One of the only times he doesn't even attempt an escape is season 7's 'The Takeback.' Judy invites Jake to his bachelor party, forcing Peralta to arrest Judy's friends when he finds out they're stealing. The clever thief usually finds a way to help the good guys and himself, all while escaping with a tidy sum. Usually, Judy manipulates Jake to help him solve a problem, like when he stages a hostage situation in season 5's 'The Negotiation' to get Jake involved when a drug dealer is threatening to kill him. Of course, by the end of the episode, we learn Judy is the Pontiac Bandit. Judy first appears in season 1's 'Pontiac Bandit,' offering to help Jake catch the episode's titular villain, named for all the Pontiacs he's stolen.
Perhaps no two TV characters more aptly embody the word 'frenemies' than Brooklyn Nine-Nine's Jake Peralta and his sometimes nemesis Doug Judy, aka the Pontiac Bandit (Craig Robinson).