During the whole 'Jeopardy' experience, I felt like I was living a bit of a double life, I would be secretly flying out to L.A. to tape new shows, hoping that none of my coworkers would notice the absence and figure out what was going on. 'Jeopardy' tries very hard to keep their secrets.

Early life
Born in Edmonds Washington Jennings grew up in Seoul South Korea (1981–1992) and Singapore (1992–1996) where his father worked for an international law firm and then as Asia Pacific Division Counsel of Oracle Corporation. Jennings attended the University of Washington during his freshman year. " Jennings had already posted a more serious comment defending Trebek that remains on his website.

S. His total was surpassed by Brad Rutter who defeated Jennings in the finals of the Jeopardy! Ultimate Tournament of Champions (first aired on May 25 2005) adding $2000000 to Rutter's existing Jeopardy! winnings. During his first run of Jeopardy! appearances Jennings earned the record for the highest American game show winnings.