Halloween II is the fourth episode of Brooklyn Nine-Nine's second season.
It's Halloween, once again, at the Nine Nine, and Jake decides to challenge Holt to a second bet. This time: Jake has to steal Holt's watch off the captain's wrist. If Jake wins: Holt once again has to do the detective's paperwork for a week. If Holt wins: Jake has to admit that Holt is an "amazing police captain slash genius" and has to work five weeks of unpaid overtime.
Elsewhere in the precinct, Terry, Amy, and Rosa are putting together Halloween Safety Buckets for the district's children while Gina is off acting stranger than usual.
Tropes present in this episode:
- Attack Backfire: Holt reveals that the other detectives in the unit except for Boyle turned on Jake purely for the joy of seeing him humiliated. Rather than feeling betrayed, Jake admits that this actually turns him on a little bit.
- Batman Gambit: Holt's plan hinged on Charles being Jake's Yes-Man, that the rest of the detectives would happily double cross Jake just to see him be humiliated, and that Jake would go to great lengths to try and win.
- Call-Back: Most of this episode references the previous season's Halloween heist.
- Comically Small Bribe: Holt managed to get most of the others to help him with his revenge plan just by asking them if they wanted to see Jake humiliated.
- Casual Kink: As mentioned under Attack Backfire, this is one of the first episodes to have a joke implying (read: all but outright stating it) Jake has a serious submissive streak.
- Crazy-Prepared:
- Jake began setting up his heist months in advance, even enlisting the help of a pickpocket, and roping in the other detectives to put together an elaborate distraction in order to get Holt's watch. Unfortunately for Jake...
- Holt began planning his revenge the moment he lost his bet with Jake the year before and spent months subliminally influencing Jake's choice of target and putting together the pieces to get the upper hand, setting up a double cross that Jake never saw coming.
- Then they start preparing for Halloween, 2015.Jake: Be warned! I started planning next year's heist just this minute!
Holt: Good. Then you're only three months behind.
Jake: You sick son of a bitch!
- Everyone Has Standards: During the reveal of his plan to humiliate Jake, Holt informs him he didn't actually have Jake's car destroyed. He instead had it washed while using a decoy car to make Jake think it was crushed.
- Eskimos Aren't Real: When Holt informs Peralta that his car was taken away to be washed, not destroyed, Peralta thinks this is just another prank, convinced that car washing can't possibly be real.
- Failed a Spot Check: Jake has apparently lived his entire life in Brooklyn without noticing the East River or the Atlantic Ocean:Jake: [Scaling a fence] Wow, look at the view from up here. I didn't know we lived near water!
- Foreshadowing: If you have a good ear, you'll be able to recognize Hitchcock, Scully, Rosa and Holt in their costumes before they're revealed. Charles is also not onscreen when he says "Jake! Party bus! Get on board!" and isn't seen on the bus or coming off of it at the impound lot.
- Funny Background Event: When Peralta gives his soliloquy about how Holt will have lost everything at midnight, Santiago and Diaz can be seen in the background giving each other looks that say "Jake has no idea how wrong he is."
- Graceful Loser: Unlike what he said in Season 1, Jake takes his defeat to Holt very well.
- Heist Episode: This time, Jake has to steal Holt's watch.
- Hidden Depths:
- Gina reveals that she's been going to night school to complete her bachelor's degree, thus explaining why she's been acting flakier than usual.
- Scully, as it turns out, is a fairly adept pickpocket.
- Hoist by His Own Petard: It's implied that if Jake had just dialed down his Unsportsmanlike Gloating a bit after beating Holt in the previous Halloween bet, Holt would have remained a Graceful Loser about things and subsequently wouldn't have utterly humiliated Jake this Halloween.
- Hubris: Thanks to his victory over Holt the previous year, Jake gets a bit overconfident about defeating Holt this year. He doesn't stop to consider that maybe Holt wasn't as zen about Jake's victory (and subsequent gloating) as he looked...
- Humiliation Conga: Holt didn't just want to win the bet, he wanted to beat Jake. Holt did so by pulling together a Batman Gambit that ensured that Jake would be utterly humiliated before even discovering that Holt had the upper hand all along.
- Holt has Fingers double cross Jake and make it seem like the pickpocket ran off with the watch.
- Holt tells Jake that the watch has immense sentimental value, thus horrifying Jake into making sure he gets the watch back.
- Fingers, in exchange for telling Jake that he hid Holt's watch in Jake's car, demands Jake's shoes, preventing him from giving chase when Amy tows Jake's car.
- Hitchcock and Scully, in disguise, pour beer all over Jake's clothes and steal his jacket and wallet.
- Terry gets Charles out of the way so that Holt can play a recording of Charles that he'd made eight months previously, guiding Jake onto a party bus.
- On board the bus, Rosa (wearing a mask) distracts Jake as Holt (also wearing a mask) pretends to be a drunken partier while stealing Jake's badge.
- Jake makes it to the NYPD impound only to discover that he lost his wallet and credentials and has to climb over a barbed wire topped fence only to watch as his car is carried off to a crusher before he's arrested and hauled to the Nine Nine's interrogation room.
- O.O.C. Is Serious Business:
- Terry realizes that Gina is depressed and does some digging to find out that she's been going to night school and became so focused on her classes that she began missing rehearsals with Floorgasm, her dance troupe, and was subsequently kicked out just before a major competition.
- Holt wants to beat Jake so badly that he drops his usual stoicism and pretends to be a drunken buffoon in order to lift Jake's badge.
- Paranoia Gambit: Jake's plan relies on Holt remembering what happened the previous year and taking precautions based on that knowledge.
- Pet the Dog: Following Holt's Humiliation Conga of Jake, he admits that he didn't have Jake's car crushed after all, and instead had it cleaned.
- Sequel Episode: To "Halloween"
- Shout-Out: As Jake is giving out code names to his heist partners, he tells Terry that his codename is Hammer to which Terry gives an approving nod. Given that a previous episode referenced Terry's love for Pam Grier, this is likely a reference to blaxploitation film star Fred "The Hammer" Williamson. It could also double as a stealth Actor Allusion as Williamson and Crews were both football players prior to becoming actors.
- Tuckerization: The name for the pickpocket, Dan McCreary, likely comes from co-executive producer Laura McCreary.
- Undying Loyalty: Holt knew that, unlike the others, Charles would never betray Jake. So part of his plan was to have Terry get him out of the picture.
