How Former DJ, Wealth Manager Benjamin Alexander Became Jamaica’s First Alpine Skiing Olympian

For more than two years, Benjamin Alexander pursued a dream of becoming the first person to represent Jamaica in alpine skiing at the Winter Olympics. Never mind that Alexander was a former DJ and wealth management employee who had only started skiing at age 32 in February 2016. Or that he knew he had no chance of competing for a medal. He thought that if he worked hard enough he could achieve his goal and take advantage of a loophole that the International Olympic Committee (IOC) instituted to lower the qualifying standards and help more countries participate.

During a race in Liechtenstein last month, Alexander did just that, clinching a spot in the Olympics giant slalom race that takes place on Sunday local time in China. But, according to the Washington Post, the International Ski Federation (FIS) is investigating that race in Liechtenstein as well as at least two other qualifying races in which skiers from Ghana, India, Kyrgyzstan, Morocco, Saudi Arabia, Timor-Leste and Taipei secured Olympics berths. As such, with questions surrounding the legitimacy of those races, the IOC granted FIS’s request to add four spots for three countries that are traditional powers in skiing: Austria, Germany and France, according to the Post. 

Alexander, speaking from China on Wednesday, told Forbes that he has been cooperative with FIS officials and reiterated he has legitimately qualified for the Olympics.

“Everything is 100% clear,” Alexander said. “The level of pettiness (other countries) got into to try to figure out a way to unwind results so they can get one of their extra racers into the Games was kind of laughable at some point. It came down to, ‘It seems like you didn’t cross the T on this application form over here. Can you explain why?’ It put a big smile on my face to see how low they would stoop to try to remove nations from the Games just so they could get their seventh or tenth best athlete into the Olympic Games.”

He added: “I think the people that have been used to dominating these Games are just not happy to see change, to see more countries coming in. That’s the overarching feeling on this point.”

For Alexander, competing in the Olympics is something he never thought about as a kid. He grew up in England and began working as a DJ as a 17-year-old, but he stopped doing so a few years later as he grew tired of the violent scenes he said he witnessed at local nightclubs. After studying engineering at University College London, he moved to Hong Kong, where he got a job at a wealth management firm.

“It was one of those things where the bank balance looked good, but the happiness balance didn’t look that great,” Alexander said. “I was wasting money on material things and champagne. I knew it wasn’t a long-term thing.”

In early 2010, Alexander quit his position and returned to DJing. Over the next few years, he served as a DJ in more than 30 countries on five continents. In late 2015, he was working at an event on a mountain in Canada when he saw people ski for the first time. He was intrigued enough that two months later he took his first ski lesson.

In 2018, Alexander attended the Winter Olympics in Pyeongchang, South Korea and enjoyed watching the top skiers in the world compete. The next month, having only skied nine times in his life, Alexander traveled to Japan to ski. He then spent the summer in the Patagonia region of South America, where he skied on mountains in Argentina and Chile, an experience that fueled his passion for the sport.

Around that time, friends would chide him about ‘Cool Runnings,’ a film released in 1993 that detailed the journey of Jamaica’s bobsled team that first competed in the Winter Olympics in 1988. Alexander knew he was eligible to become a Jamaican citizen because his father had been born in the country.

“People would always make these jokes about the bobsled team and ‘Cool Runnings’ and you should go to the Olympics,” Alexander said.

Alexander ended up retiring from DJing late in 2018 and went on a ski trip to the Revelstoke resort in British Columbia, Canada, early the next year, where he met Gordon Gray at a cocktail party. Gray, a Dartmouth graduate and former top-level skier from the U.S., was working for a technology firm in San Francisco and recently had twins, so he didn’t get to ski too often. To him, the trip was a chance to unwind, relax and have fun.

Alexander peppered Gray with questions about skiing and asked if he could join Gray on the slopes the next day. Gray reluctantly said yes, but he made it clear to Alexander that he would be getting to the mountain early. When Gray arrived at the mountain that day, he didn’t see Alexander.

“I was like, ‘Great, I’m in the clear,’” Gray said. “And then all of a sudden out of nowhere I see this guy in a onesie and this black leather jacket looking like the Fonz coming out of nowhere. I was like, ‘Who is this clown?’ It was Benji. I’m like, ‘You’re wearing a leotard and a leather jacket. We’ve got the wrong sport here.’”

