Born in 1190 in Sussex, England, 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 an attractive, 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.
Verona, Italy, 1637. MacLeod first met Hugh Fitzcairn. MacLeod worked for the prince, protecting his beautiful and supposedly virtuous daughter, Arianna. It seemed, however, that MacLeod's martial skills were no match for Fitz's amorous ones. The prince demanded Fitzcairn's head, but MacLeod demanded his right to retribution and "killed" Fitz by running him through, thus saving his life. The two became friends for life.
Chateau de Valicourt, 1696 MacLeod and Fitz vied for the hand of the beautiful Gina. To test her suitors, she enlisted their help in recovering stolen gold from Robert, Baron de Valicourt. instead of recovering the gold, however, Gina lost her heart to the daring Baron and they married. Every century, the couple renewed their vows before friends and fellow Immortals.
London, 1720. MacLeod was trying to steal the legendary Stone of Scone from Westminster Abbey for the Scots, at the same time that Fitz was trying to blow up the Abbey and King George. Fitz and MacLeod debated who had the more valid case, and finally decided to fight a duel on the field of honor; a golf course, to see whose plan they would attempt together. Unknown to MacLeod, Fitz cheated.
England, October 1929. MacLeod arrived at Fitzcairn Manor, North Tidworth, to attend Fitz's funeral. As he stood with the mourners, he
realized that the dearly departed was hiding in the greenhouse, witnessing his own funeral. Fitz told Mac that he "died" of a heart attack. Fitz had been murdered, and it was not a good time to be dead. For the first time ever he was rich, and Fitz had sunk everything he owned into American stocks for his return-from-the-dead-fund, however, he was behind on his paperwork. Meaning there was no new name to inherit the money; and he was therefore broke. He asked MacLeod to find his killer and protect his grieving widow, Juliette. The plot thickened... there were more murders. It was finally discovered that Fitz's widow was the killer. Unfortunately for Fitz, the stock market then crashed and he was bankrupted.
London, 1950. MacLeod finally discovered Fitz's golf trickery. Amanda believed the Stone to be a priceless gem and wanted to steal it, fence it, and pay off her gambling debts. Fitzcairn wanted to make up for his past deceit to MacLeod, and MacLeod wanted the Stone returned to the Scots. The three of them broke into the Abbey on Christmas. Amanda was dismayed to discover they stole a hunk of granite. She was arrested by Scotland Yard for treason and made a deal, turning over Fitz, who was arrested. MacLeod managed to get a pardon from Sir Winston Churchill and returned the Stone to the Abbey. In the end, all three of them return to the golf course.
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 Angelina de Valicourt's wedding, a decade later. Centuries later, he helped Duncan with Connor's recovery from a Dark Quickening. Fitz spoke fondly of "Brother Darius", and remarked to Duncan, that he was one of the best Immortals.
Around 1993, Hugh went to see Duncan at his barge on the Seine and told him about the disappearance of some Immortals. Upon meeting Tessa, he complimented her on her loveliness. The two went to see Darius but were met with a shocking discovery, Darius had been beheaded inside his church. When Duncan tried to take sole responsibility for dealing with the murderers; Fitz corrected him sternly saying that they would work together in finding the killers. Later, while returning to his hotel, he and Duncan were attacked by unknown men who kidnapped Fitz. Later, it was revealed that the men who kidnapped him were led by James Horton who had killed Darius, and that the men were known as the Hunters.
When Fritz revived, he watched as Horton and his men "study him like an insect". Horton told Fitzcairn, "You are an abomination before nature and in the eyes of man. There is no glory but ours. No destiny that is not of our making." Horton was about to behead Fritz using a guillotine, but he was saved by MacLeod.
Fitzcairn then settled in Paris where he was writing a cookbook and teaching at the prestigious cooking school, "Le Cordon Bleu". He had found Naomi, his latest true love, but they had problems with her former boyfriend, Patrick, who was jealous of their relationship. Kalas, on his mission to destroy everyone MacLeod held dear, killed Patrick and set Fitz up for the blame, destroying Fitz's current life. Fitz and Kalas faced off in the tunnels beneath Notre Dame, the two old immortals battled before MacLeod, who watched helplessly as his friend was bested and fell to Kalas.
Fitz was killed in a duel with Antonius Kalas in 1995 during Kalas' vendetta against MacLeod. His objective was to destroy MacLeod's friends before killing MacLeod himself.
Fitz would be remembered for his carefree, romantic style. MacLeod's epitaph for his friend, offered with a wry smile, summed up their relationship; "Fitz was a real pain in the ass. I'm going to miss him."
Fitzcairn appeared to a temporarily dead MacLeod as a guide to show him what the world might have been like had the Highlander never been born.
In the alternate timeline, he told MacLeod; "Here I've been pushing up daisies for 280 years. Some business about blowing up King George went horribly wrong, and there was no lummoxy Scotsman there to save my ass, so I had to keep an appointment with the headsman's axe. I don't know about you, MacLeod, but that 280 years was rather important to me."
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."