Ranking the Brooklyn Nine-Nine Halloween Heists

Brooklyn Nine-Nine has officially come to an end and finished its incredible eight-season run. For eight seasons, Andy Samberg and the rest of the crew took us through policing hijinks among the streets of Brooklyn. This show quickly became one of the most exciting and consistent comedies on television, and the Brooklyn Nine-Nine Halloween Heists were one of the reasons for that consistency.

The Halloween Heist became a staple for the show, as each year every member of the Nine-Nine attempted to one-up, double cross, and fool everyone in the precinct (literally, everyone). The Halloween Heists were the episodes where, as a fan, you assumed everything was going to go off the rails. You never knew who to trust, what to believe, and for the most part you never even knew who was going to win.

The Brooklyn Nine-Nine Halloween Heists became some of the most exciting television to watch, and actually became so ingrained in the shows lore that even the final episode of the entire series was a heist. I won’t be adding it to my rankings – or reviewing the episode here – but I will say that the using a heist to bring in characters of the past and give a definitive ending was a clever way to go about it.

Now, on to my rankings of every Halloween Heist in Brooklyn Nine-Nine.

Which Brooklyn Nine-Nine Halloween Heists is the best?

7. Halloween II (Season 2)

Winner: Captain Holt

This is the only win that was sort of pre-meditated. After being bested by Jake in Halloween I, you just sort of knew that Captain Holt was going to get his revenge on Jake in this episode. This heist is still impressive in how the entire night is plotted against Jake.

Getting the entire precinct in on the heist in favor of Holt was a good touch as well, but there just were better heists. Personally, I think it would have been funnier had Holt’s win come in a later season, but nonetheless Captain Holt managed to capitalize as the Best Detective/Genius.

6. Halloween III (Season 3)

Winner: Amy Santiago

Even if it isn’t the most exciting, I really like Santiago’s path to victory. This Heist began with a draft between both Captain Holt and Jake Peralta and after not being chosen by either Holt or Jake, Amy took matters into her own hands.

It really goes to show how smart Amy as she manages to best both teams of detectives. Her win was of course going to come, but literally by pinning all the odds against her, they managed to give her one of the best underdog stories of the show.

5. Cinco de Mayo (Season 6)

Winner: Terry Jeffords

Terry’s win was surprising, and it turned the running gag of him proclaiming to be out of the heists on its head. Terry was long overdue for a win, and he was ready to finally make his move. This episode was insane – mainly with Terry faking a gas explosion so that the heist could be moved to a later date – as chaos reigned throughout.

The only issue I have is that other than Terry picking up his first win, there weren’t many plot progressions. This heist kind of came and went and is even only considered as a half win for Terry. However, it was still nice to see Sergeant Jeffords crowned as champion, and there was enough chaos to where we could get our heist fix for the season.

4. Halloween IV (Season 4)

Winner: Gina Linetti

Gina wanted so much to prove to everyone in the Nine-Nine she was just as clever as the rest, and in Halloween IV she did just that. Halloween IV was the first of many things: Bill was introduced, “Gina Knows Best,” and this was the first time Terry mentioned he was staying out of the heist – which would become a running gag for the rest of the heists.

I like this heist because of what I mentioned earlier, Gina got her chance to prove herself as an equal in the Nine-Nine. She has always been one of the most clever and cunning members of the Nine-Nine, and she was able to utilize that for the heist. I think that Terry’s win might have been more insane, but Gina’s was more surprising in my opinion, because even I wrongly doubted her.

3. VallowEaster (Season 7)

Winner: Rosa Diaz

When it comes to pure insanity, VallowEaster has it all. This heist didn’t take place over one holiday, but 3 as the crew performed different heists on Halloween, Valentine’s Day, and finally Easter. The stakes had been building with every new heist, and after Terry’s win – where he faked a gas explosion – the only person who could seemingly one-up him might be the most unhinged of all of the Nine-Nine, Rosa Diaz.

This big reveal of this heist was that Rosa planned for each heist to be postponed as a way to give herself the chance to have the most wins out of all of the Nine-Nine. It’s not only clever, but it allowed for three separate heists, and gave Rosa a win before leaving the Nine-Nine in season 8.

Rosa always remained the most independent of the Precinct, and she showed her independence in this episode by not just outsmarting the precinct three times, but doing it while handcuffed to Scully of all people – which would have to give him a half win right? Either way, Rosa wins by jumping off the roof and lighting her name in fire on the ground below, so she definitely is awarded style points for her heist.

2. Halloween I (Season 1)

Winner: Jake Peralata

Halloween I is a classic, and it’s hard to beat the classics. Every great show has a running gag of episodes that become a staple for the series, and ones fans look forward to every year. For Brooklyn Nine-Nine these episodes were the Halloween Heists, and the original provided so much basis for not only subsequent Heists, but for the show as a whole.

Being the first of the Heists no one knew what to expect. The twists were magnificently done and the episode managed to be one of the most exciting of the first season. It was easy to assume Jake was going to win since he was the one who initiated the heist, but it was more interesting in how he was going to win. Jake was not the most conventional of detectives, and in the first Halloween Heist, he got to prove himself as a Detective, and a genius, to a still new Captain Holt.

We also didn’t know how important the heists would be to the show as a whole, and this heist set a precedent for the rest of the heist. It built a foundation for the heists to stand on, and still remains one of the very best of the entire show.

1. HalloVeen (Season 5)

Winner: No One?

All of the Halloween Heists are amazing in their own way, but HalloVeen stands above the rest for many reasons. Charles betrayed Jake, Holt gave us one of the best quotes of the entire series, and Jake used what had become an annual tradition to finally propose to Amy. Emotions were all over the place in this as it was the most surprising and exciting of all of the heists.

While there might be no real winner of this heist, I am going to award this one to Charles. I know Jake, Amy, and Captain Holt all claimed to have won this one, but I’m going to go a different direction, and hear me out. Charles never got a Halloween Heist win, but the outcome of HalloVeen is more than he could ask for.

For one of the first times in this show Charles went against Jake, which I just think is amazing for the character, but Charles also got something he wanted more than anything; to see Jake and Amy finally engaged. As someone who obsessed over the Peraltiago relationship more than even Jake an Amy, to finally see them engaged was the biggest win he could have.

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Which of the Brooklyn Nine-Nine Halloween Heists is your favorite?