Alexander, undeterred, joined Gray on the chair lift to the mountain top. From there, they made their way down, with Gray leading the way and looking back at Alexander.

“It was like I was about to watch a train wreck,” Gray said. “He didn’t have any idea what he was doing, but he was just going for it. I was scared he was going to be a liability, but he couldn’t get enough of it. We skied all day. He didn’t blow up and didn’t make a turn that whole day. He just kind of straight-lined it. He was like, ‘I love this sport.’”

Still, Gray understood there was a huge difference between a fearless skier and an Olympian. He explained to Alexander that he needed to dedicate himself to the sport and suggested that Alexander look to take up the giant slalom, which has the least stringent Olympic qualifying standards of all the alpine skiing disciplines.

In October 2019, Alexander took the first serious step at his Olympics dream when he moved to Jackson Hole, Wyoming and began skiing most days. In March 2020, he entered his first FIS-sanctioned giant slalom event in Sun Valley, Idaho and finished last in the 66-person field. He was nearly a minute slower than the winner and 38 seconds slower than the 65th place finisher.

Later that month, the coronavirus pandemic began and led to the slopes closing. For the next couple of months, Alexander spent time backcountry skiing, which is done outside of a ski resort’s boundary on ungroomed snow and requires walking up mountains rather than going on a chair lift. 

Alexander didn’t compete in another FIS race until February 2021, again finishing last in the 63-person event that took place in Big Sky, Montana. He was nearly 48 seconds slower than the winner and more than 20 seconds behind the 62nd place finisher. Alexander competed a few more times in the early months of 2021 but finished last each time. That year, he also tested positive for the coronavirus, leading to him taking time off from training.

After an eight-month break, Alexander returned to FIS competition in November 2021 during a race in Sweden, where he again ended up in last place. By the end of last year, he still had not met the Olympic qualifying standard, so last month he competed in the event in Liechtenstein. He finished seventh in the nine-man field and met the qualifying criteria.

“To me, the gold medal was qualification,” Alexander said. “There was no chance you could catch up with someone that’s been doing something 10 times as long as you with 10 times the budget. It’s just impossible.”

Besides the Covid-related challenges and the difficulty of becoming proficient at a new sport, Alexander knew there was a financial burden, as well. He estimates he’s spent between $120,000 and $140,000 chasing his dream the past two years through traveling, staying at resorts, buying lift tickets, paying for equipment and coaching, securing space on the money to train and other expenses.

Alexander’s friends suggested he start a GoFundMe or Kickstarter campaign and ask for donations, but he instead used his own savings and a personal loan to help defray the costs. He also was able to secure some sponsorships.

“I just didn’t like the feeling, especially during the pandemic, of me asking for money to help me on this lofty pursuit for what is classified by many as a bourgeois sport, an upper middle class sport,” Alexander said. “I never felt comfortable asking the general public for money.”

Alexander is planning on making corporate speeches in the coming months and selling a Jamaican ski team jacket with logos of companies that he’s struck deals with, so he expects to break even in terms of his investment in chasing the Olympics. Still, just being in China is something he’ll cherish forever even though strict Covid restrictions have meant he can only be in one area where the skiing, luge, skeleton and sliding events take place.

During the Opening Ceremonies last week, Alexander and bobsledder Jazmine Fenlator-Victorian held the Jamaican flag. And on Sunday, Alexander will be competing in the giant slalom. He knows he’ll almost certainly be at or near the back of the pack, but he’s hoping this will be the start of something for Jamaica. He said he has already found young skiers of Jamaican descent who dream of following in his footsteps and competing in the Olympics. He wants to be the same role model as the 1988 Jamaican bobsled team.

“Thirty four years ago those guys did something outlandish and ever since Jamaica has had a bobsled team and Jamaican winter sports has been synonymous with bobsledding,” Alexander said. “I hope 34 years from now, in 2056, we look back at this moment and we’re like, ‘That was a similar moment, a line in the sand where forever forward Jamaica had Alpine skiing as one of its sports.’”