The Untold Truth Of Robert Chambers, The Preppy Killer

Few criminal cases entice the public as much as brutal killings that involve attractive young people and potentially sordid details. That's why murderers like Jodi Arias have been able to stir up such a media frenzy, and that's why the person you're going to learn about has received plenty of coverage about things that he would presumably have preferred to keep unrevealed.

Robert Emmet Chambers Jr. has spent much of his life in the limelight, after entering the public eye as a 19-year-old youngster who was the prime suspect for the death of 18-year-old Jennifer Levin. The 1986 case was an extremely high-profile one, full of exactly the sorts of twists and turns that kept people interested. While killing another human being has obviously been the peak of Chambers' illegal activities, it's far from his only run-in with the law. In fact, the square-jawed, formerly fresh-faced man's All-American looks hide a lifetime of awful deeds and strange misadventures. Let's take a look at the untold truth of Robert Chambers, aka the Preppy Killer.

Robert Chambers' troubled studies

On paper, young Robert Chambers had everything it took to lead an incredibly successful life as a productive member of society. According to NY Mag, he was a part of New York's young elite — a mover, a shaker, an athlete, and an altar boy to boot. Per People, he was even a successful member of a drill team called the Knickerbocker Boys, which has been a traditional pastime for some of the most powerful families in America.   

However, something was bubbling under the surface. Though he maintained the façade of the archetypal prep school kid, his initially studious nature was soon shed in favor of slacking, and he started hanging with a certain subsection of the affluent circles: the party kids, who eschewed studying and hard work in favor of the club world and its drink, drugs, and casual hookups. For a time, Chambers was even a part of the Studio 54 scene. As such, his potential in academia pretty much flatlined as he drifted deeper into his new lifestyle, and finally ground to a halt when Boston University expelled him after his first year. 

Robert Chambers struggled with addiction from an early age

As Robert Chambers slowly moved from preppy world into party world in all but outward appearances, NY Mag reports that drugs and drink started to feature more and more in the young man's life. His father struggled with alcohol addiction, and despite his young age, Chambers was no stranger to beer and liquor himself. Still, a bigger issue was his use of narcotics, from his reportedly heavy marijuana use to his penchant for cocaine. In fact, People notes that this got so bad that in the spring of 1986, he did a stint in rehab for cocaine use. 

However, he was still a charming, 6'4" kid with movie star good looks, and somewhat reserved in nature. Although his friends did note that he was often stoned, he was a popular figure in his circles, and the extent of his problems appears to have remained secret from most. 

If you or anyone you know is struggling with addiction issues, help is available. Visit the Substance Abuse and Mental Health Services Administration website or contact SAMHSA's National Helpline at 1-800-662-HELP (4357).

Robert Chambers became a criminal early on

As Robert Chambers' issues with drugs increased, so did his need for money — and, as NY Mag tells us, persistent whispers insist that he took up petty theft from his friends' families to pad his pockets. One source has even insinuated that though his drug use was also a factor in getting expelled from Browning private school, part of the reason was that he stole from one of the teachers. "Getting kicked out of Browning was a big shock for Rob," a friend of Chambers' has said. "For the first time, he felt he'd been expelled from the clique. I mean, if you get kicked out of Choate, you can still go to Browning. But when you get kicked out of Browning, then where do you go?"

Though this didn't mark the end of Chambers' academic endeavors — that would come later — it didn't really teach him to mend his ways, either. According to People, Chambers racked up arrests for theft and disorderly conduct, and at the time of the Jennifer Levin murder investigation he was reportedly a person of interest in connection to numerous burglaries. As the New York Post notes, he also ended up in serious hot water in 1986 after stealing a female friend's credit card. 

The fateful establishment Robert Chambers frequented

On the fateful night of August 26, 1986, Robert Chambers met Jennifer Levin in a drinking establishment called Dorrian's Red Hand, and as People tells us, some context of the place is necessary to understand the full situation. Located near Central Park, Dorrian's ranked among the posh young kids' favorite watering holes, and it had a reputation for being a particularly good hookup spot. Regardless of its wild atmosphere, though, the clients seem to have considered Dorrian's something of a safe space.

Per NY Mag, Chambers was a regular at the bar. He was something of a popular attraction among the ladies in attendance, despite the fact that he had stolen money from many of his friends while they were there, and had even gotten caught on occasion. On August 26, he was once again present, but seemed lost in his thoughts and disinterested in the action around him. However, his own actions would soon cause irreparable damage to the bar's "safe space" street cred. 

