Season 6
By the sixth season, Cutler gets into the Aryan Brotherhood. James Robson, a disgraced Aryan, comes looking for protection from Chucky Pancamo (whom he stabbed in season 5), leader of Oz's Italian gang. Cutler agrees to protect Robson only if he becomes his "prag", or sex slave. When Robson accepts the deal, Cutler immediately sodomizes him with a dessert spoon, his initiation into a life of humiliation and pain; Robson is later seen dressed in drag, cleaning up after him, and serving him meals. In the cafeteria, Pancamo, Arnold "Poet" Jackson and Ryan O'Reily berate Robson and Pancamo takes it one further by attempting to kill him. Cutler protects Robson by assaulting Pancamo, who is then forbidden by Warden Leo Glynn from interfering with the Aryans.
Throughout the show, Pancamo and Frank Urbano approach Robson and tell them that he can get back into the Aryan Brotherhood and get the Italians' forgiveness if Cutler dies. Robson first tells prison psychologist Peter Marie "Sister Pete" Reimondo that Cutler is suicidal. She tries to schedule a psychiatric appointment with Cutler, but he rudely dismisses her. Later, after being sodomized, Robson convinces Cutler to try autoerotic asphyxiation. After Robson awakes the following morning Cutler is dead, hanging from his neck by a noose attached to the side of the bed. Cutler apparently leaves Miguel Alvarez as his sole beneficiary in his will, a surprise that baffles the Aryan Brotherhood. It's unclear as to why he did this, but his wife did point out that "he did like to fuck with her when he came to the purse strings", probably as a result of her never really loving him in their marriage.
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