The Jeopardy Hall of Fame lists Roger Craig with the highest total of $77,000 on 9/14/10 and Ken Jennings with the second highest at $75,000 on 7/23/04. Ken Jennings also holds the record for 10 of the 12 other games that were next highest with scores between $50,000 and $55,099. Brian Welke with $52,000 on 4/14/03 and Myron Meyer with $50,000 on 9/5/02 hold the other 2. see related link
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