 Madden was selected as the 7th out of 12 picks in the All-Star Games Draft in September 2018, thus becoming a member of "Team Brad" along with his former Princeton University Quiz Bowl teammate, Larissa Kelly who was the 6th pick in the draft.Team Brad won its first-round match and in the final episode, airing on March 5, 2019, "Team Brad" won the All-Star Games Tournament grand prize of $1,000,000, which was split between the three team members.After Madden's share of the prize was received, his all-time Jeopardy!