Jennifer Levin & The Preppy Killer Murder

Explicit content: sexual details of the crime

The morning of August 26th, 1986 began just like any other for 34 year-old securities trader, Patricia Riley. She was cycling through Central Park, near the Metropolitan Museum of Art, around 6am, when she came upon a body lying off in the distance. The body was that of a nude, young female, arms and legs spread out, with her clothes pulled up around her neck. There were also cuts, bite marks & bruises all over her body. After discovering the body, Patricia Riley’s next actions were to find a working payphone to call 911. This was the mid-80’s after all, and although the first commercial cell phone was released in 1983, it also cost $3995, the equivalent to just over $10k in 2021. so needless to say, not many could afford one at this price. Also, side note, it was a Motorola DynaTAC 8000X, and for its price could only hold 30 mins of talk time and store 30 numbers! Not exactly a great value at this price.

Anyway, back to Patricia. She did find a working payphone, and called the police to report the body. While she was waiting there for the police to arrive, she saw a tall man standing under some trees in the distance, wearing khaki pants. Once police arrived on scene, she believes she saw the same man about 40-50 feet away watching everything unfold, from a crouched position, arms positioned around his knees. I imagine it was like he was hugging his knees. Patricia would later testify that the reason this man stuck out to her was because unlike many other people in Central Park on that, or any other morning, he didn’t seem to be in a rush to get to work, or to anywhere, and “he had no dog, no briefcase”. Basically, he didn’t fit in as the typical park patron at this time of day.

Jennifer Levin as a child. (Source: SundanceTV / https://www.washingtonpost.com/entertainment/tv/in-resisting-the-allure-of-a-killers-good-looks-preppy-murder-series-restores-some-dignity-to-his-victim/2019/11/11/41687f3a-ff48-11e9-8501-2a7123a38c58_story.html)

Given the circumstances, it didn’t take police long to identify the body, as that of Jennifer Dawn Levin, who was 18 years old at the time of her death. Jennifer was the younger of 2 daughters born to Steven and Ellen Levin on May 21st, 1968. Her parents divorced when she was young, and Jennifer lived with her mother on Long Island, until her early teens, when she decided to move to SoHo with her father, who was a real estate developer, and her stepmother, Arlene. According to friends of Jennifer, she chose to move in with her dad, not because she had a terrible relationship with her mother, it was quite the contrary. Her mother was more like a close friend than a traditional mother. Also, she expressed to those around her that she felt as though she lived in the shadow of her older sister, Danielle. So, to carve out her own path, in her own way, she decided to live with her dad. Jennifer attended Baldwin School, which was a small, upscale, private high school on the West Side of Manhattan. She was described as being a better than average student by the principal of the Baldwin School. But, Jennifer was still a teen, and with it brought daily arguments with her dad & stepmother about typical things: cleaning her room, coming home late, not having her priorities in order, and so on. It was nothing they couldn’t resolve. Even if it got to be too much for Jennifer, she would stay at a friend’s place for the night, and the next day apologize to them both. She would even leave little trinkets, or small toys around the house with apology notes on them, saying she would do better. Anyone with a teenage daughter can probably relate to this behavior. A friend of Jennifer’s, Peter Davis, probably described her best when he said,
“…she was kind of a nerd. She was much more responsible than most of us were. She was funny, loyal and down to earth. Jennifer was the type of friend who was always there for her friends. She had a lot of friends, but she always found a way to make you feel special. She was always there for everyone. She was also very self-deprecating about herself. She wasn’t afraid to poke fun at herself. She never did drugs or even drank that much. She was just a very regular person.”

In her senior year, Jennifer started hanging out with peers at a local, preppie restaurant & bar, named Dorrian’s Red Hand. The bar was located on the Upper East side of Manhattan, between 2nd Avenue & 84th Street. It has a history of serving alcohol to underage teens, so it was a popular hangout for teens her age, and was probably viewed, ironically, as a safer place to hang with friends, as New York, in the mid-eighties had seen a large uptick in the number of homicides. Now, this could be attributed to the increase of drug use that had also become more popular around this time. And I’m not talking about weed. Nationwide, illegal drug use was growing at an exponential rate, with crack-cocaine being the leader among them. Late 1985, into 1986, it was at its peak. Combine this with a police force in NYC that was forced to make cuts due to a recent recession, and you’ve got a dangerous, even deadly mix. As Jennifer Levin would soon find out.

