Prestige, Private Schools And The ‘Preppy Killer’: An Upper East Side 'Rough Sex' Murder

It was the early morning of August 26, 1986 when 18-year-old Jennifer Levin’s body was discovered by a cyclist riding through Central Park. Found strangled, bruised, with clothes disheveled and just a stone’s throw from the Metropolitan Museum of Art, Levin’s killer would be arrested by police later that very same day.

As investigators pieced together the events leading up to Levin’s death, they discovered Levin had not only known the man who would eventually murder her, but she had had a few romantic flings with him as well. Robert Chambers Jr., 21, was quickly dubbed the “Preppy Killer” (and the event, the “Preppy Murder”) because of his privileged upbringing and reputation for flunking out of prep schools throughout New York.

On the morning of Levin’s murder, the two had been spotted flirting and drinking at Upper East Side watering hole, Dorrian’s Red Hand. They reportedly left the bar around 4:30 a.m., and Levin’s body was discovered just two hours later under a tree in the park. Chambers was arrested and arraigned for murder, but maintained that her death was an accident caused by consensual “rough sex.”

He faced a jury trial on second-degree murder charges, but after nine days of juror deliberation resulting in a deadlock, Chambers took a plea deal. He plead guilty to reduced charges of first-degree manslaughter and admitted he had intended to hurt Levin. Initially, he said the incident was an accident that occurred after Levin “painfully squeezed him” while they were having sex in the park. Chambers was sentenced to five to 15 years in state prison. At this time, Chambers also plead guilty to a separate indictment for burglary, for which he was sentenced to 5 to 15 years as well. The two terms would run concurrently, meaning Chambers would be up for parole in just five years. 

Many details about what unfolded the night of Levin’s murder remain unknown, but in an interview with CNN in 2002, Levin’s mother Ellen shares a few theories from police about how Chambers may have strangled her.

“They think that it could have been her panties, they think it could have been his arm. They found marks from his watch on her neck,” said Levin. “And we don't know for sure. He's the only one that knows the whole story, and I don't think we'll ever hear it.”

The murder sparked a media frenzy, fueled by tales of underage drinking, drugs and sex set against a backdrop of Upper East Side wealth, but for Levin’s family, there was nothing tawdry about it. Levin’s mother Ellen described the teen to CNN as a “popular girl” who “loved going out.”  At the time of her death, Levin had just completed high school at a prestigious private school and was set to begin studying at a Boston junior college.

Chambers was released from prison in 2003 but didn’t spend much time out from behind bars. He was convicted of selling cocaine and incarcerated again in 2008, this time for 19 years. 

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