Robert Chambers: The Preppy Killer

Summary

Morbid: Episode 665 - Robert Chambers: The Preppy Killer

Host/Author: Morbid Network | Wondery
Release Date: April 21, 2025

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Introduction

In Episode 665 of Morbid, titled "Robert Chambers: The Preppy Killer," hosts Ash and Alaina delve into the tragic and complex case of Robert Chambers, a young man from an affluent background who was convicted of the brutal murder of Jennifer Don Levin. This episode explores the intricate details of both the victim's and the perpetrator's lives, the events leading up to the crime, the subsequent investigation, trial, and the lingering questions surrounding the case.

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Backgrounds

Jennifer Don Levin

Jennifer Don Levin was born on May 21, 1968, in Port Washington, New York, to Stephen and Ellen Levin. Raised on Long Island's North Shore, Jennifer was known for her independence and charm. As Alaina notes, Jennifer "insisted on doing things for herself," showcasing a strong-willed and resourceful nature from a young age (06:18).

Jennifer attended the Baldwin School in Manhattan after her parents' divorce, where she thrived academically and socially. Despite her affluent upbringing, she maintained a distinctive personality, preferring adult contemporary music and embracing a healthy vegetarian lifestyle early on (08:30). Her charisma was evident; Ellen Levin remarked, "she just made people smile by just walking into a room" (07:34).

Robert Chambers

Robert Emmett Chambers Jr., born September 25, 1966, in Queens, New York, was the only child of Phyllis and Robert Chambers Sr. Raised initially in a working-class neighborhood, the family later moved to the Upper East Side. Despite attending elite prep schools like York Prep on scholarship, Robert felt socially isolated due to his modest financial status compared to his peers (12:40).

Robert's upbringing was marked by emotional distance from his parents, who prioritized education over emotional support. This environment contributed to his internal struggles and eventual descent into substance abuse. His involvement in the Knickerbocker Grays, a prestigious drill team, highlighted a facade of social success that concealed his growing sense of entitlement and insecurity (16:22).

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Events Leading to the Crime

Both Jennifer and Robert navigated affluent social circles characterized by parties, casual relationships, and substance use. Jennifer, though maintaining responsibilities like her job at Fluties, began prioritizing partying over academics and work, leading to strained relationships and declining performance (26:02). Similarly, Robert's life spiraled as his drug addiction intensified, leading him to engage in criminal activities such as theft and vandalism (27:19).

Despite brief periods of rehabilitation, Robert's inability to maintain sobriety resulted in recurrent legal issues, including burglaries and drug possession. By the summer of 1985, both individuals were grappling with personal turmoil, setting the stage for the fateful night at Dorian's Red Hand (29:38).

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The Night of the Murder

On August 25th, Jennifer and her friends planned a final night out before Jennifer moved to Boston. Concurrently, Robert had his own plans, intending to meet a new date at Dorian's Red Hand, a popular Manhattan bar. The two paths collided when Jennifer, hoping to reconnect with her ex-boyfriend Brock Pernice, approached Robert at the bar.

Jennifer, described as "very flirtatious and definitely outgoing," immediately sought out Robert (36:43). Throughout the evening, Robert appeared distracted and disengaged, leading to tension. At one point, Jennifer, frustrated by his lack of attention, threw a bag of condoms at him and stormed out (38:05).

However, their interactions continued. Jennifer insisted on meeting Robert outside the bar, leading them into Central Park. Robert's account of the incident is fraught with inconsistencies. He claimed that Jennifer became aggressive during their encounter, resulting in a struggle that led to her accidental death (42:30). Notably, Jennifer's defensive injuries, including a swollen left eye and scratches on her face, contradicted Robert's narrative of a brief and accidental altercation (49:44).

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Investigation and Trial

Defense Strategy

Robert Chambers faced charges of second-degree murder and manslaughter, with his defense attorney, Jack Lippman, advocating an insanity plea. Lippman's strategy focused on portraying Jennifer as the aggressor, suggesting that Robert acted in self-defense during a forced sexual encounter. Quotes from the trial reveal attempts to undermine Jennifer's character, such as highlighting her assertiveness and his own unintentional involvement (52:14).

Media Portrayal

The case received extensive media coverage, often sensationalizing the social status of both the victim and the accused. Articles emphasized the elite lifestyles of Manhattan's wealthy youth, inadvertently fostering a "victim-blaming" narrative around Jennifer's actions and Robert's privileged background. This portrayal contributed to public polarization and influenced perceptions of the case (54:12).

Trial Proceedings

The trial lasted 13 weeks, during which intimate details of Jennifer's life were scrutinized to support the defense's narrative. The jury ultimately became deadlocked after nine days, unable to reach a unanimous decision. This impasse led to a plea deal, with Robert pleading guilty to manslaughter in exchange for a reduced sentence of five to 15 years in prison (67:31).

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Outcome and Aftermath

Robert Chambers was sentenced to 15 years for manslaughter, serving his full sentence and facing subsequent legal issues related to substance abuse upon his release in 2003. Despite his plea, the Levin family felt justice was not fully served, expressing deep frustration over the plea deal that resulted in a manslaughter conviction rather than second-degree murder (72:26).

The case left lingering questions about the true nature of the altercation and the influence of socio-economic status on legal outcomes. Ellen Levin, Jennifer's mother, criticized the judicial process and the portrayal of her daughter, highlighting the broader implications of privilege and justice (74:21).

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Host Discussion and Reflections

Throughout the episode, Ash and Alaina express their dismay at the inconsistencies in Robert Chambers' accounts and the ethical implications of the defense's strategies. They emphasize the tragic loss of Jennifer's life and the enduring pain experienced by her family. The hosts critique the media's role in shaping public perception and the systemic issues that allow individuals from privileged backgrounds to evade full accountability for their actions.

Notable Quotes:

• Alaina: "I feel like you're arguing two very different points at the same time." (58:02)
• Ash: "The Preppy Killer is very tasteless." (79:54)
• Alaina: "Nothing you can say can bring someone back." (76:42)
• Alaina: "You shouldn't have to slit-shame a dead girl." (71:53)

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Conclusion

Episode 665 of Morbid presents a chilling exploration of privilege, accountability, and the tragic consequences of personal failings. Through detailed storytelling and critical analysis, Ash and Alaina uncover the multifaceted dimensions of the Robert Chambers case, leaving listeners to ponder the deeper societal issues highlighted by this heartbreaking event.

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Notable Quotes

• Jennifer's Independence: “Her first thought was, how can I make the money to get it, not buy it for me.” – Arlene Levin (06:53)
• Robert's Characterization: “I just realized it was a dead end.” – John Tolenko (19:31)
• Defense Argument: “He did not have to chase girls. They chased him.” – Jack Lippman (52:22)
• Family's Frustration: “Robert Chambers has literally gotten away with murder.” – Arnold Dominic (67:31)
• Judge's Statement: “Robert Chambers entered his sentencing with a statement of remorse.” (74:07)

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References

For further insights into Robert Chambers' psychological profile, Candice DeLong, a retired FBI criminal profiler, invites listeners to explore her episode on Killer Psyche. Additionally, for updates and more episodes, listeners are encouraged to join Wondery Plus for ad-free access and early listening privileges.

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Note: Timestamps correspond to the original transcript provided.

Transcript

[Ash]

Hey weirdos, it's Ash here. Ready to share a little secret. Have you heard of Wondery Plus? With ad free episodes and one week early access, it's like having an all access pass to our lighthearted nightmare. So come join us on the dark side and try Wondery Today. You can join Wondery plus in the Wondery app or in Apple Podcasts or Spotify.

