The man who’s better at picking a March Madness bracket than anyone else in America is not Nate Silver, President Obama, or Dick Vitale. It’s Craig Gilmore, a 40-year-old business analyst from Amissville, Virginia who likes a pint (or four) of Guinness and Pac-12 college hoops.
Last year, Gilmore won ESPN’s Tournament Challenge, beating out 8.15 million other entries with a bracket named after Lennay Kekua, Manti Te’o’s nonexistent girlfriend. He’s neither guru nor stat-head—“Last year was the first time I didn’t really analyze anything,” he says, only half-facetiously—but Gilmore managed to combine the right amounts of knowledge, intuition, and courage with just enough luck.
Now, with Warren Buffett offering up a billion dollars for a perfect NCAA Tournament bracket, friends, family, and even strangers are trying to pick Gilmore's brain for trade secrets.
While speaking with The Daily Beast, Gilmore received “two or three texts” from people asking about his Final Four picks. “This guy says, ‘Who’s your upset special?’ Nobody’s sent me that before. Now all of a sudden you win the bracket and you’re resident expert.”
Fortunately, the resident expert took the time to divulge his tips and tricks to The Daily Beast. Unless, of course, everything he told us is “a big farce” to lead challengers off the scent.
Have you already completed your bracket?
I haven’t completed all of it, but I do have my champion already in there. That’s the first thing I do. Everybody has a team that they kind of think is going to win, and I think as you fill out the bracket round by round, people start, either consciously or subconsciously, to massage better match-ups for them to win. So I always put my champion first. That way I don’t alter who I really think is going to win just 'cause I think it’ll be a better matchup for my champion.
When did you start watching sports?
My dad loved UCLA basketball. Even at 8 years old, me and my brother and my dad, we’d each throw like a dollar into the pool and make our brackets.
How long have you been in major March Madness pools?
Online? Probably since the earliest that ESPN has done it. But I’ve done the paper pools ever since college. That’s when we really got into it. As far as doing 20-25 bucks an entry, that was probably 20 years ago.
Do you fill out one bracket or different brackets for each pool?
I fill out one bracket. To me, part of it is just trying to get the most right. So with the bracket, either I’m gonna win or I’m not. I just go with that same bracket and I usually enter that into multiple pools.
Had you ever thought that winning ESPN’s Tournament Challenge was a possibility?
Not really. I’ve always kind of ended up in the 75 percentile, so far out of the running. The goal is just to beat all my friends. Once I hit the top 50 [on ESPN], that’s when people started sending me messages. It was mostly because of my entry name. So everyone’s like, “Dude I’m rooting for you. My bracket’s just totally blowing up, but that’s a funny name and I love it and I hate Notre Dame and I’m rooting for you.” So then I looked and I was like “Holy crap, I’m on the top 50 leaderboard.” Then I just started paying attention to me versus the rest of ESPN.
What’s your strategy?
You need to pick your four teams who you think can just get to the Final Four regardless. And then you just kind of go with trends. But it’s sort of like with everything in sports: If you overanalyze, you start to talk yourself out of things. And I use the SAT approach. I kinda go with that first gut feeling and then stick with it. I’ll make the pick, and that pick stays.
How do you keep emotion out of it?
I do pull for certain teams and I do hate certain teams, so when I pick them to either win or lose, I kind of step back and be like, “Why am I picking this team?” And I have to come up with something explainable versus if it’s just a hunch. Then that’s not good enough because I’m probably doing it because I want [Ohio State coach] Thad Matta to lose and cry. I think that’s the biggest problem that people have, that they start picking who they want to win versus who they think should win.
“I use the SAT approach. I kinda go with that first gut feeling and then stick with it. I’ll make the pick, and that pick stays.”
How much basketball do you watch during the year?
I’ll probably watch 4-5 games per week. I just like to see how other teams are playing. So I try to catch a little bit, even if I don’t watch the entire game.
What’s your March Madness watching routine?
I usually take the first Thursday and Friday off and I just watch it by myself for those two days. Now that they’ve got the games online, we’ve got three laptops as well as the TV, so we’ll keep four different games going at the same time. During a sports game, my phone goes off and I have no contact with the outside world. My whole thing is, as soon as I talk about it, I’ve jinxed it. I don’t get on Facebook. I don’t tweet anything out. I don’t email. Nothing. I’m in a cocoon.
Do you have any superstitions?
I gotta find out what the good luck mojo is, and that was one of the first things my dad ever taught me: Sports mojo. And you don’t mess with it. It’s the rally caps, it’s wearing the same clothes.
What do you look for in a team?
I like to get a feel for who plays good defense, who turns the ball over a lot, and who can score. Those are what I consider the pivotal things. I know it’s cliche, but if you play good defense, you’ll always be in a game. Defense doesn’t go into a slump. I do like bigger teams, especially down on the front court. I think just by having size you can play better defense around the basket.
