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.

Medavoy and Sipowicz go undercover as Hasidic Jews to recover a stolen Torah. Meanwhile, Simone gets a case where a father suspects his intellectually disabled son of killing his daughter. Detective Stuart Morrissey tactics with the suspect does not sit well with Lt. Fancy, despite the facts that the case match the one Simone are working on. Also, Sylvia visits a doctor who confirms that she's pregnant, and Lesniak keeps checking up on Martinez still in the hospital.

Simone and Sipowicz investigate a shooting that is related to the victim trying to leave a street gang. Meanwhile, Kirkendall and Russell investigate the death of a baby who appears to have been shaken to death by the baby-sitter. Medavoy and Martinez look into a murder at a garage where they have a suspect who looks guilty despite the fact he claims to have an alibi. That evening, Medavoy has dinner with Abby and her lover, Kathy. Also, Simone takes Russell out to a movie and proposes to her again, and this time she accepts.

Simone and Sipowicz investigate a break-in of a high-rise apartment where the wife and baby are killed and the husband injured. Vince Gotelli, now an insurance adjuster, tells Simone and Sipowicz that the man may have faked a break-in to kill his family to collect an insurance policy. Meanwhile, Fancy gets some clues about a 15-year-old unsolved murder case from a visiting old friend who is dying. Also, Russell, Martinez, and Medavoy investigate the murder of a record company executive who wasn't very popular among his co-workers.