2002 Million Dollar Masters Tournament, where he won the $1,000,000 main prize and became the largest overall money winner in Jeopardy! history. Rutter returned for the 2005 Ultimate Tournament of Champions, winning the tournament and $2,115,000. After his 2005 tournament win, in which he defeated Jennings and Jerome Vered in the finals, Rutter surpassed Jennings as the highest money-winner ever on American game shows. Jennings later regained his record by 2008 after appearing on various other game shows. There is a minor discrepancy between sources as to Rutter's total Jeopardy! winnings stemming from the prize structure of the Ultimate Tournament of Champions. Players who won in the first round earned $15,000, but Rutter was among nine top winners who received a first round bye. While some analysts suggest that Rutter's money totals should include $15,000 for a first round 'win' in this tournament, the official Jeopardy.com website does not count it (when stating that Rutter's winnings were $3,255,102 after the completion of this tournament). From February 14–16, 2011, the Jeopardy! IBM Challenge featured IBM's Watson facing off against Rutter and Jennings in a two-game, cumulative-total match aired over three days. It was the first ever man-versus-machine competition in Jeopardy!'s history. The computer program, equipped with a precisely timed mechanical "thumb", won handily, finishing with a $77,147 score, while Jennings took second place with a score of $24,000 over Rutter's $21,600 score. IBM donated its $1 million purse to two charities. Jennings and Rutter did likewise with half of their respective winnings of $300,000 and $200,000. Rutter donated $100,000 to the Lancaster County Community Foundation. Because this man-versus-machine matchup was an exhibition, Rutter's winnings and loss did not count towards official records. Rutter participated in the Jeopardy! 2014 Battle of the Decades, pitting top champions from throughout the previous 30 years of Jeopardy!. He appeared in the 1990s week of the tournament. He won the March 7, 2014, game against Mike Dupee and Jill Bunzendahl Chimka. He then appeared in the quarterfinals of the tournament on May 7, 2014, against Dan Pawson and Mark M. Lowenthal and won the game in a lock. On May 13, 2014, he defeated Leszek Pawlowicz and Tom Cubbage in the semifinals. On May 16, 2014, he won the tournament and $1,000,000, defeating Ken Jennings and Roger Craig in the finale after the former missed the Final Jeopardy! clue. With this win, Rutter regained the record