- Ani: "He was already gone."
- Winston: "He was a human being. Okay? He was human being. He didn't deserve to die like that."
- ― Winston confronting Ani about Monty's arrest and murder[src]
Early Life Edit
Not much is stated about his early life, although we can assume he was born into a well off family. Prior to the series he was enrolled in Hillcrest. He has mentioned being a fourth-generation Princeton legacy.
Throughout the Series Edit
He can be first seen at a “rich kid” party that Bryce and Monty attend, when Monty arrives Winston takes notice of his arrival.
While in a bedroom Monty arrives looking for a bathroom, Winston shuts the door and the pair look at each other before Winston moves into kiss him, Monty initially grabs Winston by the lapel, but proceeds to aggressively make out with him, and Winston gives Monty a blowjob.
After this encounter, Monty leaves the party, on his way out Winston encounters Monty and asks him to hang out sometime, Monty calls him a faggot and proceeds to beat him up, before Bryce and another partygoer pull him off Winston. He then takes $2,000 off Bryce for his silence, and demands another $5,000 the next day. Bryce and Monty leave and he tells Alex he doesn’t know why Monty attacked him.
He is later spotted at the Liberty vs. Hillcrest game photographing the match. He and Monty exchange a look.
After the game he is taking photos of the team bus leaving when he is approached by Monty, Winston begins to leave but Monty apologizes to him for his actions at the party and tells him ”he seems like a good guy”. Winston invites Monty back to his place and the two have sex, before Monty tells him that he can’t be publicly gay.
He attends the event organized at Liberty where Jessica publicly apologizes for causing the Homecoming fight and starts a wave of solidarity towards sexual assaults victims.
He is last seen at the end of the season outside of Monet’s, Ani comes out and Winston states that Monty was with him the night of Bryce’s death, and he knows that Monty is innocent. He says that Monty was a human being and that he didn’t deserve to die the way he did before walking off in disgust at Ani for framing Monty for murdering Bryce.
Not much is known about Winston. Winston is probably one of the only people to show acceptance to Montgomery, implying a kind and caring nature. Despite being violently attacked by Monty, he chooses to initially lie about their first sexual encounter when asked why he was beaten up. When asked by Ani and Clay why he kept Monty's secret, Winston replies, "That's a secret you keep," implying that he is sympathetic and understanding of Monty's struggle and difficulty in accepting his own sexuality, putting his concern for Monty before his own injuries. Later, after Winston is confronted by Monty at the Homecoming game, he is quick to forgive and invite him for another hookup. Even after Monty denies being gay, Winston does not show judgment - he kindly tells Monty that he does not have to be gay, and that he can choose to be whatever he wants to be. At this point in the story, the night of homecoming and Monty and Winston's second encounter, which the audience sees as a flashback, Winston would probably not know much of Monty's reputation at Liberty and would certainly have no way of knowing about Monty's assault on Tyler during this time (it was only in the aftermath of the homecoming game and Bryce's death that Tyler first told Clay and Jessica). We do not know if Winston and Monty saw each other again between homecoming and the night of Monty's arrest. In the aftermath of Monty's death, Winston expresses disgust at Ani for letting Monty take the blame for Bryce's death. The fact that he knows of Monty's death in jail would seem to imply that at some point he eventually became aware of the reason why Monty was imprisoned in the first place. The audience does not know what Winston's reaction was to finding out what Monty did to Tyler, nor how/if it changed his personal relationship with him. Winston walks away after this, leaving his future intentions/thoughts unclear, except that he doesn't think Monty deserved to die the way he did nor that he should have been framed for a crime he didn't commit, implying that his personal relationship with Monty still influences how he feels about him despite Monty's actions.
Physical Appearance Edit
Winston has a slender frame and pale white skin, with dark black wavy hair.
Season 3 Edit
Season 3 Edit
- ↑ Smith, Trevor Mart (writer) & Hughes, Bronwen (director). (August 23, 2019). "Nobody's Clean". 13 Reasons Why. Season 3. Episode 5.
- ↑ MacDonald, Allen, Malone, M.K., Higgins, Thomas, Tyler, Hayley, Smith, Trevor Marti (writers) & Dowling, Kevin (director). (August 23, 2019). "And Then the Hurricane Hit". 13 Reasons Why. Season 3. Episode 12.
- ↑ Yorkey, Brian (writer) & Kretchmer, John T. (director). (August 23, 2019). "Let the Dead Bury the Dead". 13 Reasons Why. Season 3. Episode 13.