[Alaina]

You're listening to a Morbid Network podcast.

[Candice DeLong]

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[Ash]

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[Candice DeLong]

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[Ash]

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[Ash]

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[Ash]

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[Ash]

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[Alaina]

Hey, weirdos. I'm Alaina.

[Ash]

I'm Ash.

[Alaina]

And this is Morbid.

[Ash]

This is Barbie Do. Hi, everybody. Hello. What's up?

[Alaina]

Not a lot.

[Ash]

No. No. Oh, I haven't checked on my Finch today. Oh. Oh, my God.

[Alaina]

I'm like, 30 days into my Finch, so we're really rocking and rolling.

[Ash]

Yeah, I'm like, 20. I think today's day 28. I'm. I'm gonna have to have you take the mic for me.

[Alaina]

Yeah, let's start today. Well, my finch is in Sydney, Australia, so.

[Ash]

Mine is in Taipai.

[Alaina]

Hey, guys, in Australia, if you see my finch, Gatsby walking around there, tell them I said hi.

[Ash]

Well, big ang. My finch said, I can't decide. Is it better to be super strong or super fast? Ooh, I think super fast. I mean, whatever you feel super fast. She says, I wish I was fast. That would mean the yellow cat that chases me would never be able to keep up with me. And she got 6.1 points for security.

[Alaina]

A.

[Ash]

She's a queen bee. This isn't sponsored. I genuinely needed to check in on my Finch life.

[Alaina]

I'm saying she's all set. Yeah, you can't just.

[Ash]

Siri. I'm not talking.

[Alaina]

Siri's like, I'm sorry.

[Ash]

She's like, I can't check in on your Finch. You have to. And I'm like, well, I did, guys.

[Alaina]

I hope you. I mean, I talked about this, like, weeks ago. The Finch app.

[Ash]

Yeah.

[Alaina]

I want to know if you guys did it.

[Ash]

Did you do it?

[Alaina]

Did you do it?

[Ash]

What's your. Finches.

[Alaina]

Just yell it really loud and I'll listen.

[Ash]

Oh, they did?

[Alaina]

Okay. Yeah, a lot of you did. I heard ya.

[Ash]

Yeah, somebody. Oh, Larry. We have a Larry.

[Alaina]

Larry. Thank you for trying.

[Ash]

Yeah. No, no. They named their finch Larry.

[Alaina]

I don't know. Oh, I thought it was Larry who tried it. No, I'm sure we have a Larry who may have tried it as well.

[Ash]

Maybe.

[Alaina]

I don't know.

[Ash]

I believe you. I'm just.

[Alaina]

We just finished watching season six. Yeah.

[Ash]

Final episode of Buffy. If you listen to the rewatcher, you know how we feel about season six.

[Alaina]

Yeah.

[Ash]

I left the room during the season.

[Alaina]

Six finale, so we're feeling type of way right now.

[Ash]

I faked a walkout.

[Alaina]

Yeah, it's true.

[Ash]

If you want to.

[Alaina]

She did like a. She did a Housewives style walkout. I did a reunion.

[Ash]

I did. I really did. But I came back and that's all that counts. If you want to hear our extra thoughts on all of Buffy. Cuz the beginning seasons of Buffy are fantastic. And we've had so much fun talking about it. And we've even had fun talking about this season. If you listen to the Re watcher, you should. We're about to end season six and go into season seven. So I have a whole new season adventure awaiting me.

[Alaina]

Join us.

[Ash]

All right. I have a bummer of a case today. We were talking, I think the last time we got together, maybe we were talking about David Carpenter.

[Alaina]

David Carpenter. The Trailside Killer.

[Ash]

The Trailside Killer. And that was just like a very. It was riddled with misjustice. Injustice, if you will.

[Alaina]

Misjustice.

[Ash]

I like that. Ms. Justice Mischief Dragon was in here, but she left.

[Alaina]

Yeah, she left halfway through that case.

[Ash]

She did, yeah. This is another case where justice is interesting.

[Alaina]

Oh, okay. Okay.

[Ash]

All right. We're going to be talking about the preppy killer, Robert Chambers, who killed Jennifer Don Levin, and we're going to talk about that entire case. So Jennifer Don Levin was born May 21, 1968, in Port Washington, New York. Her parents were Stephen and Ellen Levin, a realtor and a homemaker. Jennifer and her older sister Danielle were raised on Long Island's North Shore, Pretty much a haven for wealthier families who wanted, like, quiet home life kind of vibe, but still have access to the city.

[Alaina]

That makes sense.

[Ash]

I love Long Island. Even though she came from a wealthy family and she really didn't want for a lot, Jennifer insisted on doing things for herself when she wanted anything. Like if she wanted a new Walkman or new clothes, anything like that. She didn't go to like, oh, let me go ask my parents. She figured out how she could get it without their help.

[Alaina]

Yeah.

[Ash]

And she.

[Alaina]

So she's like, she's an independent woman.

[Ash]

She is, yeah.

[Alaina]

She's getting her shit done.

[Ash]

She did. And like at an early age, too.

[Alaina]

Yeah.

[Ash]

Her stepmother Arlene Levin said her first thought was, how can I make the money to get it, not buy it for me? Which I love.

[Alaina]

I love that. Yeah.

[Ash]

It's fantastic.

[Alaina]

That's honestly such a rare, like, viewpoint for such a young person, you know, to be like, well, I'll figure out how to get it myself. Usually it's just like, well, mom and dad won't do it.

[Ash]

That wasn't my viewpoint point. But in 1973, when Jennifer was five years old, her parents did end up divorcing Stephen. Her father moved to an apartment in Manhattan. And Ellen stayed on Long island with Danielle and Jennifer. Despite the separation, Jennifer and her sister managed to remain close to both their parents. And they even developed a good relationship with a few years later with Steven's new wife, Arlene. Ellen, Jennifer's mom, said about Jennifer, she just made people smile by just walking into a room.

[Alaina]

Oh.

[Ash]

Which is like you could feel that.

[Alaina]

Yeah.

[Ash]

And her charm and affection wasn't just limited to friends, just not limited only to family. Once, just before she was scheduled to take her driving test, she talked a Manhattan cab driver into teaching her how to parallel park. Iconic.

[Alaina]

What a savvy, savvy person. That is wild.

[Ash]

And like picture a Manhattan cab driver.

[Alaina]

Yeah.

[Ash]

They don't have time for your.

[Alaina]

No, they're always like on to the next.

[Ash]

Somehow she had the charm to be like, listen, I gotta, I got a test coming up and I gotta.

[Alaina]

Can you help me out here?

[Ash]

Yeah, help me, man.

[Alaina]

I love that.

[Ash]

So after finishing junior high on Long island, she moved in with her father and her stepmother in Manhattan, mostly so that she could attend the Baldwin School, which was a private high school on New York's Upper west side. According to Arlene Levin, Jennifer's desire to attend private school was as much a matter of fear as it was anything else. She actually believed all urban public schools were dangerous places. She was very afraid to go to public school.

[Alaina]

Oh, okay.

[Ash]

Which I don't. Maybe at the time it was like a little bit rough. I'm not positive.

[Alaina]

Yeah. I don't know how like in that area, how they are now.

[Ash]

Yeah. I'm not sure.

[Alaina]

Yeah.

[Ash]

But anyway, she thrived at Baldwin School and quickly developed her own really independent personality. She wasn't really your typical teenager. Her friends and classmates mostly kind of gravitated toward pop music and television. But Jennifer herself preferred adult contemporary music. And she said that she'd rather work out than watch tv. And she also became a vegetarian at a pretty young age just for the health benefits.

