Masters of the Game
Ken Jennings currently holds the record for the most wins ever on Jeopardy!—74 times in a row. Despite the sheer number of occasions on which Jennings walked away from the show with a winning hand, his monetary earnings didn't hold a candle to those of Brad Rutter. Rutter holds the record for the most cash won by a single player on the show: $4,688,436.
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