In June of 1986, Jennifer had graduated from the Baldwin School. Despite describing herself as “street smart, not book smart”, Jennifer would be attending Chamberlayne Junior College in Boston in the fall. But before she took off to college, she was planning a summer of fun with her friends, and some fun with people she considered to be more than just friends. One such person was a young, attractive guy by the name of Robert Chambers. Jennifer met Robert at Dorrian’s Red Hand and despite having a steady boyfriend, multiple sources claim she had casual affairs with other guys her own age. Nothing wrong with keeping your options open, especially if you’re not married, or if you are in an open-type relationship. And, that’s where Robert fit into the equation. They had a few intimate hook-ups, and although Jennifer’s opinion of him was that he really wasn’t a nice guy, she still met up with him because she claimed he was good in bed. I’m sure this “bad boy” image played into the attraction she had for him. So, let’s find out a little more about our bad boy, Robert Chambers.

Robert Emmet Chambers Jr, was born on September 25th, 1966 to Robert Chambers Sr and Phyllis Chambers. His father worked at MCA Records as a video cassette distributor and later as a credit manager. His mother was a private duty nurse. After his parents divorced, Robert Jr. decided to live full-time with his mother. And, although they lived amongst NY’s elite, Robert and his mother did not share in the same level of affluence as those around them. Phyllis worked hard to be able to enroll Robert in the most prestigious prep schools, though sometimes he needed scholarships to be able to afford it. She tried to do everything in her power to give him the best upbringing. But Robert didn’t assimilate well to the upper echelon of the Upper East side’s most elite. This led to him being described as anti-social, since he was unable to socialize well with his peers, or form any “real” friendships with any substance to them. (Interesting tidbit of information. When Robert Chambers was younger, his mother took care of John F. Kennedy Jr. when he was diagnosed with bronchitis, since she was a private duty nurse. Not long after that, she was able to set up a playdate for Robert with John Jr. I wonder if she recognized that Robert was struggling even at his young age to fit in?) It was likely Robert felt and maybe even experienced comments from his peers that fact he didn’t fit in with them, not in the same way anyway. And, he compensated by partying and acting out. His grades suffered, and for all his mother’s hard work, effort, and money in trying to make his life better than her own, Robert repaid her by getting kicked out of prep school after prep school for not maintaining academic standards or for behavioral issues.

He eventually graduated and went to Boston University. But, a change of scenery didn’t change who or what Robert was. That would travel with him wherever he went, including college. So, he picked right back up where he left off, partying all the time and not caring about his grades. Only now, Robert picked up new habits, including alcoholism and drugs. After only one semester at Boston University, Chambers was asked to leave for academic reasons. Now, back at home with his mother, he continued to party, drink, and do drugs. And, when he didn’t have the money for drugs, he would either turn to small-time dealing or petty theft to fund his habit. Somewhere along the way he went to rehab. One time it was after he was caught stealing & using a friend’s credit card illegally. His mother pleaded with the friend not to press charges, and promised she would send Robert to rehab instead. This was about 5 months prior to Jennifer Levin’s death. Ok, so I was curious whether he only had one stint in rehab or multiple. I couldn’t find anything about any other times he went, but I did see that he actually skipped out on this rehab treatment early. Apparently, he was supposed to be there until September of 1986 which would have been after Jennifer was killed.

Around this same time, Robert, at 19, began dating 16 year old Alex Kapp. (If her name sounds familiar to you, it may be because as an adult, Alex Kapp played the role of one of the “meanie moms”, on The New Adventures of Old Christine. I, myself, am not familiar with the role as I didn’t watch the show. I think the show aired on CBS and starred Julia Louis Dreyfus, who I know from Seinfeld, though I didn’t watch that show either. But, since I was researching anyway, I did look it up and found that Alex Kapp played the role of Lindsay, and appeared in 88 episodes, from 2006-2010.) But at this time, Kapp was a minor, who fell for Chambers, and believing she was the only person in Chambers life, romantically, claims she lost her virginity to him. They spent a few months together and Robert would come & stay over when Alex’s parents were out of town, at her Upper East Side apartment. The night before Levin’s death was no different at first. Robert got up to leave in the middle of the night, and asked Alex for money to catch a cab. She said for him to take $5 from her wallet. However, after he left, Alex soon found out Robert had taken all of the money in her wallet, not just the $5 she told him to take. Even though she was young, she wasn’t going to let him get away with this.

