Tim Stockwell has lived in several European countries and traveled the world during his career in hiring, training, mentoring and leading global teams — at one point working with staff and facilities in 65 countries. In the summer of 2000, he and his wife Kathleen took their family on a scuba-diving and cultural immersion trip around the world.
Yet despite his adventurous globe-trotting lifestyle, it wasn’t until July 2019 — when Stockwell and Kathleen wandered into Sloppy Joe’s Bar after moving to a houseboat in Key West — that one of his most interesting adventures began.
With his white beard and tanned complexion, Stockwell was quickly mistaken for an entrant in Sloppy Joe’s annual “Papa” Hemingway Look-Alike Contest. He was unaware of the contest and the July festivities saluting Ernest Hemingway, who lived and wrote in Key West during the 1930s. But Stockwell couldn’t resist the challenge.
Stockwell entered and competed in the contest for several years, appreciating the look-alikes’ spirit of camaraderie, and won the contest in 2025. He was the first Key West resident to earn the title of “Papa” since 1999.
Nowadays, Stockwell is deeply involved in the Hemingway Look-Alike Society, composed of contest winners and aspiring “Ernests,” and its mission of raising scholarship funds for students attending the College of the Florida Keys. To date, the society has awarded more than $350,000 in scholarships — and provides funding to Florida Keys nonprofits, a Cuban youth baseball league inspired by Hemingway and others in need.
Stockwell’s “giving back” doesn’t stop there. He’s been asked to be an ambassador for the college and is also vice-president of the Sloppy Joe’s Foundation board, which supports local nonprofits in the arts and community sectors.
Stockwell eventually plans to return to family and executive business coaching. He enjoys sharing experiences with Kathleen and their family, diving, biking around Key West and embracing the simplicity and beauty of houseboat living.
Stockwell recently chatted with the Keys Weekly, reflecting on his full and busy life.
What’s it like living on a houseboat? A lot of people live out on a hook, on a ball or in marinas where you have to keep adjusting your lines because the water level rises and drops. However, we’re on a floating dock — among the last docks out to the water, so our backyard and our view is nothing but water and sunsets. It’s incredible.
How did it feel to win the Look-Alike Contest and be celebrated on Sloppy Joe’s stage? It was very surreal. I had Kathleen come up on stage, and it was very exciting to stand there and look back at the crowd at Sloppy Joe’s and take it all in. Three of our kids and six grandsons were there for it, and my grandsons just went nuts.
What’s one of the best things about being a Look-Alike Contest winner? The Hemingway Look-Alike Society has been an absolute dream, because it’s got such great camaraderie and family focus. You make friends. I think the real magical part is the camaraderie around two causes: honoring the name and image of Ernest Hemingway, and the ability to be incredibly generous with a town that is like no other.
How did you get involved in the Sloppy Joe’s Foundation and become vice president of its board? Jeff Allen, the CEO of Sloppy Joe’s, asked if I would be interested in helping form the foundation. I had really come to love being at Sloppy Joe’s and getting to know the people there. I thought, “This is perfect. This is a great way to become a bit more involved in the community and continue to give back.” We focus on trying to help in an area that is near and dear to Sloppy Joe’s, which is performers and the performing arts.
What kinds of activities do you find most enjoyable? I love adventure — there’s almost nothing I won’t do — and I’ve traveled the world. I don’t need any excuse to get underwater, so I dive as often as I can. I have an appreciation for the ocean and the health of the ocean, as Hemingway did.
After several years living in Key West, what do you like most about it? What’s fascinating to me about Key West is that nobody cares who you are, what you have or don’t have, or what you’re running from or running to. If you’re here and you want to have a good time, that’s what it’s all about; just be kind to people. It’s still one of the most laid-back places in the U.S. I love that atmosphere — and, of course, the characters.
Have you realized yet that, as the reigning look-alike winner, you’re one of those characters? It’s creeping up on me, yes. And it’s pretty funny.
