During his time at the school, he began an affair with his teacher Grace Newman, but, when she attempted to break it off to give him a chance at a normal relationship, James lost his temper and shot her dead, subsequently taking his own life in grief.
In 1998, Buffy was given a lens into this budding relationship when she dozes off in her American history class and has a vision of Sunnydale High in 1955. In this vision, she was also in American history, although they were studying the Minutemen rather than the New Deal, and she witness James and Grace discussing the Hemingway book she lent him.
James' spirit returned, attempting to seek forgiveness for what he had done by possessing others to relive his last moments with Grace, but he was trapped in a loop; every time he attempted to undo his mistake, the participants repeated the couple's last moments, and James' host ended up shooting Grace's. This resulted in the death of one of the teachers when she and the school janitor were possessed, although Rupert Giles was able to stop the janitor before he could kill himself.
Eventually, James managed to break the cycle when he and Grace possessed Buffy Summers and Angelus respectively. Although "Grace" was still shot, Angelus's vampiric abilities allowed him to survive the injury, allowing "her" to stop "James" from killing "himself," and admit that she had always loved him. With this last act, the two kissed, their spirits finally able to pass on to the next life. Later, Giles offers counsel to Buffy who, despite being able to feel pity for James, didn't understand how Grace could forgive him.
Behind the scenes
- He was portrayed by Christopher Gorham, Brian Poth, John Hawkes, James Lurie, and Sarah Michelle Gellar.
- James shows signs of a borderline personality disorder, which includes difficulty controlling aggression, believing relationships to be more intimate than they actually are, frantic attempts to avoid real or imagined abandonment, impulsivity, and mood swings.