How much do you factor in coaching?
It’s huge. The Final Four is almost all coaching. Once you get to the Final Four, you need that Hall of Fame-type caliber coach, because all of the teams are going to be pretty similar, within close proximity of talent. But it’s gonna be who gets out-coached.
If you could choose one coach for one important game, who would it be?
[Louisville's] Rick Pitino. He’s just got that extra something and I like [his] style of play. He coaches all aspects of the game. I know he’s animated, but I just consider that being Italian, I guess. Without hesitation Rick Pitino would be my guy.
Let’s get into this year’s bracket. What team do you like this year?
Definitely Arizona. [Seven-foot center Kaleb] Tarczewski, he’s just a beast. And I think Aaron Gordon is one of the top 5 players in college basketball. They play good defense and they can score points obviously. I do have Arizona winning it all. I’ve got Arizona over Florida.
Can anyone in the West Region challenge Arizona?
The West is probably tailor-made for Arizona to go. I’m not that big on San Diego State. I don’t see Wisconsin getting by Oregon. Creighton, they rely on [Doug] McDermott and that 3-point shot. But their offense is 3-point first, and when that doesn’t fall, you’re done.
What about the South Region? Florida’s the number one overall seed.
I do see a matchup of Syracuse and Florida coming out of there. I don’t have [Syracuse] going to the Final Four just ‘cause I don’t think they have that scorer that can just take over a game, but their zone [defense] will basically keep them in it. I do like Florida coming out of that.
What about the East, Virginia’s region?
I think the East Bracket is what’s gonna keep Warren Buffett and Quicken Loans with their billions of dollars. I think this bracket will probably blow some people up. The only team I’ve made a decision on so far is Michigan State in the Elite Eight. I just don’t think Virginia can do it. If they get behind, they have a hard time coming back.
Lastly, the Midwest.
Friday, I’ll be OK with Wichita State. Saturday, I’ll second guess them. I’ve already penciled in Louisville in the Final Four. Louisville is in the top 20 in points against, top 20 in points for. I do like Michigan playing them. Obviously I liked Louisville and Michigan last year. [In 2013, those two teams met for the national championship, with Louisville winning it all.]
Which top seeds are ripe for an upset?
Wichita State. If Kentucky gets by Kansas State, I think Wichita Sate can get bounced in the second round. They’re gonna find it a little bit different this year, the hunted vs. the hunter. If that match-up happens, Kentucky’s got talent, and the players aren’t going to take Wichita St lightly.
If I go with Stanford, I’m not sure Kansas gets by that. Everyone keeps talking about Kansas and the toughest schedule in the country, and I get that. But they’ve lost to most of the tough teams in that schedule. And I tend not to like Kansas in the tournament anyway. They’re just a team that historically underachieves.
Thoughts on potential Cinderellas?
The majority of people agree on what’s going to be the most likely upset. I found that that never really happens. I don’t know if that team gets wind of it or it puts too much pressure on them, but it never hits. Before the seedings came out, I was looking at Harvard, since they upset last year, but I do like Cincinnati so I took that off the table. I do like as a 10-seed St. Joe’s. I do like Arizona State ‘cause I’ve seen them play. I don’t really see a 12 besides North Carolina State. I do like NC State as far as the lower-seed upset. I like Oregon going; they can possibly make the Elite 8.
So what are your chances of winning ESPN’s pool this year?
Jokingly, I’d give it a 50 percent chance. Everything in life is 50-50, like this year I’m either gonna win the ESPN pool or I’m not. It’s going to be funny cause my bracket will probably be blown up after the first couple days. I’d probably put it at less than one percent. With the tournament, you can do all the analysis and still, it’s crazy, you know.
Will anyone accurately predict the complete bracket and win Buffett’s billion?
A billion dollars, it could’ve been a hundred billion dollars. Nobody’s gonna touch it because it’s just insane. I think I had like 11 wrong last year [Gilmore actually had 12]. To even hit one upset is pretty significant odds, but to hit them all…
Are you cool with your bracket getting ruined if UCLA wins the national title?
People ask me this: Would you trade UCLA winning the national championship for not winning the bracket challenge? I’m like, “Oh no, I would win the bracket challenge.” I got an article in ESPN the Magazine. It’s been a blast for me. I’ve already seen UCLA win in 1995. UCLA can win the basketball championship almost anytime in my lifetime, but winning the bracket challenge is probably once in a lifetime.
How does your wife put up with this?
Any woman that was with me, if they couldn’t at least put up with sports in some form or fashion, it wouldn’t work out at all. When I was in college, there were at least two girls that I had just started hanging out with, and I was like, “Do you like sports?” And they were like, “No.” I’m like—I mean I wasn’t nasty—“This isn’t gonna work out.”