"A man grabbed me from behind and I guess he must have injected me with some kind of sedative because I went right out…[I awoke] in this man's basement. It was like a torture chamber…There was a table with restraints on it, handcuffs chained to the wall. He'd bring in a bamboo cane that he'd use to beat the back of my legs. It was medieval…[I was fed] through a slot in the door. I'd eat, then wake up, very sore, sexually violated, bruised."
—Martha Henstridge, about Paul Grady, "Old Yeller"
Detective Andrew "Andy" Sipowicz Sr. and the other detectives at the 15th Precinct detective squad have spent many years dealing with the criminal element in New York City. These are among the worst criminals they have ever dealt with.
All spoilers are unmarked. You Have Been Warned!
Seasons 1-6
- "Double Abandando": Eddie Reyna is a slimy personal trainer and smalltime drug dealer who has had multiple sexual partners and is revealed to have infected at least three of them with HIV—possibly more—uncaring that he is letting them suffer a slow and painful deterioration and death, leaving one in particular Delicate and Sickly. Trying to prevent the third known victim—his own current girlfriend Dorie—from finding out the truth, Eddie has convinced Dorie that the woman who is trying to warn her about his virus is mentally unstable. When confronted by NYPD Detectives Adrianne Lesniack and James Martinez, Eddie tries to cast aspersions on the woman who brought the allegations against him.
- "In the Butt, Bob"; "Vishy-Vashy-Vinny"; "Bombs Away": George Putnam, aka the Webster Dictionary Killer, is one of the most prolific murderers to appear on the series. Starting as a robber who killed 2 people, Putnam quickly developed a misogynist streak and started using a gun to kill couples. Putnam would leave by his victims notes with letters cut out of Webster's Dictionary to taunt the police, earning him his sobriquet. Putnam killed 5 people in New York in 1989, including a 15-year-old girl, before moving to Broward County, Florida, and continuing his killing spree. Putnam returned to NYC in 1994 and began killing couples again. Putnam begins to strangle his victims when one of them puts up a fight, eventually killing at least 11 people before he is arrested.
- "Bombs Away": Vartan Illiescu is a smug, slimy man who's so jealous of others having more that he decides to initiate terrorist attacks against them. Vartan plots a series of bombings against the elite and rich and, in his worst act, has a mother and her young kids and housekeeper strapped to the floor with bombs which will go off if they move unless he's paid. When he comes across an elderly woman, Illiescu kidnaps her and intends to murder her to cover his trail. Confronted by Det. Sipowicz, Illiescu remains a smug racist creep who even threatens to avoid telling the location of the family if they won't let him go.
- "Torah! Torah! Torah!": Roger Squires is a brutal Serial Killer who stalks women, killing 6 women overall. Squires stalks women on the subway platforms until he finds one he is attracted to and follows her home. If the woman lives on the first floor, Squires waits until she falls asleep and uses a milk grate to gain access to the window of her room. Squires then opens the window and violently stabs the woman to death, while groping her, taking trophies from her home before he leaves.
Seasons 7-12
- "Tea & Sympathy": Andrew Conover is a repeat predator and murderer from the United Kingdom. Targeting 3 women per attack period, Conover assaults women, binding their undergarments with duct tape around their ankles; inseminating their genitals, hair and face; and strangling them to the point of leaving ligature marks. Having used the name of London Detective Jimmy Cheatham—who had been pursuing Conover—as an alias, Conover obtains work as an embalmer in New York, abusing his job to molest corpses and target women. With Conover's latest crimes investigated by NYPD Detective Andy Sipowicz, Conover is revealed to have targeted eleven women overall, and attempts to target a twelfth.
- "Dead Meat in New Deli": Hector Santos is a pimp who runs a forced prostitution ring. Purchasing the teenage Luisa López, Hector forces her into prostitution by use of force and drugs. Hector also keeps Luisa and all his girls in line by threatening to kill their families if they escape.
- "Keeping Abreast" through "And the Wenner Is...'': Lucy Wenner is a seemingly timid and meek woman who is actually a deranged Serial Killer and Serial Rapist. After Lucy is rejected for a waitress job at a bar called the Time Bar, she develops a grudge against the owner when he makes a sexist comment about her. Seeking revenge, Lucy goes to the Time Bar and stalks women who leave the bar, following them home. Lucy then goes to her victim's apartment, pretending to be from a charity. Lucy then knocks out her victim with drugs, rapes them with a dildo, and strangles them. Lucy then leaves a matchbook from the Time Bar in the apartment to connect the Time Bar with the murders. When the media refuses to connect the killings to the Time Bar, Lucy pretends she was attacked by the killer to further implicate the Time Bar. When Lucy is finally caught and arrested, she claims she was killing for a righteous cause, but Sipowicz quickly deduces she was killing to gain a sense of power and control.
- "Old Yeller": Paul Grady is the owner of a local dry cleaning business who is secretly a Serial Rapist. Grady drives up to women who are alone on the street, drugs them, and then puts them into his van. Grady then takes his victim to his basement, which had been converted into a torture chamber. Grady then rapes and tortures his victims for weeks or months, eventually releasing them when he grows bored with them. Grady's wife also claims he beat and raped her. When one of his victims killed herself after being tortured and raped for 2 months, the investigation into her death led to police being able to pick up the trail that led to his arrest.
- "Peeler? I Hardly Knew Her": Rosa is a human trafficker who traffics women—including children—for sex. Rosa takes women from Latin America who cannot speak English and forces them to become sex slaves. She locks them in an apartment and forces them to have sex with men. Detectives Ortiz and Ronson discover Rosa's apartment while investigating another crime and Rosa escapes with a young girl named Corisa. Rosa is later arrested by Ortiz and Ronson and is convinced to flip on her bosses to avoid a larger prison sentence. Ortiz and Ronson go to another apartment Rosa named and save a woman who was enslaved, but Corisa is not found and is lost to the streets of New York.
- "Fish Out of Water"; "Divorce, Detective Style"; "Stoli with a Twist": Steve McClintock is a smug, slimy Con Man who makes his living by using wayward pregnant criminal women to set up illegal adoption deals. McClintock has no plan to actually honour these and will instead fake that his client had a miscarriage, to the grief of the parents wanting a child. When one of McClintock's partners objects to this cruel treatment, McClintock nearly induces an actual miscarriage in her and threatens to murder her if she speaks of this. When his newest teenage con partner has had enough and wants out, McClintock strangles the heavily pregnant woman to death and later forces his girlfriend to create an alibi for him by threatening to kill her. Weaseling out of the consequences, McClintock becomes a drug dealer before meeting his end.