The next day, August 25th, 1986 Alex Kapp invited & planned to confront Robert at, where else, the local hangout on the Upper East side, Dorrian’s Red Hand. Only it didn’t go as planned. Alex was there with a number of her friends but was anxiously awaiting for her chance to confront Robert. Unfortunately for her, he didn’t show up until hours after she expected him to, and when he did, he walked right past her and towards another group of people, including his current lover, Jennifer Levin. But this didn’t stop Alex from calling him out. She went over, shouted at him for stealing from her, and proceeded to throw a handful of condoms at him. I imagine it was quite the scene, especially in front of their friends. Robert was not amused, and was described as being very angry and embarrassed at her outburst. Jennifer, on the other hand, actually befriended Alex, and suggested they become friends and hang out together. You see, Jennifer’s relationship with Robert was casual, and so for her, seeing Alex confront him, knowing they also had a sexual relatioinship was not an issue for her. But for Alex, she loved Robert, and was under the impression he wasn’t dating anyone else but her. Now whether she thought that from things he said or not, I don’t know. She was 16, young, inexperienced, and likely this was her first real “relationship”, and I say that with air quotes around it. So, it is entirely possible he did take advantage of her, just as it is entirely possible she created it all in her head.

Unsurprisingly, Robert didn’t leave with Alex that night. Instead, just after 4am, which is the time bars close in NY, on August 26th, 1986, he left with Jennifer Levin. And, Jennifer wanted to leave with Robert. This night at the bar was her last get together with her friends, and likely Robert before heading off to junior college in Boston. Jennifer said goodbye to her friends, and headed off towards Central Park with Robert for one last rendezvous. Little did she know, the term “one last” would have a totally different meaning that morning for her.

Jennifer Levin photo. (Source: SundanceTV / https://www.washingtonpost.com/entertainment/tv/in-resisting-the-allure-of-a-killers-good-looks-preppy-murder-series-restores-some-dignity-to-his-victim/2019/11/11/41687f3a-ff48-11e9-8501-2a7123a38c58_story.html)

Something went wrong, very wrong in fact. What could or should have been a romantic hook-up one last time, led to the discovery of Jennifer Levin’s partially nude body just hours later, by our cyclist, Patricia Riley. See how we’ve come full circle now? The NYPD detectives investigating the murder of Jennifer Levin, didn’t have a difficult time trying to pinpoint what happened, or a suspect for that matter. Friends that were with Jennifer at Dorrian’s Red Hand the night before, informed detectives that she left earlier that morning with, none other than, Robert Chambers. And, that they were headed to Central Park to have sex. So, now detectives did the next logical thing, they paid a visit to Robert Chambers to see if he could shed some light on what happened earlier that morning after leaving the bar with Jennifer.

Detectives went to Robert’s home and when they arrived and saw Robert, they immediately saw his face and arms had several cuts and scratches. With that visual, and given the nature of the crime, they asked Robert to accompany them to the station for further questioning. When questioned about what happened to his face & arms, Robert told them his cat had attacked him. Not believing this to be true, detectives continued to pressure him, especially because Robert kept changing his story. Also, his cat was declawed, so that would have been impossible. His next story was that Jennifer and him were not together the whole time after they left the bar. He said Jennifer left him to go buy cigarettes at the store. Another falsity as Jennifer was not a smoker, and this was confirmed by people who knew her best. Well, they say the 3rd time’s a charm, and Robert’s 3rd attempt to explain what happened that morning is a doozy.

Robert decided to come clean to detectives about what happened between him and Jennifer at the park. Well, his side of the story anyway. Robert claimed Jennifer was the aggressor and wanted to have rough sex with him. That she used her panties to tie his hands together, behind his back, and proceeded to “masterbate” him. Supposedly, Jennifer, who was on top of him, began hurting his genitals, and he was trying to push her off of him. And during this struggle is when he accidentally strangled and killed her. So, the bites, scratches, and marks on her body were all the result of some very rough sex, according to Chambers. I want to point out that Jennifer Levin was about 5’7” tall and weighed 135lbs. Now compare that to the height & weight of Robert Chambers, who stood 6’4” tall and weighed about 220lbs. Robert went so far as to suggest to detectives that she sexually assaulted him! Detectives weren’t buying this version of the story either, and decided to arrest and charge him with 2nd degree murder.

Robert Chambers and his family retained the services of criminal defense attorney, Jack Littman. Littman was not just any old lawyer, and far from the inexperienced attorneys from the public defenders’ office. He was smart, well-educated, and well-traveled. Jack Littman graduated 1st in his class from Cornell University, with a degree in Mathematics and French Literature in 1964. By 1967, Littman graduated from Harvard Law School, and continued his education in France on a Fulbright Scholarship to study the French penal code. He attributed his love of literature, psychoanalysis, and French film, for his ability to be able to appeal to the psychology of the jury and describe his cases in narrative form. He began his career in the Manhattan District Attorney’s office and was promoted to Deputy Chief of the Homicide Bureau. And then Jack Littman decided to change sides and go to where the money was. Defending those accused of murder, such as Robert Chambers.

