Cory Raines was born in 1256, England, a foundling child raised by a family who found him. After he became Immortal, he met his teacher, Matthew McCormick. Cory was a natural thief, but under his teacher's influence, became dedicated to giving his spoils to the poor, a latter day Robin Hood.
In 1926 Missouri, he continued his trade, and found himself on the F.B.I.'s most wanted list. He robbed an armored truck when he encountered Duncan MacLeod and Amanda. Cory went to a nearby farm and gave the money to a family so that they could start a new life in California. Duncan told Cory that he was stealing, that some of the money actually belonged to people like the farmer he gave the money to. Cory then gave the family his car so they could get to California.
Duncan, Cory, and Amanda drove off to encounter the authorities waiting for them. Cory got an idea and indicated that Duncan and Amanda were hostages, Cory was shot, but Duncan dug Cory up from his grave. Cory and Amanda then went on a robbery spree, the Immortal version of Bonnie and Clyde. They would rob banks and when they got shot up, Duncan would dig them up from their graves and Cory and Amanda would go to the next state to continue their bank robbing spree, much to Duncan's disgust.In 1996, Cory turned up again, robbing a small money-lending business, as Amanda arrived with Richie Ryan to retrieve her stashed money. After the alarm was set off, Cory grabbed Amanda and they rushed to his getaway van; Richie followed them. Cory ran Richie off the road and into a creek before taking Amanda to his place; and they got his '24 Packard, and were on the road again. Cory ran Richie into the creek a second time, saying he was just having fun.
Richie and Duncan MacLeod finally tracked the pair down. Richie was not amused with what Cory did to him. Cory told MacLeod that he planned to rob the federal reserve, but unknown to Cory, the money he stole, belonged to Sam Grinkhov, a Russian mobster. Duncan was not optimistic about Cory's plans. Amanda, meanwhile, got a visit from a crooked cop, employed by Grinkhov, and was kidnapped.
Cory told Duncan about the 1.5 million dollars that he stole and Richie asked where the money was, asking sarcasticly if Cory gave the money to an orphanage, which Cory actually did. MacLeod and Cory go rescue from Grinkhov, Cory arrived at the exchange with some dynamite strapped to his chest, Duncan blows him up. After his recovery, Cory moved on, without Amanda