An Interview with Ben Stubenberg

Who am I? A writer passionate about the Caribbean—the tumultuous history, the resolute people, the unfolding events of today that tug at the heart. I don’t write about fun things to do on vacation. I seek out stories that cry for attention—poverty, wealth, overdevelopment, crime, and who gets and doesn’t get a piece of paradise.

As a former threat analyst for the Department of Defense, I like to dig deep into the changing nature of conflict, especially among gangs in Haiti. At the same time, I want to shine a light on the most vulnerable left behind in our society—the undocumented migrants and stateless children, particularly in the Turks & Caicos—and what can be done about it.

I have had the good fortune to grow up and live in vastly different cultures and landscapes, and maybe that allowed me to move easily between people and places. Born in Hawaii, childhood in Norway, high school and college in California. First jobs as a high school English teacher and reporter in St. Croix. Earned a pilot’s license and flew to just about every island in the Caribbean.

Later, I lived and worked for months in Martinique and Haiti. Those experiences stayed in my heart even as I pursued more conventional careers in law and government in Washington, D.C. Today, I’m back in the region, living permanently in the Turks & Caicos Islands, where I draw on deep connections to find out what’s happening “Behind the Scenes.”

Being able to connect with the captain of the original Jamaican bobsled team and almost everyone involved who is still alive is truly the peak of my writing career.

---

The Jamaican Bobsled Captain: Winner (First Prize, Creative Nonfiction) of the North Street Book Prize 2025

Read more about the award-winning work here!

---

Tell us the story of your book’s title. Was it easy to find, or did it take forever?

The book’s title was pretty straightforward. I wanted to describe exactly what the book was about—the “untold story” of the Jamaican bobsled captain and the original Jamaican bobsled team. Especially how the real story contrasted sharply with the Disney movie Cool Runnings, which has, unfortunately, shaped the popular narrative of the team.

How did it feel when you first saw your book cover? Or when you first held your book in your hands?

Oh, it was a thrill! This is my first book, so kind of cool to “feel” it actually be real.

Who/what made you want to write? Was there a particular person, or particular writers/works/art forms that influenced you?

Capturing struggle and perseverance against the odds. I’m lucky because when I get the story right, or even a line or paragraph right, I feel an immense high. That’s what keeps me going. Sure, like all writers, I have my frustrating stretches when things just aren’t clicking. But I just keep pushing, take a few breaks, and push some more. Usually, the right words come to me.

I got my real start in college at UC Santa Barbara when I started reporting for the college radio station KCSB. Always remember the mentors at the station who gave me the confidence and experience to get it right.

The most influential writers early on were Tom Wolfe, Kurt Vonnegut, Mario Puzo, Pierre Berton, David Wallechinsky, and then James McPherson, William Langewiesche, Malcolm Gladwell, Sebastian Junger, and Julie Checkoway. You will notice that all but two are writers of nonfiction, my favorite category. I love the way they dig deep into the background of the story—the portraits of people and forces that drive them. And that’s what I tried to do in The Jamaican Bobsled Captain.

What other professions have you worked in? What’s something about you that your readers wouldn’t know?

High school English teacher in the US Virgin Islands, Club Med sailing instructor and transportation manager, lawyer, intelligence analyst, open water swim race director, swim instructor. A rather oddball collection of jobs that are unrelated. I guess that jumbled career path provided a variety of experiences that I can hopefully tap into for storytelling from different perspectives.

In particular, I think growing up totally immersed in a foreign country, language, and culture (in my case, Norway), and then returning to the US feeling like an immigrant in my own country, helped give me perspective. I couldn’t play American sports like basketball, baseball, and football, and didn’t know how things were done. So, I often felt like an outsider. Took a while to adjust, especially during the sensitive teen years. But immigrants see things differently and often more clearly than Americans who have grown up in the US their whole lives. And having been on the outside has allowed me, I hope, to connect better with other outsiders and tell their stories.

What was the most rewarding/meaningful part of publishing your book?

Telling the full story of the Jamaican bobsled captain with all the clashes, struggles, highs and lows, and not holding back. And, of course, actually publishing and getting good reviews. Takes any writer to the next level.

If your book had a soundtrack, what are some songs that would be on it?

For sure the haunting and loud rumble of a bobsled speeding down the track. Maybe a few reggae songs.

What is one thing you hope readers take away from reading your book? How do you envision your perfect reader?

Want the reader to say, “Oh WOW! I didn’t just read about the sport of bobsledding. This book took me on a deep journey through the history and culture of Jamaica, as well as the lives of the eccentric people who made the first Jamaican bobsled team happen.”

What creative projects are you currently working on?

I continue to write articles and commentary about who gets a piece of Caribbean paradise…and who does not. Next book will reflect the struggles of the marginalized, society’s cast-offs.

---

Are you a writer, too? Submit your manuscript to Atmosphere Press.