Featured J!Buzz Contestants 12.21.2015 All-Time Top Money Winner, Brad Rutter 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