Short answers, pulled from the story.
Bradford Gates Rutter appeared on Jeopardy! for the first time on the 30th of October 2000. He won five consecutive games without losing a single match to earn $55,102 in total winnings plus two Chevrolet Camaros as prizes.
Brad Rutter won $2,115,000 during the Ultimate Tournament of Champions held in 2005. This amount made him the highest earning contestant ever on American television at that time.
Brad Rutter finished third with $21,600 during the IBM Watson Challenge which took place from the 14th through the 16th of February 2011. He donated half of his $200,000 prize to charity including the Lancaster County Community Foundation after the exhibition match concluded.
Brad Rutter won one million dollars on the 7th of March 2014 during the Jeopardy! Battle of the Decades tournament. His team representing champions from the 1990s era defeated Ken Jennings in the final round to restore his status as the highest money winner on American game shows.