Robert Chambers' relationship with Jennifer Levin

Robert Chambers and Jennifer Levin's fateful chance meeting in Dorrian's Red Hand on August 26,1986 happened after Chambers had an argument with his girlfriend, who was infuriated by the way he ignored her (per NY Mag). According to People, Chambers' legal aid would later insinuate that the killer and Levin had been an item, but the reality of their relationship was quite different. Both youths were popular and attractive, and knew each other well enough to have dated a few times in the past, but that was just about the extent of their relationship. 

Reportedly, Levin made her move after the sullen Chambers had more or less brushed off his girlfriend who, for her part, told him in no uncertain terms that they were done. According to the New York Post, Levin was genuinely interested in Chambers and wanted to start a relationship, but unfortunately, events transpired in a radically different way. An acquaintance of Chambers says that the young man was initially unwilling to hang out with Levin. "I don't think so. I don't want to deal with it," they remember Chambers saying when asked whether he'd like to meet Levin outside the bar. However, the pair ultimately talked late into the night, and left the establishment together at roughly 4:30 a.m. Levin never returned to Dorrian's Red Hand again.  

The death of Jennifer Levin

Two hours after Robert Chambers had left Dorrian's Red Hand with Jennifer Levin, a cyclist discovered Levin's body in Central Park (per People). It was not a pretty sight. According to The New York Times, she had been strangled to death, with visible marks on her neck. There were also a number of bite marks and bruises, and she was partially undressed. As the New York Post reports, it appeared that she had been killed with her own denim jacket, though it was clear that she had put up a fight.

The scene was strange and grisly enough to affect even a seasoned New York homicide detective. "I have never seen in my entire career the strangulation marks on her neck the way I did that day out of the 2,000 murders I've investigated," Detective Mike Sheehan, who was among the first to arrive on the scene, has noted. "She had all of these half-moon marks above the mustache line because she was desperately trying to pull the jacket off her mouth and nose so she could breathe." 

Chillingly, it later transpired that when the body was found, the killer was a lot closer than the police thought. As NY Mag reports, Chambers was still on the scene when the first cops arrived, observing them from outside the nearby Metropolitan Museum of Art. Allegedly, one officer even saw him.

Robert Chambers is caught

As the New York Post notes, Robert Chambers wasn't exactly sober on the night of Jennifer Levin's death. On the contrary, he had been indulging in everything from ecstasy and tequila to his go-to cocaine, which led the case's prosecutor Linda Fairstein to believe that certain performance issues might have caused the situation to escalate between him and Levin. "I don't believe as high as he was that they were able to consummate it and she may have said something to him, setting in motion a three-minute life-or-death struggle," Fairstein has opined. 

The police ended up catching Chambers very quickly because, as People tells us, they were able to peg him as a person of interest pretty easily. When NYPD Detective Mike Sheehan and his colleagues started conducting routine interviews among Dorrian's Red Hand's clientele, they soon came across a large young man with nasty scratch marks all over his face. Per NY Mag, Chambers had already acted suspiciously during a phone interview, and when a personal visit from the police revealed the facial markings, he was promptly taken in. Though Chambers initially tried to blame the scratches on his (declawed) cat, he eventually painted himself in the corner by accidentally admitting that he'd been heading toward the park with Levin. After this, he agreed to give an on-camera statement ... which ended up opening a whole new can of worms.   

Robert Chambers and the 'kink defense'

As People tells us, Robert Chambers' videotaped statement was far from the kind of confession one might expect. Instead, he insisted that although Jennifer Levin had died by his hand, this actually happened during a strange intimate encounter that involved bondage play. According to NY Mag, Chambers said that he was initially dismissive of Levin in the park, which angered her. However, he said she soon attempted to instigate a closer contact, but when things didn't proceed as planned, things took a turn for the worse and she squeezed things that aren't meant to be squeezed. "I told her to stop. She wouldn't," he claimed, saying that he eventually had to free his hands — which he says Levin had tied with her panties — and fought back. Though Chambers claimed he only hit Levin once and pulled her neck in retaliation, officials didn't buy the explanation due to the extensive evidence that Levin's death was far from instantaneous.  

