- Tyler: "These are thousand dollar cameras--"
- Montgomery: "Oh yeah, and I'll break 'em on your face."
- ― Montgomery to Tyler
Throughout the Series
He was first seen while he played video games with the other boys in Bryce's house.
At the Winter Formal, he walked up to Courtney and asked if she and Hannah are up for some fun later, implying that he knows that it's them in the picture Tyler took. Courtney proceeded to tell Montgomery a secret, which threw Hannah under the bus and protected only Courtney. Montgomery then confronted Hannah and asked where her girlfriend was. He then explains the lie that Courtney told, which left visibly pissed. She left to confront Courtney in the hallway, who was visibly upset and ashamed. Hannah angrily explained that she just wanted to be her friend. The lie Courtney told was that Hannah was dating the openly gay student, Laura. Hannah asked for a three way and not only did Justin Foley finger Hannah, but that she also went down on him. The blew up her reputation and newly mended friendship with her.
Montgomery sped through the road with Justin, to get to school and was stopped by Alex Standall, who he almost hit. The two got into a fight, which attracted a crowd of students, who watched and filmed. Mr. Porter then came to the scene to take them to the school for further consequences. After the school Honor Board had made their decision, Montgomery was sentenced 3 days of suspension, while Alex was off the hook with a warning.
5 months after Hannah's death, the trial against the Evergreen School District begun. Montgomery went to great lengths to send threatening messages and intimidating gestures to the witnesses that were to testify in court. This included: running Clay Jensen off the road, after he spotted him while he rode his bike late at night, sending a sex doll to Jessica Davis, a bullet and later a gun to Alex, leaving a dead rat in Zach Dempsey's gym bag, and vandalizing Tony Padilla's car to encourage them to keep quiet about Bryce's involvement in Hannah's death. He, along with three others, also ambushed and severely beat Clay in the locker room.
It is revealed, after Alex remembers, in a flashback that he and Alex were present at Bryce's house the night Hannah was raped. Monty looked through a window and witnessed the rape, while Alex played a game and could only hear sounds. Monty didn't alert Alex or do anything to stop it.
After the groups' efforts to destroy Bryce and the jocks, it caused enough problems for the school to cancel the rest of the sports season, Montgomery and two other jocks got revenge and they assaulted Tyler Down, Monty took it further and sexually assaulted him via sodomization with a mop handle.
Montgomery seems to be naturally violent, as he gets into fights and squabbles easily. Fighting is almost a second nature to him probably due to the fact that he has an extremely abusive father. He is an arrogant, selfish and cruel person, who regularly hangs out with the likes of Bryce Walker, Zach Dempsey, and the other jocks. However, when it comes to Bryce, he has shown a psychotic devotion to him and will do whatever it takes to protect him, including orchestrating violent attacks and attempted murder.
Montgomery, by all accounts, is a one-dimensional bully. He is often shown antagonizing and intimidating other students, such as when he taunts Hannah about the fabricated rumors about her or when he consistently attacks Tyler, often unprovoked.
He is shown to be a complete monster. In "Bye", the season finale, in the boys' bathroom at Liberty High, Tyler was brutally sexually assaulted by him, including having his head smashed through a mirror, his skull pummelled on the bathroom sink, followed by being dunked into the toilet bowl. He then used the shaft of a mop to sodomize Tyler and then left him bleeding on the bathroom floor.
In the second season, Monty is revealed to have an extremely abusive father. He is shown to sometimes run away from home to sleep under a certain bridge (which Scott knows about). He tells Alex that the reason he intimidated him and the others was that he couldn't stand to have Bryce and the jocks held responsible for Hannah's death despite their role in it, as they are his "family" and the only thing he has to protect him from his father. This is the only time where he is ever shown to have a human side to him. In the season finale, he has a cast on his arm, which Bryce believes is due to his father beating him. This shows that Montgomery, like Justin, comes from an abusive home, and releases his frustrations on other students weaker than himself, as it is the only way he knows how to release his emotions.
