Holt-Amy Relationship

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[]

Season 1
Season 2
Season 3
Season 4
Season 5
Season 6
Season 7

The Slump
Holt asks Amy to be the point person for the Junior Police Program and she's more than happy to accept
Video		Dialogue
		{{{dialogue1}}}

Old School
Holt manipulates Amy into telling him why Jake punched Jimmy Brogan, and she loves it.
Video		Dialogue
		{{{dialogue1}}}

Thanksgiving
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.
Video		Dialogue
		{{{dialogue1}}}

Christmas
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.
Video		Dialogue
		{{{dialogue1}}}

Pontiac Bandit
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.
Video		Dialogue
		{{{dialogue1}}}

The Party
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.
Video		Dialogue
The squad is invited to Holt's birthday party Amy gets caught in Holt's bathroom {{{video2}}}		Amy Santiago Everyone check your email. The greatest thing that could ever happen has just happened. Jake Peralta The girl who beat you for high school valedictorian died? Amy Santiago No. "Kevin Cozner requests your presence at Raymond's birthday party." Jake Peralta Who is Kevin Cozner? Is he the star of Danzes With Wolvez? Rosa Diaz He's Captain Holt's husband. Captain Raymond Holt. We're invited to the Captain's birthday party. Jake Peralta Oh, the Captain's party and what note. Amy Santiago I can't wait to see the inside of Raymond's house. I'm gonna learn everything there is to know about him. Rosa Diaz Apparently, my husband Kevin has invited you all to my party. There is very little street parking, no gifts and no singing of happy birthday. Should be fun. Amy Santiago Sounds fantastic! Raymond Holt Santiago, are you in my bathroom with a dog you're allergic to? Amy Santiago No...

Unsolvable
Amy forgot that she had volunteered to help Holt over the weekend and made plans to go on a romantic trip with her boyfriend, Teddy Wells. Following bad advice given to her by Gina Linetti, she lies to the captain and makes up a dental emergency for the reason she can't go. Holt, worried about her pain, sets up her up an emergency appointment with his brother-in-law and drives her to the appointment himself. Amy confesses to her lie in while in the dentist chair. She apologizes and asks for the next weekend off and Holt agrees and tells her to just tell him next time.
Video		Dialogue
		{{{dialogue1}}}

Charges and Specs
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.
Video		Dialogue
		{{{dialogue1}}}

Undercover
Amy tells Holt that the drills are too much.
Video		Dialogue
		{{{dialogue1}}}

Chocolate Milk
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.
Video		Dialogue
{{{video2}}}		Amy Santiago You're just going to let her fails us? Raymond Holt I'm sorry about your precious grade, Santiago, but this isn't about you. Amy Santiago Don't "this isn't about you" me. I'm "this isn't about youing" you! That grade is the only thing standing between me and a future where you're not my captain anymore. Wuntch failed the nine-0 and their captain was fired. Raymond Holt I attempted to cajole her but she rebuffed me. I'm not a man of unlimited cajoling. Amy Santiago Well you better become one, because I need you in command. This precinct needs you in command. Cajole up, Captain. Amy Santiago I'm sorry you had to go through that. Raymond Holt No, you were right. This is the best job I've ever had and it would be foolish to give it up over a petty feud. Here, this is for you, it's a grade for your performance over the past two days. A letter grade so as to not be weird about it. Amy Santiago Oh my god, you really shouldn't have. An "A". Thank you. Just curious, does your system have pluses in it or is it like "A" the highest?

Jake and Sophia
Holt encourages Amy to run for union rep, despite the fact that he wasn't supposed to discuss about the union rep elections.
Video		Dialogue
		{{{dialogue1}}}

USPIS
Holt tries to help Amy stop smoking by doing what worked for him with his gambling addiction, which does nothing for Amy. He later explains, by using incorrect grammar, that she's putting tremendous pressure on herself and that it's okay to make mistakes. This, of course, gets through to her.
Video		Dialogue
		{{{dialogue1}}}

The Pontiac Bandit Returns
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.
Video		Dialogue
{{{video2}}}		dialogue Raymond Holt Santiago, I want to thank you for my gift. Amy Santiago You like the scrapbook? Raymond Holt I don't know. I'm a man of my word, so I did not peruse. The gift I'm referring to was you point out my mistake. Do you know why I don't accept gifts? Amy Santiago Because you're so evolved you don't need material things. Raymond Holt Because I don't like brown-nosing. Amy Santiago Oh Terry Jeffords Youch, that was hard to watch. Raymond Holt You told me to my face that I made a mistake, and that's as far from brown-nosing as one can get. I respect you for that. Now I have a gift for you. I have the complete Brooklyn Broiler files. He was give 3 life sentences and it should have been two. So I've already contacted the D.A. about the error. Will you please help me figure out who set those other fires? Amy Santiago Ohh! More work! I know that sounded sarcastic, but... Terry Jeffords Nobody thought that. Raymond Holt Not for a moment.

