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5-time Champion Rule
S16~19
Unlimited Champion Rule

Season 16[]

Name Aired Date TW Notes
Steve Fried September 27~October 1, 1999 $45,200
Eddie Timanus October 20~26, 1999 $69,700 Passed the Jeopardy! test despite the fact that he was blind.
Darlene Lieblich-Tipton December 10~16, 1999 $35,197 Once worked for CBS, even at the time of the Michael Larson shows on Press Your Luck. She even made an appearance in Big Bucks: The Press Your Luck Scandal.
Jack Archey December 29, 1999~January 4, 2000 $51,302
Lee Lassiter January 25~31, 2000 $54,599
Jeremy Bate February 4, 21~24, 2000 $55,000 5 game run was interrupted by the 2000 College Championship.
Alternate in Million Dollar Masters.
Robin Carroll March 13~17, 2000 $64,100 2000 Tournament of Champions Winner.
Won the 2001 International Championship in Las Vegas.
Mike Blumenfeld April 7~13, 2000 $44,400
Doug Lach July 6~12, 2000 $85,400
Tad Carithers July 14~20, 2000 $60,400

Season 17[]

Name Aired Date TW Notes
Michelle Clum September 13~19, 2000 $50,200 The last retired female 5-time champion.
Last female 5-time champion before clue values were doubled on 11/26/2001.
Andrew Garen September 20~26, 2000 $56,100
Brad Rutter October 30~November 3, 2000 $55,102 2001 Tournament of champions winner.
2002 Million Dollar Masters Tournament champion.
2005 Ultimate Tournament of Champions ultimate champion.
Faced off with Watson and Ken Jennings in the IBM challenge.
2014 Battle of the Decades Tournament champion.
2019 All-Star Games champion (with David Madden & Larissa Kelly)
Faced off in Greatest of All-Time tournament with Ken Jennings and James Holzhauer.
Michael Arnone January 9~15, 2001 $54,499
Rick Knutsen March 6~12, 2001 $57,300
Bob Fleenor March 28~April 3, 2001 $55,700
Ryan Moore April 4~10, 2001 $39,800
Larry Cloud April 12~18, 2001 $66,100
Babu Srinivasan May 16~22, 2001 $75,100
Mark Eckard June 8~14, 2001 $69,600 Died October 2, 2017 at age 60.
Lan Djang June 20~26, 2001 $51,100
Kevin Keach June 27~July 3, 2001 $50,703
Alan Bailey July 12~18, 2001 $61,501

Season 18[]

Name Aired Date TW Notes
Mark Dawson September 14~20, 2001 $52,599 2003 Tournament of champions winnership.
He was a contestant on Classic Concentration from March 3, 1988, during Game 2.
Trevor Norris November 5~6, 21~23, 2001 $54,604 5 game run was interrupted by College Championship.
Last 5-time Champ before clue values were doubled on 11/26/2001.
Ben Tritle May 16~22, 2002 $78,600 Longest gap between 5-time champs under the "5-time Champ Rule" (101 games).
First 5-time Champ after clue values were doubled on 11/26/2001.

Season 19[]

Name Aired Date TW Notes
Mark Brown October 3~9, 2002 $68,094 Died on January 23, 2013 at age 48.
Travis Troyer February 18~24, 2003 $83,100
Brian Weikle April 10~16, 2003 $149,200 Sets new one-day record with $52,000 in his third game.
Retired 5-day Champ highest total winnings.
Alternate for the 1990s group in Battle of the Decades.
John Beck June 13~19, 2003 $117,099 The last retired 5-time champion.
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