Benjamin Alexander: The Jamaican Trailblazer Reflects on His Olympic Journey

As Jamaica's first-ever alpine skier, Benjamin Alexander shares the honor and gravity of representing his country at the 2022 Winter Olympics and how the experience has yet to fully sink in.
Benjamin Alexander: The Jamaican Trailblazer Reflects on His Olympic Journey
Benjamin Alexander: The Jamaican Trailblazer Reflects on His Olympic Journey / The Everyday Warrior Nation

Benjamin Alexander's journey to the 2022 Beijing Winter Olympics wasn't just about personal achievement—it was about breaking barriers and putting Jamaica on the map in a sport the nation had never competed in: alpine skiing. Reflecting on his experience, Alexander still finds it surreal to carry the title of "Olympian," a badge he admits hasn't fully sunk in yet.

"What were the feelings coming off the Olympics?" he muses. "I don't know if it's fully sunk in. You know, people call me an Olympian. That's a badge I'll have for the rest of my life."

For Alexander, the road to becoming an Olympian wasn't paved with years of training in snow-covered mountains. Instead, his journey began in 2016 on a ski trip to Whistler, British Columbia, where he had his first mountain lesson. He quickly transitioned from being a complete novice to representing Jamaica on the world stage just a few years later. In a sport traditionally dominated by countries with long histories of winter sports, Alexander knew that his presence alone would be a game-changer.

It was such an incredible experience to be out there, to compete alongside some of the best in the world,” Alexander says. “And I don’t even include myself in that category.

His humility is notable. Unlike many athletes who trained from childhood to reach the Olympics, Alexander's goal was not necessarily to win but to participate. "For me, it was about the participatory element of the Olympics, right? Bringing Jamaica into a new field, being the first-ever alpine ski racer," he explains.

Alexander’s journey is reminiscent of Jamaica’s famed bobsled team, which first competed in the Winter Olympics in 1988 and captured global attention. Just like them, Alexander carried the pride and hope of a nation better known for its dominance in sprinting than in winter sports. The chance to represent Jamaica in alpine skiing gave Alexander a profound sense of purpose. His achievement is a testament to the fact that passion, determination, and courage can push the limits of what’s possible—even in uncharted territory.

As he reflects on his Olympic experience, Alexander knows this is just one chapter in his life's story. He has conquered many worlds—from finance to DJing and now alpine skiing. His journey reminds us that success is not just about medals and accolades but about daring to step into spaces where few have ventured. And for Benjamin Alexander, representing Jamaica on the slopes was the ultimate victory.


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Mike Sarraille
MIKE SARRAILLE

Mike Sarraille is the founder and CEO of Talent War Group, a consulting and executive search firm; and Legacy Expeditions, an extreme adventure company which has set 4 x world records in skydiving. Mike is a 2023 and 2024 Top 30 Global Gurus leadership speaker, 2 x Best-Selling Author of The Talent War: How Special Operations and Great Organizations Win on Talent and The Everyday Warrior: A No-Hack, Practical Approach to Life. Mike also participated in the filming and production of two documentaries, Drop Zone Everest and Triple 7: They Said It Couldn’t Be Done. Mike started the Everyday Warrior Initiative on Men’s Journal in 2022 before moving it to Sports Illustrated On SI alongside his co-host John Welbourn. He is a former Recon Marine and Scout-Sniper, and retired US Navy SEAL