Ranking All 8 Brooklyn Nine-Nine Halloween Heist Episodes

The B99 squad in Halloween costumes: from left to right, Rosa, Holt, Hitchcock, Gina, Amy, Scully, Terry, and Jake

It’s that time of year again when all the ghosts and ghouls come out to play, and spooky events are taking place left, right, and centre. Pumpkin picking, apple bobbing, and trick or treating, to name a few. But one Halloween-themed television event that was highly anticipated up until this year was Brooklyn Nine Nine’s annual Halloween Heist

Starting in Season 1, Jake Peralta (Andy Samberg) proposed the idea of stealing Captain Holt’s (Andre Braugher) Medal of Valor before midnight struck on the night of Halloween. And thus, a drama-filled tradition was born. From Season 1 to 8, the kooky cast of characters in the 99th precinct attempt to steal a particular object every Halloween. Each year, the heist gets more and more outlandish as they all attempt to outwit each other in increasingly ridiculous ways. So, here’s my take on ranking all 8 Halloween Heist episodes!

8. ‘Cinco de Mayo’ (Season 6)

Terry dressed in gold with a banner that reads 'All Hail King Terry' behind him, Cheddar the dog by his side and a mariachi band in the background

As the episode title suggests, this heist doesn’t take place on Halloween, which sadly removes the spooky festivity. Due to a gas explosion, the Heist is delayed. Six months later, on Mexican holiday Cinco de Mayo, the heist is proposed as a way to distract Terry (Terry Crews) from the nerves leading up to his Lieutenant’s exam. Scully’s (Joel McKinnon Miller) medical bracelet is the object to vie for, which is locked in a supply closet alongside Hitchcock (Dirk Blocker). This year’s teams are Jake and Terry, and Holt and Amy (Melissa Fumero), as Rosa (Stephanie Beatriz) opts out and Charles (Joe Lo Truglio) is excluded due to Bill’s (Winston Story) absence.

Even more betrayals than the previous year ensue, with not only a healthy dose of double-crossing, but also the involvement of Holt’s husband Kevin (Marc Evan Jackson) and Scully’s secret twin brother Earl (?!). It’s extremely convoluted in a way that feels very over-the-top. In the dramatic reveal, Terry turns out to be the champion as he is in possession of the bracelet. Everything was his plan, from delaying the Halloween Heist to manipulating everyone against each other. It’s very well-planned and executed for an unexpected sixth winner. At this point in the show though, it feels like they made Terry the winner purely for shock value, since he isn’t big into silly games. The episode in general also doesn’t have the same spirit as other Halloween Heists—mostly because it doesn’t take place on the usual holiday. 


  • Bill being ‘dead’ but later revealed to be alive in a pretty dark lie.
  • Amy, Jake, and Holt arguing over who actually won last year’s Halloween Heist.

7. ‘Valloweaster’ (Season 7)

Jake and Holt by the 'Infinitude Gobbler' as Jake introduces the Halloween Heist

On Halloween 2019, the next heist begins. Based on Thanos’ Infinity Gauntlet, the players have to collect three gems to put in the ‘Infinitude Gobbler’. All three are inside Bill’s pocket; I do think this was a little lazy, as surely it would make more sense to scatter them and increase the difficulty of the challenge. Each team is handcuffed together to force them to work in tandem. Jake is paired with Holt, Amy with Charles, and Rosa with Scully, as Terry opts out and Hitchcock is excluded. It’s later revealed that the teams were once again rigged or intentionally manipulated.

Hence the name ‘Valloweaster’, the heist ends up getting postponed and occurring on various holidays due to both Cheddar and Scully swallowing the gems. After the latter is eliminated, Rosa’s partner is replaced with a filing cabinet. Amidst all the chaos in the Easter heist, Rosa steals the gems and jumps off the roof onto a trampoline, lighting her name in fire—she wins in style. As she reveals, she stole all three sets of gems each holiday by replacing them with fakes, with the additional help of Terry. Rosa was a worthy (and perhaps overdue) winner, and arguably three-time winner since she stole the gems on three separate occasions. Incorporating three different holidays is a fun new take on the heist, but it does unfortunately mean the events are diluted by the multiple postponements. There’s not much in the way of action and the challenge itself, so it feels lacklustre. But, worth it for Rosa getting crowned!


