Here's how every Halloween Heist on Brooklyn Nine-Nine was won. Halloween may be a time to embrace candy and costumes for some, but for the detectives on the show, the holiday is all about who will be the next winner of the Halloween heist. Since Jake Peralta (Andy Samberg) first challenged Captain Holt (Andre Braugher) to a contest of wits in season 1, episode 6, "Halloween," members of the 99th precinct have ruthlessly competed to win the title of "Ultimate Detective/Genius" — or, after season 4, "Ultimate Human/Genius." The prize may vary, but victory always includes bragging rights.
Like many holiday traditions, the heist started as a whim and grew into a must-have event. The heist begins when, after Jake comments that he would be a better criminal than any of the perps he arrests, Holt questions his ability to outsmart the police. Jake quickly turns the unspoken challenge into a real contest, betting Holt that he can steal the Medal of Valor from his office before midnight. As an incentive, Jake promises to work the next five weekends without overtime if he loses.
Holt's acceptance marks the start of an annual heist that spans seven seasons, evolving each year as the characters grow and change. Members of the Brooklyn Nine-Nine squad often form teams, shift alliances and lie to one another in an effort to win. But the one thing all the victors have in common is that they are one step ahead of everyone from the jump. Winners of the heist always claim the crown by doing the unexpected, taking advantage of everyone's preconceived notions about what the heist is and what the rules are. The truth is there are no rules. So who won each heist and exactly how did they do it?
Halloween: Jake
The first Halloween heist in Brooklyn Nine-Nine is the least complicated, with Jake teaming up with Rosa Diaz (Stephanie Beatriz), Terry Jeffords (Terry Crews), Amy Santiago (Melissa Fumero) and Charles Boyle (Joe Lo Truglio) to steal Holt's Medal of Valor. Each person takes a different step toward stealing the medal, with Rosa picking the lock to Holt's safe, Terry and Amy unlocking his window, and Boyle finding his safe combination and stealing the medal. Throughout the heist, Jake acts as a distraction, using different ploys to draw Holt out of his office.
The first heist is the only one that truly embodies the spirit of teamwork, as Jake subverts Holt's expectations by getting the help of other members of the 99th Precinct. One of the major themes in the first season is Jake's struggle to ask for help — in this heist, he proves to Holt and himself that he can step out of the spotlight and work as part of a team to get the job done.
Halloween II: Holt
In Brooklyn Nine-Nine's second Halloween heist, Holt succeeds in avenging his previous loss by using Jake's confidence against him. After Jake's win last year, he believes his plan to use a pickpocket to steal Holt's watch will be easy to pull off. Holt, however, is more invested than Jake suspects. After learning Jake's plan, Holt turns the pickpocket Fingers (Appolo Robbins) into a double agent, having him steal the watch and then return it in one smooth move. Fingers gives a replica watch to Jake, and Holt then pulls a series of pranks on Jake to keep him from realizing the truth and to have a little fun. By the end of the night, Jake has been thoroughly beaten and Holt's honor has been restored.
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Halloween, Part III: Amy
In the third year of Brooklyn Nine-Nine's Halloween heist, Amy crashes the Jake-Holt party by turning the two against each other. After Jake and Holt both refuse to pick Amy for their teams out of fear she'll betray them, she decides to teach them both a lesson. While Jake and Holt are watching each other with laser-like focus, Amy sneaks under the radar, tapping into Holt's bug to learn his plan and keeping an eye on Jake.
The item in play is a plastic crown, which Jack steals first, as per Holt's plan to let him gain confidence. Holt later makes a play to steal the crown using Terry's wife and two children as a distraction, but his exit is compromised by a motion-triggered Halloween prop that cackles when he walks by. When Holt is forced to deviate from his plan and hide the crown in a trash can, Amy makes her move. Disguised as a janitor, she steals the crown from the trash can and leads Holt and Jake on a wild goose chase up 31 flights of stairs, only to reveal that she was playing them all along. For the first time, a woman is crowned Queen of the 99.
Halloween IV: Gina
Until season 4 of Brooklyn Nine-Nine, the Halloween heist was always a contest between detectives in the precinct. But after three years of being left out of the spotlight, civilian administrator Gina Linetti (Chelsea Peretti) walked onto center stage. Despite her forceful and sparkling personality, Gina is often overlooked by members of the 99th precinct, including during previous heists. Gina takes advantage of this to remind everyone on the squad that she is not someone to be ignored.
