Brooklyn Nine-Nine Wiki

Every year, the 99th Precinct has their annual Halloween Heist to decide who is the Ultimate Detective/Genius (Season 1-3), and later the Ultimate Human/Genius (Seasons 4-8).


Season One[]


Jake attempts to take Holt's Medal of Valour from his office before midnight.

  • Jake tries to steal the Medal of Valour from Holt's office while he is at his meeting, Holt hears Jake hiding in the ceiling and moves his Medal to his safe inside a locked cabinet.
  • Jake dresses as a janitor to sneak into Holt's office, but is once again caught by Holt. Holt fails to see Rosa sneak in and pick the lock on the cabinet as he drags Jake out of his office, Jake complaining that the distraction that he set was mistimed. A garbage bin then suddenly bursts into flames, creating a distraction that allows Rosa to sneak out.
  • Jake places pigeons into the air vent to lure Holt into the copy room, allowing Amy and Terry to break into Holt's locked office without being seen. Amy unlocks a window and sneaks out again.
  • Jake hires royal babies to swarm the bullpen. One of the babies swipes Holt's key and he is so concerned about getting it back that he doesn't notice Terry stealing his phone.
  • Charles dusts the phone for fingerprints, the greasiest smudges revealing the 4 numbers he uses the most, thus his passcode. Jake suspects, given Holt's age, his password is the same for everything.
  • Jake gets him arrested on purpose, drawing Holt into the interrogation room. Charles stuffs himself through Holt's window and opens the safe.
  • Jake reveals that he got the squad's help by telling them he would do all their paperwork for the night. Since Holt is doing Jake's paperwork, he also has to do all of the squad's paperwork as well.
  • At Shaw's Bar, Holt declares Jake the " Ultimate Detective/Genius."

Season Two[]

Halloween II[]

Jake attempts to steal Holt's watch from off his wrist.

  • Jake hires a criminal known as "Fingers" to pickpocket Holt's watch
  • Fingers takes Holt's watch and then secretly puts it back in Holt's pocket. Afterwards, Jake meets with Fingers.
  • While Jake is talking with Fingers, Amy places a fake fire hydrant in front of his car and tows it away.
  • Jake and Boyle attempt to chase down the tow truck that took Jake's car, but are stalled by a group of party-goers, two of whom (Hitchcock and Scully in bear outfits) take Jake's jacket and wallet while Terry kidnaps Boyle. A recording of Boyle's voice lures Jake onto a nearby party bus.
  • Rosa and Holt, in disguise on the bus, take Jake's ID and gun, leaving Jake unable to prove he is a cop at the impound lot, thus leading him to try and jump over the fence to retrieve his car, getting himself arrested. Holt then reveals his successful plan to Jake, and with the squad watching (and recording), Jake declares Holt to be the "Best Police Captain/Genius."

Season Three[]

Halloween, Part III[]

In a tie-breaker heist, Jake and Holt both attempt to steal a crown.

