There's some slight confusion surrounding how long Detective Jake Peralta went undercover between Brooklyn 99 seasons 1 and 2, and whether or not the storyline created a plothole. Although the police work in much of Brooklyn 99 is quite fictitious and geared towards comedy, the main characters do sometimes take on more serious assignments. Jake's infiltration of the mafia marks one of these significant operations, but just how long was he gone for exactly?
The episodes «Charges and Specs» and «Undercover» from Brooklyn 99 seasons 1 and 2, respectively, see Jake (Andy Samberg) going undercover in New York as part of the mob. Although most of his exploits during this period aren't shown, Jake revealed a few key details upon his return during a 12-second recap, claiming he had "fixed a boxing match, smoked a whole cigar without vomiting, [and] was once in a room with ten guys named Sal." A flashback also reveals Jake performing Billy Joel karaoke with fellow mafia members. Except for one man who escapes the bust, Jake's undercover assignment is a success.
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There is some inconsistency when it comes to how long Jake was actually undercover with the mob, however. Although he and his coworkers refer to his absence as being six months long, Jake later says he was undercover for 63 days—which is of course much closer to two months. This could be a Brooklyn 99 plot hole, but there's also a simpler explanation, potentially, which is that Jake was only undercover for 63 of the days he was gone on assignment.
In «Charges and Specs,» the final episode of Brooklyn 99 season 1, Jake tells the squad that "they're saying this assignment will last about six months," but "the assignment" can refer to
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