Trinidad and Skibago

Of the excuses for missing class that Anthropology professor Michael Sheridan has ever received, Nikhil Alleyne’s ’28.5 ranks among the best. Instead of reading and attending lectures, Alleyne took the first nine days of the semester to do something nobody else had done before: ski for Trinidad and Tobago at the Winter Olympics. 

On Feb. 14, Alleyne descended the giant slalom (GS) course in Bormio, Italy — a flash of bright red weaving between gates, with the national flag on his left shoulder — as he officially became the first athlete to represent the Caribbean nation in alpine skiing at the Games. 

Alleyne’s path to his own bit of history began in California. Starting at two years old, his father would take the family skiing in Tahoe every weekend. Alleyne soon joined a development program and began his racing career thereafter. He trained and competed at the Sugar Bowl Academy, a ski school in California, through his teens, though recurring shoulder injuries set him back as he approached college recruiting. 

Despite being unable to ski for a varsity program, Alleyne had an opportunity to compete at the Olympic level. Having dual citizenship through his Trinidadian father, Alleyne began to race under the nation’s International Ski and Snowboard (FIS) license. As the Milan-Cortina Games approached, Alleyne faced a decision about making his Olympic chances a reality. 

“I got convinced that it could be a cool experience and it might mean a lot for the country,” Alleyne said. He had a chance to do something special both for Trinidad and Tobago and, equally important to Alleyne, for his family.

Nevertheless, his shoulder injury — a torn labrum from repeated dislocations — kept Alleyne from recording any ski results for a year. Reaching the Olympics would require him to go all in, and to make up for the year of lost training, Alleyne decided to take the 2026 fall semester to train.

Alleyne joined Sugar Bowl’s post-graduate team to train and race full-time. He competed in several FIS races, simultaneously spending up to two hours per day tending to his skis between practices and competitions. Without his own equipment staff, it was Alleyne’s responsibility to tune the bases and sharpen the edges of his skis, along with shaping the sidewalls on a new pair of skis he received as the Olympics neared. Alleyne flew to Europe to train in the month prior to the Games, and soon he was in Italy preparing for his first run. 

Months of intense training and practical organization were expected challenges that Alleyne faced in reaching his Olympic GS debut— but contracting norovirus in the days prior to the event came as a surprise.

“I had norovirus, so I was feeling pretty sick in my GS start,” Alleyne said. “That was kinda tough for me.”

It would be “kinda tough” for anyone to race the GS at the Olympics for the first time in their nation’s history, let alone with norovirus. Regardless, Alleyne remained cool and, to his surprise, finished the first run. “I just pushed out of the start and hoped for the best.”

Then came a second curveball: still sick, Alleyne badly injured a rib in training the next day. 

“It still, like, really hurts. I think I might’ve broken it,” Alleyne explained, gesturing towards his ribcage.

The slalom was planned for the next day. Only 44 of 96 competitors finished the race, many falling victim to the inclement conditions. Factoring in illness and an injured rib, Alleyne joined the ranks of disqualified skiers after Saturday’s first run. He had missed a single gate, for which there is no forgiveness at the Olympics.  

“It was not that good, honestly,” Alleyne reflected about his performance. “But I didn’t really go there for a result […] so I’m not too upset about it.”

The overall experience of representing his country mattered more to Alleyne. For instance, all nations have pins of their respective flags at the Olympics, and the pins of some lesser-known teams, such as Trinidad and Tobago, were in high demand — a true collectible for some fans. 

“Everyone wanted ours […] just walking around the street, people would ask you for pins all the time,” Alleyne said. 

He was also responsible for a much larger national symbol, standing as Trinidad and Tobago’s flag bearer in the opening ceremony. 

“I think they just gave it to me […] I didn’t know until a couple days before,” Alleyne said.

Alleyne was not the sole Trinidadian competitor at the games. Emma Gatcliffe, a junior at St. Lawrence University in upstate New York, also skied in the GS and slalom, and the nation brought a bobsled team as well. Nonetheless, of the fun facts an admissions tour guide can tell prospective Middlebury students — from having a large window, to inventing quadball and the common agent in teargas — sending a member of the student body to represent Trinidad and Tobago in alpine skiing for the first time in Winter Olympic history certainly carries its own weight.