  • Jake and Holt hold a draft and select their teams. Team Jake consists of Jake, Charles and Rosa, while Team Holt consists of Holt, Terry and Gina. Both teams exclude Amy, with Jake citing Amy's willingness to do anything to please Holt as his reason and Holt referring to Amy as 'Peralta's paramour' and declines to have her on his team. The crown is locked in a briefcase and placed in the interrogation room.
  • Both teams send a lookout into the observation room (separated from the interrogation room by mirrored glass so as to provide a view into the interrogation room from the observation room) to guard the crown. Charles represents Team Jake, and Gina represents Team Holt.
  • Amy talks to Jake about how much he hurt her feelings by leaving her off his team. During this conversation, Jake accuses Amy of being in cahoots with Holt, declining her offer once again. When Jake leaves, he jumps at a cackling witch dummy. Holt jumps at the same time (inside his locked office) which tips Amy off to the presence of a bug on Jake's desk. She subsequently taps into its frequency.
  • Amy then has a similar conversation with Holt, during which Hitchcock interrupts (an interruption planned by Amy) and creates a gap in the blinds on the premise of watching Scully during their 'Foot Fungus Heist'. After Amy gets Hitchcock to leave, she exits the office soon after and can read Holt's lips through the blinds.
  • In the interrogation room, Team Jake initiate operation 'Oh crap, wrong vent!' in a play for the crown. Charles releases cockroaches from his trousers (a ruse which was supposedly meant to distract Gina) and Jake enters the observation room through a vent and starts arguing with Charles 'accusing' him of marking the wrong vent. During this, Rosa breaks into the interrogation room and steals the crown, replacing it with a fake.
  • Rosa and Jake discuss the success of the plan, and Jake locks the crown in his top desk drawer.
  • Holt, overhearing the conversation on the bug frequency, activates his plan to steal it back. He employs a Dutch fencing tactic - one which lets your opponent gain points early to instill a false sense of confidence. In order to prove his point, he turns the bug on and Terry and Holt hear Jake boasting about how he is 'the smartest man alive! I am never gonna die!'.
  • Terry gets Rosa out of the building by showing her some motorcycle handlebars and implying that they came from her motorcycle.
  • At this point, Terry's wife Sharon enters the building with Cagney and Lacey, and they go to take a photo with Jake. She attempts to get Jake into the briefing room to pose for the photo, but Jake rebuffs her attempts because he is worried Holt will make a play for the crown.
  • Sharon agrees to take the photo at Jake's desk, and as she distracts him, Holt crosses the roof outside and enters through the window to get behind the drawers, unscrewing the back and stealing the crown. He stands up and showcases the crown just as Sharon takes the photo.
  • Holt moves into the break room to stash the crown, but the cackling witch (moved by Scully) activates and Jake goes to investigate. Under pressure, Holt stashes the crown in a nearby rubbish bin.
  • After Jake pats Holt down, he is satisfied that he doesn't have the crown and leaves.
  • Rosa tells Jake that the "handlebar thing was fake" and that they must have been making a play for the crown. Jake tells Rosa he had his hand on it the whole time and says they couldn't possibly have gotten it - before realizing they did, in fact, get it when Rosa discovers the loose screws.
  • Both Jake and Holt make independent attempts to get the crown back, and after these fail, they assume the other must have it.
  • The two confront each other, and eventually realize neither of them have it. Rosa goes to pull the security tapes while Jake attempts to distract Holt and Terry.
  • From the security tapes, both teams realize that a janitor called Al is the person who took the crown from the rubbish bin.
  • Both Holt and Jake realize the only person who knows his address is Amy, and so they attempt to make it up to her in various ways. Ultimately, Amy gives them both the address and calls them selfish.
  • Jake, over his two-way radio, says "Charles, I need your butt. Meet me in the parking garage' and Holt calls his team, saying "Alpha Team, this is the Golden Sparrow, meet me at Drop Zone Yankee.' Jake asks Holt how he possibly came up with all those code names.
  • Both teams arrive very close to each other, but due to the out of order elevator they are forced to take the stairs. All 31 floors later, they arrive on the roof and see a silhouette, whom they assume is Al. (The elevator was not actually out of order, it was just a sign placed there by Amy.)
  • As it turns out, the silhouette is actually Amy in disguise, who is revealed as the mastermind behind the entire heist.
  • Amy details how she defeated the other teams using various methods, and claims the title of "Ultimate Detective/Genius" in the heist's third edition.
  • Her official coronation as the 'Queen of the 99' takes place in Shaw's Bar.

Season Four[]

Halloween IV[]

Amy, Jake and Holt try to steal a plaque by midnight.