Payback
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.
Video		Dialogue
		{{{dialogue1}}}

Boyle's Hunch
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.
Video		Dialogue
		{{{dialogue1}}}

Halloween III
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."
Video		Dialogue
		{{{dialogue1}}}

9 Days

Video		Dialogue
		{{{dialogue1}}}

Monster in the Closet
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.
Video		Dialogue
		{{{dialogue1}}}

Skyfire Cycle
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."
Video		Dialogue
		{{{dialogue1}}}

The Last Ride
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.
Video		Dialogue
		{{{dialogue1}}}

The Slaughterhouse
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.
Video		Dialogue
		{{{dialogue1}}}

The Big House Pt. 2
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.
Video		Dialogue
		{{{dialogue1}}}

HalloVeen
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.
Video		Dialogue
		{{{dialogue1}}}

Return To Skyfire
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.
Video		Dialogue
		{{{dialogue1}}}

99
Jake figures out Holt’s sabotage of their return to New York, but doesn’t understand how Holt is compromised. Amy knows exactly what it is; Seamus Murphy’s deal to get Jake and Rosa out of prison.
Video		Dialogue
		{{{dialogue1}}}

NutriBoom
On her first day as Sergeant, Amy struggles to deal with an annoying know-it-all police officer. When she asks everyone else for advice they tell her the tactics they used to avoid her, none of which work. When she asks Holt for advice he tells her to listen to him because managing someone like her is a pleasure because they’re useful and valuable.
Video		Dialogue
		{{{dialogue1}}}

Jake & Amy
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.
Video		Dialogue
		{{{dialogue1}}}

Honeymoon
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.
Video		Dialogue
{{{video2}}}		Raymond Holt Since the rejection, a great sadness has enveloped me. I kept expecting this dark feeling to pass, but it's only gotten worse. Amy Santiago Not getting the job you want stinks. In first grade, I was passed over for line leader, and I'm still pissed. Kyle D's lines had curves and gaps and cutting galore. It was a frickin' carnival. Jake Peralta Yeah. What's a line leader? Raymond Holt Well, it's not just that I didn't get the job. It's that John Kelly did. He's already released a memo detailing his vigilant policing initiative. It's essentially a return to stop and frisk. Choosing him is a betrayal of everything I stand for. Amy Santiago I feel the same way about Kyle D. Raymond Holt I tried to suck it up and go back to work. I put on my uniform and got in my car. And next thing I knew, I was on a plane to Mexico. I didn't even pack a bag. I bought a bundle of novelty shirts at a nearby gift shop. This one says "What's up beaches?" Instead of bitches for humor reasons. Amy Santiago But you hate humor. Raymond Holt Well I'm a joke now, so it suits me. Jake Peralta Mm-kay. But how did you end up here in Mexico, at the exact same tiny resort as us? Raymond Holt Gina's been talking this place up for years Jake and Amy Referral code Gina30 Raymond Holt I had no idea you'd be here. Jake Peralta You know what? It's fine, sir. A lot of people go on their honeymoon with their boss. Nope, I though if I said it out loud it would normalize it, but it's weird. Amy Santiago It's gonna be okay. HOw long are you staying, sir? Raymond Holt Just until I get my head right. But don't worry. I'll steer clear of you two. You won't even know I'm here. Amy Santiago This place is so romantic. Jake Peralta Yeah, and so... intimate. Raymond Holt Don't worry. I'm not listening to you. I'm just thinking about how this sea bass is cold. But not as cold and cruel as the hands of fate that have thrust my entire life into darkness. Jake Peralta Ah, damn it. I just ordered the sea bass. Amy Santiago How dare you call Jake selfish? He just wasted his entire honeymoon trying to take care of you while you wallowed in your misery like a little baby. Raymond Holt That seems a little harsh. Amy Santiago Oh, does it? I don't give a hoot. Jake Peralta Oh, damn. Amy Santiago For the last five years all I've done is give a hoot about you and what you think. I gave a hoot about you as a boos. I gave a hoot about you as a mentor. I gave a hoot about you as a friend. Jake Peralta She gave so many hoots. Amy Santiago Not anymore. After the way you've acted and what you just said to Jake, I don't give a hoot what you think, and I really don't give a hoot if you decide to quite the NYPD, so do it! I'm all out of hoots. I'm hootless! [Holt apologized] Raymond Holt Listen, I'm on the next plane back, but I wanted to pay for you two to extend your stay so you can have a proper honeymoon. Amy Santiago Oh, sir, thank you. That's very nice, right Jake? Jake Peralta Yeah, super cool.

Gintars
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.
Video		Dialogue
		{{{dialogue1}}}

Cinco de Mayo
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.
Video		Dialogue
		{{{dialogue1}}}

Captain Kim
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.
Video		Dialogue
		{{{dialogue1}}}

Debbie
Holt and Amy engage in a speed reading contest.
Video		Dialogue
		{{{dialogue1}}}

Lights Out
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.
Video		Dialogue
		{{{dialogue1}}}

Running Gags Featuring Amy Santiago and Raymond Holt's Relationship[]

Amy Embarrassed In Front Of Holt[]

Read full article on Amy embarrassed in front of Holt

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.