Montgomery de la Cruz

"Do you know what I got Alex? I got my friends, I got the team. I don't get to be all boo-hoo I'm sad my friend died, I'm gonna put a bullet in my head so the whole world feels sorry for me. Jesus, you wave that gun around like I give a s**t. I don't man. If I sell out Bryce or lie either way my life falls apart. I got no one else on my side. I can't run home that team's my home. Going to playoffs, winning state, being an athlete? That's not about fun for me it's about survival. It's all I got. It's everything."

- Monty telling Alex his motives for his crimes.

Montgomery "Monty" de la Cruz is the secondary antagonist of the Netflix Original series 13 Reasons Why, serving as a supporting antagonist in the first season, one of the main antagonists (along with Bryce Walker) of the second season, and the main antagonist of the third season.

Montgomery has been known to mess around and pick on the Baker's Dozens as a way to silence the victims of Bryce Walker any of the jocks in Liberty High along with eventually antagonizing Bryce Walker in the third season.

He is portrayed by Timothy Granaderos.

Biography
Montgomery is casually vicious and callous to the other students (especially Tyler Down) and uses physical cruelty the most often, seemingly just for the pleasure of it. Despite his behavior, his status as a popular athlete in baseball protects him from any consequences within the school. He is a member of Bryce Walker's bully friends and is passionately loyal to him. This is proven in season 2 where he consistently tries to protect his friend Bryce Walker from facing legal consequences for his rape allegations, he goes as far as being an accomplice to his rape of Hannah Baker (who later killed herself partially because she felt she could not handle the trauma the rape caused her), and an attempted murder to Clay Jensen to keep him silent, to protect Bryce.

Personality
Monty initially comes off as very one dimensional. He is a cruel, sadistic, unsympathetic, and naturally violent bully, most likely because of his abusive history with his father. His violent tendencies may also be a result of his abuse of steroids as well.

In the second season, Montgomery's character is shown to be more than just a one-dimensional bully. Monty is a manipulative and scheming survivalist, willing to side with whoever he believes will keep him safe even if the person is guilty. While Monty is extremely loyal to his friends and teammates, especially Bryce, it is not out of care or compassion but rather as a necessity because he believes they are his best chance at surviving his abusive home. Even though Monty knows Bryce is guilty of raping multiple girls he still sides with him because of Bryce's family's influence and therefore his best chance of survival, despite knowing Bryce would never go the lengths Monty went to help Monty. He is neither sympathetic nor empathetic towards any of his victims or Bryce's victims. He also goes a step further when he rapes Tyler with a mop stick in the high school bathroom.

In Season 3, he is still violent and psychopathic but slightly more subdued than in season two, as well as being revealed to be a repressed homosexual. He also becomes even more paranoid when the police begins to search the sports teams lockers for drugs, particularly steroids. Though he remains completely callous and heartless towards others, such as mocking Justin's drug addiction, Clay for being a suspect in Bryce's murder, as well as making kissing noises at Tyler after his rape of him. Monty's psychopathic behaviour becomes so disturbing that even Bryce, who has committed a fair amount of atrocities, is disturbed and appalled at Monty's actions. We later see that his virulent and obsessive homophobia is likely a result of some sort of self-loathing that he hides deep inside through his cruel and sadistic nature.

Season 1
This season Montgomery is the least villainous and he is mostly an antagonist because of his brutish nature.

At one of Liberty High School's school dances, he goes up behind Courtney Crimsen and forces himself on her body, asking her sexually for some fun later on, although he does stop touching her when she pushes him off.

Later, Montgomery was driving recklessly with Justin Foley on their way to school where he almost hits Alex Standall. Remorseless, he laughs vacuously in response to Alex angrily yelling that people were walking. The two then get in a fight, which Montgomery easily overpowers, and later Montgomery is suspended for 3 days.

After his suspension Montgomery torments Tyler Down despite the latter's unprovoking actions. He once shoves Tyler to the floor when he passes him in the hall, and another time pins Tyler against the wall and threatens to break Tyler's expensive cameras against Tyler's face. Alex steps in and Montgomery backs off. This is his final antagonistic appearance in the season.

