Seattle’s Ken Jennings has returned to the “Jeopardy!” stage this week as one of three all-star contestants on ABC’s “Jeopardy! The Greatest of All Time.” He defeated James Holzhauer and Brad Rutter on Tuesday to win the first night. On Wednesday, Holzhauer won the second night of the tournament.

The prime-time competition features the quiz show’s three most successful players, and will last until one player wins three matches. The winner will receive $1 million and be crowned the “greatest of all time.” The two runners-up will each receive $250,000.

“Jeopardy!” host Alex Trebek, left, with contestants James Holzhauer, Ken Jennings and Brad Rutter on the set of “Jeopardy! The Greatest of All Time.” (Eric McCandless / ABC)
“Jeopardy!” host Alex Trebek, left, with contestants James Holzhauer, Ken Jennings and Brad Rutter on the set of “Jeopardy! The Greatest of All Time.” (Eric McCandless / ABC)

Jennings holds the record for the longest winning streak in “Jeopardy!” history with his run of 74 games in 2004. His streak was so stunning that host Alex Trebek called the “Super Tournament” that took place in 2005 the “quest for Ken.”

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In 2011, Jennings returned to “Jeopardy!” to compete against fellow champion Brad Rutter and IBM’s Watson computer system. Both Jennings and Rutter committed to donating half of their winnings to charity, and IBM donated all of its winnings to charity. Jennings chose the Seattle-based nonprofit VillageReach.

He said he chose the Fremont-based nonprofit, which focuses on infrastructure and logistics for distributing medical supplies in Africa, because of its “innovative approach to improving access to health care and commitment to documenting the results of their work for donors.”

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Watson beat its human opponents by a large margin, winning $41,413 for the day ($77,147 for both games), while Jennings reached $19,200 ($24,000 overall) and Rutter reached $11,200 ($21,600 overall). For defeating its rivals, Watson won a total prize of $1 million, which IBM said went to the charities World Vision and World Community Grid. Jennings came in second place and won $300,000; Rutter won $200,000.

While some were concerned by the outcome of this battle between man and machine, Jennings accepted his loss with humor.

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“I for one welcome our new computer overlords,” Jennings wrote alongside his correct Final Jeopardy response (“Dracula” author Bram Stoker), apparently trading on a line from “The Simpsons.” Clearly Jennings is a good sport with a sense of humor.

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“Jeopardy!” contestant Ken Jennings was defeated by IBM’s Watson in 2011. He wrote “I for one welcome our new computer overlords” alongside his Final Jeopardy answer. (Seth Wenig / The Associated Press, file)
“Jeopardy!” contestant Ken Jennings was defeated by IBM’s Watson in 2011. He wrote “I for one welcome our new computer overlords” alongside his Final Jeopardy answer. (Seth Wenig / The Associated Press, file)

Jennings showed his sense of humor again in 2016, when successful Seattleites shared their first seven jobs on Twitter. While local artists and business owners joined the thousands of people sharing their first few jobs, Jennings chose to share his knowledge of Billy Joel lyrics.

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In June 2019, James Holzhauer won $2,462,216 over his stretch of consecutive victories, which fell just shy of the $2,520,700 Ken Jennings won during his 74-game run. When Holzhauer’s 32-game “Jeopardy!” winning streak ended, Seattle Times columnist Matt Calkins spoke with Jennings.

“He looked so unbeatable. I was like, ‘This guy is going to be playing until the year 2100, when we’re all just heads in jars.’ But a ‘Jeopardy!’ game is such a fragile thing. You never know which one is going to have your name on it. Two things go right for you, it can change everything. Same if two things go right for the other person. That’s what happened.” 

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Since his “Jeopardy!” streak ended, Jennings has become a bestselling author. His books include “Brainiac,” which delves into trivia in American culture; “Ken Jennings’s Trivia Almanac,” a book of 8,888 trivia questions; and “Because I Said So!,” which challenges parenting clichés. He has also written a series of Junior Genius Guides, one of which was a finalist for the Washington State Book Awards in 2015.

Jennings, born in Edmonds, now lives in North Seattle with his wife, two children and dog. He has said he lives in a house that “‘Jeopardy!’ built,” explaining that he could not have afforded a house in Seattle if not for his winnings on the game show.