Montgomery is portrayed with a tall, strong, handsome appearance, with spiked up brown hair. He appears to have great physical strength.
In Season 1, Bryce and Montgomery appear to be friends. They are shown together on numerous occasions. In particular, Montgomery is shown with Bryce, Justin and Zach pushing Clay and Alex into a drinking contest, and later is at a party at Bryce's house. He and Bryce are seen together with other jocks at the winter formal, and they both, at some point, harass Hannah and Courtney over the kiss photo. He and Bryce both moon Tyler after Clay takes a photo of his ass. He is also at the party at Bryce's house when Justin calls Bryce a rapist. He and Bryce are later shown hitting baseballs together and discussing the next season, and the past. It appears, however, that Bryce does not trust him with everything. When Montgomery asks how Bryce injured his hand, Bryce lies and claims he punched the wall (he actually punched Clay Jensen). Later, when Montgomery and Tyler fight (which Montgomery initiated), Bryce breaks it up.
In Season 2, Montgomery is concerned about what could happen to Bryce as a result of the trial. Bryce simply reassures him that everything will be fine. They are shown together on the field and off it regularly throughout the season. However, Montgomery disregards Bryce's advice and takes matters into his own hands, threatening the tape subjects and Tony by leaving intimate objects and threatening notes in their lockers behind Bryce's back. It is also revealed that he saw Bryce rape Hannah, but did nothing, though he was far enough away to not see much, so he may have assumed the sex was consensual. He even uses Bryce's car to run Clay off the road and damages Tony's car. He is also shown to sometimes sleep under a bridge, which Bryce does not know about. When Bryce finds out that Montgomery is the one who threatened others on his behalf, he is disgusted, but still gives Montgomery his lawyer to make sure charges are not pressed, though he admits he only did this because Montgomery used his car, and he knows after the rape charges have been filed, no jury would believe he had no idea. After Montgomery wants to get revenge on Tyler for his actions despite Bryce's probation, Bryce becomes even more disgusted, and ends their friendship, hurting Montgomery, which may have been a contributing factor to his assault on Tyler.
Montgomery and Tyler hate each other. Montgomery is sometimes shown slamming Tyler into walls through Season 1, never provoked. He also moons Tyler after a picture of the photographer's ass is shared throughout the school. Tyler eventually fights back, and at the end of the season, Montgomery's picture is shown on Tyler's photographic "hit list", implying Tyler may want to kill him in revenge for bullying him.
In Season 2, their relationship does not change. Montgomery is still a bully to Tyler, and Tyler still despises him. Tyler takes revenge on the entire team, by burning the field. After Tyler is caught, he is sent to a program to control his anger. When he returns, Montgomery confronts him, due to the fact that his actions caused the season to be cancelled. Tyler attempts to apologize for his actions, showing some regret, but Montgomery refuses, and beats him up, before sodomizing him with a mop.
In Season 1, Montgomery and Clay appear to be mere acquaintances who don't interact at all unless brought together by circumstance. Montgomery accompanies Bryce, Justin and Zach to push Clay into a drinking contest with Alex, and afterwards, he waves Clay off when he leaves. In a flashback, it is shown that Montgomery harassed Hannah over the picture in front of Clay, and afterward, called him Cory, showing he does not even bother to learn Clay's name. After he nearly hits Alex with his car, Clay is among the honor board that suspends Montgomery for three days.
In Season 2, Montgomery again calls Clay "Cory" before being corrected by Bryce. Though it is unknown at the time, he is the one who runs Clay off the road, and later he and three other jocks beat Clay up in the locker room in an attempt to silence him. After finding out that Montgomery is the one intimidating them, Clay is among the group of male students that force him to give the polaroids back, though it turns out he doesn't have them.