The trial of the People of New York vs. Robert Chambers Jr. began on January 3rd, 1988. Litman’s defense of Robert Chambers was simple, yet calculated….Smear the victim. Through countless interviews with media, Littman painted a picture of his client as the victim, and that the true victim, Jennifer Levin, was just a sex driven young woman, whose death was an unfortunate accident that occured during rough sex, because she got too rough with his client. It was literally coined the “Rough Sex Defense”. And Robert Chambers was dubbed the “Preppy Killer”. It didn’t help the prosecution that Chambers was tall, dark, and handsome. Women were attracted to him, because he dressed nicely, looked like he came from money, and photographed very well. In fact, in the time leading up to and during the trial, Robert’s face was plastered everywhere. Newspapers, magazines, television, you name the media outlet, his face was on it. His attorney continued to slander, slut shame, and describe Jennifer Levin as promiscuous, claiming she even had a sex diary that detailed all of her conquests. In actuality, this diary only mentioned Chambers a few times, and was far from being graphic or a sex diary. Litman introduced a letter from Cardinal Thomas McCarrick that described Chambers as a literal choir and altar boy. (I will also mention here that interestingly, the same Cardinal Thomas McCarrick lost his status as a Cardinal after being dubbed a serial pedofile in 2018. Not sure if Chambers was a victim of his or not. This was not explored in anything I read.)
The prosecution, led by Linda Fairstein, painted a very different picture of Robert Chambers. One of anger, rage, lack of control, who was a drug & alcohol abusing, petty thief that graduated to murder. (FYI – lead prosecutor, Linda Fairstein, is the same Linda Fairstein who is a New York Times best selling author of criminal fiction books.) Now back to Robert.

Robert Chambers Jr., second from right, leaves court with his attorney Jack Litman, left, and father, right. (Source: Charles Frattini/NY Daily News Archive via Getty Images/SundanceTV / https://www.washingtonpost.com/entertainment/tv/in-resisting-the-allure-of-a-killers-good-looks-preppy-murder-series-restores-some-dignity-to-his-victim/2019/11/11/41687f3a-ff48-11e9-8501-2a7123a38c58_story.html)

The court of public opinion was beginning to change against Robert Chambers. Female advocacy groups were protesting and taking a stand against the smear campaign that was lodged against Jennifer Levin. And, Chambers while out on bail, wasn’t doing himself any favors. A video surfaced on the network TV show, A Current Affair, that showed a home video of Robert at a party, surrounded by a group of scantily clad girls wearing lingerie. In the video, he makes a mockery of Jennifer’s death by pretending to choke himself. As if this wasn’t abhorrent enough, he then is seen playing roughly with a barbie doll until its head pops off, saying, “Oops, I think I killed her”, and then just smirks.

With the case having gone to the jury, and this information and video being out of their purview, the jury deliberated for 9 days. At the end of those 9 days, they were deadlocked, and coming to a decision one way or the other, seemed unlikely. So, the prosecutor, Linda Fairstein and defense council, Jack Litman came to an agreement on a plea bargain. Instead of 2nd degree murder, Robert Chambers agreed to plead guilty to manslaughter in the first degree and one count of burglary. For that, he received a sentence of 5 to 15 years in prison. The only solace for this lesser conviction is that he did serve the full 15 years, because of his behavior while behind bars. He was released on February 14th, 2003 and moved to Georgia to be with his new girlfriend, Shawn Kovell. Perhaps the biggest mistake Robert could have made after being released, was making the decision to move back to the Upper East Side of Manhattan with Shawn, as he soon began getting in trouble with the law once again. Only this time, it wasn’t for murder. First, it was for driving on a suspended license in 2005, where he had a short stint in jail. Only a couple years later, in 2007, Robert still was using, and to fund his habit, turned once again to dealing from his apartment, this time with his girlfriend. They were both arrested, and Robert pled guilty to the criminal sale of a controlled substance in the 1st degree and assault in the 2nd degree. He was sentenced to 19 years in prison, and his earliest possible parole date is 01/25/24, with a maximum release date of 10/15/26.

There was a made for TV movie that was televised as a 3 part series in November of 2019 depicting the events that surrounded the death of Jennifer Levin, as well as the conviction of her killer, Robert Chambers Jr. It was entitled, The Preppy Murder: Death in Central Park. In the 3 part series, they look at the details of the murder, court case, the “Rough Sex” defense, and the way the media handled the coverage of Jennifer Levin’s murder. Chambers refused to be interviewed for the documentary.

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Jennifer Levin & The Preppy Killer Murder

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