During his 'Jeopardy' run, the study/data showed that based on this average score winnings (which was almost always well over $70,000), he would surpass Ken Jennings' consecutive cash winnings record at the time he wins his 32nd or 33rd game. Oddly, James ended up being defeated in his 33rd game, just $58,484 short of surpassing Kens' record.