From the moment Raymond Holt is appointed captain of the 99th Precinct, Amy Santiago tries desperately to impress him, which he refuses to pander to. While Amy spends half of the series attempting to enlist Holt to be her mentor, it is revealed in the fourth season that he had been mentoring her the whole time.
Yet Holt is not the only mentor in the relationship, as Amy helps him acknowledge his emotional immaturity throughout the series. She teaches him how he hurts the people he cares about which motivates him to take corrective action, something he hadn't learned by the time he came to the 99th Precinct.
Ultimately their relationship develops into one of mutual respect which culminates in the final season, when Holt enlists Amy's help to develop the NYPD Police Reform Program and finally, in the penultimate episode, promotes her to Chief, bringing her on to help run the unit.
Amy Santiago & Raymond Holt's Relationship By Season[]
The Slump | |||
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Holt asks Amy to be the point person for the Junior Police Program and she's more than happy to accept | |||
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Old School | |||
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Holt manipulates Amy into telling him why Jake punched Jimmy Brogan, and she loves it. | |||
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Thanksgiving | |||
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Amy invites Holt to her Thanksgiving with the plan to officially ask him to be her mentor. She never gets the opportunity to read him her 10 page toast, but Gina gives it to Holt. He read it, provided feedback, spell checked and labelled the awkward parts. Amy interprets this as her first official mentoring from him. | |||
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Christmas | |||
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Amy tells Holt that she would have loved to be Holt's bodyguard. Holt tells her that he'll consider her next time. She accidentally embarrasses herself by saying she couldn't wait for Holt to get another death threat. | |||
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Pontiac Bandit | |||
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Holt tries to get Amy to take the puppies but she can't as she's allergic. She tries to hide it because she does not want to say no to him, but her uncontrollable sneezing gives it away. | |||
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The Party | |||
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Kevin Cozner invites the squad to Holt's birthday party and Amy is excited for the opportunity to learn all she can about Holt. She goes through his kitchen cabinets and in his bedroom to see what tv shows he's watching. | |||
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Charges and Specs | |||
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Amy can't believe that Jake doesn't trust Holt enough to inform him about his investigation of Lucas Wint. She then tells Jake that she appointed Holt executor of her will. She stands up to Holt and, against his orders, helps Jake convince Holt that Wint is guilty. | |||
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Undercover | |||
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Amy tells Holt that the drills are too much. | |||
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Chocolate Milk | |||
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Holt's nemesis, Madeline Wuntch, comes to the precinct and Amy is upset to see that she might give the precinct a bad review and close it. Amy stands up to Holt, telling him to be the bigger man so that Wuntch gives them a good review. | |||
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Jake and Sophia | |||
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Holt encourages Amy to run for union rep, despite the fact that he wasn't supposed to discuss about the union rep elections. | |||
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The Pontiac Bandit Returns | |||
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While making Holt the scrapbook of all of Holt's highlights, "From Ray to Z", Amy discovers a mistake in one of Holt's cases and tells him. He thanks her for the gift of telling him he was wrong and asks her to work the case with him. | |||
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Payback | |||
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Holt and Amy reopen the Brooklyn Broiler case and stakeout a shop he owns. While staking out the shop Amy convinces Holt to eat "street meat" which gives Holt stomach problems. They discover the Brooklyn Broiler died and Holt spends the day visiting the toilet. Amy apologizes and Holt puts her at ease by sharing an anecdote that assures them both they'll be able to laugh about it. | |||
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Boyle's Hunch | |||
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Holt selects Amy as the first NYPD employee to feature as a "good cop" on his new Public Relations campaign. After Gina tries to dissuade him from doing it, Amy takes Holt's side. She brings in a defaced poster of herself and explains that Gina was right all along and the two of them come up with a better campaign, which Gina approves of. | |||
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Halloween III | |||
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Amy tries to team up with Holt for the Halloween Heist after Jake pissed her off by not picking her for his team. Holt responds by yelling into her boobs as if there were a hidden camera. He apologizes for saying "cleavage." | |||
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9 Days | |||