[Alaina]

Damn, she sounds cool as hell.

[Ash]

She does sound cool. I want to be her friend.

[Alaina]

Yeah.

[Ash]

Now. Also, unlike her peers who relied mostly on their parents for money. As soon as she was able to, Jennifer got a part time job as a hostess at Fluties, a bar in lower Manhattan. I feel like I don't know if I've been there, but I've definitely heard familiar. Yeah, right.

[Alaina]

It really does.

[Ash]

I don't know if it's like from something, but her manager said never once did I see her come to work with anything but a smile. More. On her job at Fluties later. There's like another anecdote in my tail here. But when it came to romance and relationships, Jennifer, who had been voted best looking in her senior class.

[Alaina]

Oh, Jennifer.

[Ash]

Snap, snap. She was pretty non committal. You're in high school, you don't need to be committal.

[Alaina]

Exactly.

[Ash]

So when she started dating in her junior year, she spent a lot of time with Brock Pernice, a student at York Prep, which is an elite prep school. Pretty similar. Similar to Baldwin.

[Alaina]

That sounds fancy as hell.

[Ash]

Pretty much all of them are fancy as hell.

[Alaina]

Anything prep sounds like. Whoa.

[Ash]

I always think that.

[Alaina]

Yeah.

[Ash]

Now, Brock said Jennifer was a really cute girl. Fun, happy, go lucky. She loved the club scene and she was very innocent. I took her to a Billy Idol concert on our first date.

[Alaina]

Oh my God.

[Ash]

Yeah, that's what a sick ass first date. And then he said, but it wasn't until weeks later that I first kissed her at the Peppermint Lounge. And then I couldn't leave her. Oh, it sounds like he really, really liked her a lot. It's, it gives me butterflies.

[Alaina]

Wow.

[Ash]

Yeah, it's, it's very like young love.

[Alaina]

Brock surprised me because to be honest, the name Brock, like it's fair, gives me pause sometimes.

[Ash]

We're conditioned.

[Alaina]

I don't.

[Ash]

From a certain time, I was gonna.

[Alaina]

Say I've been conditioned, but actually, two.

[Ash]

Television shows where my Reba fans at.

[Alaina]

Yeah. So it's like. I, I, I love that. I love that about Brock.

[Ash]

I do too. Now, around that same time, Jennifer and her friends all managed to get fake IDs.

[Alaina]

Whoa.

[Ash]

You gotta. You are a New York Upper East Sider. Don't do that. I'm not telling you to, but I'm just saying retroactively, you had to.

[Alaina]

Retroactively, yeah, of course.

[Ash]

So they became regulars at Dorian's. Red Hand, great name for her.

[Alaina]

Wow. I love that.

[Ash]

Yeah. It was a Manhattan bar popular with college students.

[Alaina]

Damn.

[Ash]

Now, even though she was dating Brock Pernice at the time, Jennifer also started casually dating a couple of the guys that she met at Dorian's. Because remember, you can do whatever the fuck you want to do.

[Alaina]

Yeah.

[Ash]

And she's casually dating. She's in high school.

[Alaina]

Yeah, it's. It's high school.

[Ash]

It's high school. It doesn't matter at all. But that included a short period where she dated Robert Chambers, a guy who had attended York Prep with Brock himself.

[Alaina]

Whoa.

[Ash]

Now, I also feel like guys date multiple women all the time, and it's hard.

[Alaina]

You don't even need to feel like that, that's. That's reality. That's just a fact.

[Ash]

And it's never a part of the story. No, but as soon as a girl dates multiple guys, it becomes part of the.

[Alaina]

It becomes part of her personality, part of her character, part of every facet DNA that's goes on her, you know, resume.

[Ash]

Like it's normal to date around and find out what you like and who you want to hang out with. And like, you're. You're not dating to marry in high school. And if. I mean, maybe you get so lucky that you meet that person that you're going to marry.

[Alaina]

But. Yeah, I wish I had dated, like, more different people in high school.

[Ash]

I wish I had dated less people.

[Alaina]

Than the same person that I dated for all of high school.

[Ash]

Yeah, you heard.

[Alaina]

Yeah, but with purd, you know? Yeah.

[Ash]

But I support this. And it. I'm harping on it because it becomes a major aspect of this case and it pisses me off. Yeah, she gets. She gets very much railroaded for it. Yeah. So let's talk about Robert a little bit. Robert Chambers.

[Alaina]

Sure.

[Ash]

Robert Emmett Chambers Jr. Was born September 25, 1966, in Queens, New York. He was the only child born to Phyllis and Robert Chambers Senior, a nurse and an employee for mca. For the first few years of his life, the family lived in the working class neighborhood of Jackson Heights, and then they actually moved to a more upscale neighborhood in the Upper east side. Oh, I just can't, like, hear the Upper east side without thinking of Gossip Girl.

[Alaina]

I think of Cruel Intentions. Oh, I'm the Marcia fucking Brady of the Upper east side. And sometimes I want to kill myself. That's a direct quote, not me movie.

[Ash]

Yeah, I love that movie. I'm gonna go watch that later.

[Alaina]

She's a icon in that movie.

[Ash]

She's so good in that movie. So honestly, so scary. Everyone is so good in that movie.

[Alaina]

Oh, everyone's a plus in that. That movie is a plus. The fact that they tried to remake it. Don't get me started.

[Ash]

I think they're actively remaking it into a TV show right now.

[Alaina]

Yeah, stop. Because you can't. You can't remake that. You can't bottle.

[Ash]

Stop.

[Alaina]

You can't bottle that time.

[Ash]

No, you can't.

[Alaina]

In that kind of cast. You cannot bottle that so good.

[Ash]

Like, you just can't. And just the.

[Alaina]

It's got Tara Reid in it. You can't. What are you doing? Trying to make that again?

[Ash]

I always forget that terror.

[Alaina]

She starts the whole damn thing.

[Ash]

She sure does.

[Alaina]

Hell yeah.

[Ash]

Oh, My God. Her crying scenes are always the best.

[Alaina]

That movie. That movie is in my DNA.

[Ash]

It's a retweet. Me too. I cry every time.

[Alaina]

Oh, my God. When she's going up the escalator.

[Ash]

Yeah. Oh, and the end when she drives across the bridge.

[Alaina]

Black and egg white.

[Ash]

Oh, my God. We've gone on too long. So the Upper east side, period.

[Alaina]

Yeah, sorry. That's what makes us think of that.

[Ash]

By a lot of accounts, Robert's parents were, in a lot of ways, pretty hands off. And they were kind of emotionally unavailable. Like, they struggled to provide the best education for him. That was a. That was a drive that they had. But they didn't really support him, like, emotionally and, like, they didn't support his social development.

[Alaina]

They just wanted the best education. But they weren't thinking of, like, making.

[Ash]

Him a well rounded individual. Exactly. They were very focused on education, which is great. Great.

[Alaina]

Yeah.

[Ash]

But there's more aspects of a child's upbringing.

[Alaina]

There's definitely more to life.

[Ash]

Yeah, exactly.

[Alaina]

More to a human.

[Ash]

Yeah. Now, he would be portrayed by the press, interestingly, later in his later years, but Robert Chambers background was a lot more modest, actually, than it appeared throughout a lot of his life. He attended elite prep schools, but his mom worked nights as a nurse in order to pay for his tuition.

[Alaina]

Oh, wow.

[Ash]

And her income rarely covered the entire tuition. So the fees he were covered by, like, a scholarship. He was there on scholarship and by his mom's hard work.

