Simone and Sipowicz investigate a case where two transvestites witnessed a murder that they say was committed by a 'gay-basher' who's supposed to have been in jail for a previous crime. Meanwhile, Fancy's former foster son is arrested and charged with possession of a kilogram of heroin. He tries to make a deal with Sgt. Ray Kahlins, the "blow hard" from the DEA who worked out of the squad room the previous year, to nab the drug dealers. Medavoy finally asks out Abby Sullivan, the beat cop from the anti-crime unit upstairs. But she turns him down by revealing that she is a lesbian. Elsewhere, Russell gets more deeper involved in her undercover work which puts a strain on her relationship with Simone. But the psycho Jimmy's malevolence puts Russell's life in danger when he puts a drug in her drink.

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.

Simone and Sipowicz investigate a story that a diamond dealer and his partner report that one of the dealer's sisters is missing with a bag of diamonds worth a million dollars, but the sister's boyfriend is actually responsible. Meanwhile, Martinez, Medavoy and Russell look for the assailant of Gina who badly slashed her face up while she was on her way to work, and Martinez cannot cope with this sudden turn of events. Simone and Kirkendall go out on their first date, while Russell cannot cope with the fact of being alone again.