Diane Wittlesey - Season 1 (1997)

Season 1 (1997)

Whittlesey is the supervisor of the guards in Emerald City, Unit Manager Tim McManus' experimental cell block. She helps to keep prisoners' records and to stop any conflicts between inmates. Eventually, she and McManus fall in love and even have sex inside an empty cell. However, when the two receive flak from their fellow staff members over their relationship, she breaks it off with him.

Eventually, Whittlesey gets some bad news — Oz had made a contract with the Department of Corrections that, as a condition, will no longer allow officers to work overtime. More trouble arises for her when Scott Ross enters Oz. He was a biker on the outside; he and her ex-husband used to be in the same biker gang. He is obsessed with Whittlesey, and on the outside he tried many times to have sex with her behind her husband's back. Ross decides to "help her out" with her situation at home; he proposes that she smuggle cigarettes for him and he will give her extra cash. She agrees reluctantly, but when McManus finds out, he tells her to stop. He doesn't fire her, knowing she's only trying to make money for her family. When Ross gets wind of this, he threatens to tell Warden Leo Glynn and take from Whittlesey everything she has worked for.

Whittlesey gets caught in a riot in Emerald City. She is taken hostage, but eventually the SORT team breaks in and ends the riot. Ross shoots McManus (who volunteered to be captive in return for letting two critically injured officers out for treatment). Whittlesey later takes the gun and kills Ross, shooting him in the head, heart, and genitalia.