Dargan Ware’s journey to Jeopardy! started at 12-years-old when his grandmother paid him to read encyclopedias.
Today, at 49, he is a winning contestant of the classic game show Jeopardy!
“It was a wonderful experience, a lot of fun,” Ware said.
Last night, Jeopardy aired its championship episode, where past winners compete head to head, which Ware, a Bessemer resident, participated in. While he did not move onto the next championship round, he did win and fulfill his longtime dream of competing.
Ware said he has tried to become a Jeopardy! contestant for almost 30 years.
As a child of a National Park Service member, Ware moved around a lot as a child, from Arkansas to Alaska.
But no matter where he went, his love for knowledge and trivia was always close behind.
“I read all the encyclopedias, and I started getting into playing trivia and watching Jeopardy! And I knew by the time I was 15 that I wanted to do it,” Ware told AL.com.
He participated in quiz bowls throughout school, joined local trivia groups and always watched the show.
His first tryout for the show was in 1996. As a University of Arkansas student, Ware drove from Fayetteville to New Orleans to compete for a coveted collegiate spot.
After graduating with a bachelor’s degree in medieval history, Ware went on to take the LSAT, passed with flying colors and attended the University of Alabama, one of the top law schools in the country, in which he graduated within the top 5% of his class, and landed a federal court clerkship.
All the while, he was still pursuing his Jeopardy! dream.
Over the years, Ware said, he has taken the test to become a contestant 25 times, passing most of them. He had been invited for interviews six times, and done two in-person tryouts, one in Memphis, the other in Nashville.
But he was never asked to move forward.
“I honestly thought they were never gonna pick me,” Ware said with a smile. “But I kept trying, and I’m glad I did.”
After 30 years of trying, Ware finally got the call he had been waiting for for 30 years.
In preparation, Ware read through hundreds of the show’s online archives, rewatched past episodes, created flashcards, and practiced with his friends and trivia group members.
In September 2025, Ware was invited to participate in his first Jeopardy! competition filmed in Los Angeles, where he won two games and took home $47,801.
Ware said the entire experience, from watching the show with the other contestants and having his wife support him in the audience to competing against other players, was thrilling.
The episode aired in October. He was later invited back to the show to play in the championship against past winners.
In a sharp suit, Ware sped through the first round, answering questions about geography and famous figures and earning $3,200 before his opponents added any money to their own scoreboards.
“After the first round, I’m thinking ‘Okay, I could win this thing’,” Ware said.
But after speeding past his competitors in the first round, things took a turn.
“It was kind of intimidating with a bunch of other people that were champions…I think it made me over-confident. I buzzed too much,” he laughed.
“I thought everything was falling apart when it really wasn’t. If I had kept it together better after that, I think I would have been better off.”
By the end of the game, Ware had earned $2,200, while his competitor, Stella Trout, who started the game in the negatives, made an impressive comeback and won with $26,401.
Despite losing the game, Ware said he was grateful to be a part of Jeopardy! again.
“It was a wonderful experience,” Ware said. “I really, really did enjoy it.”
Throughout his life, Ware has worn a lot of hats. He was an encyclopedia expert, a truck driver and Walmart employee.
Today, he is a consumer protection lawyer with Davis and Norris, president of the Alabama State Poetry Society, a novelist and a winner of Jeopardy!
With his winnings from the show, Ware is working to publish his next novel, The Legacy of Colgan Toomey, sequel to The Legend of Colgan Toomey.
“I would play it every day. If they would let me do it, I would play Jeopardy! for a living, all the time,” Ware laughed.
“It was fun. That’s the main takeaway…I encourage everybody to try out for Jeopardy!”
