Ken Jennings Wins 'Jeopardy! The Greatest of All Time' The 45-year-old took home $1 million after claiming victory in the fourth match of the series. He defeated James Holzhauer, the show's third-highest earner and Brad Rutter, who has won the most money in 'Jeopardy!' history. Both of the runners-up received $250,000 for their efforts. Jennings earned nationwide fame back in 2004 when he won a record 74 straight matches on the popular game show. The software engineer is now America's all-time game show winnings leader. Alex Trebek, via 'Jeopardy'
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