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. Alex Trebek, via 'Jeopardy'