Brooklyn Nine-Nine: Every Halloween Heist Winner, Ranked Least Surprising To Most Surprising

As long as Brooklyn Nine-Nine stays on the air, there’s one thing that audiences can be 100% certain that they’ll see during the season – the Halloween Heist episode. It’s a staple unlike any other on the show that fans look forward to every year (Doug Judy installments are a close second) and it always leaves audiences guessing who is going to take home the title of “Amazing Human/Genius.”

The tradition began in the very first season and has carried on throughout the entirety of the series (quite impressive considering the last two seasons haven’t aired during October) and the writers do a great job of keeping the annual ideas fresh while still surprising the fans with whoever is going to walk away with the title each year, with some winners being much more surprising than others.

7 Captain Holt

Be honest, nobody expected Jake to win the heist two years in a row. At this point in the series, fans didn’t know that the Halloween Heist was going to become a tradition, so the return of it was a joyous occasion. However, when Jake recruited the entire precinct to help him take down Captain Holt for a second consecutive year everybody agreed just a little too easily.

Not only that, but Jake ran into so many problems throughout the night that it mirrored what happened to him the first season and the writers weren’t going to repeat the exact same twist. Holt may have slightly underestimated Jake in the first season, but Jake severely underestimated Holt for this win.

6 Amy

The outcome was definitely satisfying, but don’t make the mistake of thinking that “satisfying” is synonymous with “surprising.” In its third year, Brooklyn Nine-Nine decided to switch the heist up a bit by having Holt and Jake try to steal the same item (a crown) instead of the usual situation of Jake stealing something of Holt’s.

Unfortunately, both men have the option of drafting the other precinct members to help them in their task and both exclude Amy due to her divided loyalties. In response, Amy plays both of them for fools, wins the crown for herself, and takes the title of “Amazing Detective/Genius” as well as being dubbed Queen of the Nine-Nine.

5 Rosa

The most recent Halloween Heist winner (despite taking place over Halloween, Valentine’s Day, and Easter) was Rosa, whose win falls into the same category as Amy’s – it was impressive, but not that surprising. The whole point of the heist (and why it stays a fan-favorite every year) is because the writers change things up with who the winner is/how they do it.

For the seventh season, instead of individuals or two separate teams, the precinct split up into pairs to see who could steal the Infinity Gauntlet – every pair contained a previous winner except for Rosa’s team. After seven seasons, this one wasn’t too difficult to figure out. Making her a three-time winner was nice twist, though.

4 Jake

The episode that started it all. Only six episodes into the first season, Brooklyn Nine-Nine managed to create a staple so prominent, creative, and clever that it has continued throughout the entire series and fans look forward to it every year. By this point in the series, audiences (and the writers) were still figuring out the logistics of the relationship between Jake and Holt and how the two would ultimately affect one another in their work.

So, when Jake made a bet with the Captain on their first Halloween together that he could steal the Holt’s medal of valor, fans weren’t sure what the outcome to be. Include that with the fact that Holt seemed to stymie Jake at every turn and it surely seemed as though the Captain would take home the prize. But in true heist fashion, Jake assembled a crew and won the bet at the last minute. Jake truly earned the title “Amazing Detective/Genius.”

3 Terry

The series deserves a standing ovation for how they’ve managed to not only keep the Halloween Heist around (again, the seasons haven’t aired in October so that’s quite impressive) but also keep the winners/twists fresh. Fans were heartbroken for Terry in season 4 when he revealed that he took the Lieutenant’s exam and failed, and it also meant he had to wait another two years to retake the test.

The writer’s stuck to continuity and gave Terry his second chance in season 6 to take the exam and he was understandably nervous beforehand, prompting the precinct to suggest a “Cinco De Mayo” heist to help take his mind off it. The Nine-Nine goes through their typical Halloween hijinks (which includes a twin Scully) and end up accidentally knocking Terry out right before his test, only to get bamboozled by Terry himself who wins the heist and reveals that he had already passed the Lieutenant’s exam.

2 Gina

Be honest, the writer’s fooled everybody with this one. While Terry’s win in season six might have been a surprise twist, there was no twist more surprising than when Gina Linetti took home the title of “Amazing Detective/Genius.” After all, she’s not a detective and the rest of the precinct often underestimates her for it – just like the audience did.

In season 4, the writers kept things going how they had from the previous year with all former heist-winners drafting other precinct members for teams as they tried to steal an item (a plaque). Things take a turn when Gina knocks her two front teeth out and has to leave in the middle of the event. Pair that with the fact that the writers cleverly hinted that Terry would be the winner this year and Gina’s victory results in a complete blindside. Major props to Gina – beating several seasoned detectives, a sergeant, and her captain all out of spite. Respect.

1 Jake, Amy, Holt

What a twist. Jake had barely gotten out of prison, everyone at the Nine-Nine was still settling into the new season, and the writers decided to hit audiences with an absolute curve-ball. The fifth season heist itself wasn’t exactly the best out of all the episodes, especially considering that the premise was virtually exactly the same as the previous year (teams try to steal an item, a championship cummerbund) and it had the typical pranks and double-crosses that the heists usually have.

But a heist is only as good as its twist and because of the repeated antics, audiences couldn’t quite pin who was going to walk away with the title since the previous year’s winner, Gina, was out on maternity leave. Lo and behold, Jake surprised Amy (and everybody watching) by swapping out the championship cummerbund with a marriage proposal cummerbund and the two got engaged. However, this is easily the most surprising winner since it’s still not clear who actually won this season.

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