Whittlesey is introduced as the supervisor of the guards in Emerald City, Unit Manager Tim McManus' experimental cell block, first seen when a new group of inmates, including Tobias Beecher and Miguel Alvarez, arrive at Oz. She helps to keep prisoners' records and to stop any conflicts between inmates. Eventually, she and McManus form an attraction and even have sex inside an empty cell while avoiding the execution of Jefferson Keane. However, when the two receive flak from their fellow staff members over their relationship, particularly by Mike Healy, she breaks it off with McManus, who despite his reputation for bed-hopping and womanizing reacts poorly.