  • Amy hiring an actor to be Jake’s ‘therapist’ to plant the idea of dressing as bunnies during the Heist.
  • Rosa taking advantage of a loophole by still having part of the filing cabinet handcuffed to her.

6. ‘Halloween IV’ (Season 4)

Amy and Rosa looking annoyed from the decorated break room as Gina stands triumphant outside

To break the three-way tie between Jake, Holt, and Amy, the fourth Halloween Heist commences. The aim this time is to steal a plaque from Amy’s childhood caboodle in the middle of the precinct by sunrise (since they’re on the night shift). Amy picks her teammate first (Rosa), then Holt picks Charles, and Jake is left with Gina (Chelsea Peretti) since Terry refuses to participate. This immediately throws a spanner into the works for Jake, since his whole plan revolved around working with Charles, including hired body double, Bill.

One of my favourite tactics from this one is Jake still utilising Bill by dressing him in a wig and Gina’s hoodie to function as her body double instead of Charles’. Gotta use your resources! Bill soon ends up being Jake’s only heist partner since Gina rollerskates into a pole and loses her front teeth. It’s a shockingly violent moment that stands out from the other heists, and I respect it for being so brutal.

In a mass of confusion, every team later realises they have the same plaque. Turns out Gina faked her accident and pulled the strings behind this heist, even framing Terry with the wording on the plaques (‘heists are dumb’). She also has a dig at Amy by saying she dressed in one of her bland pantsuits so she was hiding in plain sight—it wouldn’t be a Gina-centric episode without a comment at Amy’s expense. Feeling left out by the ‘detective’ part, Gina also changes the winning title to the “ultimate human/genius”, as it remains for the rest of the show. It’s extremely satisfying to see such an iconic character win out of the blue, even if this episode feels quite predictable compared to the others. By this point, we know if someone is eliminated or excluded, they have an ulterior motive. Even so, the drama suits Gina perfectly.


  • Jake and Holt both making ridiculously over-the-top entrances to declare the Heist.
  • “Come on Amy, show me the binder” – Rosa exciting her teammate.
  • Jake straight up forgetting that Gina lost her front teeth as a kid.

5. ‘HalloVeen’ (Season 5)

Jake proposing to Amy in the evidence room

Due to the previous two dark horse winners, the Halloween Heist is open to everyone in Season 5. The aim is to steal a cummerbund (or belt, as Jake claims) inscribed with the words “amazing human/genius” by midnight. Everyone gets their best insults in as the competition heats up. To spice up the events, the cummerbund is hung from the ceiling in plain sight, but as soon as it is, the lights go out and it’s stolen straight away!

This particular heist involves a lot more betrayals, which are always the most entertaining part. The cummerbund changes hands at an alarming rate as characters from The Handmaid’s Tale are utilised as a distraction, and GPS trackers are planted in the winning object and people (namely Terry, via lots of yoghurt). I love that some characters (especially top three: Jake, Holt, and Amy) are willing to go to the lengths of actively poisoning a colleague to win now. The pressure is on so much more than in previous years, making it a much more intense watch.

As all players race to the cummerbund, Jake and Amy go into the evidence room, where Amy finds it. However, it’s inscribed with something different: “Amy Santiago, will you marry me?” It’s the perfect proposal and wonderfully surprising way to end the heist. It does mean that there is no winner this time though! Since the inscription was changed, as Holt points out, it doesn’t count. The next year, Holt claims he found the actual cummerbund during the engagement celebrations; however, this took place after midnight, rendering it obsolete. It’s hilarious how this fact preoccupies Holt so much rather than his two beloved colleagues getting engaged. We wouldn’t have him any other way!


  • “Letting me into your life was the worst mistake you ever made” – Amy getting competitive with Jake at the start.
  • “You’re not Cheddar, you’re just some common bitch!” – Holt discovering his dog was replaced.

4. ‘The Last Day’ (Season 8)

From left to right: Holt, Jake, Amy, Charles, Terry, and Scully locked in the storage unit with golden balloons around them

It’s understandable why this one would be pretty high up on the ranking considering it’s a) the finale of the whole show, and b) a heist two-parter no less! As Jake sets it up, he explains the goal is to steal a medal (modelled off Holt’s Medal of Valor from the first ever Heist) from a ‘golt’ tube that will release at midnight. However, his real motivation is to give himself the ‘perfect goodbye’ since he’s leaving the Nine-Nine, as he tells partner-in-crime Amy—he replaces the tube with a bunch of fakes containing presents for each of his colleagues.

