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Florida lawyers dominate annual Key West ‘Hemingway Look-Alike Contest’

Senior Editor News in Photos

Jonathan Auvil, a 64-year-old Dade City attorney, had it in spades on a recent Saturday when he boldly took the stage in a Key West bar and walked away with the 41st annual 'Hemingway Look-Alike Contest' title

Jon Auvil

Dade City lawyer Jon Auvil claimed the 41st annual “Hemingway Look-Alike Contest” sponsored by the iconic Sloppy Joe’s Bar in Key West July 16. Auvil’s victory in the look-a-like contest ended eight years of competition and he says the real prize is membership in the “Papa” fellowship, and an opportunity to promote the competition’s lesser-known charitable efforts. The look-alike contest, a feature of the “Hemingway Days Festival,” began in 1981 for reasons not altogether literary or historical, Auvil acknowledges. “They came up with the concept because it is so miserably hot in Key West in July, and businesses were starving,” he said. “This has become the most profitable week of the year, at least for Sloppy Joe’s.”

Ernest Hemingway defined courage as “grace under pressure.”

Jonathan Auvil, a 64-year-old Dade City attorney, had it in spades on a recent Saturday when he boldly took the stage in a Key West bar — suffocating in a wool sweater in the merciless July heat — and calmly delivered a 120-second pitch.

“We put an unbelievable amount of time into figuring out that two minutes,” Auvil recalls. “A lot of guys wear the sweater, and at that time of year, I will tell you, it is cruel and unusual punishment.”

It was enough for Auvil to claim victory in the 41st annual “Hemingway Look-Alike Contest” sponsored by the iconic Sloppy Joe’s Bar.

Auvil’s triumph over 124 other contestants scored headlines in the New York Post and London’s The Guardian, among many, many other publications and platforms.

Five finalists

Jonathan Auvil, holding the conch shell, and the four other “Papa” finalists, including Pensacola lawyer Christopher Dutton, the young Hemingway to right of Auvil, and Tampa lawyer Paul Phillips, one of the other three Hemingways pictured.  

Auvil says the victory was even sweeter because he got to share it with two other Florida Bar members who landed with him in the top-five — Christopher Dutton of Pensacola and Paul Phillips of Tampa.

After plunking down the $35 entry fee, the winner, like other contestants, gets a t-shirt, but not much more than bragging rights. Champions agree to quit competing and return the next year to judge and help organize the friendly chaos.

“It’s people from all over the country, and it’s not just fun,” Auvil said. “It’s serious business.”

For Auvil, the real prize is membership in the “Papa” fellowship, and an opportunity to promote the competition’s lesser-known charitable efforts.

Auvil fell into the fellowship when he was a teenager, and met an original organizer named Fred Johnson.

“I’ve always been interested in the unusual…but [it began when] a fellow named Fred Johnson certified me for SCUBA when I was 12 years old,” Auvil said.

Johnson is widely admired in the look-a-like inner circle for winning the competition on his first try in 1986.

According to its website history, Sloppy Joe’s opened the day Prohibition ended, December 5, 1933. There were name changes, but it migrated to its current location on Duval Street five years later.

Hemingway, a Key West resident since 1931, befriended the owner and became a regular. Before he moved away in 1939, Hemingway wrote “For Whom the Bell Tolls,” and parts of other novels, as well as the short story “Snows of Kilimanjaro.”

Hemingway’s legacy stuck. The look-a-like contest, a feature of the “Hemingway Days Festival,” began in 1981 for reasons not altogether literary or historical, Auvil acknowledges.

“They came up with the concept because it is so miserably hot in Key West in July, and businesses were starving,” he said. “This has become the most profitable week of the year, at least for Sloppy Joe’s.”

Auvil considers himself a Hemingway fan. “Islands in the Stream,” is one of his favorite novels. But Hemingway the person — hard drinking contributed to his suicide in 1962 — was admittedly flawed, Auvil said.

“He was a complicated person,” Auvil said.

Auvil’s victory in the look-a-like contest ended eight years of competition. The triumph was tempered somewhat when he contracted COVID-19 the following day and was forced to deal with mild symptoms on his nine-hour return drive.

He’s looking forward to going back next year.

“It’s mostly fun, but some guys go crazy with it, there are cheering sections,” he said. “It’s more of a fraternity than anything else.”

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