Brooklyn Nine-Nine: Every Halloween Heist RANKED!
4. Halloween II (Season 2 Episode 4)
Having been shamefully defeated in the first heist, Captain Raymond Holt vows to take vengeance upon Detective Peralta, hatching a devilish scheme to outplay Jake at his own game and prove that he is the more deserving holder of the prestigious title of Amazing Detective/Genius. He tasks Jake with stealing his watch from right off his wrist, a tricky task which sets up a whole host of spooky shenanigans.
Jake swaggering around in his cheap magician's outfit flying a drone through the precinct as Scully sings Carmina Burana is a sight to behold, as is Boyle pushing Jake in a shopping trolley as they desperately chase a truck that's towed his car (which happens to also contain the Captain's stolen watch).
It's somewhat tragic to see Jake, brimming with overconfidence at the start of the heist, have his plans go completely sideways like this after months of planning. But it's oh-so-satisfying when it's finally revealed that Captain Holt was behind everything, keeping one step ahead of Peralta all along thanks to a full year of planning.
Turns out Holt is in possession of both the real watch and the fake one, having employed the pickpocket who we all thought was working for Jake in advance, and instructed Amy to tow away his car. Holt celebrating his victory as he explains to Jake every detail of how he manipulated him is a fantastic final scene that proves this heist is a trick and a treat all in one.