[Alaina]

His mom sounds like a badass in that retro in that respect.

[Ash]

She does. Definitely.

[Alaina]

Really Working her ass off for a kid.

[Ash]

She was. Yeah. And his status as one of the least wealthy kids in school usually made him feel kind of inferior. Socially isolated. Think Dan Humphries.

[Alaina]

I was just gonna say this sounds very, like, written by a showrunner.

[Ash]

It does. You know, it's. It's very. That.

[Alaina]

Yeah.

[Ash]

But the thing was, even though he felt that way, like, internally, outwardly, he seemed pretty popular. He had a lot of friends. His classmates liked him. So this was very much an internal struggle that he was going through.

[Alaina]

Okay.

[Ash]

But outside of school, he was an altar boy at the family's church. He was a member of the Children of the American Revolution, which is always interesting. It always makes me think of Gilmore Girls.

[Alaina]

It always makes me think of that.

[Ash]

And he was an officer in something I've never heard of before, but gives very American Revolutiony vibes. And he was an officer in the Knickerbocker Grays, which is a drill team for children of wealthy New York Families.

[Alaina]

That doesn't even sound real.

[Ash]

I know.

[Alaina]

That sounds like something somebody made up.

[Ash]

It does.

[Alaina]

To make me feel stupid. Maybe they'd be like, this is a real thing.

[Ash]

Maybe they did.

[Alaina]

Wow.

[Ash]

Well, Phyllis, his mom, served as the board president of the Grays at the time.

[Alaina]

Wow.

[Ash]

And she told a reporter, it's a very tough world out there. A boy who receives this training is less likely to fall by the wayside later on. The Grays teaches what society should be about. The niceties of life.

[Alaina]

Wow.

[Ash]

It's very, like, pinkies up.

[Alaina]

Yeah. See, I'm. I'm psyched about my kids knowing karate.

[Ash]

There you go.

[Alaina]

And how to, you know, beat the shit out of someone in the throat. There you go. But, like, I guess, yeah, different jokes for different folks, different vibes for what's important, I guess.

[Ash]

I think you should go be the president of the Knickerbocker Grays.

[Alaina]

Personally, it sounds wild. I'm looking it up right now because I just never heard of this.

[Ash]

I had never heard of it before either.

[Alaina]

I mean, the good News is their 142nd season is starting. A lot of seasons.

[Ash]

I didn't realize they had seasons. Yeah, apparently, it's like a team.

[Alaina]

This is very interesting.

[Ash]

It is. Well, like I said, Robert might have felt like an outsider, but the messages he got from his peers pretty much contradicted his self image entirely. Like I was just saying.

[Alaina]

Yeah.

[Ash]

He was six'four he weighed 220 pounds. He's sturdy guy. He was very popular with the girls, and they were all drawn to his, quote, shy and secretive charm. Oh, yeah.

[Alaina]

Secretive charm.

[Ash]

I don't know. It was a different time. So the combination of his sense of inferiority and the overwhelmingly positive encouragement that he got from his classmates resulted in him becoming the kind of guy with a chip on his shoulder.

[Alaina]

Ah.

[Ash]

Like 100%. And a very huge sense of entitlement also.

[Alaina]

Oh, I could. Yeah, I could. I could feel that vibe starting to come.

[Ash]

He's giving, like, tortured poet.

[Alaina]

Oh, yeah.

[Ash]

Without writing poetry.

[Alaina]

See? And let me just, like, quick little thing. Secretive charm is never charming unless his secret is he's like a vampire. Like, that's the only.

[Ash]

And even then, that's a little messy.

[Alaina]

That's the only. Like, a real vampire.

[Ash]

Like, that's legit, baby. Legit.

[Alaina]

Yeah. You never want secrets. It's not a good. Good thing to go after.

[Ash]

Yeah, no, no. See, secretive charm isn't really, like, a descriptor. I've heard before.

[Alaina]

Secret. Secrets are no fun.

[Ash]

Secret secrets hurt someone. But he started to deal with his insecurities by engaging in some casual drug use. Casual. Casual. And other illegal activities like petty theft and vandalism.

[Alaina]

Very casual.

[Ash]

You have to deal with your secret charm in a certain way. Soon his grades began to slip. He lost his scholarship, which is real shitty because his mom worked her ass.

[Alaina]

Off, I was gonna say.

[Ash]

And he was also kicked out of school. Oh, yeah.

[Alaina]

Damn. Yeah, you buried that lead.

[Ash]

So your secretive charm didn't get you anywhere, bud. This increasingly destructive behavior even took a toll on his relationship with his oldest friends. His closest friend at the time, John Tolenko, said, I just realized it was a dead end. One night, a group of us were hanging out at this bar on East 85th Street. I remember thinking how pathetic the conversation was. We were just joking around in this cynical matter manner that we have. But I had stopped drinking a few weeks before, and I couldn't relate to it at all. I stood up and told them to go to hell and walked out.

[Alaina]

Whoa.

[Ash]

This whole thing is like a TV show slash movie.

[Alaina]

It is. It's very dramatic.

[Ash]

Yeah. Looking back, John Delingo said that, you know, he wished he'd been more honest with Robert and tried to help him make some kind of positive change before it was too late. But hindsight's 20 20.

[Alaina]

Yeah. And that's not totally up to everybody else.

[Ash]

No. And also, he's a teenager, so he doesn't have all the resources that he needs to make Robert better, you know?

[Alaina]

Exactly.

[Ash]

But thankfully, Robert was able to enroll at York Prep, a new school. But it was with the understanding that he would get his life together, work hard to graduate, and get into a good college. It's unknown whether he maintained good grades during his senior year at York, but what is clear is that his drug use unfortunately did not stop. Actually, if anything, it got worse. Throughout that year, he got in trouble for alcohol abuse. He developed a very serious cocaine habit. And that cocaine habit affected almost every part of his life, of course, as it does. But somehow, even with all that going on, he did manage to get accepted to Boston University. Yeah. In large part, according to one former friend, because of his high test scores.

[Alaina]

That's a good school, man.

[Ash]

That's a great school. It's very impressive.

[Alaina]

Yeah.

[Ash]

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[Ash]

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[Ash]

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[Ash]

So after his graduation from York in 1985, so he did graduate, he moved to Boston.

[Alaina]

Boston, I was gonna say yeah.

[Ash]

And he started the year in Boston University's Basic Studies program, which basically it Was established by the school to help students who struggled social or emotionally during high school.

[Alaina]

Oh.

[Ash]

Which is really cool.

[Alaina]

I didn't even know that was the thing.

[Ash]

Yeah. So the new city and the supportive program work. This big chance for Robert to start over and establish some new, more responsible habits.

[Alaina]

Yeah.

[Ash]

Get his life back on track.

[Alaina]

For sure.

[Ash]

And that's a big chance. You get into Boston University and you get this, like, kind of like. I don't want to say hand holding, but. But for lack of a better term. And you, like, you got to do the most with that. You gotta do the most with that. Unfortunately, he did not.

[Alaina]

Oh.

[Ash]

He fell back on old habits. And according to his friends, he, quote, used the school as an excuse to party and hang out.

[Alaina]

Oh, what? That's such. And it's like, why bother?

[Ash]

I'm sure that program was beneficial for so many other people.

[Alaina]

That's the thing. Who didn't get to use it because you took their spot.

[Ash]

Yeah, like. And. Exactly. But like, that pisses me off.

[Alaina]

Yeah. Somebody who would have actually used it.

