What ‘Preppy Killer’ Robert Chambers confessed in prison

The first time John J. Lennon set eyes on Robert Chambers — the man notoriously branded the “Preppy Killer” by the media — he was slouched in an oversized prison-issue green shirt and dirty Skechers, just another convict at New York’s now-shuttered Sullivan Correctional Facility.

Lennon was struck by the contrast.

“He was hardly the symbol of privilege I’d seen on TV,” he writes in “The Tragedy of True Crime: Four Guilty Men and the Stories That Define Us” (Celadon Books), out Tuesday. Then 54, Chambers was, Lennon says, still tall and broad-shouldered, his jawline sharp, but his thick hair was gray and thinning.

What Lennon saw was not the Upper East Side prepster immortalized by tabloids, but a man finishing a 19-year sentence for drugs, a conviction that had followed the 15 years he served for killing Jennifer Levin in Central Park in 1986.

That killing had electrified New York City, in the worst way. The circumstances were sordid and sensational: two teenagers fueled by alcohol and cocaine, a hookup after a night out at Dorrian’s Red Hand bar on the Upper East Side and a body discovered beneath an oak tree.

For the public, it was more than a crime; it was a parable about privilege and sexual deviance.

Lennon notes that the case “turned into a cautionary tale about the ’80s, the era of excess and inebriation — young people in the throes of addiction, uninhibited and numb.” In a year when New York City recorded 1,309 homicides in its first 10 months, most in poor neighborhoods, the murder of Jennifer Levin by a boy from the Upper East Side shook the perception that privilege insulated people from violence.

Decades later, Lennon met Chambers not as a journalist parachuting in but as a fellow convict.

His vantage point was unusual: a man serving his own life sentence for murder, who had turned to writing from prison and knew firsthand the way true crime flattens complicated people into archetypes.

Lennon had grown up in Brooklyn housing projects before moving to Hell’s Kitchen, where he fell in with the Westies and hustled on the streets. In 2001, during a drug-dealing dispute, he shot and killed a man from his old neighborhood.

Convicted of second-degree murder, Lennon was sentenced to 28 years to life. He arrived in prison in his twenties, and slowly reshaped himself into a writer, publishing essays and articles in outlets like The Atlantic, Esquire and The New York Times. That transformation gave him both credibility and suspicion among other inmates.

But if Chambers “was going to talk to any journalist, he wanted it to be me,” Lennon recalls.

Pressed to describe the night Levin died, Chambers — who cooperated with the book, according to the publisher — faltered. “I said, ‘Come on, let’s go.’ Then she didn’t move. And I looked at her and her eyes were open. And then I freaked out, backing up, all the way to the rock wall by the path,” Lennon says he told him.

Chambers admitted that panic took over, that he hid. Lennon asked why, decades later, he couldn’t simply own it. Chambers went silent. To Lennon, it seemed as if Chambers still could not fully comprehend what he had done.

“My best guess is that he still can’t understand how one minute he was walking into the park and talking with Jennifer, and then, minutes later, strangling her,” Lennon writes. “How do you explain something you can’t believe you did?”

Even at 19, Chambers’ words betrayed denial. Arrested days later with scratches on his face, he told police they came from a cat. Hours later, under questioning, he admitted they were from fooling around with Jennifer.

“I liked her very much,” he told detectives. “She was a very nice person. Easy to get along with. Easy to talk to. She was just too pushy.”

Those words, recorded in transcripts, cast a long shadow over how he was perceived. In the end, prosecutors and defense cut a deal: a plea to first-degree manslaughter. He served the full 15 years. When he walked out in 2003, he did so “an untreated addict,” Lennon notes.

Sobriety never took hold. Within a few years, Chambers was caught in a drug sting and sentenced to 19 more years. Addiction defined nearly everything. “Even though I was, like, 36 when I got out, I was still 19 in my mind,” he allegedly told Lennon.

Chambers struggled with remorse. He told Lennon he envied the essay Lennon had once written to the family of his own victim. “I guess I feel like, how could I not have figured out how to do that?” Chambers said. “I think it was always something I felt like I needed to earn.”

In 2019, AMC aired “The Preppy Murder: Death in Central Park.” Younger inmates and correctional officers who had never heard of his case suddenly saw it splashed across the TV in the dayroom. For Chambers, it was a gut punch. Prison had been, in its way, a shield from the relentless coverage. Now the story followed him even behind bars.

Chambers once attempted to explain himself in writing. In 2018, in a Sullivan college class, he allegedly turned in a essay called “Lust in the Clutches of a Dreamsleep.” Lennon describes it as “an East Coast version of Bret Easton Ellis’ ‘Less Than Zero.’” The piece evoked a shadowy secret society, the Seven Silver Keys, where adults anointed chosen teenagers with promises of money, sex, drugs and power.

“Everything was for the taking. But once you take, you will give forever,” Chambers wrote. One figure, a “Hitler in an Armani suit,” delivered sermons of prejudice and greed. Chambers claimed he ran errands to Wall Street offices, carrying envelopes he suspected contained insider information. At 15, he wrote, he had “secret money, a secret apartment, and more secrets of the who’s who of politics and finance than I knew what to do with.”

He described a seven-month affair with an older married woman who whisked him to MoMA, McSorley’s and the Hamptons. “I was scared of her,” he admitted. “I loved her.” Fact or fiction, it painted the picture of a teenager racing through Manhattan, consuming and consumed, his future already burning out.

When Lennon began writing about Chambers, friends and pen pals warned him off. One female penpal remembered the case and told him that showing empathy would ruin his reputation. Another, a French friend named Anne, watched the docu-series and visited him afterward. “You must have respect for Jennifer when you write this book, John,” she said, eyes watery.

Lennon does not flinch from the tragedy. “Robert Chambers has so completely absorbed the external media narrative about himself as an irredeemable figure that it is hard to imagine him finding the wherewithal to ever become more than his crime,” Lennon writes.

On July 25, 2023, Chambers walked out of Shawangunk Correctional Facility with a commissary check, $40 in release cash and a bag of socks and underwear.

“Countless tabloid stories, prime-time specials, made-for-TV movies, books … Rob’s internalized it all,” Lennon writes. “And so, I imagine, have the Levins.”