Jeopardy

We spoke with “Jeopardy!” star James Holzhauer to learn just what being a professional sports gambler entails. 

By Michael Shapiro
May 14, 2019

A version of this story appears in the May 20, 2019, issue of Sports Illustrated. For more great storytelling and in-depth analysis, subscribe to the magazine—and get up to 94% off the cover price. Click here for more.


Long before James Holzhauer racked up $1.69 million as a contestant on Jeopardy!, he made a living as a sports gambler in Las Vegas. Far from a traditional occupation of most contestants, Holzhauer has spent the last 12 years bankrolling his life with bets on MLB home run titles and college football futures.

So how did Holzhauer get into the gambling business, and how has it informed his dominant Jeopardy! strategy? Sports Illustrated spoke with the 22-game champion.

Michael Shapiro: You’re introduced on Jeopardy! as a sports gambler. What does that entail?

James Holzhauer: So a lot of time went into the research and development of how to handicap games, but the day-to-day is often spent checking odds for different upcoming events. It’s not like the stock exchange where you get the best available price anytime you want to buy, here you have to shop around and find who’s giving you the best odds on the team you want to bet on that day. If a price will get better, I’ll wait to place my bet until it does. So that’s really the bulk of the day, doing the trading itself and staying up to date on news, too. If there’s injury news there’s very little time to react on the market before someone else does.

MS: When did you start sports gambling?

JH: So in college [at Illinois] I was an online poker player and I also ran a poker strategy website where people would click through links to go sign up at online card rooms and they’d pay me online referral fees for that. And I played fantasy sports heavily in my college years, so the idea of analyzing numbers to see who would be the best teams and players the next year was already something I was doing anyway. So the idea that I could make some money doing this was a natural fit. I turned 21 in 2005 and the 2006 World Baseball Classic was a big event for me, I did very well on that. That season I bet a lot of baseball futures and won two big ones. I bet [Phillies first baseman] Ryan Howard would win the home run title at 40/1 odds and he did. I then got 100/1 odds on the Tigers to win the AL pennant and make the World Series and they did. That provided me with the bankroll to be more heavily invested moving forward into 2007.

MS: Do you have a go-to sport or team or type of wager?

JH: One of the things I specialize in that not many people do is keeping a close eye on futures markets, trying to find teams that are underpriced there. Sometimes it gets to a point that I bet so much futures on a team that I’ll end up betting against them when the playoffs start. It’s kind of like running a long-short hedge fund in some ways. There’s definitely times where I’ll take one side of the game on the spread and the other team on the money line. A big part of it is handicapping teams right, but possibly an even bigger part is knowing the math, and finding the mathematical edges that exist.

MS: Where do you have the biggest success?

JH: One thing I specialize in is halftime and in-game bets. As a general rule, the less time a bookmaker has to set his odds the softer the odds are going to be. At halftime he has five minutes to put a line up whereas the line for the whole game has been up all week. If every time there’s a commercial break they’re putting up new odds, they’re going to make a mistake. If you’re paying attention you can clean up for sure.

MS: Do you have any other jobs, or are you fully a sports gambler right now?

JH: The last real job I had I was 16-years-old slinging fried chicken in my hometown of Naperville, Ill. I spend more time parenting than anything if that counts. Managing my public life has also been a big job over the past month, but it’s basically been all sports for a while now.

MS: What have you applied to Jeopardy! from your gambling career?

JH: The aggressive betting on the daily doubles is one of my trademarks. People should be betting big, and people who have a normal day job may not feel as comfortable betting this much money, though really it’s just points on a scoreboard until you actually win the game. I think there’s a mental block for betting big amounts that doesn’t exist for me but it does for other people. So that’s a big advantage my background gives me.

MS: Have you set any goals for your Jeopardy! run? Are there any records you are eyeing?

JH: When I went up there I was hoping to win one game, and that seems a little silly now but that was just the goal, just play the one game in front of you, don’t worry about streaks or dollar totals, though I did want to win exactly $110,914 because that’s my daughter’s birthday. That was the one specific goal I had.

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