Born circa 1844 in Jamaica, Winston was taken in by parents who themselves were former slaves. Possibly around 1859, Winston was sold on the auction block in Kingston, Jamaica for the sum of forty-three guineas.
After seeing first-hand the brutally repressive tactics employed by British troops in Jamaica, Winston became a passionate fighter for Jamaican freedom. When he witnessed his foster parents shot to death by a British soldier, Winston charged the soldier in a blind rage, and was bayoneted to death, after which he revived as an Immortal.
During the 1940s, following Jamaica's independence from Great Britain, Winston became a globetrotting mercenary. He traveled to North Africa, hoping to take advantage of the chaos caused by World War II, where he met Jacob Kell, who then recruited him as a follower into his Immortal “posse.” Afterward, Kell started hunting Immortals all over the world, largely disregarding the rules, and formed a gang of Immortals who hunted other Immortals for him. Winston became part of the group, and assisted Kell for a long time in his quest.
In 1972, Winston encountered Carlos Dash when the latter attempted to sell marijuana to him; Winston brought Carlos before Kell, and convinced Carlos to join Kell’s evil crusade against Connor MacLeod.
In 2004, Winston followed Kell to the Watcher Sanctuary. Winston and the others of Kell's cadre arrived on their motorcycles, and let themselves be shot by the guards, giving Kell the needed distraction to infiltrate and kill them. After they revived, Winston and the others follow Kell to a cave were several Immortals were connected to life support machines. Kell beheaded all the Immortals except Connor MacLeod. Soon thereafter, they attacked Duncan MacLeod in the ruins of Connor's antiques store in New York City. Winston and the others couldn't defeat Duncan, and Jin Ke took over from them. The fight was broken off by Kell, but Carlos Dash shot Duncan, making him fall out of the building. With Duncan out of reach, they left.
Some time later, Jacob Kell gathered his followers for their last supper, taking two swords and beheading them. When Winston saw that he had been tricked by Kell, he could do nothing more than smile at him before he also lost his head.
The Highlander: Endgame screenplay gives the date of Winston's sale as “August 14, 1813,” but the DVD timeline gives Winston’s date of birth as 1844, while Jamaican emancipation actually occurred 1833-1838.