Eventually, Whittlesey gets some bad news — Oz has made a contract with the Department of Corrections that, as a condition, will no longer allow officers to work overtime, severely impacting her finances. More trouble arises for her when Scott Ross enters Oz. He was a biker on the outside and used to be in the same gang as Whittlesey's ex-husband. He is obsessed with Whittlesey, and on the outside he repeatedly tried 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 a cut of the profits. She agrees reluctantly, but is quickly discovered by McManus. He doesn't fire her, knowing she's only trying to make money for her family, but demands she put an end to it. Ross however, threatens to tell Warden Leo Glynn and take from Whittlesey everything she has worked for unless she continues.