The Brief A 39-year-old Tampa resident took home the top prize at the annual Key West Hemingway look-alike contest last weekend. A Tampa man made history in Key West over the weekend by becoming the first younger contestant to win the annual Ernest Hemingway look-alike contest. Key West Hemingway contest winnerWhat we know:Chris Dutton, 39, earned the prestigious title after competing in the contest for seven years. Florida Hemingway look-alike societyThe backstory:Dutton shares a deep connection with the organization, traveling to Cuba with the group three times and never missing an official event. Key West contest judgingWhat we don't know:Official judging criteria for the competition remain unclear to the public.