The article highlights the stories of the Jamaican and Trinidad & Tobago bobsled teams at the 2026 Winter Olympics. Jamaican mechanic Dave Kiernan, based in Utah, maintains the team's sleds, emphasizing the technical challenges faced due to the sport's noise and vibration. Despite the comedic portrayal in the 1993 Disney film 'Cool Runnings,' the real Jamaican team, including Olympian Devon Harris, acknowledges the grit and determination required to compete at such a level. The film's inaccurate accents and caricatured depiction of Jamaicans remain points of critique among locals, yet it has played a significant role in shaping international perceptions and nostalgia. Meanwhile, Trinidad and Tobago's team, led by Axel Brown, finished 25th out of 26 in the two-man bobsleigh event, with a total time of 2:51:05. Brown, a former American football and taekwondo athlete, switched allegiance from Great Britain to revive Trinidad and Tobago’s bobsled program, which had previously participated in three Winter Olympics from 1994 to 2002. Their goal was modest—to avoid finishing last—and they succeeded, calling their effort 'mission accomplished.' Brown expressed pride in competing without government funding and highlighted the personal significance of representing his country. Both teams exemplify the perseverance and cultural significance of bobsledding for Caribbean nations, challenging stereotypes and inspiring future athletes. The article also notes the upcoming opportunities for these nations to improve their standings and the broader impact of their participation on national pride and international perception.