Charles Westmoreland

A relatively quiet and gentle man, Westmoreland took great pains to stay out of other people's business, including Michael's escape attempt, despite Michael's efforts to recruit him. He and Captain Brad Bellick enjoyed a mutual respect for many years until Westmoreland refused to tell Bellick what he'd seen after a guard was murdered outside Westmoreland's cell during a prison riot. Shortly thereafter, Westmoreland found Marilyn dead in his cell. Westmoreland quietly retaliated by starting a fire in the guards' break room and making it appear as if Bellick's negligence had caused the fire. This also allowed Michael and the P.I. crew access to the guard's room in order to dig a hole for their escape.

Upon learning that he would not be allowed to visit his terminally-ill daughter until after her death, Westmoreland became desperate to escape. He finally confirmed that he was D.B. Cooper by showing Michael a one hundred dollar bill matching the serial number of the first bill from the fabled hijacking. After becoming a member of the break-out team, Westmoreland participated in the first failed escape attempt. He would eventually form a friendship with fellow escapee C-Note, bonding over the fact that they were both fathers and talking about their families. C-Note was one of the few people entrusted with Westmoreland's true motive for escape; his dying daughter.

Westmoreland attacked Bellick when Bellick discovered the hole the team dug in the guards' room. He successfully subdued Bellick but was severely wounded by a piece of glass, piercing his torso. During the escape, he collapsed in the infirmary from loss of blood. He told Michael to go on without him, but not before making him promise to visit his daughter (a promise Michael would later sadly be forced to break) and then revealing the location of the D.B. Cooper money (under a silo at the Double K Ranch, just outside of Tooele, Utah), and revealing that sum was $5 million, rather than the one million generally assumed. He is later found dead by Warden Pope.