Cindy Stowell
Tragically, Cindy Stowell was diagnosed with terminal cancer just after she qualified. Thus, the Jeopardy! producers were able to rush the filming process to get her on. With Stage 4 cancer, she competed, fulfilling her lifelong dream and winning $105,803. The chemical engineer donated all her winnings to charity. Sadly, she passed away in December of 2016.
Ken Jennings
Seriously, we hope this second highest winner has a solid financial advisor, considering he took home $3,270,700! Amazingly, Ken Jennings holds the record for most consecutive Jeopardy! games won (74). Since his unbelievable success, the computer scientist/author wrote about his time on Jeopardy! and American trivia culture and history. Seems like a good next step after experiencing such a wild ride on television.