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.