Season 2
Montgomery is a villain in this season and many consider him the main antagonist (even more than Bryce Walker) of the season. As one of Bryce's friends, he goes at great lengths to protect Bryce from any legal consequences due to the rape accusations Bryce faces. Montgomery's deeds consist of:


 * Montgomery de la Cruz and Bryce Walker taunts Tyler Down about the photo Clay Jensen took on Tyler Down when he was naked with a remark saying "Nice a**."
 * Giving out hostile notes and papers to the people who received subpoenas, telling them to stay quiet.
 * Attempting to hit Clay Jensen with Bryce's jeep, which almost certainly would have killed him if he succeeded.
 * Attempting to force Alex Standall (a recent suicide survivor) to kill himself by leaving a bullet in his locker and also a diagram of a target shooting dummy, and later a gun.
 * Leaving a naked female sex doll on Jessica Davis' (who was raped by Bryce Walker ) porch, hanging from a noose, calling her a slut.
 * Defacing Tony Padilla's car, which he loves.
 * Vandalizing the Bakers' drugstore, spraying words like "She's dead" in order to taunt them about Hannah's death.

When he is confronted, he ditches the crippled Alex Standall in an abandoned building and snatched the gun Alex had. Later it is revealed that he witnesses Bryce Walker raping Hannah Baker from inside Bryce's pool house, however he chose to not intervene and remained silent about it without a shred of guilt.

He vows for revenge on Tyler Down when the latter indirectly ends baseball season abruptly before state by vandalizing the baseball field.

Later he and two of his lackeys run into Tyler Down in the boys bathroom. Angry at Tyler for ruining the season, he accuses Tyler of ruining his life then assaults him by smashing the back of Tyler's head into the mirror, breaking it. He then proceeded to slam him head first on the side of one of the sinks. He vulgarly calls Tyler a faggot and begins shoving Tyler's head in the toilet while Tyler cries out that he's sorry repeatedly. Montgomery then tops it off by shoving the end of a mop in the bathroom up Tyler's anus while his two lackeys hold Tyler down, thus anally raping him. He pushes the stick so far up Tyler's anus that it bleeds and he later is revealed to be unable to defecate without bleeding. Montgomery and his two friends leave Tyler behind in tears and agony, not knowing that this was the last straw for Tyler and they indirectly pushed him so far he decides to go through with his plan to shoot up the school at their Spring Fling Dance.

Season 3
Montgomery takes a less active role in this season than he did in season two. He harasses Tyler on occasion, showing no regret over raping him and mocks Clay for being the prime suspect of Bryce's murder and Justin for still consuming drugs.

When Bryce takes him to a "rich kid" party, he meets a boy named Winston Williams and the two briefly hook up. As Montgomery and Bryce are about to leave, Winston tries to speak with Montgomery, inviting him to hang out later on. Out of fear of being outed, Montgomery calls him a faggot and beats him senselessly. As a result, Bryce is forced to pay out a total of 7000$ to Winston in exchange for his silence.

On the night of Bryce's murder, Monty apologizes to Winston for beating him up and he invites him over to his house where they have sex, though Monty continues insisting he's not gay. Monty is finally arrested for his sexual assault on Tyler. Monty's father visits him in prison and angrily scolds him, not only for the crime itself, but for assaulting a male. He warns Monty that he will get beaten up by the inmates for what he hid and Monty finally stands up to his father for the first time, saying that while he may get beaten in prison, he won't by his own father for once. He then asks Monty if he's gay, which he bravely admits, before the man spits on his face in response before turning to leave.

The group subsequently frames Monty for Bryce's murder in order to protect the true culprit - Alex Standall - before being informed that Monty was killed in his cell hours ago. Feeling sorry that Monty and Bryce are dead, Ani nonetheless convinces Deputy Standall to close the case by blaming the murder on Monty and that they should "let the dead bury dead". Despite his cruel nature, Monty was mourned by Clay and his friends. Winston, who is also upset about Monty's death, confronts Ani about lying to the police, since he knows Monty is innocent and he didn't deserve to die like he did.

Trivia

 * Ironically, despite playing such an active role in later seasons, Montgomery is not even on the tapes.
 * Montgomery de la Cruz was a really close friend to Bryce Walker. Bryce would cover for his negative behavior with Winston Williams. Justin Foley even says that both he and Monty cared for Bryce at some point.
 * Montgomery is more of a sociopath since he has been traumatized throughout his childhood possibly from his father as implied and pointed out. This would explain his sadistic behavior and constant homophobia towards others, despite engaging in homosexual activities himself which would make him a hypocrite.
 * Montgomery has internal homophobia and would get insecure and angry towards others because of his abusive homophobic father. This would make Montgomery de la Cruz have more of a insecure side to him.