The Jamaican national bobsleigh team represents Jamaica in international bobsledding competitions. The team first gained fame during their debut in the 1988 Winter Olympic Games in Calgary, Alberta, where they were seen as underdogs as they represented a tropical nation in a winter sport. The team returned to the Winter Olympics again in 1992, 1994, 1998, 2002, and 2014. The team failed to qualify for the 2006 and 2010 Winter Olympics. Led by driver Winston Watts, Jamaica qualified for the 2014 Winter Olympics in the two-man bobsled.
The team, consisting of Devon Harris, Dudley Stokes, Michael White, Freddy Powell, and last minute replacement Chris Stokes, debuted at the 1988 Winter Olympics in Calgary, Alberta. The team was coached by Howard Siler, an Olympic bobsledder for the United States in 1972 and 1980. They quickly became very popular, largely because of their status as the ultimate 'underdog' story of the games. Alongside the novelty of a tropical country competing in a cold-weather sport, the team had very little experience going down a bobsled track, and borrowed spare sleds from other countries to compete. In a show of sporting camaraderie across national boundaries, other bobsledders were quick to give them guidance and support. They did not officially finish after losing control of the sled and crashing during one of their qualifiers. The movie Cool Runnings is loosely based on their experience at the 1988 games.
The team returned to the Olympics in the 1992 Winter Olympics in Albertville, France, but finished poorly. They qualified again for the 1994 Winter Olympics in Lillehammer, Norway. There, the Jamaican four sled stunned many of their critics by finishing in 14th place, ahead of the United States, Russia, Australia and France.