Lesniak deals with a perpetrator and his "high priced lawyer and shrink" when he repeats the offense. Meanwhile, Detective Solomon uses a fast pull to take a possible serial killer case away from Simone after he brings in a possible suspect. One of Fancy's old contacts, Vinnie Greco, brings in a tip about a couple of guys looking for some heavy arms to do an armored car job and Sipowicz works with him, but Greco is working for someone else against Fancy. Sipowicz invites Andy Jr. over at his place for dinner where his son tells him that he is joining the Air Force. Also, Sipowicz proposes marriage to Sylvia and this time, she accepts.

After discovering a key piece of evidence, Simone gets his chance by Detective Archie Solomon to question the serial killer suspect George Putnam. Meanwhile, Sipowicz, Medavoy and others work on how to stop the armored car robbery and Fancy has a confrontation with Haverill about using his informant, Vinny, as a pawn to try to bring him down and plays a tape for Haverill which he reveals his true attitude which results in his resignation as the zone commander. Also, Martinez and Lesniak arrest an odd extortionist, while romantic feelings for each other begin to appear, and Simone also develops romantic feelings for his writer friend Benita Alden.

Simone and Sipowicz investigate the brutal murder of the teenage daughter of a woman whose ex-husband has made threats against her. Meanwhile, Lesniak and Martinez's latest case involves them trying to nab a con artist who sells a black box to homely women, promising them beautiful skin. The new zone commander, Captain Clifford Bass, checks in and lets Fancy know his overtime policy, which doesn't sit well with Sipowicz when it compounds their investigation. Elsewhere, while Simone's romance with Benita becomes more serious, he also deals with a childhood friend, named Ray, who is now involved with a nightclub that is frequented by wise guys and other criminals.

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.

Martinez is shot in the back during a scuffle and the doctor's report is possible that he may be paralyzed for life. But Martinez's assailant, a government witness in a relocation program, will probably go free and Simone contacts reporter Benita Alden, his former girlfriend, to help put pressure on the D.A. to prosecute their protected witness. Meanwhile, Russell, on the road to recovery from her alcoholism, wants Sipowicz to let Simone know she's doing okay but she is on the brink of falling off the wagon. Donna expresses to Simone that she has feelings for him, and Sylvia tells Sipowicz that she may be pregnant.