"Halloween II" is the fourth episode of the second season of the American television police sitcom series Brooklyn Nine-Nine. It is the 26th overall episode of the series and is written by consulting producer Prentice Penny and directed by Eric Appel. It aired on Fox in the United States on October 19, 2014.
The show revolves around the fictitious 99th precinct of the New York Police Department in Brooklyn and the officers and detectives that work in the precinct. Jake Peralta (Andy Samberg) is an immature yet very talented detective in the precinct with an astounding record of crimes solved, putting him in a competition with fellow detective Amy Santiago (Melissa Fumero). The precinct's status changes when the Captain is retiring and a new commanding officer, Cpt. Raymond Holt (Andre Braugher) is appointed as the newest Captain. This creates a conflict between Jake and Holt over their respective methods in the field. In the episode, Jake and Holt continue with their annual Halloween contests. This time, Jake has until midnight to steal Holt's watch or he will do five weeks of overtime for free. Jake, with help from the precinct, manages to get the watch from a criminal. However, the criminal runs away with the watch and upon learning of the importance of the watch, Jake sets to find him. Meanwhile, Gina begins to skip duties unexpectedly.
The episode was seen by an estimated 5.22 million household viewers and gained a 2.5/7 ratings share among adults aged 18–49, according to Nielsen Media Research. The episode received positive reviews from critics, who praised the writing and Braugher's performance.
Plot
In the cold open, Boyle tries to have the squad pick his Halloween costume, dressing up as a peach, William Shakespeare, and He-Man.
After his victory the year prior, Jake proposes to continue the bet with Holt. Jake's assignment last time was to remove Holt's medal from the wall (which was removed by Holt and put in a safe to make it even harder for Jake) before midnight. This time, Holt's wrist watch is the target. If Jake wins, Holt will do Jake's paperwork for one week, but if Jake loses, Jake will do five weeks of overtime without pay.
Getting help from the precinct, Jake brings in a pickpocket to help him steal the watch. It proves successful and the criminal gets on to steal the watch. However, problems arise when the criminal runs away with the watch and Jake learns from Holt that the watch belonged to his husband Kevin's father before he died. He and Boyle (Joe Lo Truglio) meet with the criminal and gives him his money and shoes in exchange for knowing the location of the watch but are told the watch was already in his car. When they go to retrieve it, they find that the car has been towed. Meanwhile, Amy (Melissa Fumero) and Rosa (Stephanie Beatriz) are upset when Terry (Terry Crews) doesn't punish Gina (Chelsea Peretti) for skipping out on her duties at the precinct to attend dance practice. It is revealed that Gina has been secretly going back to college which has caused her to miss dance rehearsals.
While passing through a crowd of party-goers, Jake manages to get on a party bus to get to the impound lot but loses track of Boyle. When he arrives to impound, he finds he lost his badge and his ID and can't claim his car. He tries to sneak through the fence but is arrested by guards. In the interrogation room, he is told by Holt that he orchestrated everything for a year, that he annoyed Jake into wanting to steal his watch, and that the watch never left his person to begin with. The criminal was already on Holt's payroll, and Holt had organized everyone to go against Jake as everyone wants him humiliated. However, Boyle was taken before he boarded the party bus because he might have told Jake the plan.
In the end, Captain Holt and the group celebrates Holt's victory at the bar and Jake is forced to admit that Captain Holt "is an amazing police captain/genius" in addition to the five weeks of unpaid overtime. Jake tells Holt that he has already started planning for the next year's heist, to which Holt replies that he is only three months late in planning.