In Season 1, Alex and Montgomery had a slight friendship. Montgomery is shown pushing Alex into a drinking contest and later playing video games with him at Bryce's house, which Alex wins. However, he later nearly hits Alex with his car and laughs. After he and Alex get into a fight because of this, he blames Alex for it. He is suspended, while Alex is not. This appears to end any friendship they had. He and Alex are later both shown at the party at Bryce's house where Justin admits Bryce raped Jessica, though they do not interact. Later, Alex stops Montgomery from antagonizing Tyler, and brings up his recently ended suspension, which Montgomery does not take kindly to.
In Season 2, they are no longer friends. He even intimidates Alex away from testifying by sending him a target, a gun and a bullet. It is also revealed that he and Alex played video games at Bryce's house the night Hannah was raped, and he saw it, but did nothing and told Alex it was nothing to worry about. Alex confronted him about this later, and he warned Alex to shut up, refusing to take responsibility for his actions. During the fight between the jocks and other boys, Alex hits Montgomery with his cane when he attacks Zach, and after Montgomery retaliates, Alex tells him he will go to jail. Alex later figures out Montgomery was the one intimidating them, and is among the group that confronts him, even threatening him with a gun and going with him to get the polaroids. When Montgomery is revealed to not have the polaroids, he calls Alex's bluff on shooting him and escapes with the gun, leaving Alex stranded. Alex is presumably the one who told the police what Montgomery did, as his father asks Montgomery about the gun when he is questioned.
Scott and Montgomery appeared to be friends in Season 2. They are often shown hanging out, and Scott even knows about Montgomery sometimes sleeping somewhere other than his house and keeps his word not to tell Bryce about it. However, after Scott finds out from others that Montgomery is threatening them, he tells them about the place under the bridge, and helps them intimidate him into giving the polaroids back, which shocks Montgomery. Before this, he tries to get Montgomery to understand that they have been protecting Bryce, the rapist, for long enough, though Montgomery does not appear to agree. It is unknown how their relationship continues after this, as they are not seen together again after this.
|“||If I sell out Bryce or lie, either way, my whole 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. So you wanna shoot me? Shoot me.||”|
|— Monty to Alex in The Box of Polaroids|
- Montgomery's arch-enemy seems to be Tyler, who constantly gets slammed into the wall by Montgomery. They hate each other.
- He is a rapist: in "Bye", he takes his hatred for Tyler to an extreme extent and assaults and brutally sodomizes Tyler with the handle of a mop. He walks out leaving him half-naked and bleeding on the floor.
- This scene caused controversy over being 'too graphic' and 'taking it too far'.
- Montgomery is not mentioned by name in the book.
- His hideaway is called a 'Hobo-hotel' for when his dad got to be too much.
- He is revealed to be the one who was intimidating many of the people that were testifying. Most of the messages he left were written with red paint.
- He painted on Tyler's pictures and had 'you ain't seen shit' written on it.
- He hung a sex doll with 'slut' written on it in front of Jessica's house.
- He left a note in Jessica's locker that said 'keep your fucking mouth shut'.
- He made a mess of a classroom.
- He sent Alex's a note with a picture of a target and the text 'Better luck next time' on it.
- He almost drove Clay on his bike off the road.
- He set the sign in Marcus' yard on fire.
- He put a dead rat in Zach's sports bag.
- He threw a brick through Mr. Porter's car window with a paper around it that said 'know your place'.
- He broke into the Jensens' house and stole Justin's gun.
- He put pictures of Zach's sister in Zach's locker.
- He destroyed Tony's car.
- He broke into and vandalized the Baker's Drug Store.
- He sent Alex the gun he had stolen with a note that read 'How could you live with yourself?'.
- He followed Clay and Justin when they drove away from Bryce's house.
- He left Justin a death threat on Clay's car.
- See also: Category:Images of Montgomery de la Cruz
- ↑ Son, Diana (writer) & Shaver, Helen (director) (March 31, 2017). "Tape 2, Side A". 13 Reasons Why. Season 1. Episode 3. Netflix.
- ↑ Sheff, Nic (writer) & Alvarez, Kyle Patrick (director) (March 31, 2017). "Tape 3, Side B". 13 Reasons Why. Season 1. Episode 6. Netflix.