The prize in the fourth heist is a plaque reading "The Ultimate Detective/Genius." After becoming a member of Jake's team, Gina steals the plaque by swapping it out with a fake. She distracts the squad by faking a skating accident in which she seemingly knocks out her two front teeth, also allowing her to leave the precinct and proceed with the rest of her plan. She then returns in Amy's clothing which "makes her invisible," and replaces the real plaque with a fake every time someone new steals it.
By the end of the heist, Amy, Jake and Holt all believe they have the real plaque, when in fact they have replicas. Gina uses the replicas to lure everyone into the interrogation room, where she locks them in. As Gina claims victory, she demands the plaque's inscription be changed to read "The Amazing Human/Genius," making the heist open to anyone who wants to participate.
HalloVeen: Jake
The winner of Brooklyn Nine-Nine's fifth Halloween heist is debated to this day, with Jake, Amy and Holt all claiming victory. The prize in question is a championship belt, or as Holt would say, a "championship cummerbund," inscribed with the words "Amazing Human/Genius." The heist is derailed however when Jake uses it to propose to Amy.
The belt is first stolen by Jake and changes hands twice before Amy steals it herself. Amy uses her knowledge of Charles' and Holt's plans to steal the belt and also seems to be one step ahead of Jake for most of the episode, having been dating him since season 3. After stealing the original belt from Amy, however, Jake uses her familiarity with him to lure her into the evidence locker, where she finds a replica belt inscribed with the question, "Will you marry me?" Amy, of course, says yes, in a tearful engagement that has Charles fainting.
It's later revealed in season 6, episode 16, "Cinco de Mayo," that Holt found and stole the original belt while Jake and Amy were celebrating their engagement at the bar, although he stole it after the midnight deadline. Holt argues he won because he found the original belt and Amy argues she won because she found the replica belt. The real winner, however, is Jake, who not only has possession of the original belt at midnight but also pulls off a second scheme to pop the question to Amy. His layered plan, which only he knows all the details of, bests Amy and Holt and embodies the spirit of the Halloween heist.
Cinco de Mayo: Terry
The most notable feature of the Brooklyn Nine-Nine's sixth Halloween heist — that it doesn't take place on Halloween — is the result of a months-long master plan orchestrated by Terry. In a brilliant and slightly insane move, Terry fakes an emergency gas line explosion on All Hallow's Eve to postpone the heist and gain the upper hand. As Terry later explains, he had to find a way to postpone the heist so he could upend the plans of Jake, Amy and Holt and stand some chance of winning. Terry uses nerves about his upcoming lieutenant's exam, which he's already passed, as an excuse to kick off the heist on Cinco de Mayo.
As the members of the squad attempt to steal Scully's medical alert bracelet, they use their personal relationships as leverage, lying to each other and stabbing each other in the back. Many of the flare-ups and arguments between members of the squad are Terry's doing, as he has been "sowing discord" for months. The bracelet changes hands a few times before reaching Holt, who hides it in a dog toy belonging to his adorable Corgi, Cheddar. That's when Terry makes his move, swapping out the dog toys and using a magnetic collar to have Cheddar deliver the real medical bracelet to him at One Police Plaza, where he reveals his successful plan and celebrates his promotion.
Valloweaster: Rosa
In season 7 of Brooklyn Nine-Nine, the Halloween heist takes on an epic scale as members of the team try to steal three infinity gems from Charles' body double, Bill (Winston Story), and claim ownership of the Infinity Gauntlet. Rosa, a skilled and dangerous detective, has been a valuable addition to different teams in past years with her ability to perform physical stunts and her criminal know-how. So by season 7, it's past time for her to be crowned the winner.
In true Rosa fashion, she implements her plans alone despite being forced to partner with Scully and later, a cabinet. Rosa takes a page out of Terry's book by postponing the heist multiple times, using the interruptions as a way to steal all three gems on Halloween, Valentine's Day, and Easter, making her win a triple victory. On Halloween, Rosa swaps out the real gems with fakes before Cheddar the dog swallows them. On Valentine's Day, she pulls a similar switch before Scully swallows the gems. And on Easter, she uses Terry as a distraction while she steals the gems.
The Easter heist is the biggest and most confusing yet, with members of the squad taking over the entire precinct at multiple times throughout the year with their shenanigans. It's hard to imagine how Brooklyn Nine-Nine could outdo themselves in season 8, but whoever the winner of the heist is, they're sure to be the last person anyone suspects.