Born in 1190 in Sussex, England, as a latent Immortal, Hugh Fitzcairn's first death in 1224 summed up his habit of getting himself into sticky situations over women: he was skewered by a jealous husband. He was first taught in the ways of the Immortal by Henry Fitzmartin. Fitzmartin either shared Hugh's exuberant ladies' man nature or spent his time exasperated by the young man. Fitz was a carefree man. Well loved by his friends, among them Duncan MacLeod, he was the life of every party and could charm any lady in the room.

Fitz was also a friend of Connor MacLeod and Darius. He flirted with a Montague woman named Selene, who was involved with Connor at the time, and called Connor a "renegade who would break her heart". Connor was so angry at Fitz, he refused to attend Robert and Gina DeValicourt's wedding, a decade later. Centuries later, he helped Duncan with Connor's recovery from a Dark Quickening, in early 1987. Fitz spoke fondly of "Brother Darius", and remarked to Duncan, that he had been one of the best Immortals.

According to Charles Anthony, the Watcher's Bladed Weapons Curator, "Fitzcain was a man of impeccable taste with an exaggerated sense of style. It stands to reason that he would adopt the most fashionable sword of the period...by 1696...Fitzcairn had adopted... the cup-hilt rapier...his weapon of preference for more than a century."