List of NYPD Blue Characters - Adversaries

Adversaries

• James Sinclair, Esq.—A brilliant but very sleazy attorney who could always be counted on to represent the very worst of the bad guys that the 15th's cops were able to arrest for heinous crimes. The only exception to this rule came in Season 2 when he won a lesser manslaughter conviction against Office Licalsi. He got under Andy's skin in a way few other adversaries even came close to doing. Sinclair appeared for a last time defending crooked IAB Captain Pat Fraker and successfully getting him acquitted for the murder attempt against Lt. Tony Rodriguez. Played by Daniel Benzali.
• Alphonse Giardella—A gross mobster with a bad toupee, who hated Andy and was hated by him in turn. Set up Andy with a prostitute after Andy humiliated him, and shot the detective several times. He was later arrested for the crime but became a state's witness to save his skin, only to get assassinated by a mob hitman.
• Kwasi Oloshula—Formerly known as Kenny Parker, Kwasi was an outspoken community activist in the housing projects located in the 15th precinct. Kwasi organized a basketball game in memory of a young boy who died in police custody only to have the game be taken over by local drug lords who would start a gun fight at the game. Kwasi was intensely distrustful of the NYPD and would often get belligerent to the cops at the 1-5 with or without provocation (with the exception of Lt. Fancy, whom he had a cold but respectful relationship with) due to past racial problems he endured with police. Kwasi provoked Sipowicz into using the word "nigger" causing further conflict between Fancy and Sipowicz during a homicide investigation. Kwasi was found murdered later on with Sipowicz solving the case and apologizing to Kwasi's ex-wife and daughter for his past language against him. Played by Tom Wright.
• Jimmy Liery—A thug with IRA connections whom Det. Russell was asked to resume an undercover operation with in Season 4. Jimmy knew Diane as "Mouse" and distinguished himself through anti-Semitic violence, talking about being molested by nuns, and slipping Diane a roofie to undisclosed results. Bobby got angry enough to barge in on the operation and beat up and arrest Jimmy, and later he and Andy spread false information that led to Jimmy being murdered by his partner in arms-smuggling.
• Malcolm Cullinan—A very rich man who appeared in Season 6, Cullinan hired PAA Dolores Mayo as a prostitute, watched as she died of a heroin overdose and later buried her body in New Jersey. PAA John Irvin punched Cullinan in the face when he saw this on tape, and it later emerged that Cullinan deliberately gave prostitutes high-grade drugs so he could watch them die, and also that he tried to hire sleazy ex-cop Mike Roberts to kill Irvin, only to arrange for Roberts' death when Mike reached out to try to turn Cullinan in. After his actions indirectly led to the death of Sylvia Costas, Cullinan broke down and finally confessed when a nearly-silent Andy told him "Why don't you just cut it out?" and said he should confess so "You don't have to do this anymore".
• Don Kirkendall—Jill's unbelievably scummy ex-husband and father of her two boys, Don returned to Jill's life in Season 7. She claimed to believe that he was legitimately working, but quickly learned he was part of a major drug-trafficking ring. However, Jill's inability to turn him in or let him get arrested nearly ended her career before Don was apparently killed by the drug cartel. It later emerged that he and Det. Denby faked the death and began their own dealing, and Jill's career did get destroyed in the aftermath of her hiding this information (Don had kidnapped one of her sons for leverage). Diane, Andy, and the others did arrest Don for kidnapping and he was murdered by his former narcotics partners while in Rikers.
• Craig Woodruff—An ex-con who was suspected of murdering his ex-wife. The only witness in the case was his son Michael, a good kid whom Baldwin Jones took under his wing, to Craig's anger. Craig later assaulted Michael's aunt, but a lecture from Andy to Michael provided enough evidence to arrest Craig. After he was acquitted on the charges, he had a confrontation with Baldwin that led to a fistfight, but he then made himself scarce. In the final season, Craig was shot to death, and both the married woman he'd been having an affair with and her husband told police they killed him, with the case remaining unresolved.