It all started in July of 2019, just three days after we had moved to Key West from Kansas City, Missouri. We had arrived after navigating our houseboat from DeLand, FL, up the St. John’s River to Jacksonville and then across to Mayport. We headed down to Miami along the Intercoastal Waterway to Key Largo and then to Key West.
After getting the boat settled into her slip, Kathleen and I, along with our good friends who traveled from Key Largo to Key West with us, went into Sloppy Joe’s Bar. Unbeknownst to us at the time, that visit for a couple of beers would change our lives!
When our waitress arrived at the table, she asked if I was entered in the contest, and I asked what contest. She was very kind and explained to me that in just a couple of days, they were having the Ernest Hemingway Look-Alike contest, which they hold every year in July at Sloppy Joe’s. I explained that I wasn’t aware of the contest and was not there as a contestant. After a few minutes, a woman appeared at our table with an application to enter the contest. I politely thanked her for the application, and as I was folding it to put it in my pocket, she gently put her hand on my shoulder and simply said,” I’ll wait”. I had no excuse, so I took a couple of minutes, filled out the application, and paid the $35.00 fee. We thought it would be a fun way to get into the Key West lifestyle as newly minted citizens of the Conch Republic.
The adventure begins. It started for me on Thursday, July 18th, 2019, my first-ever visit to the stage at Sloppy Joe’s bar for my 15-second speech, telling the Papas that I was a newly minted citizen of Key West and the Conch Republic and would do my best to represent the Hemingway Look-Alike Society. For whatever reason, that speech must have resonated because I was voted through to the Saturday night semifinals. Quite an accomplishment for my first year’s effort.
On stage, that Saturday night, I had one minute to speak to the Papas, of which I don’t recall anything of what I said. I was just thrilled to have made it to the semifinals my first year.
As a first-year contestant, you realize very quickly the generosity of the Hemingway Look-Alike Society and the camaraderie that occurs throughout those four days. I hadn’t known that the real mission of the group was to raise money for scholarships given to the College of the Florida Keys. Also, given out each year to high school students in the Keys. That year, I believe we raised $100,000.
One other strong attraction is the camaraderie of the contestants and their spouses. We made many great connections that are still great friends, even though it is a competition; many of the long-time contestants offer advice to the newbies on what to expect.
Later that year, I was invited to visit Cuba with 10 other contestants and the new Papa 2019, Joe Maxey. What an extraordinary opportunity and eye-opening experience. We went to support an ongoing effort, sponsored by Honorary Papa Brian Gordon Sinclair, of keeping alive the Little League team that Ernest Hemingway had originally started for his sons and the young boys of the San Francisco de Paula area, on the grounds of Finca Vigia.
The guys who traveled to Cuba that year bonded like brothers, and I was now deeply hooked into the group!
2020, as everyone knows, brought a stop to virtually everything in the United States, including the Hemingway Look-Alike Societies contest at Sloppy Joes.
We all looked forward to having the contest again in 2021, which turned out to be a very well-attended event, and I started the contest on Thursday evening, giving my 15-second speech to the Papas and making it to the semifinals that Saturday night. My confidence was growing, and while not making it to the top 5, I was very excited to continue my work for the group while living in Key West.
The 2022 contest started out with another well-attended Hemingway Days. As was becoming my tradition, I went onstage Thursday evening and gave a more focused 15-second pitch to the Papas and was rewarded with another trip to the semifinals on Saturday night. Unfortunately, I began to feel unwell on Friday and tested positive for Covid-19, and withdrew from the contest out of concern for the other contestants as well as the Papas and Mamas.
The contest in 2023 marked a turning point for me. Starting off again on Thursday night and making it to Saturday’s semifinals. When you make it to Saturday night and the semifinals, you’re up against generally 23 other gentlemen in an attempt to make it to the top five. Once you make it to the top five, you’re in the queue to be selected as Papa. So, this Saturday night I did my one-minute speech to the Papas and was thrilled when they called my name as one of the top five.
2023 also saw my return to Cuba, now with an expanded group. Instead of 12, we had 20 of the contestants and Papas travelling with us. I believe the trip for everyone, including myself, was again very eye-opening and rewarding at the same time as we worked with the All-Star team at Finca Vigia and their parents from the San Francisco de Paula area.
2024 started very quickly with our mid-year meeting in Key West. In 2023, Papa Gerrit Marshall and Mama Sharon decided to bring the event back home to Key West.
The contest in 2024 was attended by 136 wannabes hoping to become the next Papa! I made it to the semi-finals again. I wish I could recall what message I gave that Saturday, as it propelled me to another top 5 placement. I was rooting hard for my friend Bat Masterson and was thrilled when they called his name as Papa 2024.
I spent a lot of time in 2024 recruiting sponsors for the contest and secured 5 initial businesses to support our scholarship program.
2025 was also a busy year, with our mid-year held in Daytona Beach and very well attended. I started work earlier in 2024 to recruit sponsors for our scholarship program and secured a total of 25 generous businesses and individuals. We were able to kick off the contest with a nice nest egg.
We drew 130 contestants for the contest, and the competition was fierce. We had an 8-year-old entrant who wowed the crowd with his poise and humor. He and I both made it to the semi-finals.
Saturday night came around with 25 semi-finalists, and I used my one-minute speech to talk about Hemingway and how he demonstrated living a life well-lived as a model for all of us. I was fortunate to make the top 5 again.
I then had two minutes to speak to the type of Papa I wanted to be. Citing the wonderfully written ‘The Homerun Kid’ by Oscar Blas Fernandez Mesa (Cayuco). In the narrative, he outlines his personal account of Hemingway’s direct involvement with the Cuban baseball team he organized at Finca Vigia. I was particularly influenced by how Cayuco described Hemingway’s generosity, joyful paternal nature, and his efforts to teach the kids how to play, work, and behave as young men.
I was thrilled that so many of my family members and friends had traveled to Key West to cheer me on that night.
There is something surreal that happens when they announce your name as the new Papa!
2025 proved to be my year, and I am thrilled to be Key West’s second local winner of the 44th annual Hemingway Look-Alike Society as Papa 2025!
Mama Kathleen and I are grateful for the opportunity to represent HLAS here in the Florida Keys and will work hard to continue its success.
Come to the contest out of curiosity, stay for the charitable contribution opportunity, and return for the camaraderie.