As Terry once again opts out, he leaves a trail of clues for the rest of the squad in a very treasure-hunt-esque style to kick off the final heist. I love this inclusion of actual puzzles, especially since they hold nostalgia; a trip down memory lane takes place, as the characters visit locations linked to significant plot moments. We see a few familiar faces throughout the story: Mlepnos (Fred Armisen), Teddy (Kyle Bornheimer), Pimento (Jason Mantzoukas), and even Wuntch’s (Kyra Sedgwick) grave. It makes for a sweet send-off as well as an extra-special heist for fans who have stuck with the show since Season 1.

As it usually tends to go, many betrayals occur as each player has their own agenda. In the end, the squad get trapped in a storage unit from the first case they worked with Holt. Aww. After escaping, they return to the precinct only to find Hitchcock, who they assumed was on a vacation in Brazil following his retirement, holding the real tube. He ends up being crowned the ‘Grand Champion of the Nine-Nine’, much to everyone’s (and my own) dismay. Sure, it’s a surprise twist, but I couldn’t help feeling disappointed since I dislike Hitchcock and Scully so much. But that’s just me. The episode even ends on a flash-forward to Halloween next year, where Jake, Holt, Rosa, Amy, and Gina return to the Nine-Nine to surprise Terry with another Halloween Heist. They know how to play to their audience alright!


  • Gina stealing the diamonds from evidence and leaving (or just her whole return in general).
  • Amy making Jake think he was in a coma for seven years. Just wow.
  • Terry’s Kool Aid Man moment.
  • Holt’s Kevin-Cheddar tattoo!

3. ‘Halloween’ (Season 1)

Jake looking happy in his winning crown while Holt announces him to be an 'amazing detective/genius', wearing an eyepatch

In the pioneering Halloween episode, there are a couple of sub-plots alongside the heist, making the event itself a lot more stripped back. It’s pretty much only Jake and Holt involved in a 1v1 battle as the other squad members are preoccupied with working cases. Remember when they actually did their jobs on Halloween? Ahh, simpler times…

It all starts when Jake asserts that he’d made a great criminal who wouldn’t be caught by any of his fellow detectives. Holt instantly protests this, saying he’s “100% sure” Jake would be caught. And so the bet is proposed, along with some ground rules:

“I will bet you that by midnight tonight, I can steal the Medal of Valor from your office. […] If I lose, I’ll work the next five weekends, no overtime. And I won’t tell anyone here about the time I saw you wearing short-shorts outside of work. But if I win, you have to do all of my paperwork tonight, the busiest and spooookiest night of the year. And you have to publicly state that I’m an amazing detective-slash-genius.”

Crashing through the ceiling of Holt’s office after getting caught (a great slapstick moment, might I add) marks the beginning of all of Jake’s failed attempts to steal the medal. These failures consist of the following: dressing as a janitor (fake mustache and all) and getting caught, wrongly timing a diversion, holding a bunch of pigeons up to a ventilation shaft to send the feathers through into the office, using people dressed as royal babies as another distraction, and getting arrested after scaling the side of the building with a blowtorch. To say the heist wasn’t the whole focus, and the episodes are only 20 minutes, there’s a decent amount of shenanigans involved here!

Alas, while Jake is handcuffed in an interrogation room, he explains to Holt how all of his actions were very much intentional and resulted in him successfully stealing the medal before midnight. Charles, Amy, Rosa, and Terry were also all recruited to help him. It’s an excellently pulled-off scheme, and the pay-off is fantastic. Seeing Holt so disappointed with Jake’s supposed stupidity only to become reluctantly impressed is a fantastic ending. The audience is also fooled alongside Holt, which is very clever.


  • First ever ‘title of your sex tape’ joke.
  • Jake making a bunch of puns aimed at a guy dressed as a banana stuck in revolving doors as he attempts to escape after robbing a bank (“I’m sure you’ll get out on “a peel”).

2. ‘Halloween II’ (Season 2)

Jake rejoices in his magician's outfit while Amy and Rosa smirk in the background

Holt pretends to be uninterested in a follow-up Halloween Heist in the second season, but Jake manages to convince him with another bet involving overtime and paperwork. Upping the stakes this time, Jake proposes stealing the watch off of Holt’s wrist. In a meeting with his previous allies, Jake claims he’s been planning his scheme for three months. Love the dedication.

