Despite Ken Jennings’ impressive run, the highest cumulative amount won by a single contestant belongs to Brad Rutter, a player whose combined totals of his 2002 streak and 2005 “Ultimate Tournament of Champions” streak netted him $3,255,102. Ken Jennings has racked up $ 2,520,700 thus far. Ken does, however, hold the highest one-day total record: $75,000.