'Jeopardy!' champ eyeing MLB GM position?

Holzhauer, a lifelong Cubs fan, considered front-office job a dream early in life

May 2nd, 2019

As a kid growing up outside of Chicago, James Holzhauer came home from school, turned on the TV and indulged in his two great loves: Cubs baseball games and "Jeopardy!" episodes, both of which aired in the afternoon.

“My dad would come home from work and turn the TV off,” Holzhauer said, smiling at the memory. “But I had already had my fun.”

Most kids are asked at least once in their childhood that standard question: “What do you want to be when you grow up?” Holzhauer had two items on his list: be a contestant on "Jeopardy!" and work in a Major League Baseball front office.

Needless to say, one-half of that to-do list has been checked off. Could the second be lurking around the corner?

Wearing a Cubs jersey while speaking with MLB.com via Skype from his home in Las Vegas, Holzhauer, a professional sports gambler, is more focused these days on what’s happening in real time. He’s been thrust into the national spotlight behind the strength of his sheer dominance on "Jeopardy!," the popular trivia game show that pits three contestants against each other in a test of intelligence, quick-thinking and the ability to buzz in ahead of the competition.

The 34-year-old Holzhauer, as of Wednesday, has won 20 days in a row, with his winnings reaching $1,528,012. With one more win, he'll be the only contestant other than Ken Jennings to reach more than 20 wins.

Until recently, Holzhauer’s story wasn’t really a baseball one. That changed when he responded to a Washington Post op-ed questioning unconventional methods he’s using to crush his opponents. He tweeted, “I always dreamed of working in an MLB front office and ruining baseball, but I have to settle for ruining @Jeopardy instead.”


“I kind of put it aside the last 10 years or so, but when I was a teenager, I was idolizing guys like Billy Beane and Theo Epstein, who were really bringing the statistical revolution to the masses,” Holzhauer said. “I don’t know if I’m the kind of networking/interpersonal skills guy who could become a GM, but being a guy who can help the team on making decisions on which guys to trade for and sign as free agents, that was the dream back then.”

It’s the dream of a lot of young, mathematically-minded whipper-snappers who are mapping out their post-college careers. What makes Holzhauer different is that he has employed a lot of the logic front offices use to assemble their rosters, and he’s doing it front of millions of viewers every night on a revered, decades-old game show.

Using his sports-betting background to strategize how he approaches the "Jeopardy!" board of clues, Holzhauer leverages the limited time he has to accumulate the most assets. He starts at the bottom, where the higher-dollar “answers” are placed, builds up equity then searches for the hidden "Daily Double" clues, where he can bet the house and double his already sizable total.

His stoic risk-taking may be his biggest advantage over the competition. As a sports bettor, wagering large -- even eye-popping -- sums of money doesn’t faze him. Holzhauer lets probabilities dictate his every move.

Sound familiar?

Front offices, filled with masterminds searching for every little opening to exploit a market inefficiency, rely heavily on probabilities when projecting a player’s long-term value.

Who remembers the famous 2014 Sports Illustrated article foreshadowing the Astros’ 2017 World Series title? The story opened with an anecdotal account of then-Astros executive Sig Mejdal working a blackjack table, post-college, in a Lake Tahoe casino, where he “learned that human beings do not always make decisions that serve their own long-term self-interest, even when they are equipped with a wealth of experience and knowledge of the mathematical probabilities that ought to guide their choices.”

Holzhauer, armed with plenty of experience and knowledge, makes a living off of crunching numbers and high-stakes wagering. Front offices do the same thing, without the monetary wagering, of course.

“It is exciting for me to see the stats guys winning the battle and getting into MLB front offices,” Holzhauer said. “I see a lot of people commenting, ‘Oh, everyone’s shifting now. There are so many more home runs and strikeouts.' But that’s kind of just the natural direction of the game for people to figure out -- shifting works, home runs work and these are things that help our team win games. Above all, that’s what people care about.”

With a steady income, comfortable lifestyle and schedule that allows him to be an engaged parent to his young daughter, Holzhauer is not feeling overly motivated to pursue a career change, even if it involves working for a Major League team.

But that doesn’t mean it’s off the table completely.

“I’ve got a family and job that I really love with super flexibility,” he said. “I wonder, even if they come knocking, if I would actually accept. But part of me does wonder what it would be like to realize that childhood dream. I would have to at least think about it if the right offer came along.”

What are the odds?