  • Amy, Jake and Holt announce the heist and choose teams. Amy goes first, choosing Rosa. Holt chooses Boyle, derailing Jake's plan. Jake then takes Gina after Terry says he doesn't want to participate.
  • Jake tells Gina that he got a body double for Boyle, and his plan has been totally derailed by it.
  • Jake improvises by getting Bill (the body double) to dress as Gina.
  • Gina then roller skates behind a mail cart to lock the door to Holt's office (Team Holt) and the break room (Team Amy). Jake then exits the briefing room and breaks the lock off of the caboodle, stealing the plaque, throwing it to Gina, and allowing her to exit.
  • To try and catch Gina, Holt breaks the window of his office.
  • Gina instead fakes a skating accident and pretends to lose her two front teeth, allowing her to leave and resume her own heist without the others knowing.
  • After a reset, during which Charles partially collapses at the pressure of standing up to Jake, Team Amy then steal the plaque by bringing dozens of pizza delivery guys into the precinct, with Rosa hidden among them to steal it.
  • Holt then discovers where the plaque is hidden by stressing Amy out (asking her to do something and then cancelling it) and following her to her cigarette stash. He then tasks Cheddar with the quest to retrieve it.
  • Jake threatens Charles with replacing him as his best friend. Charles reveals that Holt stashed the plaque in a box marked 'Cold Cases 1972'. Jake finds it and puts it in his desk.
  • It is at this point where Holt exits his office, taunting Jake. Charles stops him by saying he told Jake where the plaque was, and Holt denies he would leave it in a box unattended. Jake then says that he did, and pulls the plaque out of his desk, and in reply, Holt calls Cheddar and shows Jake his plaque. Team Amy then arrives and Amy exclaims "What?! We just got it out of the vent to rub in your faces!', which leads to a classic 'Title of your sex tape.'
  • Suddenly, the lights turn off, revealing ultraviolet black lights that turn on. After showing their disgust at the precinct, especially the desks of Hitchcock and Scully, the detectives discover the plaques all have a word on them that is fluorescing.
  • The words are initially arranged as 'Are heists dumb' but Holt and Amy swap to reveal the message 'Heists are dumb.' This leads the three teams to rush to the interrogation room to confront Terry, as this is a variation of one of his catchphrases: ________ is/are dumb.
  • They interrogate and insult Terry, even going to the heights of saying that his daughters would grow up to be failures.
  • The suspicion towards Terry is further elevated by the fact that Hitchcock and Scully fell asleep, and Terry did not wake them up.
  • After they rush in, the door is locked from the outside, and Gina shows herself from through the one way mirror.
  • Gina reveals that after the accident, she replaced the plaque in her possession with a fake and later disguised herself in a suit (taking a stab at Amy in the process) to blend in with the rest of the precinct, replacing the plaque with one of her false ones each time it was taken.
  • She explains that she stole the plaque to teach them a lesson, and forces them to change the name of the plaque (forever) to the 'Ultimate Human/Genius'.
  • The episode ends with Gina being proclaimed the Queen of the Nine-Nine.

Season Five[]


  • Holt, Jake and Amy explain that the heist is open to everyone in this edition, and the aim was to steal a cummerbund.
  • Holt and Jake hang the cummerbund on the ceiling, but the lights go out and, as they turn back on, it is revealed that the cummerbund is gone.
  • 'Wolf Gina' then appears on all the computers in the precinct and explains that she stole the cummerbund. She explains that for every piece of baby equipment put together by the detectives, a clue will be revealed to them.
  • It is then revealed that Jake, Charles and Bill were conspiring together to steal it. Charles turned off the lights while Bill stole the cummerbund and portrayed Wolf Gina.
  • Charles then betrays Jake and handcuffs him to a file cabinet. He reveals that he was in cahoots with Rosa and Terry, forming the alliance 'The Tramps'. Charles leaves Bill to watch Jake.
  • The Tramps hide the cummerbund underneath a server courtesy of Terry, as it is something nobody else can lift.
  • Holt then lifts the server using a stationary bicycle and pulley set up, and sends Cheddar to retrieve it.
  • Outside, Holt waits for Cheddar to appear, but immediately discovers that Cheddar has been replaced by a fake.
    • "You're not Cheddar. You're just some common bitch." - Raymond Holt
  • After breaking free, Jake discovers in the security room that Amy stole Cheddar, as she sneezes due to her dog allergies.
  • Amy returns Cheddar to Holt by releasing him into the bullpen, after securing the cummerbund in her safe.
  • Jake's next plan is to fill the bullpen with characters from the Handmaid's Tale. Bill steals Amy's safe and replaces it with an identical replica.
  • Amy then discovers Jake, and after some conversing, Amy discovers her key no longer fits her safe. Jake then opens it and acts surprised at it being empty.
  • Terry explains that he put a transmitter in the cummerbund, and he and Rosa both run to chase after it.
  • Amy, Holt and Jake all explain that they fed Terry GPS transmitters via gifts of yogurt.
  • After the rest of the detectives all chase after the cummerbund in their own directions, Amy and Jake both head separately to the evidence room, where Amy discovers the cummerbund.
  • Jake then encourages Amy to read the inscription on the cummerbund, and discovers that it says 'Amy Santiago will you marry me? Jake and Amy then become engaged, causing Charles to faint in delight.
  • Jake's plan to use the heist as a proposal is a success, while he also retains the original cummerbund (Not shown during the episode). Holt, while congratulating Jake and Amy, ensures that everyone knows that since the inscription was changed, there was no 'technical' winner this year (Until Cinco de Mayo, where Holt reveals that he found and stole the original cummerbund during the engagement celebration). However, since he stole it after midnight, there's no champion in this Halloween Heist

Jake, Amy and Ray claim victory of Heist V. Jake insists that he was in possession of the altered cummerbund at midnight which was enough. Amy's claim is based on the fact that she was holding the altered cummerbund at midnight. Raymond claims that as he became in possession of the real cummerbund he was the winner, however he did not have the belt until after midnight. As not any contestant was in possession of the real original cummerbund at midnight, no victor is given.

