Featured J!Buzz Contestants 12.21.2015 All-Time Top Money Winner, Brad Rutter To view videos on this site, you need to enable certain cookies.Privacy Settings From his first appearance on Jeopardy! through multiple subsequent tournament victories, Brad Rutter remains the record holder for All-Time Winnings with $4,938,436. Flashback through some highlights of his wins. Jeopardy! Flashbacks Brad Rutter You May Also Like Contestants 10.19.2015 Roger Craig Sets the 1-Day Winning Record News & Events 09.01.2014 Meet Jeopardy!'s Super Stylish Mega-Champion News & Events 06.22.2015 Watson IBM Invitational