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