Kelly begins moonlighting as a security guard for Susan Wagner, a wealthy woman who's married to an abusive husband. But things take a turn when the husband is shot and killed, and Mrs. Wagner becomes a suspect. Meanwhile, Sipowicz is paired with the hard-nosed Detective Walker who arrests a man for a robbery and double-murder. While Detective Walker thinks he's guilty, Sipowicz thinks differently. Laura quits her job and plans to move into a position with the District Attorney's office, prosecuting narcotics. The increasingly edgy Josh Goldstein has Kelly appear at a tenant's readiness group regarding crime, and he is later killed trying to save an elderly woman from a mugging on a subway platform.

Kelly, Medavoy, and Martinez investigate the brutal murder of a entire upper class family. Meanwhile, Inspector Lastarza orders Janice to cooperate with the mob even though it results in the death of the person whose license plates she ran through the computer, and Kelly deals with his relationship with her who tries to keep him out of the situation she's in. Also, Sipowicz takes a statement of a gay writer whose Academy Award was stolen.

Sipowicz has a cavity and decides to have it taken care of by his son's dentist. At the dental office, Sipowitz finds himself unsuccessfully trying to prevent the suicidal Dr. Fleishman from jumping off a 28th floor ledge. Meanwhile, Medavoy and Martinez work on a strangulation murder case that appears to be the work of a cross-dresser. LaSalle's first case for the squad involves a woman who was raped and she, Kelly, Sipowicz try to catch the most probable suspect. Janice joins the undercover squad and is partnered with the hot-tempered Roy Larson to assist with LaSalle's case, while Sipowicz suspects that Larson's short temper and odd behavior points to a drug problem. Also, Lois Snyder (the prostitute who set Sipowicz to be shot in the premiere episode) returns to try to apologize to him about the incident and also wants to renew their romance. But Sipowicz turns her down and goes back to start whatever relationship she has with D.A. Sylvia Costas.