Regular Game[]
He first appeared on Jeopardy! on October 30, 2000, where he became a five-time undefeated champion (at the time, returning champions were limited to five games) and accumulated $55,102.
| Game No. | Air Date | Final score | Cumulative Winnings | Additional Notes |
|---|---|---|---|---|
| 1 | October 30, 2000 | $10,201 | $10,201 | Brad's first game without a runaway. |
| 2 | October 31, 2000 | $14,000 | $24,201 | |
| 3 | November 1, 2000 | $10,601 | $34,802 | Brad's second game without a runaway. |
| 4 | November 2, 2000 | $15,200 | $50,002 | |
| 5 | November 3, 2000 | $5,100 | $55,102 |
Tournament of Champions[]
In the fourth quarterfinal game, he faced 5-day champions Doug Lach and Bob Fleenor. He gave 36 correct responses (including all DDs) and two wrong responses and entered Final with a runaway game. Final Jeopardy was a Triple Stumper, he wagered $0 and advanced to the semifinals. His opponents were eliminated from the tournament as they didn't score high enough.
In the third semifinal game, he faced 5-day champions Larry Cloud and Mark Eckard. He gave twenty-two correct responses (including two DDs) and only one wrong response. He and Larry got Final right. He wagered $6,201 and advanced to the finals.
In the finals, he faced 5-day champions Tad Carithers and Rick Knutsen. In game one, he gave seventeen right responses and three wrong responses. Final Jeopardy was a Triple Stumper and he wagered $3,500. In game two, he gave eighteen right responses (including two DDs) and only one wrong response. He and Tad got Final right. He wagered $7,801 and won $100,000.
Million Dollar Masters[]
In the second quarterfinal game, he faced 4-day champion and Tournament of Champions semifinalist Claudia Perry and 4-day champion, Tournament of Champions wildcard semifinalist and Super Jeopardy! quarterfinalist Kate Waits. He gave 26 correct responses (including one DD) and four wrong responses. He and Claudia got Final right. He wagered $7,001 and advanced to the semifinals.
In the second semifinal game, he faced 5-day champion, Tournament of Champions semifinalist, Tenth Anniversary Tournament second runner-up and Battle of the Bay Area Brains player Leslie Frates and 5-day champion and Tournament of Champions semifinalist India Cooper. He gave 33 correct responses (including one DD) and four wrong responses. Everyone got Final right, but a $0 wager from Leslie meant that Brad advanced to the finals.
In the finals, he faced Teen Tournament winner, Tournament of Champions semifinalist, Super Jeopardy! semifinalist and Teen Reunion Tournament winner Eric Newhouse and 5-day champion, Tournament of Champions winner and Super Jeopardy! first runner-up Bob Verini. In game one, he gave 26 correct responses (including two DDs) and four wrong responses. Final Jeopardy was a Triple Stumper and he wagered $4,000. In game two, he gave eighteen correct responses and two wrong responses. Everyone got Final right, he wagered $201 and is the show's first millionaire.
Ultimate Tournament of Champions[]
He earned a bye into Round Two. In round two, game twelve, he faced 5-day champion and Tournament of Champions quarterfinalist John Beck and 5-day champion, Tournament of Champions first runner-up and Super Jeopardy! quarterfinalist Bruce Naegeli. He gave 36 correct responses (including two DDs) and two wrong responses and entered Final with a runaway game. Bruce was the only player correct in Final; however, his runaway put him through to the quarterfinals.
In the first quarterfinal game, he faced 5-day champion and Tournament of Champions semifinalist Steve Chernicoff and 5-day champion and Tournament of Champions semifinalist Michael Rooney. He gave seventeen right responses and four wrong responses (including two DDs). He was the only player correct in Final and advanced to the semifinals.
In the second half of the semifinals, he faced 5-day champion and Tournament of Champions wildcard semifinalist Chris Miller and 5-day champion and Tournament of Champions semifinalist John Cuthbertson. In game one, he gave 30 right responses (including one DD) and four wrong responses (including one DD). He was the only player to get Final wrong. In game two, he gave 30 right responses (including two DDs) and two wrong responses (including one DD). He was the only player correct in Final and he advanced to the finals.
In the finals, he faced 5-day champion and Tournament of Champions second runner-up Jerome Vered and 74-day champion Ken Jennings (he had a bye into the Finals). In game one, he gave eighteen correct responses (including one DD) and two wrong responses (including one DD). Everyone got Final right and he wagered $4,200. In game two, he gave seventeen right responses and only one wrong response. He was the only player correct in Final. In game three, he gave 30 correct responses (including one DD) and only one wrong response. He was the only player correct in Final and won $2,000,000 and the record for most money won on a game show (until Jennings won $500,000 on Are You Smarter Than a Fifth Grader in 2008).
IBM Challenge[]
Rutter and Jennings returned in February 2011 for a two-day exhibition match against the IBM supercomputer Watson. This was Rutter's first defeat overall as he finished in third place. However, this did not count towards official show records since the event was an exhibition.
Battle of the Decades[]
In 2014, Rutter was invited back to play in the Battle of the Decades tournament. In the finals, he again faced off Ken Jennings; again, he prevailed over Jennings, taking home $1,000,000 and reclaiming the game show record.
All-Star Games[]
And in 2019, Rutter and Jennings were two of six team captains for the All-Star Games. Both of their teams (named Team Brad and Team Ken, respectively) advanced to the finals, where they faced Team Colby Burnett. Like in the two aforementioned tournaments, Brad's team won the All-Star Games, and the $1,000,000 top prize was split between Rutter, Larissa Kelly, and David Madden.
The Greatest Of All Time[]
Shortly after James Holzhauer won the 2019 Tournament of Champions, it was announced that Rutter, Holzhauer, and Jennings would compete for $1,000,000 in the Jeopardy! The Greatest of All-Time special, which aired in January 2020 on ABC. This time, Ken Jennings defeated Rutter, who didn't win a single match (he was outplayed by Jennings and Holzhauer) and thus finished as the second runner-up taking home $250,000. This was his first defeat to a human opponent.
After this game, like James, it was his last activity as a Jeopardy contestant. Contestants cannot compete on the show if they know anyone working on the show, and Ken's duties as a consulting producer and guest host made this the last of his Jeopardy career. However, the three of them have remained good friends and now star as the three chasers on ABC’s version of The Chase.