[Ash]

Yeah. Like some. Maybe somebody who didn't get into it. Or even there was people there that probably like. Yeah, exactly. So after just one semester at Boston University, he was kicked out of the program for academic reasons and just returned back to his parents in New York, where it seemed like. Yeah, it seemed like he picked up right where he left off there. His father was away on business trips a lot, and his mom was still working nights at the hospital. So he spent a lot of his nights at the bars, at the clubs in Manhattan, just acting basically like he was still in high school with no responsibilities whatsoever.

[Alaina]

Awesome. Yeah.

[Ash]

Fantastic. Now, Jennifer, on the contrary, by the time she had reached her senior year up Baldwin, she started having difficulties with her parents. According to friends, Jennifer had moved in with her father and her stepmother not only to attend Baldwin, like I was saying, but also for the added discipline that she felt that environment would offer.

[Alaina]

Okay.

[Ash]

One journalist wrote, though she was close to her mother, she told friends that her mother was more of a friend than a parent, which. That can be difficult. And that relationship might not have provided the structure that she was looking for. But it seems like life with her father and her stepmother in Manhattan also left a lot to be desired in a different way. Friends remembered that she constantly resented her stepmother, and that often led to fights with her father or with her father and stepmother.

[Alaina]

Oh, man.

[Ash]

Yeah. One of her close friends said, she used to call me in tears and come sleep over at my house because of fights with her dad. They were just about the usual things. Coming home late, cleaning her room, getting her priorities straight. But she never really felt comfortable living there, which is sad. It's also, I think, a very common problem amongst teenagers.

[Alaina]

Well, I was gonna say it's also very teenager. Yeah, like angsty teenager.

[Ash]

Yeah. And also, I think, like, having divorced parents, like, you leave one house because it's not super desirable and you think the other house is going to be this great place where nowhere's perfect. Yeah, nowhere's perfect. Exactly.

[Alaina]

Yeah.

[Ash]

But like Robert Chambers, Jennifer did also turn to substance use and partying as a kind of escape from the pressures that she felt at home. It doesn't seem like she developed the same addiction problems that Robert was going through. But her desire to party oftentimes outweighed her responsibilities like school and work, which.

[Alaina]

Again, very typical of a lot of teenagers.

[Ash]

Yeah, this is exactly who I was, like, 100%. And obviously the fact that she's prioritizing, partying over school, over her responsibilities at work and home, it's resulting in bad grades and probably some more tension at home.

[Alaina]

Yeah.

[Ash]

According to Daniel Kimball, the principal at Baldwin, Jennifer was a, quote, good, average student. She probably wasn't expecting to get into Harvard or Yale, but she was studious and responsible enough to get accepted to some very reasonable schools or, excuse me, respectable schools. Now, for her friends, who knew her best, the change in her personality started right around the summer of 1985. At that time, she was working actually at a boutique in the Hamptons. She wasn't actually working at Fluties yet. And she was spending more and more time with some new friends that she'd met in the club scene.

[Alaina]

Okay.

[Ash]

You can imagine probably not the best influences. Brock, her first boyfriend there, said. Said. I remember when I met her, she was a little Miss Innocent. I saw her change grow up real quick in the city. Yeah, he said the unchained. The. The change was unwelcome and pretty disappointing.

[Alaina]

Oh, man.

[Ash]

He said, I tried to do other things with her, like, other than go to the club.

[Alaina]

Yeah.

[Ash]

He said, we went to the theater, formals, restaurants, but she always had to go by Dorian's. That's where our friends were.

[Alaina]

Oh, man.

[Ash]

Yeah. So remember, these are like very, very wealthy kids with literally no adult supervision whatsoever. Oh, yeah. So they were living like adults. Yeah, but they didn't have the emotional maturity that usually comes with age, which is very like.

[Alaina]

I'm not trying to be, like, silly here when I say it's very Gossip Girl esque, like, you know, like the Whole, like kids living very adult lives, having very adult drama. Yeah, but in like a kid's setting.

[Ash]

And it comes with adult problems and, you know. Yeah, exactly. A close friend said, we act like we were adults. Most of us have credit cards, we all drink, we all fool around, have flings, like, truly very gossip.

[Alaina]

Yeah. Straight up, like Sex and the City style. Like.

[Ash]

Yeah, but these are kids.

[Alaina]

But kids.

[Ash]

So that summer, while she was still seeing Brock, Jennifer again casually dated a few different guys, like I said, including Robert Chambers, who was also working on the Hamptons that summer. And their social circles kind of overlapped with each other's. Nothing really came of the brief relationship with Robert Chambers, actually. But for Brock, it was the beginning of the end. That winter, he and Jennifer broke up for the first of what would be short, several short breakups before finally ending things for good a few months later. And Jennifer wasn't the only one struggling to find her place. In 1985, after he got kicked out of Boston University, Robert Chambers life was spiraling out of control. It was a very slow spiral at first, I think when he left school. But then things really started gearing. Gearing up. Oh, he managed to find work at like some low paying jobs. He actually even took a few college courses at Hunter College. But his drug use was overtaking everything. It was becoming his biggest priority. Yeah, he wasn't really hurting for money. But that fall he fell in with a group of young guys from wealthy families who just broke into people's houses around the city for fun.

[Alaina]

Oh, cool.

[Ash]

Yeah. You know, as. As groups of young men do, just.

[Alaina]

You know, just kids being boys being.

[Ash]

Boys, guys being dudes. Yeah.

[Alaina]

Guys being bros. Yeah, that's casual. Yeah, that's fine.

[Ash]

They stole jewelry, other expensive items like that, just for fun.

[Alaina]

Yeah.

[Ash]

An acquaintance of his, of Rob.

[Alaina]

Like the Bling Ring.

[Ash]

Yeah, I know, honestly. Yeah, it really does. An acquaintance of his said, we went out to dinner in America once and he pulled out a credit card that wasn't his and joking, jokingly said, should I use this tonight?

[Alaina]

What the.

[Ash]

No, you douchebag. What the.

[Alaina]

But this is so entitled, like, spoiled rich kid behavior.

[Ash]

It's very cliche.

[Alaina]

Yeah. Like this part of it, like that's. It's very like what you think spoiled rich kids in Manhattan are gonna be. You know, it's got like, not necessarily what they are, but like, this is very, what, atypical. It's very typical of what you would think.

[Ash]

Yeah, it's very stereotypical. Yeah, it's very like clueless bling Ring Gossip Girl. Like, it's got all of those vibes. Even remember the Sex and the City, like, prequel that they did? I don't think you watched it. Yeah, it was a banger. I think it only got, like, one or two seasons. I loved it.

[Alaina]

I'm a purist.

[Ash]

I get it.

[Alaina]

No sequel, no reboot.

[Ash]

No, I get it. The. The prequel was pretty good, though, and it reminds me.

[Alaina]

Yes.

[Ash]

But anyway, as the year went on, so did Robert's excessive drug use and now theft. Before long, he moved on from stealing from strangers to just straight away up stealing from people he knew, like his friends. On nights when people. When Robert had been at their homes, his friends and acquaintances would notice that money had gone missing.

[Alaina]

Wow. Which is like, if he's willing to do it to people he doesn't know, of course he's going to start doing it. Like, you can't trust that.

[Ash]

But that's such a big escalation.

[Alaina]

It is.

[Ash]

Like, stealing in general is so up, and stealing from strangers is up. Stealing from your friends is up on a whole other level.

[Alaina]

Of course, it is wild.

