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Brian Cullen suffered his first death in 1314, when he fought under Robert the Bruce against the English. In the centuries that followed, he earned a reputation as the best swordsman in Europe. Over time, this led inevitably to repeated challenges from both mortals and immortals alike in hope of building a reputation on a dead man's shoulders.
In May 1810, Cullen traveled with Duncan MacLeod from Sion to Lausanne by the Swiss Rhone Valley. Shortly before Lausanne, the young mortal Alan Kelley challenged him. Cullen tried to send him away, but eventually he fought Kelley, whom he defeated and killed.
Brian Cullen, in 1810
In 1854, Cullen was in San Francisco. His fame and constant dueling had developed in him a fear, he no longer wanted to face the contant battle that was his life, he developed a streak of paranoia. He began to take refuge in saloons and opium dens to forget the fear. By chance, he met his old friend Duncan MacLeod. This fear Cullen expressed with MacLeod before the fight with Zoltan Laszlo. Duncan tried to help his friend, but he could not get through to him and his dependence on drugs took deep root.
Cullen tried to run from the Game by going to the Yukon, he nearly froze to death in the wilderness, and tried to reinvent himself as a fur trader. He was rumored to have both run from challenges and otherwise ambush challengers before taking their heads
This trend continued over the decades, with him eventually becoming a drug dealer in Albuquerque, NM in 1994,
Cullen at an opium den in San Francisco, 1854
Cullen tried to run Richie off the road when their paths crossed, and then tried for Richie's head. While playing "chicken" with Richie on a mountain road, Cullen crashed head-on into a bus, killing many. MacLeod tried to convince Cullen the error of his ways, to remind him he was once the greatest of the warriors, to stop using the drugs, but a paranoid Cullen believed MacLeod was just trying to render him helpless. Finally, MacLeod had no choice but to confront his former friend and behead him. Having to kill his friend left Duncan devastated.