A look back at Monty and Winston’s relationship 13 Reasons Why as he attempts to avenge his death

Season four has seen Hillcrest student Winston transfer to Liberty High – but why is he snooping around Bryce's murder?

Monty and Winston 13 Reasons Why

Warning: this article touches on subject matter that some readers may find distressing

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The fourth and final season of 13 Reasons Why landed on Netflix on Friday, introducing some new characters – including Estela de la Cruz – but also bringing back a few minor characters from last season.

One of the returning familiar faces is Winston Williams – a Hillcrest student who recently transferred to Liberty High and has become fast friends with Alex Standall and Tyler Downs.

But with Winston’s previous links to Monty de la Cruz, who was imprisoned for assaulting Tyler and subsequently framed for Bryce’s death after dying in jail, the gang can’t help but be suspicious of the new student and his sudden interest in Bryce’s murder.

Here’s everything you need to know about his connection to Monty last season…

What was the nature of Winston and Monty’s relationship?

Winston was introduced as a minor character in season three, when it is revealed that Monty met Winston at a party full of rich Hillcrest students. They kiss in the bathroom at the party and Winston performs oral sex, but after the encounter, Monty, who is in-denial about his sexuality, calls Winston a homophobic slur and beats him up. Bryce then pays Winston $2,000 to keep quiet, but Winston demands another $5,000 the next day.

This is all revealed when Clay and Ani find the ID of another boy named Winston in Monty’s car. They track down the actual Winston Williams, who explains that the other boy took his exams for him and that Bryce and Monty were blackmailing him with this information to keep him quiet about the assault.

Monty and Winston then see each other again at a Liberty High vs Hillcrest game, as Winston is his school’s student photographer. After the game, Monty approaches Winston and apologises for his actions at the party. He invites Monty back to his house, where they have sex, however, Monty tells Winston that he does not want people to know that he is gay.

13 REASONS WHY (L to R) DEAKEN BLUMAN as WINSTON and MILES HEIZER as ALEX STANDALL in episode 404 of 13 REASONS WHY Cr. DAVID MOIR/NETFLIX © 2020
Winston with Alex Standall – Bryce’s killer (Credit: Netflix)

At the end of season three, when Monty, who was imprisoned for assaulting Tyler, has died in jail and framed for Bryce’s murder, Ani sees Winston outside of coffee shop Monet’s. She goes outside to talk to him, and Winston tells her that Monty was a human being and that he didn’t deserve to die the way he did. He also reveals that he was with Monty the night that Bryce died, and therefore knows that Monty could not have killed Bryce. He then walks off, leaving an anxious Ani.

Although Winston says that he was expelled from Hillcrest, the fact that he transfers to Liberty High implies that his feelings for Monty were deeper than revealed in season three – this is confirmed when we see Winston looking at a picture of Monty in the school’s previous yearbook.

Whether or not Monty and Winston were fully dating before Monty died, it is clear that Winston wants to uncover the truth about Bryce’s death from the questions he’s been asking Tyler in yearbook club.

As for any other intentions Winston might have, I’m sure they’ll be revealed as season four plays out…

Who plays Winston on 13 Reasons Why?

Winston Williams is played by Deaken Bluman in 13 Reasons Why. Bluman previously appeared in various web series and shorts, with 13 Reasons Why being his first TV acting credit.

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Season four of 13 Reasons Why is now available on Netflix – check out our lists of the best TV shows on Netflix and the best movies on Netflix, or see what else is on with our TV Guide