A lawyer and CEO from London, United Kingdom...

Chuck Forrest

A law student at the time of his five wins in 1985, Chuck used his Jeopardy! winnings to pay for law school outright rather than take out student loans. In the years since he became the winner of the second Tournament of Champions in 1986, he has worked for the U.S. State Department and the United Nations, traveled to over 70 countries, and is presently the CEO of a human rights organization based in London, England. "I have spent most of my career living and working outside the U.S.," he says, "but everywhere I go, people remember me from Jeopardy!"

Hi, I'm Chuck Forrest, winner of the 1986 Tournament of Champions. Watch me participate in Jeopardy!'s Million Dollar Masters tournament. Right now you're watching me on jeopardy.com.

When did you first appear on Jeopardy!?
My first appearance on Jeopardy! was in 1985. I won five games and $72,800.

Any special strategy for the competition?
Not really--I haven't been watching Jeopardy! all these years, because I've been living outside of the country, so I'm, uh, not sure who I'm up against.

Did you get recognized from your previous Jeopardy! appearances?
I have been in the past--all over the world. Americans who've seen me on Jeopardy! Places as far away as Saudi Arabia and Australia.

What is your fondest memory from your previous appearances on Jeopardy!?
Uh, from my first appearance, it was just the, you know, winning the money, I really didn't have any expectations, and when I won five shows, it was just kind of a total shock to my system, I think.

"He became a winner of the second-ever Tournament of Champions in 1986. Now a CEO for a human rights organization based in London, this is..."

2024 Jeopardy! Invitational Tournament quarterfinalist: $5,000.
2014 Battle of the Decades semifinalist: $25,000.
2005 Ultimate Tournament of Champions Nifty Nine (players with byes into Round 2) member: $25,000.
2002 Million Dollar Masters tournament semifinalist: $25,000.
1990 Super Jeopardy! quarterfinalist: $5,000.
1986 Tournament of Champions winner: $100,000.
Season 2 5-time champion: $72,800.

A contestant early in Season 2, Chuck would remain the regular play winnings record holder with $72,800 until Season 6, when Bob Blake earned a cumulative total of $82,501 in his fifth game, #1152, aired 1989-09-12.
Chuck's style of play was typified by the Forrest Bounce, a clue selection strategy he employed to potentially confuse opponents.

Co-author with Mark Lowenthal of the 1992 book Secrets of the Jeopardy Champions.