasn't perfect, but he was closer to it than anyone else, predicting Louisville's win over Michigan and even Florida Gulf Coast's first-round upset of Georgetown. Now old college friends, colleagues and even his own mother have been in touch, asking Gilmore to reveal the method behind his March Madness.
"There's really no big secret," he says. The 40-year-old Gilmore is a business analyst for a health care company in Virginia, but he didn't employ any algorithms or actuarial witchcraft when he filled out his fateful bracket. Instead, he attributes much of his success to the four pints of Guinness he'd drunk before he made his selections. "I didn't overanalyze it," he says. "I just kind of went with my gut."
Luckily, Gilmore's beer-filled gut is just as familiar with the infinite alchemy of tournament basketball. He filled out his first bracket when he was 8, joining his father and brother in a $3 pool. His lifelong love of college sports has since given him an unshakable philosophical foundation: He likes well-balanced teams with tall, physical guards and veteran coaches who stress defense. He almost always picks Syracuse to go deep, for instance, because of Jim Boeheim's confounding 2-3 zone.
He's also a student of history who recognizes that every March has its share of upsets, and Georgetown is often one of them. "I knew nothing about Florida Gulf Coast except that they were probably on the Florida Gulf Coast," Gilmore says. "Georgetown just always underachieves." He likewise doesn't think Kansas will make it past this spring's second round. Michigan's come-from-behind overtime win against the Jayhawks last year secured both Gilmore's bracket and his belief in bad tournament juju.
Gilmore's abiding faith in hunch and superstition is almost charmingly antiquated in our analytical age. The Guinness was new to his usual pretournament routine -- "I'm definitely going to do that again this year," he says -- but he's always started his brackets with his champion, then top two, then Final Four, quickly backfilling those teams to the first round without additional thought, never risking an opening for self-doubt. Last year he missed perfection in three of the four regions by a single game. One of them, California's upset over UNLV, he had right, only to change his mind after a more stringent calculus. "That won't happen this year," he says.
In between Gilmore's brain and his gut is his least used weapon: his heart. He's a Southern California native and loves UCLA, but that didn't stop him from correctly tipping Minnesota to beat the higher-seeded Bruins. "You can't confuse who you want to win with who you think will win," Gilmore says. This year he likes multifaceted Arizona to take it all and three-point-dependent Creighton to be among the surprise early knockouts. The more complicated the padlock, he argues, the harder it is to pick.
That's also why a far more analytical man can bet a billion dollars against bracket perfection. According to the Book of Odds, you are 18 times more likely to be killed by a waterspout than to forecast an entire 63-game tournament accurately. "I think it's possible," Gilmore says, "but I'm probably not the right person to do it." He points out that he was thrown out of a college statistics class for arguing, semi-seriously, that at some level even the remotest probability is a coin toss: It will either happen or it won't.
Maybe that makes Gilmore exactly the right person to do it. He knows that March will never be won by math alone. When Florida Gulf Coast upset Georgetown, he had watched the game lying in bed with his 8-year-old daughter, because she had hurt her ankle and needed to prop up her foot on a pillow. That meant her foot stayed on that same lucky pillow for the rest of the tournament. Did the placement of a little girl's ankle in Virginia affect the outcome of college basketball games played thousands of miles away? Of course it didn't. But Craig Gilmore believes, and belief is how perfect always begins.