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Season 39 Jeopardy winner Jake DeArruda is a man of simple tastes for his newfound wealth

“I was 23 years old when my games aired last year, so I did what anybody under the age of 25 would do,” DeArruda said on Wednesday’s show. “I promptly spend the check on sports gambling and women and alcohol.”

DeArruda’s quip was met with laughter from the crowd and shock from host Ken Jennings, but the quote was all in good fun, having not actually blown the more $86,000 he net from the show.

“And by that, of course, I spent 20 bucks on a college football pick ’em that went horribly wrong, 20 bucks to take my date and I to the top of the Gillette Stadium Lighthouse, and several four packs of hard cider to get through the awful Patriots season that I endured.”

Sports gambling wasn’t officially legal in his home state of Vermont until Jan. 11, 2024, so DeArruda’s reference to a college football pick ’em likely relates to a PrizePicks sort of daily fantasy gaming.

DeArruda was on a hot streak during the 2023 Jeopardy circuit, walking away with more than $86,000 after he won three consecutive games.

The delivery dispatcher is originally from Ludlow, Vt. and had been a controversial figure on the show, with fans complaining about his on-screen behavior, including his facial expressions and interruptions of Jennings.

But it doesn’t seem like Jennings, nor the producers of the show, are bothered by him.


  Jeopardy host Ken Jennings was nearly speechless when hearing Jake DeArruda’s response to how he spent his winnings. Jeopardy, ABC Jeopardy host Ken Jennings was nearly speechless when hearing Jake DeArruda’s response to how he spent his winnings. Jeopardy, ABC

“He’s only 23 years old,” show producer Sarah Foss previouslytold TV Insider. “Ken joked in a post-game chat he’s got t-shirts older than Jake. [He] was inspired by Matt Jackson, who was another very strong champion back when he was 23 and just mowed down the competition.”

DeArruda was seen on the show mimicking a basketball jump shot while opening his final episode in 2023.


  Jake DeArruda’s boisterous attitude rubbed some fans the wrong way, throwing up the three fingers after his third consecutive win. Jeopardy, ABC Jake DeArruda’s boisterous attitude rubbed some fans the wrong way, throwing up the three fingers after his third consecutive win. Jeopardy, ABC

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“I’m encouraging everyone to show a little more compassion on the message boards,” Foss said to the cult-like following that “Jeopardy” receives.

DeArruda did not advance to the next round, having finished in second place.

He did walk away with $5,000, certainly enough to spend on more dates, alcohol and sports gambling.

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