The catch is, everything genuinely goes wrong for Jake in this heist. He hires a criminal called ‘Fingers’ (Apollo Robbins) to carry out the theft, who scams him after stealing the watch. Jake ends up on a wild goose chase to retrieve the watch that culminates in his arrest like the first. Holt reveals he was planning how to outwit him since last Halloween! I’m obsessed with how Holt’s focus and work ethic translates into being so good at such a silly yet elaborate game, purely to wreak vengeance on his co-worker. He actually hired Fingers to double-cross Jake, and convinced the rest of the squad (minus Charles who is far too loyal) to help him too on the basis of wanting to embarrass the previous champion. As much as we love Jake, it’s a great comeuppance for him. The prankster has to be pranked every so often!

My personal favourite part of Holt’s scam was him and Rosa disguising themselves as partiers on the Halloween party bus. It’s easy to root for him with the amount of effort that went into his scheme, especially when he says he already started planning the next heist three months ago.


  • The squad teasing Charles for his costume obsession once again.
  • Gina shirking her work responsibilities for her dance group.

1. ‘Halloween, Part III’ (Season 3)

Jake poses for a picture with Terry and Sharon's children, Cagney and Lacey, as Holt photobombs holding the crown

Aaaand the top spot goes to the third Halloween Heist! Holt and Jake both agree to it as a tie-breaker to see who deserves the title of “ultimate detective/genius”. A crown locked in a suitcase in the interrogation room must be stolen. For fairness, they pick teams to help them this time. On Jake’s side is Charles and Rosa, and on Holt’s is Terry and Gina. Amy is upset to be excluded from both teams; neither Jake nor Holt trust her due to her close relationship with both of them. A highlight is both characters yelling into Amy’s boobs thinking she’s bugged.

Jake starts with the upper hand as Rosa steals the crown for him. As it turns out, Holt has bugged Jake’s desk and so he is aware of where Jake has stored the crown: in a vault inside his desk. Using Terry’s wife and kids as a distraction, Holt breaks into the vault and steals the crown for himself. Holt photobombing Jake and Terry’s kids while posing with the crown is my absolute favourite moment—petty Holt is the best Holt. 

Both teams confront each other as they realise neither of them have the crown. Security tapes show a janitor named ‘Al’ took the crown from the bin, but the only person who knows his address is Amy. Jake and Holt both beg her for it, in a very satisfying moment that firmly kicks them off their high horses. Amongst all the heist betrayals, it’s always amusing seeing a team member come crawling back to someone they turned their back on. Staying neutral (and of course to cause extra fighting between them), Amy gives the address to both of them.

In a dramatic turn of events, ‘Al’ is revealed to be Amy after all. She played both teams since they didn’t trust her and assumed she’d only participate out of loyalty to one of two men in her life. Rightfully, she stole the crown to spite them both. I also love that in the process of this, Amy put up an ‘out of order’ sign on the elevator, forcing Jake and Holt to run up 31 flights of steps. What an icon. I particularly like the set-up of this episode, as it makes it all the more rewarding that Amy is the mastermind. She’s a very deserving winner who has a solid reason behind playing for the crown rather than just to cause drama (not that there’s anything wrong with that either). All hail Queen Amy!


  • Gina rejecting a man Charles tries to set her up with; “buh-bye, whore”. 
  • Amy’s janitor disguise parallels Jake’s in the first Heist.
  • When trying to get the address from her, Jake fake-proposes to Amy; two years later, he proposes during the Halloween Heist for real.

And so ends my ranking! It’s a shame we won’t be getting any more Halloween Heist episodes (or any more Brooklyn Nine-Nine in general, for that matter), but it’s always there to rewatch during spooky season. Let me know your thoughts in the comments!

Written by Robin Moon

Robin writes for 25YL and Horror Obsessive as much as their scattered brain will allow. They love dark fantasy, sci fi, and most things horror-related, with a huge soft spot for vampires. Don't make the mistake of mentioning Buffy around them or they won't shut up about it. Seriously. They're also a fiction writer and aspiring filmmaker; in other words, they much prefer spending time in made-up places and far-off universes than in the real world.

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