[Ash]

But at popular hangouts like Dorian's Red Hand, even the customers frequently complained to management that money and credit cards were going missing from their pocketbooks, their coats. And a lot of times, people knew that it was Robert, but they just didn't want to confront him because, you know, he's this, like, wealthy kid. He comes from a good, wealthy family, so there was rarely any consequences, but everybody knew what he was doing.

[Alaina]

Yeah. And he was just allowed to get away with it.

[Ash]

Yeah. Now, that spring, he went to Palm beach to visit some friends, and while he was gone, his mother was cleaning up his bedroom, and she found evidence of his ongoing drug use. And she called. This is actually really smart. On her behalf. She called him, and she said he needed to come home immediately because somebody was sick.

[Alaina]

Whoa.

[Ash]

But when he turned home, it turned out they were having an intervention for him, like, he was the one who was sick. And a few days later, he did agree to go to a drug rehab facility. He went to Hazelden foundation in Minnesota, and he spent the next month there detoxing and learning the skills that he would need to, you know, stay clean once he got back home. But I think that's so smart, the way she did that.

[Alaina]

Oh, yeah, of course it is.

[Ash]

Made sure he got home.

[Alaina]

And she's not lying.

[Ash]

Yeah. Someone.

[Alaina]

Because she's saying someone's sick.

[Ash]

Yeah. You know, so he went to rehab. He cleaned up. He spent a month there. He came Back to New York from Minnesota in late May of 1986 and enthusically announced that he had kicked his cocaine habit for good and he was ready to start fresh.

[Alaina]

Wow. I mean, sounds good.

[Ash]

Yeah, it would have been exciting, but here we are talking about it.

[Alaina]

But here we are. He's on morbid, so it's not good.

[Ash]

He actually even found work as a painter. He was a caretaker for his neighbor at this time. But a lot of people around him who are closer to him were questioning how he was actually doing. A close friend said, in a way, he was too positive. Most people, when they got out of rehab are realistic, but Rob always wanted to think that he could handle anything. And it soon started to become obvious to those again, close to him, around him more frequently, that he was still struggling. And he started drinking again in no time and then smoking pot. And then it escalated.

[Alaina]

Oh, man.

[Ash]

Meanwhile, Jennifer had also started making major changes in her life. In late spring, she spent some time visiting colleges in Boston.

[Alaina]

Boston, Boston, baby.

[Ash]

And she eventually applied and was accepted to Chamberlain Junior College, which is a school with Mount Ida. I feel like people talked about Mount Ida all the time around here.

[Alaina]

Yeah.

[Ash]

So many people go there.

[Alaina]

Yeah, everyone goes there.

[Ash]

Everybody. Mount Ida, Mount Ida. When she got back to New York, she found. That was when she found her part time hostess job at Fluties.

[Alaina]

Oh, okay.

[Ash]

And according to friends, the job interview at Fluties actually didn't go as well as she hoped it would. But like she had so many times before, her charm just worked for her and eventually she won them over.

[Alaina]

I love it.

[Ash]

Her friend Betsy remembered she had to wait three or four hours for an interview, which I'd leave at that point.

[Alaina]

So like, good for her, seriously.

[Ash]

And when the guy saw her, he told her she wasn't right for the job. So she grabbed him by the shoulders and told him she was great with people and about all the jobs she's had. She had had selling and made him fall in love with her. And she got the job.

[Alaina]

Wow.

[Ash]

Yeah.

[Alaina]

Jennifer sounds like such a badass.

[Ash]

Like a hot ticket.

[Alaina]

That's exactly what she sounds like, you know? Yeah.

[Ash]

And like, imagine having that chutzpah at that age, like grabbing the man by his shoulders and being like, no, I got this, dude. She's.

[Alaina]

She sounds. Sounds to me like I'm like a. Like a young Blanche Devereaux.

[Ash]

Yes.

[Alaina]

You know, like she's got that vibe to her where she's just like, it, I can do it.

[Ash]

Yeah. She's a straight shooter.

[Alaina]

She's a Sass master. I like it.

[Ash]

She is. So things were looking up for her at this point. Her future was very bright. Everything was on the up and up. But things were not going as well for Robert. All through the summer, he kept telling his friends and family that he was working on getting his life back on track. He was going to enroll in courses at Columbia. But by the end of August, he hadn't enrolled in any classes, hadn't found a permanent job. He was also stealing from friends and acquaintances again. Everybody was like, oh, he's backsliding and this is not good. And it was not. On the evening of August 25th, Jennifer and some of her friends decided to go out to Dorian's Red Hand for one last night out on the town. She's going to be leaving soon. She's going to be moving to Boston, starting her new life. And as it turned out, actually, Brock had been accepted to Northeastern. So Jennifer hoped that they could reconnect and start seeing each other again.

[Alaina]

Ah, yeah.

[Ash]

It was true that she had gone on a few dates with Robert Chambers, but insisted, quote, her thing with Chambers was no big thing, just a crush. Nothing at all like the serious relationship she had with Brock. She was really hopeful.

[Alaina]

I really. I like Brock.

[Ash]

I do, too.

[Alaina]

Okay, good.

[Ash]

Yeah, I do, too.

[Alaina]

I was like, tell me I can like Brock.

[Ash]

I only know very minimal things. But what for what I do know, I know.

[Alaina]

I like.

[Ash]

Yeah. Now, that night, Robert Chambers had made plans also to meet up with a girl that he'd been dating for a short time, and they decided to go to Dorian's Red Hand together again, like I said, very popular spot. They had been there a few hours by the time Jennifer and her friends arrived just before midnight, and everybody had been drinking. Despite her stated desire to reconcile with Brock, Jennifer was still pretty excited when she saw Robert that night. And she told friends, apparently, that she, quote, wanted to go home with him later. Remember, they dated before. Yeah, casually. She was excited about the future, but she still wanted to live it up and have, you know, one last hurrah before leaving the city. I get it.

[Alaina]

Why not?

[Ash]

According to Larissa Thompson, one of the girls that Jennifer had been out with that night, Jennifer, quote, immediately made a beeline for Robert's table when she saw him at Dorian's and seated herself at the table. One of the customers at the bar said she was very flirtatious, definitely outgoing. Robert Chambers, on the other hand, was distracted, it seemed, and occasionally even disinterested. People said he chatted with Jennifer for a little bit but at multiple points throughout the night, he would just get up and walk away, only to return a short time later, which to me says something. Something.

[Alaina]

It says.

[Ash]

Yeah, it says a break.

[Alaina]

Maybe some stuff's going on.

[Ash]

Lots of people go to New York bathrooms for this.

[Alaina]

They do. Just as. I mean, they yell about it on Housewives Seasons.

[Ash]

They do, I think. What are people doing in your bathroom?

[Alaina]

Yeah.

[Ash]

Now, when asked about his mood that night, Robert explained that he was depressed about a friend from rehab who had recently died. Who knows?

[Alaina]

Yeah.

[Ash]

Whether it was his emotional upset or his interest in talking to Jennifer, he spent most of the night ignoring the girl he was on a date with.

[Alaina]

Wow.

[Ash]

So finally, after an hour had passed without him speaking to her, she approached the table that he was sitting at and threw a bag of condoms in his face and told him he could, quote, use these with someone else, because you're not going to get the chance to use them with me. Me. And stormed out of the bar again.

[Alaina]

Wow.

[Ash]

Is this like.

[Alaina]

I'm like, what?

[Ash]

That's a. That's a queen move right there.

[Alaina]

So that's wow.

[Ash]

Like, wow. If your date is ever ignoring you, do that.

[Alaina]

Yeah. If I saw someone do that slow clap. I would talk about it for the rest of my life.