Chambers' sordid statement and the preppy circles he ran with were more than enough to earn the attention of the public, and the tabloid newspapers were soon on the case. As the New York Post notes, it didn't take long for Chambers to earn his new, unsavory nickname: The Preppy Killer. 

The trial of Robert Chambers

According to the New York Post, Robert Chambers' trial in 1988 was not an easy one for the prosecution, not only because of its incredibly high-profile and tabloid-friendly nature (via Bustle) but because there were no witnesses. Although the media barrage had uncovered no less than two joggers who may or may not have seen Chambers and Levin in the park (per NY Mag), the actual legal back-and-forth soon proved that Chambers' explanation of the events was more than enough to deadlock the jury. 

It was evident that it would be hard to lock Chambers up on a murder charge. The situation was ultimately resolved with a plea deal that saw him plead guilty for manslaughter, though some of his lawyers have expressed an opinion that the deal was simply a smart business move, and doesn't necessarily reflect their true views about the case. "So the question was how could we not accept such a favorable plea bargain," Chambers' lawyer Roger Stavis said in 2016. "To this day, 30 years later, I continue to believe that what happened in Central Park on that evening was a terrible accident and that Robert Chambers never intended to kill Jennifer Levin." 

Terrible accident or not, Chambers' prison stint proved he was far from harmless. In fact, he turned out to be such a dangerous prisoner that he ended up serving the full 15 years, and spent nearly a third of it in solitary confinement. 

Robert Chambers continued his criminal ways after prison

Robert Chambers was released from prison in 2003, and as Bustle tells us, he went on to become a ... prisoner. After the initial barrage of media coverage, he resumed his life as a free man, though this went slightly less well than he may have hoped. According to People, by 2005 he was back in court for possession of heroin and cocaine. This time, he got away with just a 100-day sentence, but as it turns out, his lengthiest prison stint was still ahead of him. 

According to Reuters, Chambers' new life saw him take up drug dealing, and in 2007, he and his girlfriend were arrested and brought to justice. To make things somehow even worse for himself, Chambers assaulted an officer during the arrest. As such, in 2008 the Preppy Killer was sent back to prison after yet another plea deal — and this time, he received a sentence of 19 years and four months. Judging by the way his earlier sentence went, one would be forgiven for thinking that he's unlikely to get released early for good behavior.

The civil lawsuits

Robert Chambers may have been able to get a plea deal for the crime itself, but as UPI tells us, he was all out of fight when Jennifer Levin's parents came calling with a lawsuit of their own. In 1988, Chambers said he was fine with the Levin family's $25 million wrongful death lawsuit, which means that whatever income he'll ever earn must be paid directly to the Levins (per People). This wasn't the Levins' only courtroom battle, either. Outlets like the New York Post have reported that Chambers had been drinking copious amounts of alcohol on the night of the crime, and the Levins sued the owner of Dorrian's Red Hand for serving the clearly worse-for-wear killer. This case was settled in 2009.

Per Today, Jennifer's mother Ellen Levin has gone on to devote her life to fighting for victims' rights, and has been instrumental in passing New York's rape shield laws. Unsurprisingly, she still doesn't much care for Chambers. "As far as I'm concerned, he doesn't exist to me," she's said. "I thought it was outrageous that he got more time for selling drugs then he did for killing Jennifer."

Robert Chambers in popular culture

The Preppy Killer case was an extremely high-profile one, and as People and Bustle tell us, it has influenced a number of artists in many ways. Apart from a fitting mention in Bret Easton Ellis' transgressive yuppie killer novel "American Psycho," the case received its own TV movie, "The Preppie Murder" – as well as a 2019 docuseries called "The Preppy Murder: Death in Central Park." On the more fictional side of things, Season 5 of HBO's prison drama "Oz" features a very Robert Chambers-like character called Adam Guenzel, who was indeed inspired by the man, and goes through a series of very, very unfortunate events during his time in the Oswald State Correctional Facility. Both "Law & Order" and "Law & Order: Criminal Intent" have also drawn inspiration from the case. 

Per the BBC, the case has even made it to the land of music. Apart from a Sonic Youth track called "Eliminator Jr.", The Killers (pictured) based no less than three songs on the Preppy Killer: Their 2004 songs "Jenny Was a Friend of Mine" and "Midnight Show," as well as the 2007 "Leave the Bourbon on the Shelf."