Sipowicz investigates the murder of a pimp in which evidence points to a cop that Sipowicz once helped out with a problem of his. Later, Simone mentions the case to his girlfriend reporter Benita, and soon regrets it when the story hits the papers which leads to the suspect committing suicide. Benita denies leaking the story, but Simone refuses to believe her and ends their romance. Meanwhile, Donna's former boyfriend, Harold, a ex-New York Ranger hockey player, returns to the city and meets with Donna, while Meadvoy overreacts with jealousy. Donna confides her situation with her sister, Dana, but she manipulates Donna by sowing seeds of anxiety into her about Medavoy and his neurosis. Elsewhere, Martinez begins to develop feelings for Lesniak.

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.