The Drill
Because it’s a show which subverts our expectations for what real police work is often like, we rarely get huge moments of catharsis and action from Brooklyn Nine-Nine. But occasionally an episode like “Windbreaker City” comes along which is able to give that to us, while still staying true to the tone of the show.

Like last season’s “Tactical Village,” this episode places the entire group in a scenario where they can act as the action heroes Jake wishes they could every week. This time, they’re invited to Homeland Security’s anti-terrorism drill, but because they’re not well respected, they’re given the role of the hostages.

It should be pretty obvious to anyone who knows Jake that he’s not going to take this well, and he immediately starts plotting to get them out and have them beat the fictional terrorists. It doesn’t help that the Homeland Security guys are so rude to them, especially Agent Kendrick (played by guest star Nick Kroll).

Once it gets going, the second half of the episode plays out like Brooklyn Nine-Nine’s take on an action movie. We can sort of see the one that Jake has planned to look cool in his head, but in reality it’s just people shooting paintballs at each other and Charles trying to get a brick-oven pizza.

But even though it’s pretty silly and not real, the episode actually does a solid job of setting up the stakes here. It’s hard not to compare this to Community’s paintball episodes, and I don’t think Brooklyn Nine-Nine does quite as good of a job. In Community the stakes are pretty high at least for the characters and we’re genuinely invested to see who wins. In “Windbreaker City,” the stakes aren’t really that high; it’s just a matter of us hating the Homeland Security guys, loving the Nine-Nine team, and wanting them to win. But if they lose, nothing actually happens.

Still, I couldn’t help but get caught up in the action of this episode, and “Windbreaker City” ended up being one of the most fun episodes of Season 2. Like a lot of the best episodes, it makes great use of its ensemble, with just about everyone placed together in the scenario and playing off each other in a brilliant way.
Unexpectedly, the Brooklyn Nine-Nine crew doesn’t win, though, which is kind of a downer ending to the episode. However, they do sort of succeed in helping Jake getting over Sophia, helping distract him from constantly checking his phone to see if she texted back. He ends the episode by his own calculations 20% less devastated than before, so it wasn’t a total loss.

Santiago and Rosa
This is a pretty minor storyline in the episode, but throughout the hostage scenario we also have an argument between Santiago and Rosa, who both want the day off on Saturday but one of them has to work. Santiago has tickets to a Ted talk and Rosa has to go to dinner with her parents. Santiago isn’t totally unwilling to work, but she doesn’t believe that Rosa is actually just going to dinner with her parents.

The stakes are raised when during the shootout they decide to place a bet: the highest body count in the game wins. Santiago wins, but it’s only by cheating and shooting Rosa, because technically they didn’t say they couldn’t do that. But in the end, Santiago ends up volunteering to work, both because she feels bad for cheating and to help Rosa out. It seemed pretty obvious this dinner had something to do with Marcus, and we find out that Rosa is introducing him to her parents. This is a pretty minor storyline, but it fits in pretty well with what we know of both of these characters: Rosa being stubborn and unwilling to admit her feelings, and Santiago being overly enthusiastic but with a genuine caring heart at her core.

Holt and Gina
Finally, we get to see a pairing we don’t see too much this episode when Gina asks Holt to take a personality test for her class. Holt is prepared to get an unfavorable test result, and we get a hilarious flashback to him at the doctor’s office freaking out that his blood pressure is only “normal.”
As it turns out he gets a great score, being rated as a strong leader, but he’s confused when Gina gets the same rating as him. His ego and desire to be the best makes him not want to be in the same category as Gina, and I can’t really blame him too much considering how lazy and uncaring Gina is. But this episode suggests that though she comes across that way, her strong personality can actually make her a great leader that can get things done, and Holt realizes that by the end of the episode, giving her more responsibility around the office. Though this is probably a nightmare scenario for Gina, it should be a lot of fun to see her step up and have some position of authority over everyone else.

Other highlights:

-Terry threatens to take Jake's phone away in the cold open: "I'd like to see you try. Oh, well, you did that very easily."
-Boyle gives Jake a list of cathartic exercises. “It’s the middle of winter, so where would I dance in a fountain?” “Indoor malls, Jake. Indoor malls.”
-Nobody cares about Santiago saying NINE NINE, but loves when Terry does it. “I don’t get it.” It works later in the episode though, and she is so happy.
-“Welcome to the big leagues, Boyle.” “Say that again, I want to record it and use it as my ringtone.”
-“That guy doesn’t matter. Sarge I was wrong, he totally matters.”
-“You just made fun of us for that.” “For practicing, that’s the first time we’ve ever tried it.”
-“Waiting for your mom to text?” “No actually I’m waiting for a girl who broke up with me to text.” “That’s way worse.”
-“I have a dog tag.” “That is badass Boyle! Oh, no, it’s an actual tag for a dog.”
-Jake tries to rip off “HOSTAGES”, left with “HOS.” "Really meant to rip off the whole thing but I say we go with it. Come with me, HOs!
“It’s a regular paint bath.” “Like bubble bath.” “No, like blood bath…”
-“No way this is brick oven...they’re playing us Jake!”
-“That’s a terrible apology from content to tone.”
-“Is this a rain man impression?”