‘Jeopardy!’ champ Holzhauer learned early lesson about betting with heart

James Holzhauer, who on Monday returns to “Jeopardy!” after a two-week hiatus, has frequently discussed how his affinity for sports betting helped his record-breaking run on the popular game show.

How did he get his start as a sports bettor and how has sports gambling influenced the way he plays the syndicated show?

Holzhauer said he placed his first bet when he was 10, wagering on Super Bowl XXIX between the San Francisco 49ers and the San Diego Chargers with classmates in his native Naperville, Illinois.

The 49ers were favored by 19½ points and covered the largest spread in Super Bowl history in a 49-26 rout. Holzhauer lost his allowance on the Chargers.

“I bet on the Chargers because I was a Chargers fan that year. Just straight up, even money, even though they were enormous underdogs; I was a believer,” Holzhauer wrote in an email to the Las Vegas Review-Journal. “I lost about twenty bucks to eight different classmates, and I learned a lifelong lesson about betting on emotion.”

To be clear, Holzhauer said he lost a total of about $20.

“A dollar here, three dollars there,” he said. “Luckily I had a small allowance.”

To this day, the lifelong Chicago Cubs fan said, he doesn’t bet with his heart. No matter who’s playing.

“I try to bet strictly according to what my numbers say,” he said. “Sometimes this causes conflicts. I bet against the Cubs winning the 2016 World Series, so I wasn’t able to enjoy that historic moment as much as I could have.”

His fascination with sports and numbers continued into college, when he majored in math at the University of Illinois. But he likes to say he really majored in online poker. He used his online poker profits to build his sports betting bankroll and said he increased it with winning wagers in 2006 on the World Baseball Classic, Ryan Howard to win the MLB home run title at 40-1 and the Detroit Tigers to win the American League pennant at 100-1.

“I’m not naturally drawn to the emotional ups and downs of gambling, but I do love being able to see something the bookmaker missed,” he said. “Forecasting game results is the kind of thing I’m interested in anyway, so I figured I might as well make some money doing it.”

Holzhauer said he thinks of sports bets like an investment bank.

“In-game betting is basically day trading; futures markets are a hedge fund; handicapping is fundamental analysis; reading the market is technical analysis; actually placing bets is being in the trading pit,” he said. “The more of these skills you can master, the better off you’ll be.”

Holzhauer answered a record 187 consecutive clues correctly on “Jeopardy!”, but he said he’s never had a long streak of winners against the spread.

“I’m not really one to lay on the heavy favorites all the time, so four, maybe five,” he said of his longest sports betting win streak.

‘Advantage player’

DraftKings sportsbook director Johnny Avello, a former Wynn Las Vegas sportsbook director who has been in the industry for 33 years, has been impressed with Holzhauer’s sharp intellect and betting acumen since taking his wagers at the Wynn in recent years.

“He was an advantage player who won a little or broke even,” Avello said. “He bet mostly futures and series prices.”

Advantage players use legal methods to gain an advantage. These include arbitrage trading, or scalping, which is betting on both sides of a game or prop at different books for a guaranteed profit. Advantage players also simply shop for the best line, and multiple industry sources put Holzhauer in that category, saying he follows the market closely and always bets the best numbers.

For example, if a team climbs to a 7-point favorite at most books and only one book still has the line at 6½, Holzhauer will bet the 6½.

“To be a successful sports gambler, you have to balance multiple skills,” he said. “I definitely do my own handicapping, but it’s also vital to get the best available odds every time you bet, and that requires monitoring the market closely.”

Bookmaker.eu, an offshore sportsbook, has posted odds on whether Holzhauer will surpass all-time “Jeopardy!” champion Ken Jennings’ 74-game win streak and total winnings of $2,520,700.

According to Bookmaker odds consultant John Lester, the book has taken five figures worth of bets on the props. Most of the money is on Holzhauer, who has been bet up to a minus 500 favorite to eclipse Jennings’ winnings. That means a bettor would have to bet $500 to win $100.

But the odds on winning 75 games in a row are a toss-up. Yes and no are both minus 115, meaning bettors must put up $115 to win $100.

James vs. Jennings

Jennings, of Edmonds, Washington, set the show’s records in regular play in 2004. Holzhauer is second in both categories, winning 22 straight games and $1.69 million through May 3 before taking a break for the show’s annual Teachers Tournament.

Avello made Holzhauer a minus 140 favorite over Jennings in a hypothetical best-of-3 match mostly for his aggressive betting strategy and buzzer skills. That means a bettor would have to wager $140 to win $100 on Holzhauer, who has credited his career as a pro gambler with giving him the nerve to bet big on “Jeopardy!”

Holzhauer said he wouldn’t bet on himself as a big favorite over Jennings in a head-to-head match.

Bookmaker.eu made Holzhauer a minus 300 favorite over Jennings in a potential showdown.

“Ken Jennings has said that he is too old to play at his peak level, but we saw in February’s All-Star games that he is still top notch,” Holzhauer said of the 44-year-old. “I would bet on myself at even money but not at (minus 300).”

Lester said a Jennings win would be a major upset.

“While both players have stellar knowledge of all topics, Holzhauer’s strategic play of question ordering and Daily Double usage is superior, even game changing,” Lester said.

Regardless of how Holzhauer’s “Jeopardy!” run ends, a duel with Jennings would be must-see TV.

Jennings is still quick on the buzzer. Criticized recently on Twitter by a “Jeopardy!” fan for being “ultra conservative” and “almost afraid to lose” during his win streak, Jennings shot back, “ok bro, drop me a line when you win your 75th game so you can explain Jeopardy to me.”

Holzhauer retweeted Jennings’ post with the comment, “Challenge accepted!”

Contact reporter Todd Dewey at tdewey@reviewjournal.com. Follow @tdewey33 on Twitter.