It's a sortable list of the biggest winners in Jeopardy! history. made the Tournament of Champions ; or; won over $50, (unadjusted). Kenneth Wayne "Ken" Jennings III (born May 23, ) is an American game show contestant and author. Jennings holds the record for the longest winning streak on the U.S. syndicated game show Jeopardy! and Early life · Streak on Jeopardy! · Jeopardy! Tournaments · After Jeopardy!. Jeopardy! is an American television game show. Its format is a quiz competition in which .. Brad Rutter (born January 31, ) is the biggest all-time money winner on Jeopardy! and briefly held the record for biggest cumulative game show Fleming era (–79) · Trebek era (–present) · Bob Harris · Ken Jennings.