[Ash]

For the rest of my life.

[Alaina]

That would be the first thing I brought up. Any new person I met, I'd be like, can I tell you this crazy thing that I saw? Yeah, yeah, Absolutely.

[Ash]

I would.

[Alaina]

Yeah. Most people forgettable. That girl, not forgettable.

[Ash]

Well, the date's theatrical exit from Dorian's was also a great opportunity for Jennifer because, you know, she wanted to hang out with Robert that night.

[Alaina]

Yeah.

[Ash]

So now this girl's not on her way.

[Alaina]

Well, she left.

[Ash]

So she wasted no time settling in next to Robert at the table. But for all her directness and enthusiasm, for some reason, she wasn't comfortable propositioning Robert directly. Like, I get that. You don't want to be like, you want to get out of here, man.

[Alaina]

Yeah. And, I mean, he's just had a bag. A literal bag of condoms thrown at him.

[Ash]

Yeah.

[Alaina]

In public. Yeah.

[Ash]

He might be.

[Alaina]

So that might have made it a little weird.

[Ash]

It probably did.

[Alaina]

Yeah.

[Ash]

Yeah. So instead, she had a friend ask him to meet her outside of the bar. The friend later said he just tilted his head like, she's driving me crazy, and said, I don't think so. I don't want to deal with it. Which is rude. Go tell her that yourself.

[Alaina]

Yeah.

[Ash]

Now, he might not have wanted to meet Jennifer outside the bar. But that definitely didn't mean that he was uninterested. Because when Jennifer's friends left Dorian's a little past 2am they remembered seeing her still sitting at a table with Robert and engaging in what appeared to be a very serious conversation.

[Alaina]

So what the.

[Ash]

Yeah, they're clearly, like, carrying on.

[Alaina]

Yeah.

[Ash]

So a little before 4:30am Several more friends saw Robert and Jennifer get up from the table and leave Dorian's headed in the direction of Central Park. A friend said usually she'd come over and give me a big hug and tell me she'd call me tomorrow, but this time she didn't. I remember she looked sort of mellow, putting her jacket over her shoulder, pulling her hair, and crossing the street like there was no problem. So she didn't seem, like, agitated or, like, upset, anything like that. She seemed fine with Robert.

[Alaina]

Yeah.

[Ash]

But it was a little weird that she didn't say goodbye to anybody. Like, it wasn't like her.

[Alaina]

Yeah.

[Ash]

So that's why it's pretty unclear why the two of them did go into the park that morning. Because they did go into Central Park. Friends of Jennifer's insisted that she would. She wasn't the type of person who would have wanted to have sex outside, because that's ultimately the story that gets told.

[Alaina]

Oh.

[Ash]

And several friends of hers were like, no, she wouldn't do that.

[Alaina]

Yeah.

[Ash]

That's not her vibe at all.

[Alaina]

That doesn't make sense.

[Ash]

And also, remember, she's like. Like when I was saying earlier that she didn't want to go to public school. She has a fear of danger in, like, dangerous situations.

[Alaina]

Yeah. She's not reckless.

[Ash]

Yeah. So she wouldn't have gone into that park if she didn't feel like she was safe with Robert Chamber. So she very clearly did. Did. But this wasn't the first time that Robert had brought a girl into the park for a romantic evening. In fact, a few weeks earlier, he brought another date there, and friends said that the park held special meaning for him. So it's possible he hoped bringing Jennifer there would be a similarly romantic experience.

[Alaina]

Well, it's like, that doesn't line up with, like, how he was acting earlier.

[Ash]

No.

[Alaina]

Unless that was just, like, directly from the girl, like, throwing a bag of condoms at him.

[Ash]

Yeah, maybe.

[Alaina]

Maybe he was just like. Like, thrown off for a minute.

[Ash]

Maybe.

[Alaina]

I don't know.

[Ash]

But he was also weird, too.

[Alaina]

It all sounds weird.

[Ash]

The night itself seemed like nobody was really acting. Yeah. How they typically would have.

[Alaina]

Yeah.

[Ash]

But I feel like that happens when these kind of things happen. Even though you don't know that, like, something awful is gonna happen, it can be like, in the air sometimes.

[Alaina]

It's just like some kind of tension happening.

[Ash]

Yeah, exactly. So Robert and Jennifer entered the park around 4, 4:50 in the morning at an entrance near the Metropolitan Museum of Art. What happened next is only known to Robert himself. And he has changed his story multiple times over the years.

[Alaina]

Awesome.

[Ash]

So nobody really knows the exact truth, but this, in my opinion, is not the truth. According to him, he was not interested in Jennifer romantically and initially actually declined to go to the park with her. But Jennifer insisted, he said. So he finally relented and agreed to join her. According to him, she was clearly interested in him and he thought that she wanted to have sex in the park. But he declined her advances and said he was interested in other people and he'd see her around. But he said she freaked out. She, like, got up and knelt in front of me and scratched my face.

[Alaina]

What?

[Ash]

Like that would have escalated so quickly.

[Alaina]

And she knelt in front of him.

[Ash]

He said she got. She, like, got up, knelt in front of me and scratched my face. Face. Which when you see the scratch marks on his face later because they are photographed, it wouldn't have been like, she scratched my face, like in a cute way or like, yeah, like they're deep scratch marks on his face. He said after that, after that happened, he got up to leave, but that Jennifer apologized and he agreed to stay and keep talking since she had apologized. And despite asking her to sit far away from him, he said she came up behind him and started massaging his shoulder. Shoulders. And he said she. She said I looked really cute and that I would look cuter tied up.

[Alaina]

Okay.

[Ash]

According to the statement that he gave police, he didn't think she was serious until she held his wrists together and using her underwear, started to tie them together. Once his hands were bound. Chambers claimed that Jennifer tried to take off his pants, but she was hurting him in the process. And he said she, quote, kind of laughed in a weird way. Like more like a cackle or something.

[Alaina]

Okay.

[Ash]

And then he said that his protests only made her more aggressive. And she started scratching his chest and his face and was, quote, laughing and giggling and making weird laughing type sounds while digging her nails into me. This is unbelievable. I. I don't believe this.

[Alaina]

I'm looking at those scratches on his face right now too.

[Ash]

They look defensive.

[Alaina]

They. Absolutely. In my opinion, in my opin opinion.

[Ash]

In my opinion, in our opinion, with.

[Candice DeLong]

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[Ash]

Like I said at the top, you're.

[Candice DeLong]

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[Ash]

That is way too late.

[Candice DeLong]

Simplisafe's active guard outdoor protection, though, can help prevent break ins before they even happen. Visit simplisafe.commorbid to claim 50% off a new system with a professional monitoring plan and get your first month free. Whoa. That's simplisafe.com morbid there's no safe like Simplisafe.

[Ash]

Why are there ridges on Reese's peanut butter cups? Probably so they never slip from her hands. Could you imagine I'd lose it?

[Alaina]

Luckily, Reese has thought about that.

[Ash]

Wonder what else they think about. Probably chocolate and peanut butter. So Robert claimed that his screams caught the attention of a nearby jogger, who eventually came over to investigate. But the jogger left the area when Jennifer insisted everything was fine. Okay, then. He claimed he could not take the pain that Jennifer was inflicting on him anymore. So he reached up and grabbed her, putting his arm around her neck and pulling hard. He told detectives it was just really quick. She flipped over and then landed and she was kind of twisted on the tree. So you flipped her over into a tree. At that point, she wasn't moving, and Robert thought that she was trying to frighten him. But when he shook her and got no response, he said he realized she was dead and walked across the park and found a place to sit on the wall where he could still see her body from that position. He said he eventually saw a cyclist enter the park, come upon the body, and then leave and return a short time later with paramedics. Once the ambulance arrived, Robert himself left the scene, went home, showered, and went to bed. Okay, three words. In what world? I. Yeah, in what world?

