A math whiz with a competitive streak and a childhood love for a popular, televised game confronts that same game as an adult years later, exploding its ingrained fallacies and applying an analytical, data-based approach to the game’s essential strategies — which proves to be wildly successful, but also subject to a backlash from traditionalists and aesthetes.
Long before James Holzhauer beat the game of “Jeopardy!” — becoming the second-longest-running champion in its history, with 22 straight wins and $1,691,008 in earnings, and the possibility of more to come when he returns to the show May 20 — he watched a handful of people with similar sensibilities succeed with that same approach in the only game he loved more than Jeopardy! as a child growing up outside Chicago: baseball.
“I didn’t look at anyone else’s strategy in ‘Jeopardy!,’” Holzhauer, 34, said in an interview with MLB Network on Tuesday. “I thought, I’m going to build this from the ground up. What do I need to do to win at ‘Jeopardy!’? If I’ve never seen a Jeopardy! game before, how would I play it to maximize my winnings, maximize my chances of winning?”
If that sounds like the approach that statistics pioneer Bill James or longtime Oakland Athletics executive (and protagonist of the “Moneyball” book and film) Billy Beane took to baseball a generation or two ago, it is no coincidence: Holzhauer, a lifelong Chicago Cubs fan who is a professional gambler by occupation, has cited James and Beane as models for the theories he has applied in both his professional and game-show lives.
Until now, the links between Holzhauer’s methodical dominance of “Jeopardy!” — second only to Ken Jennings — and its baseball-related underpinnings have been little more than a curiosity:
Holzhauer has said he always wanted to be the general manager of a baseball team. He wore a Cubs jersey for his MLB Network interview. He has suffered a backlash from “Jeopardy!” fans who think his analytics-based approach — he uses high-value clues to build a bankroll, then seeks out Daily Doubles using probability data compiled from previous games — has “ruined” that game the same way concepts such as defensive shifts and launch-angle swing theory has “ruined” baseball.
But now, baseball people are also taking notice of Holzhauer, and the merging of his success in “Jeopardy!” and his passion for baseball is no longer a mere curiosity — it may be the start of a new career. Assuming baseball can afford him, that is.
“My first thought when I saw him,” said Beane, the Athletics’ executive vice president of baseball operations, “was: We have to get this guy in baseball.”
“Absolutely, yes,” said Boston Red Sox President and chief executive Sam Kennedy, when asked about Holzhauer’s prospects in baseball. “We put a huge premium on analytical abilities both on the baseball side and business side. Without question, when we interview young professionals coming out of college, that skill set is hugely important.”
If you’re skeptical that people with Holzhauer’s skill set could land a job in a baseball front office, or that baseball front offices would hire someone like him, here’s the answer to both: They already have.
“Absolutely. He’s very intriguing,” Baltimore Orioles Vice President and Assistant General Manager Sig Mejdal said, when asked about Holzhauer’s suitability for a baseball job. But in a nod to Holzhauer’s reigning-champion status on “Jeopardy!,” he added, “It looks like his days are still pretty busy.”
If anyone understands how there could be a place in baseball for someone with Holzhauer’s background and skills, it is Mejdal.
A former A’s fan and fantasy baseball player with degrees in aeronautical engineering and cognitive psychology, Mejdal, 53, was working as a biomathematician for NASA when, in 2005, the St. Louis Cardinals offered him a job in their analytics department. Seven years later, he moved to the Houston Astros to be their “director of decision sciences” — essentially building out the analytics department that soon became an industry leader and helped lead the franchise to its first World Series title in 2017.
In Holzhauer, Mejdal sees parallels “not only to myself, but to many successful analysts and decision-makers in baseball. I see a similarity in how we think. Of all the analysts we’ve hired in St. Louis, Houston and Baltimore, none have come from the baseball industry. They’ve all been from outside. They may have been involved in baseball research as a hobby, but it wasn’t their primary occupation. What there was, was a passion for the sport.”
Mejdal, in fact, knows something about the gambling industry himself, having once worked as a blackjack dealer in Lake Tahoe to help pay for college, absorbing the lessons of probability and human tendencies across those green-felt tables.
“Hitting a 16 against a dealer’s seven, it doesn’t feel right. With a $100 bet, it feels even less right,” Mejdal once told Sports Illustrated. “But that doesn’t mean it isn’t right.”
