How Jamaica’s 1988 Bobsled Team Became an Unlikely Global Sensation

Before the 1988 Winter Olympics, the sight of the Jamaican flag in the snow would have been more of an oddity than a symbol of national pride. But thanks to the history-making turn of Jamaica's first bobsled team in Calgary, Alberta, the image has symbolized hope and endurance ever since.

As the pioneering driver of that team, Dudley “Tal” Stokes literally had a front seat to all the action. “It was a hard sell,” he said of organizing a team from the tropics to compete in a winter sport, but Americans George Finch and William Maloney—who conceived the idea of a Jamaican bobsled team—saw the idea through. 

There was just one problem: “They couldn’t actually convince anybody in Jamaica to try it,” Stokes said. That is, until they approached the Jamaican Defence Force, and military officials agreed to help find contenders among its servicemen because they regarded bobsleigh as an “army sport.”

But not just any soldier would do. Finch and Maloney requested those with specific physical strengths and skills. For example, they sought an individual with proven hand-eye coordination to drive the sled. Enter Stokes, a military helicopter pilot. He’s not sure he would have signed up for the team had he not been under orders.

“The whole undertaking looked very risky,” he said. “Never mind the sport, but also the funding, the travel and the fact that we were planning to become an Olympic team in five months from ground zero. Those were ambitious, ambitious things.”

What followed were five grueling months that Stokes describes as “some of the most difficult of my life.” The team—Stokes, Devon Harris, Michael White and Caswell Allen—arrived in Calgary for training just as Finch, who was bankrolling the effort, lost his fortune in the October 1987 stock market crash known as Black Monday. That development forced the entire team to crowd into one extended hotel room with a kitchenette as they trained for the Olympics by borrowing sleds and learning to drive them by observation.

The International Bobsleigh and Skeleton Federation didn’t make matters easier by introducing one rule after another for this unprecedented Caribbean team, including requiring them to finish a World Cup race in Igls, Austria, to compete in the Olympics.

In this scenic resort town with views of the Alps, Stokes and his teammates lived in an army facility with little cash, selling T-shirts and sweatshirts to get by. But their persistence paid off when Time magazine sent out a photographer to document their effort and published a story about them. 

“That’s when we knew that this was serious, serious publicity,” Stokes said.

They qualified for the Olympics and were able to finally enjoy some good meals when the Jamaica Tourist Board routed money their way.  When they arrived in Calgary, the reception they received came as a shock. “You would think that we would be shunned and not accepted as athletes,” Stokes said. Instead, he added, “We were very popular with every team, including teams from behind the Iron Curtain, the East Germans and the Russians. Everybody treated us well because, unbeknownst to us, we were famous.”

While living in what Stokes described as an “Olympic bubble,” they didn’t realize word had spread about them globally. When the Winter Games began, Stokes was filled with emotion representing Jamaica. He carried the nation's flag into the stadium in a moment he describes as “one of the proudest moments of my life, and it remains so to this day.”

But the competition itself brought chaos and disappointment. In the middle of the Games, the team decided to enter a four-man bobsled event, replacing injured Caswell Allen at the last minute with Stokes’ brother, Chris, a sprinter who was cleared to compete within hours. Then came a crash in the third run, televised to a global audience of millions. “For me personally, that was an intense embarrassment,” Stokes admitted. “I was unaccustomed to failure in my life up to that point.”

Following the crash, Stokes and White participated in the two-man bobsled event in which they finished 30th out of 41 teams. But the crash continued to sting for Stokes, particularly because he thought it might contribute to the widespread perception that Black people were inept at sports that required mechanical skill, he said. When he crashed, Stokes not only felt that he had let down himself and his country but also the Black diaspora more broadly. That the public viewed the Jamaican team’s foray into bobsled as a valiant effort and uplifting story surprised him. 

”I thought that this would be devastating and that I would be ridiculed and that people would shun me,” he said. “I was surprised at the reception, which, in retrospect, had to do with the sheer audacity of going into the snow … It looked very strange to Jamaicans who had never seen anything like this, and that endeared us to the population.”

Stokes went on to compete in the Winter Games through 1998, a turn of events he never predicted. Not even Finch expected the team to persist beyond Calgary. But the crash made Stokes determined to compete again. 

“I decided that this story couldn't end here,” he said. “I had no idea where it was going to end, but I knew we had to go on.”

In 1994, the four-man bobsled team finished 14th overall—ahead of teams like the United States and France—and placed 10th in two of the four runs. 

“It's still the highest finish by a Black male driver in Olympic competition,” Stokes said. 

But he knows the 1988 Winter Games will always stand out as the year the Jamaican national bobsled team made a splash—and then a crash at the Olympics. 

Kathleen Pulito, who is heading media relations for Team Jamaica at the Milano Cortina 2026 Games, describes 1988 as the blueprint for Jamaica’s winter sports teams. 

“Without them, we wouldn't be where we are,” she said.

Stokes has no doubt that the team’s determination broke barriers. “Today there are lots of Black drivers around, especially the women have had lots of medals between them, and the men—that's just a matter of time.”

Even Black competitors outside the sport have been inspired, he said, noting that Formula One champion Lewis Hamilton is one of many inspired by their story. The 1993 Disney film Cool Runnings cemented the team’s status as legends, though Stokes didn’t always appreciate the movie’s comedic take on their experience. After all, he was striving to be taken seriously as a competitor. Now, he is grateful for the movie's lasting impact. 

“I have gained a lot of respect for the people who made it and the concept and the way they worked it, and I have accepted that it's not a documentary about me,” he said.

Pulito said the film led to the perception that Jamaica’s winter athletes are “cute” but not competitive, the opposite of the truth, given that the nation’s bobsled team won their first-ever gold medal in a global competition—the IBSF North American Cup—in November 2025.  

When people see the fun-loving characters in Cool Runnings, they don’t realize the characters don’t reflect “the true personalities of who the team members were,” she said.  “And I think sometimes they don't expect the bobsledders to have such grit and determination and competitiveness.”

In fact, persistence is what won the nation’s first bobsled team global acclaim—even after they crashed. 

“Literally, four Black guys from the tropics on the ice giving it their all—that’s an inspiration to anybody, anywhere, in any time,” Stokes said. “And I am proud of that.”