Tonight is “Brooklyn Nine-Nine”‘s Halloween episode, and it focuses on the relationship between Jake and Captain Holt–this time in a match of wits. Jake’s not only eager to prove that he’s a great detective, but he also wants to prove that he’s not so predictable to the highly observant Captain Holy.
Jake’s caught a banana trying to rob a bank, and with the parade of petty costumed criminals in the station, Jake declares that he’d make a better criminal than anyone. He somehow convinces Captain Holt to accept his challenge–if Jake fails to steal the medal by midnight, he’ll work the next five weekends without overtime and still complete his regular coursework. If he succeeds, Holt will stay behind on Halloween to complete all his work, and (more importantly to Jake’s ego) announce that Jake is a brilliant detective.
Jake tries multiple absurd ways to divert the observant Captain Holt–he crashes through Captain Holt’s office ceiling while lying in wait for the Captain to head off to a meeting, and the Captain makes the task even more formidable by putting his medal in a safe in a locked cabinet, and then keeping the key on his person. After Jake bruises his ego (and his head), Sergeant Jeffords reminds him that the Captain is a genius and “has [your] number at every turn.” This inspires Jake to go for even crazier schemes: dressing as a janitor and setting off an ill-timed garbage can bomb; releasing a flock of stray pigeons into Captain Holt’s air vent; using a group of Royal Baby-costumed theft suspects to unsuccessfully steal Captain Holt’s key, and finally, scaling the side of the precinct with a blow torch and getting locked up in an interrogation rule.