Spoilers ahead for 13 Reasons Why Season 3. The teens of 13 Reasons Why may have found a way to protect Bryce's real killer(s) for now, but Winston and Monty's relationship could prove to be everyone's undoing in Season 4. Though Monty is dead, Winston knows the truth about where he was the night Bryce died — and he may not keep quiet.
As we learned throughout the course of Season 3, Monty met Winston at a Hillcrest house party that he'd gone to with Bryce over the summer. The two noticed each other immediately from across the party, and when Monty later stumbled upon Winston alone in a bedroom, they hooked up. However, when Winston asked Monty if he could see him again once they were back with the other kids, Monty responded by punching him.
As becomes clear from Monty's interactions with his dad toward the end of the season, his family is homophobic, and Monty has internalized that. In turn, he's become a macho, violent jock who masks his own self-hatred through bullying and bigotry. It's a tired trope, but one that helps us to better understand Monty, though it certainly doesn't justify what he did to Tyler or anyone else.
Anyway, after the party, Winston and Monty didn't see each other again until the homecoming game in early November. Winston was there taking pictures for Hillcrest's yearbook, and after the fight broke out on the football field, he and Monty ran into each other in the parking lot. Monty actually apologized for what happened over the summer, saying Winston seemed like a good guy, and Winston forgave him. One thing lead to another, and the two spent the night (or maybe even the whole weekend) together at Winston's house.
Despite Monty's violence toward him, Winston was understanding about what he was going through. When Monty insisted, as they cuddled in bed, that he was "not f*cking gay," Winston responded simply, "OK. Cool. You can be whatever you want to be." But Monty disagreed. "No. I can't," he said, tears welling up in his eyes.
After getting arrested for assaulting Tyler, Monty did tell his dad he was gay, only to receive a response of disgust; later, Monty died in his jail cell. This gave Ani the perfect opportunity to frame Monty for Bryce's murder, get an innocent Clay off the hook, and ensure that the investigation didn't turn toward Alex and Jessica. The only problem? Winston knows Monty didn't do it, and he could easily go to the police and give Monty's alibi, thus re-opening Bryce's case. "He was a human being," Winston told Ani in the Season 3 finale. "He didn't deserve to die that way."
Winston and Monty's relationship may have been brief, but it was meaningful enough that Winston could seek to clear Monty's name in Season 4. And if he does go to the cops, not only will it put Alex and Jessica in jeopardy, but everyone who helped to cover up the truth.
If you or someone you know is seeking help for mental health concerns, visit the National Alliance on Mental Health (NAMI) website, or call 1-800-950-NAMI(6264). For confidential treatment referrals, visit the Substance Abuse and Mental Health Services Administration (SAMHSA) website, or call the National Helpline at 1-800-662-HELP(4357). In an emergency, contact the National Suicide Prevention Lifeline at 1-800-273-TALK(8255) or call 911.