Simone and Sipowicz investigate the race-related murder of a Puerto Rican teenager who was attacked while spray painting graffiti in Little Italy. Meanwhile, Medavoy meets Donna's former boyfriend, Harold, when he comes to the station to file a car vandalism report, while Donna makes a tough decision about her relationship with Medavoy. Also, Sylvia is mugged and she later tells Sipowicz a secret from her past about being raped as a teen.

A woman comes into the station to report that there's a bullet hole in her wall. The gun is found in Jimmy Liery's apartment and Simone arrests Jimmy, but has to let him go as there isn't enough evidence to hold him. Simone finds out that Russell unsuccessfully attempted to scare Jimmy by firing a shot over his head. Simone decides to remove Jimmy unlawfully by setting him up to take a fall. Meanwhile, Sipowicz is still angry at Fancy who thinks he held up his promotion. Following a tip from a young runaway teenage boy, named Marco, Medavoy and Martinez investigate the murder of an apartment building tenant. Also, artist Walter Hoyt (from ep. UnAmerican Graffiti) returns and wants the detectives help to get his paintings returned from some mob guys that he is a witness against.