Season Six[]

Cinco de Mayo[]

The squad attempt to steal Scully's medical bracelet.

  • Jake, Amy and Holt all claim to have won the 5th Halloween heist. Jake by proposing to Amy, Amy by finding the altered cummerbund at midnight, and Holt by recovering the real cummerbund after the midnight deadline.
  • The heist was originally meant to take place during Halloween, but doesn't due to Terry realizing that to stand a chance of winning the heist, he couldn't let it be on Halloween, as he would have no control over the events. Thus he fakes a gas explosion on Halloween for the heist to take place at a later date.
  • Over the next six months, Terry sows seeds of conflict among the other detectives, riling them into taking their respective heist plans "too far":
    • While Amy and Holt are within earshot, Terry that he is sick of Jake calling himself the only two-time heist winner. Amy and Holt both claim that they are the only two-time winners of the heist.
    • Terry tells Charles that everyone thinks he is worthless in the heist, due to his fingers being too big to steal stuff.
    • Terry even gets Kevin involved. While at Holt and Kevin's home, Terry points out the prominent location of the cummerbund from the fifth heist to Kevin.
  • The heist is suggested as a way to distract and help Terry before his Lieutenant's exam. Despite this, everyone made plans anticipating the heist would take place on Cinco de Mayo, as "Terry hates tests!"
  • Due to the "suddenness" of the heist, it is decided that the target would be Scully's medical bracelet, which is initially locked (along with Hitchcock) inside a supply closet. Jake and Terry make one team, Holt and Amy make another, with Rosa opting not to take part and Charles being left out because Bill had died before the heist.
  • Jake reveals that Scully has a twin brother called Earl, and brings him in to distract the other teams while Terry gets the bracelet. Jake double-crosses Terry and locks him in the lineup room with Scully, but upon hearing Earl was at the precinct Scully breaks through the glass, resulting in Terry also getting out and chasing Jake down.
  • Scully confronts Earl (to the others confusion) and Terry reveals Jake has the bracelet, but Boyle (disguised in a suit and beard) stole the bracelet while everyone was distracted (also revealing he introduced Earl to Jake) and rendezvous with Rosa, who he was secretly working with. Rosa immediately betrayed him, having put chloroform in his beard, and when Boyle passes out she puts him in a box shipping to New Jersey, before returning to Holt, who she was actually working with.
  • Holt called in Kevin to bring in the cummerbund, along with Cheddar and a chew toy to hide the bracelet in.
  • Jake reconciles with Terry before enacting his next plan, secretly filling Cheddar's water bowl to prompt him to use the bathroom, at which point Holt lets him onto the roof to go, where Terry (disguised as the gold statue of Gina) swaps the chew toy with a fake. While here, Terry fits Cheddar's collar with a magnetic latch for his later plan.
  • On reuniting with Jake in the evidence room, Jake handcuffs Terry to the metal gate and takes the bracelet.
  • Later, Terry escapes and reveals to everyone that Jake took the bracelet, but a massive argument breaks out among the participants, including Charles who just returned as to who was working with who, who betrayed who, and who had the bracelet, also revealing Kevin's betrayal of Holt and Bill being alive, ending in Terry snapping at everyone for taking things too far and shouting "You all suck!" which is the voice command for Jake's banner, which unfurls and hits Terry on the head, concussing him.
  • The gang gets Terry to the exam room, but on walking in to an empty room Terry reveals himself to have the bracelet, his plan including the delaying of the heist, manipulation of everyone and training of Cheddar. He also reveals to the squad that he is already a Lieutenant, having passed the exam weeks ago, thus making him the sixth Heist champion. Terry also reveals his own banner, crowning him King Terry.

Season Seven[]


The squad attempts to steal three gems from Bill.

