Once every year, the 99th precinct breaks into a factions for the annual Halloween Heist competition on Brooklyn Nine-Nine. Beginning with a simple bet between Jake (Andy Samberg) and Holt (Andre Braugher), the event has become some sort of a tradition over the years - and it's one of the most anticipated episodes every season for fans of the popular sitcom.
The Halloween Heist has a simple premise: participants will agree on an object to steal. Depending on how many participants there are, the main cast of Brooklyn Nine-Nine forms their own teams. Whoever possesses the chosen object after a set period will be declared the winner. From seasons 1-3, the winner is dubbed "The Ultimate Detective/Genius," but as the competition expanded, the official title now is "The Ultimate Human/Genius." From Jake emerging triumphant in the first heist to Holt technically becoming a two-time winner, here's everyone who has won the annual Halloween Heist.
Starting with "Halloween," episode six of season 1, Jake goads Holt to agree on a bet that he can steal his Medal of Valor before midnight. Holt eventually says yes, feeling extremely confident that he can keep his accolade by putting it inside a locked safe in his office. With time running out, Holt - still sure that he's winning the wager - conceitedly started questioning Jake's intellect after a series of supposed failed attempts to nab the medal. Little did he know that Jake, with the help of the rest of the precinct, was able to accomplish his mission.
The next year, in the episode titled "Halloween II," Jake and Holt go at it for another round. This time, they decide that Jake has to try and steal the Holt's watch from his wrist. Turning the table on his adversary, Holt taps the help of the rest of the Nine-Nine (and a skilled pickpocket), brilliantly outsmarting his subordinate and revealing that he had planning the scheme since the first Halloween Heist.
With a tied record, Jake and Holt go for round three in the episode "Halloween, Part III." This time, however, they're tasked to steal the same object, making it a fair game. Caught up in their desires to win, they leave out Amy (Melissa Fumero) for fear that she might betray them due to her relationship with them (she's dating Jake and a suck-up to Holt). Insulted, Amy undermines the whole competition and decides to play the game herself, emerging as the winner of the third Halloween Heist.
Motivated by her interest in winning the Halloween Heist herself, Gina (Chelsea Peretti) executes an elaborate plan for "Halloween IV" to steal "The Ultimate Detective/Genius" plaque. Initially teaming up with Jake, she deviates from their plan and sets up everyone to believe that they have the object of interest. After supposedly suffering an injury during the game, she gets sidelined - only to reveal in the end that she has the real plaque. Gina's success leads to the winner's new title: "The Ultimate Human/Genius."
On its fifth year, the Halloween Heist takes a different turn. Starting as an open for everyone competition, the episode "HalloVeen" makes a cumberband the focal object. As every year, the event was marred with various twists and turns, but the biggest shocker came toward the end, when it was revealed that instead of working to win this year, Jake was setting up everything to propose to Amy. Due to how things panned out, there wasn't a winner for this year. That is, until it was revealed during the rescheduled event now taking place during Cinco de Mayo that Holt stole and had the original cumberband while everyone was celebrating Jake and Amy's engagement.
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The first Cinco de Mayo event saw Terry (Terry Crews) outsmart everyone and win the competition. But despite a new date for the Halloween Heist, fans can expect nothing but more shenanigans from Brooklyn Nine Nine's 99th Precinct crew just to become "The Ultimate Human/Genius."