|First appearance||"Next Stop, Valhalla" (episode 5.04)|
|Last appearance||"A Failure to Communicate" (episode 6.04)|
|Reason/Cause||Murdered by Chris Keller|
|Date of Conviction||January 14, 2002|
|Date of Death||January 26, 2003|
|Affiliations||Adam Guenzel & The Aryans|
|Episode Count||8 Episodes|
|Portrayed by||Andy Powers|
A well-off, educated, suburban white male, Winthrop is imprisoned because he assisted his best friend Adam Guenzel in beating and raping a woman while intoxicated. Inside, he is immediately targeted as weak and becomes the sex slave of Vernon Schillinger and the Aryan Brotherhood. Later, he offers Schillinger a deal to join the brotherhood, and gets in. He dies at the hands of Chris Keller shortly afterwards.
Winthrop arrives in Oz with Adam Guenzel for raping a woman, and is sent to Unit B. Guenzel is sent to Em City with family friend Tobias Beecher. Winthrop and Guenzel are both unfit for prison and thereby ideal sex slaves for both black and white inmates. Inside Unit B, Winthrop is approached by an overweight black inmate named Clarence Seroy, who attempts to rape him.
Winthrop is "saved" by Aryan Brotherhood members Vernon Schillinger and James Robson; As Winthrop is new to prison, he does not realize that the Aryans in Oz are sexual predators themselves who pull this routine often to turn naive white inmates into their sex toys. He is told that he will be protected, but the protection will cost him sexual servitude to the Aryans. Still in shock, Winthrop realizes he has no choice and allows the Aryans to rape him. In the cafeteria, Robson parades him with a tied up shirt, pigtails, and makeup. He is whistled at by various inmates as Guenzel looks on in disgust.
When Guenzel, who is extremely homophobic, is transferred to Unit B, he insults Winthrop. Schillinger rapes him shortly afterwards, and eventually sets Guenzel up, by convincing him to undertake a dangerous escape plot that results in his death. Beecher, who agreed to sell Guenzel out to the Aryans, is so guilt-ridden that he testifies against Schillinger, who is sent to solitary. Winthrop remains as the Aryan's main prag.
Winthrop eventually tires of being the Aryans' toy, and asks to be a full-fledged member of the gang. Schillinger initially refuses, but Winthrop offers to kill Beecher's father, who is helping inmate Chris Keller appeal a death sentence. Schillinger accepts Winthrop's deal. Winthrop pays off a guard to lock Beecher's father in a hall, and Winthrop stabs him to death. Winthrop is then let into the Aryan Brotherhood as a soldier.
Once Keller's death sentence is overturned on appeal, he avenges Beecher's father by luring Winthrop into a closet in Unit B and snapping his neck. When he found out about it later, Schillinger was apathetic to Winthrop's death, claiming "He was not meant to be with us anyway".