The largest overall winner is Brad Rutter, who has won over $4.2 million in various tournaments over the years. Since Rutter's regular play appearance occurred when they still had a five game limit he remains undefeated by a human being, having only ever lost to the IBM computer Watson in an exhibition game.
In terms of money earned in regular play, ie not including tournaments, the highest money winner is Ken Jennings, who earned over $2.5 million over the course of 75 shows.
