Rutter entered the tournament having never lost a match against a human, only coming up short in an exhibition match featuring him and Jennings taking on Watson in Jeopardy!: The IBM Challenge in 2011. Rutter still holds the record as the highest-earning contestant (primarily from special tournament events) on Jeopardy! with a total of $4,688,436 entering the tournament. He later defeated Jennings and Roger Craig in the 2014 Battle of the Decades tournament, winning an additional $1,000,000 and reclaiming his spot at the top of the all-time winnings list from Jennings, who had retaken it in 2009. Rutter defeated Jennings and Jerome Vered in the final to win the tournament, and the prize money made him the new all-time American game show winnings leader. Shortly after Jennings’s run as champion ended, Rutter was one of the many former champions invited back for the 2005 Ultimate Tournament of Champions, where two of the former champions in the field would face Jennings in the final match for $2 million. He was invited back in 2002 for the special Million Dollar Masters Tournament with several past champions, and emerged victorious again to become the first Jeopardy! contestant to win over $1 million. After winning $55,102 in his initial run, Rutter qualified for and won the 2001 Tournament of Champions, which at the time was played for $100,000. He first appeared on Jeopardy! in October 2000, during the era of the program where contestants were retired after winning five consecutive matches and before the show doubled its question values. Rutter was the highest-earning American game show contestant of all time entering the tournament. He agreed to compete largely out of respect for Alex Trebek and because it would be "almost certainly last time" as a contestant. Jennings said he took part in the competition reluctantly, fearing that because of his age and repeated tournament losses to Rutter (Rutter having won every head-to-head matchup between the two except the IBM Challenge), he was past his peak as a Jeopardy! contestant. Entering the tournament, his total Jeopardy! winnings totaled $3,372,700, which was second-highest behind fellow competitor Rutter. He won 74 consecutive matches, and his total of $2,522,700 is a record for non-tournament winnings. Jennings first appeared on the program in 2004 and set two Jeopardy! records that he still holds. The contestant with the highest combined score from the two games would win the match, and the first one to three match wins won the tournament. Scores were in points instead of dollars. Each game was played as normal with the Jeopardy! and Double Jeopardy! rounds followed by Final Jeopardy!. The tournament began on January 7, 2020, and each match consisted of two games. With the $1 million prize added to his previous winnings across several game show appearances, Jennings surpassed Rutter as the highest-earning American game show contestant of all time, a record he had previously held twice. Jennings won the tournament on January 14, 2020, with Holzhauer finishing second and Rutter third. The tournament featured former champions Ken Jennings, Brad Rutter, and James Holzhauer competing for a $1 million top prize and the recognition of being the show’s greatest champion of all time. JEOPARDY RECORDS SERIESThis was the first time any Jeopardy! competition aired on network television since 1990, when the special tournament series Super Jeopardy! was carried by ABC. The tournament was produced for ABC and aired on the network in prime time. Jeopardy! The Greatest of All Time was a special tournament limited-run series of the game show Jeopardy! that took place in January 2020.
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