Lucky No. 7: Tampa Lawyer Makes History as First “Young Hemingway” Winner (Video)

Perseverance paid off Saturday night in Key West, as Chris Dutton made history becoming the first “Young Hemingway” ever to win Sloppy Joe’s 45th Annual Hemingway Look-Alike Contest. The 39-year-old lawyer from Tampa captured the title, joining a brotherhood dedicated to preserving Ernest Hemingway’s legacy through friendship, tradition and service.

Dutton’s road victory was far from easy. He emerged from a field of 134 registered contestants, in two preliminary rounds before defeating 23 other finalists to claim the title on his seventh attempt.

And while most contestants portray the older, white-bearded version of Hemingway, Dutton embodies the younger writer who lived and worked in Key West during the 1930s. Other “Young Hemingway’s” had reached the finals over the years, but none had ever won…until now.

The judges, each a former Look Alike winner known affectionally as a “Papa”, look for more than a familiar face. They evaluate resemblance to Hemingway, stage presence, character and the ability to represent a society devoted to preserving the celebrated author’s legacy. Twenty-four finalists each had one minute to make their case before the top five earned two additional minutes on stage. In the end, the Papas chose Dutton.

Dutton credited seven years of unwavering family support, a keepsake from a past winner, and one well-kept secret for helping him capture the prestigious title.

“Papa David Douglas gave me this sweater,” said Dutton. “I’ve had it for a few years and I never told anybody.”

Douglas, the contest’s 2009 winner, passed down his trusted sweater to Dutton, who wore it with pride as he took the title Saturday night. But winning, he says, wasn’t the best part of the experience.

After his first appearance at the look-alike contest, he discovered what keeps generations of contestants coming back: the friendships. In 2019, a past Papa invited him on a trip to Cuba, where Hemingway also briefly lived. Experiences like that, he said, revealed the true spirit behind the competition.

“It’s about the brotherhood, the friendship, and that’s why we all keep returning,” Dutton fondly recalled.

Dutton’s new role is only beginning.

He now moves from contestant to judge, helping select future winners while supporting the Hemingway Look-Alike Society’s scholarship program, which has awarded more than $350,000 to Florida Keys students. He also becomes one of the tradition’s ambassadors, helping ensure Hemingway’s enduring influence continues for future generations. Dutton said he would do everything in his power to keep the tradition going.

Hemingway lived and wrote some of his most famous works in Key West through much of the 1930s and was a regular at Sloppy Joe’s Bar, where the contest was held. Today, the annual contest remains the signature event of the six-day Hemingway Days celebration honoring the 127th anniversary of his July 21 birth.

The new Papa admitted the victory still hadn’t fully sunk in.

“I haven’t completely digested it yet. But I’m ready. Ready to get to work.”