Montgomery de la Cruz isn't exactly a guy you’d want to grab a coffee with. Actually, in the world of 13 Reasons Why, he’s arguably the most terrifying presence Liberty High ever produced. He’s the "villain’s villain." While Bryce Walker was the face of the show's initial conflict, Monty became the shadow that truly haunted the later seasons.
Honestly, people still argue about him. Was he just a monster? Or was he a tragic product of a cycle of abuse that he couldn't break?
The truth is somewhere in the messy middle. He did some of the most unforgivable things ever put on a streaming platform—specifically that graphic season two finale—but his character arc also highlights a very specific, dark reality of repressed identity.
The Brutality of the "Brotherhood"
Monty lived for the football team. For him, the "Blue and Gold" wasn't just a sports jersey; it was his entire moral compass. He was the enforcer. If someone threatened the team or the status of their leader, Bryce, Monty handled it.
But his loyalty was toxic.
He didn't just bully people; he hunted them. He spent the first two seasons as a background menace, planting threats in lockers and terrorizing the "tapes" group to protect Bryce. It was all about the code.
Then came the bathroom scene.
You know the one. Even years later, that scene with Tyler Down is cited as one of the most controversial moments in modern television. It was brutal. It was hard to watch. It shifted Monty from a "typical jock bully" to a character that many fans found impossible to redeem.
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Why the Winston Williams Story Changed Everything
In season three, the show threw a massive curveball. We found out that Montgomery de la Cruz was gay.
It wasn't a "coming out" moment in the traditional, heartwarming sense. It was desperate. He met Winston Williams at a party, and after a hookup, Monty's immediate reaction was to beat Winston to a pulp.
This is where the nuance kicks in.
Monty’s aggression was largely a mirror of the violence he faced at home. We finally got a glimpse of his father, Mr. de la Cruz, who was depicted as a physically abusive homophobe. Monty was terrified. He was trapped in a house where being himself was a death sentence and a school where being a "man" meant being a predator.
Timothy Granaderos, the actor who played Monty, has talked a lot about this. He didn't want to make Monty "likable," but he did want to make him human. He once noted that Monty’s behavior often came from a place of "personal pain and a lack of being able to properly understand those emotions."
Winston was the only person who saw the "real" Monty. Or at least, the Monty that could have been.
The Framing of a Dead Man
The ending of season three is where things get really controversial for the fans. Monty is arrested for the assault on Tyler. Shortly after, it’s announced that he was killed in his jail cell.
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Convenient, right?
The Liberty High group—Clay, Ani, and the rest—needed someone to take the fall for Bryce Walker’s murder. Alex Standall was the one who actually pushed Bryce into the water, but they couldn't let him go to jail. So, they pinned it on Monty.
He was dead. He couldn't defend himself.
This move split the fanbase. On one hand, Monty was a rapist who "got what was coming to him." On the other, the "heroes" of the show became murderers and liars who used a dead boy as a scapegoat.
It’s dark. It’s messy. It’s exactly why people are still talking about Montgomery de la Cruz in 2026.
Breaking Down the Timeline
- Season 1: Monty is a background player, mostly just an annoying jock.
- Season 2: He becomes the primary antagonist, culminating in the horrific assault on Tyler.
- Season 3: We see his relationship with Winston and his abusive home life. He is framed for Bryce’s murder after dying in prison.
- Season 4: Monty "returns" as a hallucination, representing Clay’s crumbling mental state and guilt.
What Timothy Granaderos Brought to the Role
It's worth mentioning that Granaderos is nothing like Monty. He’s actually a soccer player from Michigan who didn't even start acting until his mid-20s.
He originally auditioned for Justin Foley. Can you imagine that? He also tried out for Tony and Jeff Atkins.
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Landing Monty meant he had to deal with a lot of real-world heat. He even received death threats because he played the character so convincingly. That’s the "curse" of being a good villain actor. People forget there's a human behind the script.
The Legacy of the "Ghost"
In the final season, Monty haunts Clay. He isn't a ghost in a supernatural sense, but a manifestation of trauma.
Every time Clay looked at Monty’s sister, Estela, or saw Winston, he was reminded that they destroyed a person’s legacy to save their own. Monty became a symbol of the show's central theme: that everyone is "13 reasons" away from a breaking point.
What You Should Do Next
If you're revisiting the series or just trying to understand the character better, there are a few things to keep in mind.
First, look at the cycle of abuse. Monty’s story is a textbook case of how trauma is passed down. His father’s belt created the monster that attacked Tyler.
Second, check out Timothy Granaderos’ other work. He’s been in Tagged and Walker: Independence. Seeing him in a different light helps separate the actor from the trauma of the character.
Lastly, pay attention to the subtext in season four. The way the show handles "Wonty" (Winston and Monty) isn't just about a romance; it's about the tragedy of what happens when someone is never given the space to be honest about who they are.
Montgomery de la Cruz was never going to get a happy ending. But his story serves as a brutal reminder of what happens when society—and families—prize "toughness" over empathy.
Actionable Insight: If you're interested in the psychology of characters like Monty, research the "Internalized Homophobia" studies by Dr. Ilan Meyer. It provides a massive amount of context for why characters in Monty’s position lash out with such specific, targeted violence.