Seamus Murphy (guest star Paul Adelstein) returns to redeem the favor Holt owes him, the precinct searches for a loophole that will allow Holt to uphold his end of the bargain without breaking the law.
Seamus Murphy returns to request the favor that Captain Holt owes him, after giving him the evidence that allowed Jake and Rosa to be released from prison. Murphy tells Holt that if he refuses, he has evidence that shows Holt asking for intel, threatening to show his bosses. It is revealed that Murphy wants a block party permit. However, Holt believes that Murphy wants to use the permit as a cover for criminal activities. Jake tells Holt that there is a possible way to do the favor without raising suspicion from Seamus, and allow Holt to keep a clean conscience. He comes up with a plan that involves Kyle Murphy, a supposed weak-link in the crime family, believing that they can retrieve information about any plans happening.
Meanwhile, Amy and Rosa go to the Street Activity Permit Office, to get the permit required for the favor. After not being able to get the permit the first time, and finding out that a rules regulator had been incompetent at her job, they find a loophole that allows a previous form that had been written to get the permit.
Terry and Gina discuss her return to the precinct, and she tells him that she needs a place to pump milk for her baby. However, she has been leaving the pump and going back home. She tells Terry that she feels like a failure after not being a good mother. Terry comforts her by telling her that he had felt the same way when raising his twins.
Jake and Charles go undercover to gain Kyle's trust. He brings them to his apartment, however, they discover that Kyle has been kicked out of the crime family due to being a liability and losing Seamus' car. They come up with an idea that would allow Kyle to bring back the lost car, regaining Seamus' trust and bring him back into the family. They give Kyle the car, who gives the keys back to Seamus, in which they have bugged so they can hear any conversations about the plan.
They find out that Seamus was planning to steal $20 million in bonds from a truck. Charles says that Seamus wanted the block permit so that the street would be closed, making for an easier robbery, due to the truck having to use an abandoned alley. Jake says they changed the truck's schedule so that the bonds would not be there to be stolen. However, after listening to the bug after the failed heist, Jake finds out that Seamus would "take care" of Kyle, believing that he told someone about the heist. Jake tells Holt that they have to help Kyle and they end up "arresting" him for parking violations.
Two days later, Seamus confronts Holt about what had happened and tells him that the arrest had been a cover for Kyle helping them stop the heist of the armored truck. Holt denies any collusion with Kyle, and tells Seamus that his debt has been repaid. Seamus refuses to believe the story and tells Holt that he will go after Kevin.
|Andy Samberg||...||Jake Peralta|
|Stephanie Beatriz||...||Rosa Diaz|
|Terry Crews||...||Terry Jeffords|
|Melissa Fumero||...||Amy Santiago|
|Joe Lo Truglio||...||Charles Boyle|
|Andre Braugher||...||Captain Ray Holt|
|Chelsea Peretti||...||Gina Linetti|
|Dirk Blocker||...||Michael Hitchcock|
|Joel McKinnon Miller||...||Norm Scully|
|Paul Adelstein||...||Seamus Murphy|
|Mike Mitchell||...||Kyle Murphy|
|Jane Morris||Florence Tinj|