James Duffy (Formerly Jimmy Wagner) is an old classmate to Adrian Monk and Sherry Judd who is an art curator and painting restorer. As a youth, he was a pacifist who was friends with Adrian and Sherry, but became the apple of Sherry's eye, even though he wasn't really trying to woo her. In the present day, he now works at an art gallery where he is a curator and painting restorer. He and Sherry reconnected when she brought him her painting to restore after it was vandalized in a home invasion/murder.