Key West, Fla. – Perseverance, a lucky sweater, and an uncanny resemblance to one of the world’s most iconic authors. That was the winning formula that helped a 69-year-old man from Key West, Florida, win the Hemingway Look-Alike Contest title this weekend in the Southernmost City in the U.S.
A Key West local, Tim Stockwell, captured the coveted title, beating out more than a hundred contestants to make the top 5. And it was in that final round that he offered a compelling story as to why he deserved to be “Papa 2025.”
His lucky charm? A thick wool sweater, like the one Hemingway wore, which he bravely donned in the sweltering July heat.
“Seven other previous winners have worn this sweater, and I’m very grateful and glad to be able to call it the eighth,” said Stockwell, who moved to the island from Michigan in 2019 and has participated in the event ever since.
This year’s contest took place over three nights, starting with 131 contestants, then 24 semi-finalists, and finally the top 5. The location? Sloppy Joe’s Bar — a frequent hangout for Hemingway when he lived and wrote in Key West during the 1930s.
The contest featured three younger look-alikes, including six-year-old Keefer Haynie from Baton Rouge. The whimsical tribute is all part of the annual Hemingway Days Festival that honors the enduring legacy and literary mastery of the author who wrote “For Whom the Bell Tolls,” “To Have and Have Not” and other classics during his Key West years.
During his plea to judges, Stockwell recounted his favorite story about the iconic author that showcased the author’s softer side. He shared that 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 recalled.
Stockwell is the latest ambassador for the bearded brotherhood known as “The Hemingway Look-Alike Society,” an organization that combines camaraderie and scholarships to support Florida Keys college students.
“He broke all the barriers for those kids,” said Stockwell. “They had a great opportunity. I’d like to continue that. And that’s why I’m proud to call these guys my brothers.”
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