Robert Chambers Jr. was 19-years-old when he was arrested for the death of 18-year-old Jennifer Levin in 1986. Her bruised and strangled body was found under a tree by a cyclist riding through Central Park one morning. Two hours earlier, Levin and Chambers were seen flirting and drinking at an Upper East Side bar. They left the bar together around 4:30 a.m. Chambers was arrested that same day. At first, he blamed the multiple scratches on his face and arm on a cat. Police also found multiple cuts and bruises on the woman’s neck, from the strangulation and from her own fingernails as she clawed at her perpetrator’s arms. Chambers later admitted to killing Levin but maintained that her death was an accident caused by consensual “rough sex.”
Chambers was dubbed the “Preppy Killer” in the media (and the event, the “Preppy Murder”) because of his privileged upbringing and prep school past. He didn’t exactly make a good impression on the public. According to The New York Times, a 1988 broadcast of a home video by "A Current Affair" showed Chambers hanging out with four girls in lingerie at a party when he was free on bail. In it, he began choking himself with his hands while making loud gagging noises. He then twisted a Barbie doll's head off, and said, "My name is…Oops! I think I killed it." Chambers is even referenced in the novel "American Psycho" when its sociopathic protragonist/serial killer Patrick Bateman talks about trying to start a defense fund for him.
Chambers initially faced second-degree murder charges for the death in a jury trial. But, that resulted in a deadlock after nine days of deliberation. Afterwards, Chambers took a plea deal, pleading guilty to reduced charges of first-degree manslaughter. Chambers was sentenced to five to 15 years in state prison. During his plea deal, he claimed that he hurt Levin after she “painfully squeezed him” while they were having sex in the park. Chambers also pleaded guilty to a separate indictment for burglary, for which he was sentenced to 5 to 15 years. The two terms ran concurrently.
Chambers struggled to stay out of trouble, even while incarcerated. He assaulted a correctional officer and was cited repeatedly for weapons and heroin possession infractions. As a result, almost five years of his term were served in solitary confinement. He was released in 2003. The same day of his release, Chambers maintained during a televised interview that he killed Levin accidentally in an attempt to stop her from injuring him during rough sex. He denied that he was disciplined in prison.
After prison, Chambers moved to Georgia with girlfriend Shawn Kovell. The two knew each other for a long time and she had even appeared in the infamous Barbie doll video made before Chambers’ sentencing. Chambers worked at a dye factory, and the two lived in Georgia for nearly nine months before moving to an East 57th Street Manhattan apartment in New York City. Chambers began working at a limousine company in Queens, and later at a New Jersey sports trophy manufacturer's engraving plant.
In 2004, Chambers was stopped in his Saab for driving with a suspended driver's license. Police found heroin and cocaine in the car. Chambers pleaded guilty in 2005 for the charges, and was sentenced to a reduced sentence of 90 days in jail.
In 2007, he was arrested again, along with his girlfriend. Chambers and Kovell were charged with running a cocaine operation out of their apartment. Chambers, then 41, fought with police during his arrest. One detective suffered a broken thumb.
Former Assistant District Attorney Linda Fairstein, who had prosecuted Chambers for Levin's death, said following his 2007 arrest: “Doesn't surprise me. I always believed his problem with drugs and alcohol would get him in trouble again. He's had the opportunity in prison to detox and take college courses, to straighten out his life, but that clearly is of no interest to him. He's learned nothing in the last 20 years.”
By 2007, Chambers was reportedly using 10 to 12 bags of heroin a day in addition to cocaine, marijuana and prescription drugs. Prosecutors claimed Chambers had sold about $2,800 in heroin to undercover police. In 2008, Chambers pleaded guilty to selling drugs. He was sentenced to 19 years in prison. His earliest release date is in 2024.