For a sport with a long, queasy history with gambling — a sport that still won’t let Pete Rose into the Hall of Fame because he gambled on his own games — Holzhauer’s background might create some problems. He acknowledged having bet heavily on baseball, especially in his early days in the profession, applying advanced statistical concepts that the Las Vegas sports books had not yet discovered — and cashing in big before the houses got wise. (He said his primary sport is now college football.)
“When I got started, baseball was the best game in town,” he said Tuesday. “They were making some big mistakes, especially in the futures markets, pricing the long shots incorrectly. That was how I got a big enough bankroll to play with. … Early in the 2000s, I was quick to adopt a lot of the new stats they had out there, and I think the books took a long time to incorporate the new stats into their oddsmaking. So for a while, the stats guys were really ahead of the curve. I know some other people who also cleaned up on baseball. It’s a lot harder game now.”
But baseball has also softened its stance somewhat toward gambling, reaching an agreement in November with MGM International Resorts as its official casino partner, with MLB sharing proprietary Statcast data with MGM. Personnel working in baseball are still prohibited from gambling on the sport, but the agreement underscored the links between gambling and fantasy baseball, as well as fantasy baseball and the real thing.
“We’re sort of all in the prediction business,” Mejdal said. “[Gamblers] are just trying to predict tonight’s game. But with us, we’re not only trying to predict the outcome of that night’s game — using data on pitching matchups and analysis of individual performances — but also in a longer time-frame than they are, over entire seasons and multiple seasons. We’re in the prediction business just like them.”
“Gambling has always been taboo in baseball,” said Beane, who is also a minority owner of an English soccer club. “But if you look at the analytics influence in European football, the guys at the forefront are gambling guys, because gambling has been legal there, and a major part of sport. The best and brightest in football and gambling come from the same space.”
Though plenty of baseball executives have voiced their admiration for Holzhauer, and pondered a future in the sport for him, none has gone on the record to acknowledge real interest in hiring him. That, however, doesn’t mean the interest isn’t there, or that inquiries haven’t already been made. In his MLB Network interview, Holzhauer mentioned “some interesting offers [that] have been floated my way … some potentially life-changing stuff out there.”
But to hire Holzhauer, baseball teams will confront the same problem the sport has faced for years now in its search for new talent in the analytics realm: fierce competition. As the analytics movement has grown, teams have had to compete for talent not only against each other, but against other sports — and other, higher-paying industries.
“I’m going to go out on a limb,” Beane said, “and say when he’s done with [“Jeopardy!”] he’s going to have an opportunity to work in any sport he wants. Or any industry — because all industries are based on data and making predictive decisions.”
Just as a new generation of GMs imitated Beane’s work with Oakland, and an even newer generation has modeled their operations on the Astros’ success — to the point where analytics has crept into every organization and every facet of the game — so, too, will Holzhauer’s success almost certainly spawn a generation of imitators. But as the most progressive baseball teams have found, when everyone is operating with the same theories, it becomes harder to find an advantage.
It also increases the degree of the backlash. Already, critics have linked Holzhauer’s success to the so-called “ruining” of baseball, opining that the cold, evidence-based approach has taken all the fun and nuance out of the game.
Not surprisingly, Holzhauer cited the cold, hard data reflecting “Jeopardy!”’s bottom line — viewership has soared as his winning streak has grown — to defend his approach.
“There’s definitely some people who don’t like the product they’re seeing on screen right now,” he said. “But I don’t think the producers are complaining.”
In baseball, the smart-guys-are-ruining-the-game argument is perhaps best exemplified by the application of defensive shifts — essentially positioning the fielders in the places where batters are most likely to hit the ball — which have helped bring the leaguewide batting average (.244 entering Wednesday) to its lowest point in 47 years.
“I’ve heard the same thing, and I just laugh,” Beane said. “Baseball teams could’ve shifted 100 years ago, and nobody did. But in the last five years, a lot of really smart people have come into the game, and it’s thrown the whole game upside-down. It’s an unemotional, rational way of doing things.
“It’s the same thing [Holzhauer] is doing: It’s bringing order to something that’s inherently chaotic. If he’s ruining “Jeopardy!,” and if we ruined baseball, then ruin away.”