10 years prior to Silent Hill 3, Douglas worked as a police detective and retired. Shortly after, he and his wife divorced. The Book of Lost Memories calls Douglas a "widower", indicating that his ex-wife died after they divorced.
Douglas had one son who was killed while attempting to rob a bank because his family was burdened with financial concerns. Douglas feels his son's death was his fault, calling himself a "penniless good-for-nothing." He eventually became a freelance independent private investigator.