Ernest Hemingway Lookalike Winner Chosen in Key West

69-year-old Key West local Tim Stockwell has been crowned winner of the Hemingway Look-Alike Contest title, beating more than 130 contestants.

Mr Stockwell, who moved to the island from Michigan in 2019 and has participated in the event ever since, said his lucky charm was a thick wool sweater, similar to the one Hemingway wore, which he happily donned in the sweltering July heat. “This sweater has been worn by seven other previous winners," he said, "and I’m very grateful and glad to be able to call it the eighth."

This year’s contest took place over three nights at Sloppy Joe’s Bar which was a frequent hangout for Ernest Hemingway when he lived and wrote in Key West during the 1930s. The contest featured three younger lookalikes including six-year-old Keefer Haynie from Baton Rouge.

During his speech to judges, Stockwell recounted his favorite story about the author that showcased the author’s softer side. He recounted how Hemingway formed a baseball team of Cuban youngsters called 'Gigi’s Stars' and provided a group of boys, including his own sons, with a field on his property. He also gave them new uniforms, bats, balls, and gloves, pitched for both teams, and never kept score.

“The way he taught those young men to become young men, how to play fair, how to be honest, how to be straightforward…he taught those kids how to live a life well-lived, and they benefited from his generosity and his kindness,” he said.