For a certain segment of the population who you can probably picture quite clearly, it’s easier to get into Harvard than to go to jail. Such was the case of Robert Chambers, a major asshole who’d gotten away with pretty much everything his entire life until he made the mistake of victimizing one of his own a little too hard to ignore in an incident known to the press as the “Preppy Murder.”

Robert Chambers

Robert Chambers

(Marilyn Church/picryl​​)

We don’t wanna say too much about Robert Chambers because he’ll be released soon and we don’t wanna be revenge murdered, but his only apparently positive quality was being super hot by mid ‘80s James Spader standards. Despite appearances, he was only a “preppy” by way of private school scholarships, and he got into drugs and petty crime at an early age. Still, he always managed to escape consequences for his actions; he’d occasionally get kicked out of school, but there was always a new one. In the days before Jennifer Levin’s death, he was talking about going to Columbia.

Jennifer Levin

Jennifer Levin's school

(Beyond My Ken/Wikimedia Commons)

Friends’ descriptions of Jennifer Levin sound like something out of Gossip Girl, a “fun, happy-go-lucky” 18-year-old with rich divorced parents and a fake ID that let her into all the hottest places for rich 18-year-olds to get drunk. She’d hooked up with Chambers a few times, and apparently, a week away from leaving New York City for college in Boston, she was determined to give him one last go.

The Preppy Murder

Levin found Chambers on August 25, 1986 at Dorrian’s Red Hand, a bar they both frequented, and although he was in a sullen mood after a fight with his girlfriend and initially tried to brush her off, they ended up talking late into the night and then heading to nearby Central Park for a little more privacy. What happened after that is still kind of a mystery, but despite what teen sex comedies have led us to believe, friends of both insisted it would have been super weird if either of them left with the intention of dicking down in hobo town.

The Next Day

Central Park

(Ingfbruno/Wikimedia Commons)

It’ll never be totally clear what happened between Chambers and Levin that night, but her body was found in the park the next day, with injuries suggesting strangulation and, weirdly, a lot of biting. It was later discovered that at least two joggers had witnessed a sort of blurry struggle before a third had noticed the body and Chambers had stuck around, watching the investigation from across the street like some kind of definite murderer.

Chambers’s Story

Cat scratching

(Milada Vigerova/Unsplash)

After friends told them Levin left the bar with Chambers, police found him at home with scratches all over his face that he claimed were from his cat. After it was determined the cat had been declawed, he admitted that he “might have accidentally” killed Levin after she tied his hands together with her underwear, started doing sex stuff to him, and then squeezed his balls too hard and refused to stop. It’s worth noting that the prosecutor suggested Chambers had so many drugs in his system that it was unlikely he could achieve an erection and “she may have said something to him” about it. Just a theory, folks.

Media Sensation

It didn’t take long for the media to latch onto the story of privilege, death, and ball-squeezing. They dubbed the case the “Preppy Murder” and Chambers the “Preppy Killer” because they weren’t as good at coming up with nicknames back then as they are today.

Catholic Sex Abuse Scandal Break

Theodore McCarrick

(World Economic Forum/Wikimedia Commons)

Those tabloids got even more fodder, though it wouldn’t pay off for some time, when Archbishop Theodore McCarrick, an old family friend, wrote to the judge of Chambers’s case to ask for his release on bail. Thirty years later, McCarrick was stripped of his collar following reports of sexual misconduct, but the judge didn’t have a time machine, so it worked. This gave Chambers the opportunity to be filmed at a party ripping the head off a Barbie doll before laughing, “Oops, I think I killed her.”

Jack Litman

Jack Litman

(Marilyn Church/picryl​​)

Chambers’s family hired Jack Litman to defend him, which was as big of a score as getting Snoop Dogg to be your weed sommelier. Litman became famous the previous decade for defending a Yale student who murdered his girlfriend, so he knew from preppy killers.

Litman’s Defense

Litman argued fairly successfully that Chambers had no reason to kill Levin, speculation of penile impairment aside, and even then, he was known as a “wimp” who rarely gave into anger despite his absolute unitness. He was less successful at convincing anyone that Levin’s injuries were more consistent with a type of chokehold that can cause death in as little as two seconds that Chambers could have used when he pulled her off him, to which the prosecution responded, “No, they aren’t.”

Slut Shaming

One of Litman’s dirtier tactics was trotting out Levin’s sex life for all to see, introducing her journal (which he called a “sex diary”) into evidence on the grounds that it established a pattern of “kinky and aggressive sexual activity.” It was a strategy appreciated by the press, who wrote articles with titles like “How Jennifer Courted Death,” but not so much by the actual court.

Chambers in Prison

Chambers ended up serving the full 15 years of his sentence because he was really bad at being in prison. He racked up “numerous drugs and weapons infractions” and even spent five years in solitary before being released in 2003.

Dorrian’s Red Hand

Gossip Girl loft

(dumbonyc/Wikimedia Commons)

The only one who seems to have come out on top in the whole situation was the owner of Dorrian’s Red Hand, whose liquor license was only briefly suspended, which he insists was government retaliation for securing Chambers’s bail and not because he was loudly serving minors. The bar has since not only retained its elite clientele but become a morbid “rite of passage,” attracting a whole new class of celebrity customers. It was even featured in an episode of Gossip Girl in one of the show’s top 10 moments of poor taste. Top 20, for sure.

Top image: Marilyn Church/picryl​​

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