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Monster in the Closet | |||
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Amy assigns Holt the task of decorating Shaw’s for Rosa’s upcoming wedding. He fixates on a balloon arch and spends the day creating more and more arches until Amy finally tells him she hates it and didn’t want to say anything because he’s her boss. | |||
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Skyfire Cycle | |||
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Holt and Kevin come to Rosa and Amy for help with a riddle they've been arguing about. Rosa points out that they just need to bone, and Amy responds by calling Kevin and Holt their "dads." | |||
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The Last Ride | |||
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Amy thanks Holt for mentoring her, even if he didn't see himself as her mentor. He reveals that he had been mentoring her the entire time. They go through his 9 year mentor plan quickly in 1 day and when the precinct doesn't get shut down Holt reveals what they had done that day was volume 1. | |||
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The Slaughterhouse | |||
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Holt discovers Amy is incapable of getting angry at him, so he tries different ways to remedy it. Telling her to not be angry doesn’t work so he uses reverse psychology. She gets angry without realizing it then gets a little too angry. | |||
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The Big House Pt. 2 | |||
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Amy is approached with information on Melanie Hawkins in exchange for a favor by the crime boss, Seamus Murphy. Holt advises her not to take it to prevent ruining her career. She does what he says and works the information Seamus mentioned. Holt, instead, makes the deal with Murphy and uses the information to get Jake and Rosa out of prison. | |||
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HalloVeen | |||
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Jake wakes up at 3:00 a.m. to get a head start on Halloween Heist prep but Amy surprises him already fully dressed and awake. Holt surprises them further by being in full uniform sitting in the dark in their bedroom. | |||
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Return To Skyfire | |||
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Amy and Holt get distracted during their forensic science course taught by Dr. Yee by trying to prevent Boyle from ruining it with his incessant talking. While the only thing they can focus on is getting their certification they lose sight of Boyle as a person. | |||
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Jake & Amy | |||
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Holt officiates Jake and Amy’s wedding where Holt tells them that he’s proud of them and loves them both and gives them permission to say it back. | |||
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Honeymoon | |||
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Jake and Amy spend their entire honeymoon trying to cheer Holt up. When Holt calls Jake selfish Amy snaps and lets him know how rude he's been and that she's done caring about him. He apologizes and corrects his actions by paying for Jake and Amy to have a honeymoon without him. | |||
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Gintars | |||
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Holt and Amy geek out and become bullies to Rosa and Terry over forensic entomology and force them to bring in Dr. Yee who they trip over themselves trying to impress. | |||
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Cinco de Mayo | |||
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Amy and Holt argue the entire time over who the reigning Halloween Heist champion is, since there wasn’t technically a winner due to the proposal. Holt picks Amy as his teammate and they betray one another. | |||
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Captain Kim | |||
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Amy calls Holt out for wearing sneakers, which he only wears for their intended purpose, sneaking. Holt gets why Jake’s into Amy after she spells out the pun chaperowned. | |||
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Debbie | |||
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Holt and Amy engage in a speed reading contest. | |||
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Lights Out | |||
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When Amy was in labor at the precinct Holt performed the dance Terry taught him in the elevator during the blackout as a distraction for Amy from her pain. | |||
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Running Gags Featuring Amy Santiago and Raymond Holt's Relationship[]
Amy Embarrassed In Front Of Holt[]
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A running gag throughout the series is Amy constantly creating awkward situations between her and Captain Holt. She tries harder than anyone to impress him, however, it usually backfires, leaving her feeling embarrassed. Ex: "Raymond, those slacks are a knockout."
Trivia About Amy Santiago and Raymond Holt's Relationship []
- Like Jake Peralta, Amy also views Captain Raymond Holt as a father figure. When Rosa states that Holt needs to "bone" Kevin to overcome his family problems, Amy exclaims, "Gross! Rosa, those are our dads! I mean- [chuckles nervously] that's not what I think. Captain Dad is just my boss. Never mind, I'm teaching father the math!"
- Jake and Amy are the only two members of the detective squad to say and receive an "I love you" from Captain Holt.