Brooklyn Nine-Nine has had a number of recurring themes over the years, but two that have stuck to a one-appearance-per-season schedule are Doug Judy and the Halloween Heist. The Halloween Heist is a fun bet turned competitive show of detective skills and prowess, in which the members of the Nine-Nine compete against one another to retrieve a certain item of value within an allotted time limit.
The eighth and final season of Brooklyn Nine-Nine also featured a heist, but nothing about it was Halloween related. Rather it was focused on giving multiple characters a meaningful goodbye at the end of the show. This heist-of-sorts cannot truly be compared to the other heists for a number of reasons, but it brings the annual tradition and the show as a whole to a satisfying close. Every edition of the Halloween Heist introduced new fun ideas and thematic differences, ultimately resulting in different winners every year.
7 Season 7, Episode 11 – “Valloweaster” (8.3)
Following on from the premise of the previous year’s heist, the heist in “Valloweaster” is also not limited specifically to Halloween. When Cheddar eats the target-valuables, the gems, the heist is forcibly delayed and rescheduled for four months down the line. Scully then also swallows the gems, with the heist once again being postponed until Easter.
Rosa eventually wins, and the reasoning and explanation gets evening more outlandish and over the top, with it even emerging that Rosa technically wins all three heists, despite the postponements.
6 Season 1, Episode 6 – “Halloween” (8.5)
The original Halloween Heist episode was in the season one episode aptly named “Halloween.” It originated when Jake wanted to prove that he could commit a crime without being caught, and subsequently made a bet with Captain Holt, instigating the first ever heist of the Nine-Nine.
Although later editions of the heist completely dominate the episode and require everyone’s attention, the initial episode still features side-stories with the detectives doing their jobs. The heist is full of failed attempts from Jake until his final reveal at the end of the episode, detailing how he managed to win. It is a fun first edition and the start of a hilarious tradition for the show.
5 Season 2, Episode 4 – “Halloween II” (8.8)
“Halloween II” is the second edition of the Halloween Heist, taking place in the second season of Brooklyn Nine-Nine. While there once again is another side-story involving Terry and Gina, the heist takes more of a center stage, focusing on Jake’s side of things every step of the way.
The heist appears to be going well for Jake, but the step-by-step walkthrough of his plan foreshadows that ultimately he isn’t going to win. Jake’s various misfortunes are hilarious, and the inevitable reveal that Captain Holt was behind everything is entertaining, albeit rather predictable. Captain Holt conned Jake into raising the stakes, while he had everything meticulously planned out and prepared.
4 Season 4, Episode 5 – “Halloween IV” (8.8)
By the time that the fourth season’s Halloween episode comes around, the entire squad is involved in the competition, adding an air of uncertainty and unpredictability regarding who is likely to emerge victorious. Holt, Amy and Jake pick a partner each, with Hitchcock and Scully keeping an eye on Terry who claims to not be playing.
The heist is the sole focus of the episode, with each team’s strategies being shown. The eventual winner is Gina, who fakes an injury and heist mishap in order to remain undetected and eventually emerge victorious, changing the victor’s title to “Amazing Human/Genius”.
3 Season 3, Episode 5 – “Halloween III” (9.0)
“Halloween III” is the third edition of the 99th Precinct’s annual Halloween Heist, and is seen as the deciding contest, with Captain Holt and Jake each having one win apiece. The rules are different to previous editions with both of them attempting to steal the same item on this occasion: a crown locked inside a briefcase.
Captain Holt and Jake both refuse to take Amy on their teams which ultimately hurts her feelings and motivates her to win the heist all by herself. With separate teams being allocated for the heist, the heist takes up the entire episode, eventually leading up to the reveal of Amy’s victory.
2 Season 6, Episode 16 – “Cinco De Mayo” (9.2)
Season six’s edition of the Halloween Heist is the first to have a twist in terms of the date, and not just with the unfolding events and winner. An explosion prevents the annual Halloween Heist from taking place, with the squad eventually proposing that the heist takes place on “Cinco de Mayo” instead, in a bid to distract Terry from his upcoming Lieutenant’s exam.
This version of the Halloween Heist has more twists, turns and betrayals than any other Brooklyn Nine-Nine heist and ends up with Terry winning with the most elaborate of plans, making it one of the most impressive heist victories of the entire show.
1 Season 5, Episode 4 – “HalloVeen” (9.5)
Not only is the fifth edition of the Halloween Heist, titled “HalloVeen,” the most entertaining in terms of the heist itself, its premise and the plot twists, but it also has a significant ending result that affects the show beyond the heist itself.
There is no official winner of the heist, as it turns out that Jake used this year’s heist as a cover to surprise Amy and propose to her, leading everyone away from the belt apart from Amy in order to ensure the success of his plan. Jake feels as if he won due to his plan being executed perfectly, but as Captain Holt continues to angrily mutter in disgust, there was no winner of this Halloween Heist.
About The Author
