Jeopardy! viewers who have played against Ken Jennings spoke out about what that experience was like. Some contestants also played against him on another game show, The Chase. Ken Jennings had an amazing 74-day winning streak and participated in 75 episodes. So, that’s 150 different people he would have competed against, as he would have faced two different people each night. His original run was in 2004, and then he went on to compete in numerous tournaments. He racked up $2,520,700 in winnings for regular gameplay, which is the highest ever, according to the Jeopardy! website. Brad Rutter had the highest total of winnings of all time, which includes tournaments. Jennings is currently in second. “Did anyone here face Ken Jennings? Is there anyone in this sub that went up against Ken Jennings in his original 75-episode run?” a Reddit user wrote. “I actually went up against him in a team Quiz Bowl...