  • This is the first heist to occur on three different holidays. The heist was originally planned on Halloween, but subsequent incidents result in the heist being postponed mid-action twice. Therefore the heist takes place on Halloween, Valentine’s Day, and Easter: ergo the title is a portmanteau. Val-Low-Easter.
  • Jake makes a rule that each player must play as a pair and be handcuffed to their selected partner, or is otherwise disqualified from competing (Jake is paired with Holt, Amy with Charles, and Rosa with Scully). Terry voluntarily retires, and Hitchcock is nonchalantly snubbed. The rule is suggested as a way to prevent betrayal of any kind as has happened in the past, particularly the last heist. (It is later revealed that Jake rigged the envelopes to team up with Holt, and manipulated Rosa into picking Scully. It is also revealed that Amy wanted Jake to do this, as Jake and Holt would not be able to work together.)
  • In the first attempt on Halloween, Jake fills the bullpen with smoke, and he and Holt retrieve the gems from Bill in an orderly sequence before knocking over a moved chair and dropping the gems on the floor.
  • Holt uses Cheddar to search for the lost gems. He and Jake were to be initial champions until Cheddar swallowed the gems, forcing the first postponement of the Heist.
  • In the Valentine edition of the heist, Rosa fills the bullpen with people delivering flower bouquets for Bill. She and Scully retrieve the gems with Scully holding them in his mouth. Scully then accidentally swallows the gems, forcing yet another postponement.
  • In the Easter edition of the Heist, Rosa replaces Scully with a filing cabinet as her partner and Jake fills the bullpen with people in bunny costumes, which he and Holt use to blend in. Amy, having learned of Jake's plan, also has herself and Charles dress up as bunnies, causing confusion.
  • Rosa wins the heist by having Terry take her place with the filing cabinet, and wearing the same bunny costume, steals the gems in the chaos before jumping off the roof, falling on a crash mat and igniting a fire that spells her name on the ground while everyone deduces the winner. She still has part of the cabinet chained to her to exploit a loophole in the heist ruling.
  • Rosa purposefully postponed the heist each time to claim victory for winning the most heists, as it is revealed that Rosa has claimed all three versions of the gems from each heist. During the first attempt, she swapped the gems with fake ones before Cheddar could spot them; in the second attempt, she exchanged the new gems during the bouquet debacle before putting the old ones in Scully’s mouth; the third was with the fake ones that discolored after Scully ate them.
  • While celebrating at Shaw's, Rosa escalates the heist-related arguments between the detectives.

Season Eight[]

The Last Day Part I and The Last Day Part II[]

The squad attempt to be in possession of a replica of Holt's Medal of Valor, which will be stored in a pneumatic tube, by midnight. The Squad decides to forget all previous heist winners and only the new winner will count and be crowned as "The Grand Champion of the Nine-Nine", however this sentiment is later revoked by all. Jake and Amy ploy the heist as a perfect goodbye for Jake from the NYPD. The winner was Hitchcock.

Official Heist Leaderboard[]

Champion Count Champions Notes
Jacob Peralta 1 Heist I (2013) Jacob claims to be a two time winner, winning Heist I and V
Deputy Commissioner Raymond Holt 1 Heist II (2014) Raymond claims to be a two time winner, winning Heist II and V
Chief Amy Santiago 1 Heist III (2015) Amy claims to be a two time winner, winning Heist III and V
Gina Linetti 1 Heist IV (2016)
Captain Terry Jeffords 1 Heist VI (2018/19)
Rosa Diaz 1 Heist VII (2019-20) Rosa claims to be a three time winner, winning on Halloween 2019, Valentines Day 2020 and Easter 2020, by manipulating the heist.
Detective Michael Hitchcock 1 Heist VIII (2021)

Heist Champions[]

Heist Champion
Heist I (Halloween 2013) Jacob Peralta
Heist II (Halloween 2014) Raymond Holt
Heist III (Halloween 2015) Amy Santiago
Heist IV (Halloween 2016) Gina Linetti
Heist V (Halloween 2017) No Winner / Disputed
Heist VI (Halloween 2018, Cinco De Mayo 2019) Terry Jeffords
Heist VII (Halloween 2019 - Valentines Day 2020 - Easter 2020) Rosa Diaz
Heist VIII (Halloween 2021) Michael Hitchcock

  • A winner of Heist V is given as no contestant was in possession of the real cummerbund at midnight
  • It is unknown what occurred on the Halloween of 2020, however, given the Covid-19 pandemic and that Heist VII concluded on East of the same year, the halloween heist was cancelled for the year, postponing Heist VIII to Halloween of 2021