An Immortal, Kragen was born in Boston in 1754 in the British colony of Massachusetts.
Kragen was a pornographer, though he saw himself as an artist. In the late 1800s, he started with paintings. The girls he used as models were often still children. A prominent clergyman tried to get him arrested, but there were no laws against what he was doing at that time. Somewhere before the 1880s he met the mortal woman, Genevieve, when she was 13. They were together for some time, but she eventually escaped from him. He searched her out; eventually finding her in 1886. At that point she had married the Immortal, Alec Hill.
Before Alec and Duncan MacLeod could stop him, Kragen hurled himself and Genevieve from a nearby cliff. Genevieve died and Kragen revived and escaped.
He eventually moved on to photography, and when moving pictures came into being, he was one of the first to use film as his medium. He made a great deal of money to fund his "empire".
When video was invented, Kragen was on board from the start. There were a lot of others who did the same, and to his surprise, the audience didn't see the difference between his "art" and the "smut" the other directors made.
In 1996, Kragen was working at the Anchor Studios as a producer and director of adult movies.
Alec Hill had at ast tracked down Kragen and went to the studio to fight him. Alec, however, never reached Kragen. He was killed by Richie Ryan, who he picked a fight with when the younger man was in his way. Richie was in a bad mood as well, and the two fought.
Everyone assumed, it had been Kragen who killed Hill, and Hill's wife invoked the vow that Duncan had sworn; that he would kill Kragen if Hill could not. Some time later, when he had just finished filming for the day, Duncan MacLeod entered the studio in order to make a challenge. Kragen put up a good fight, but in the end he was beheaded by Duncan who received his Quickening
Kragen never took The Game lightly; he used an English hand-and-a-half sword, and was very skilled with it.