[Alaina]

That is.

[Ash]

World.

[Alaina]

That's a no for me.

[Ash]

That's.

[Alaina]

That's a no for me.

[Ash]

One of the most bizarre stories.

[Alaina]

That is a very. That is bizarre is the perfect way to describe that. Bizarre. Not one bit of that makes sense.

[Ash]

No.

[Alaina]

Whatsoever.

[Ash]

No, no.

[Alaina]

You're literally saying that you put your arm around her neck and like, really quick, though you made sure to say really quick.

[Ash]

Really quick.

[Alaina]

Somehow flipped her into a tree.

[Ash]

Yeah.

[Alaina]

And then she just died in the tree. Really quick. And you just knew that. That's my favorite part is I realized she was dead.

[Ash]

Yeah. Interesting.

[Alaina]

Like that. I'm sorry if that. If. If I got into a little tussle with someone and I. They just flipped into a tree, I wouldn't automatically assume that they were dead. Like, that would be. I'd be like, wow, that was weird. Let me help you up.

[Ash]

Like that would be.

[Alaina]

And I wouldn't just be like, wow, I bet you're dead.

[Ash]

And then also like, what?

[Alaina]

How did that. Like, he's just like, yeah, I just realized.

[Ash]

You realized she was dead, and then you went and sat on a bench nearby and watched somebody discover her dead body. Leave. Go get help. You watched that help arrive, and you watched her body be taken away in a body bag and in an ambulance.

[Alaina]

And then you just went home and showered and went to sleep.

[Ash]

And at no point did you intervene and tell them, like, what happened here was an accident. Like, let me.

[Alaina]

Just went to sleep.

[Ash]

Let me tell you. Interesting that you showered.

[Alaina]

That's a bonkers story.

[Ash]

It's crazy. It's a bonkers story, in my opinion. Does not line up with the way that her body was found.

[Alaina]

Very strange story.

[Ash]

Yeah. Well, later, detectives showed up at Robert Chambers apartment to question him, and then they took him to the station for further interrogation, where he gave a videoed statement to police.

[Alaina]

Wow.

[Ash]

Now let's talk about the crime scene. The crime scene was, unfortunately a pretty familiar one to investigators. A young woman found dead in the park, an apparent victim of sexual assault. Her body was slumped in front of a tree. Her shirt was pushed up. Up, and her bra was wrapped around her neck.

[Alaina]

What the.

[Ash]

At the time, they thought that she had been killed, maybe somewhere else and dumped in the park since there were tire tracks leaving the scene and somebody spotted a car around the same time that the body was discovered. But that would quickly be dismissed once she was identified. Now, the crime scene didn't yield a lot of clues or evidence, but there were obvious signs of a struggle. It appeared that she'd been physically Assaulted and hit in the face. According to the medical examiner, the left eye was swollen, discolored, and just about closed. On the bridge of the nose, there was a dark mark. Her mouth was caked in dirt and what appeared to be dried blood.

[Alaina]

Yeah. Those scratches are defensive, in my opinion. In my opinion.

[Ash]

Yep. One of Jennifer's front teeth was also loose. And there was a dark red mark around her neck from where her killer had strangled her with her bra. Bra.

[Alaina]

Wow.

[Ash]

None of that.

[Alaina]

That's not lining up.

[Ash]

None of that aligns with him swiftly.

[Alaina]

Flipping her over into a tree and how awful. Like that. This poor girl's last moments were filled with that.

[Ash]

Her front tooth was loose. That's a violent struggle. A violent struggle, yeah. According to the pathologist, the bra had been twisted around her neck, but it was also still hooked in the back. Back. So there was a possibility that her shirt and bra had been pushed up. And maybe the strangulation was an accident. But there was also, like. That is what they thought on a cursory glance.

[Alaina]

Yeah.

[Ash]

But there was petechial hemorrhaging in the eyes that indicated. Indicating that the blood flow to her brain was restricted, which would have been unlikely if it was just a matter of her bra getting wrapped around. Yeah, your bras aren't that tight.

[Alaina]

It's. We've. We've said it before. It's very difficult to strangle someone. It takes a lot minutes, a lot of, like, pressure and time.

[Ash]

Consistent pressure.

[Alaina]

Consistent pressure and cons. Yeah.

[Ash]

Yeah. So the pathologist said in court later, I thought the deceased was strangled, like, definitively. The murder and Robert's arrest, though, came as a shock to residents around New York, not only because of the brutal facts of the case, but also because of the social status of the young people involved. Jennifer's death shined a light on a social scene that few outside of it knew existed. Both the victim and her killer were not out of their teens, but the lives that they lived reflected a world usually populated by adults, like we were saying, complete with problems like addiction and violence. When asked for a comment about his daughter's death, Stephen Levin said, I have lived in New York City for 19 years, and I have hesitatingly come to the conclusion that it is no longer a fit place to live. It is a social experiment that failed.

[Alaina]

Wow.

[Ash]

It's really Sad.

[Alaina]

Damn.

[Ash]

On October 28th, Robert Chambers was arraigned on a charge of second degree murder, which is interesting.

[Alaina]

Yeah.

[Ash]

And it was during his arraignment that his lawyer, Jack Lippman, revealed The beginnings of his strategy. In his statement to the court, Lippman explained that Jennifer had been pursuing Robert for several weeks and, quote, that night, she was the aggressor. According to Lippman, Jennifer's death was simply an accident that occurred when his client was trying to defend himself against sexual assault by Jennifer Levitt.

[Alaina]

Wow.

[Ash]

Yeah. Lippman preemptively defended against accusations of rape by pointing out how popular Robert Chambers was with women.

[Alaina]

Wow.

[Ash]

He said he didn't have to chase girls. They chased him.

[Alaina]

Oh, yeah. So that. That clears it up.

[Ash]

Yeah. Attractive people aren't rapists.

[Alaina]

No, of course not. Because everyone wants to have sex with him.

[Ash]

Yeah.

[Alaina]

Because he is conventionally, according to some people, attractive.

[Ash]

Yeah, totally.

[Alaina]

Yeah, that. Totally. That checks.

[Ash]

That's a perfect argument. That's not based on opinion at all.

[Alaina]

Yeah. People don't have varying, like, attraction levels. Attraction. Attractive. Definitely not.

[Ash]

But he said that being the case, there would have been no reason for his client to pursue Jennifer, much less sexually assault her.

[Alaina]

Wow.

[Ash]

Yeah. Yeah.

[Alaina]

Wow.

[Ash]

Yep. The elite status of the defendant and the victim were completely unavoidable, though, from the moment Jennifer's body was discovered. And it was an element of the case that the press simply could not resist. In article after article, young people that made up Jennifer and Robert, social groups groups. Were discussed as distinctly different from teenagers their age. They made this a zoo. In a New York Times article, one reporter wrote, many of them are under 21 and get past the bartender with skillfully applied makeup and expensive clothing that makes them look several years older and with elaborately faked identification. It's like you're talking about women there. You're not talking about the entire social.

[Alaina]

Yeah. Group, which involves males as well, but cool.

[Ash]

So that's cool. One teenager who went to the city's hottest nightclubs and restaurants said, you walk in here, no one's gonna challenge you. It's an attitude. So they're very much making this. Putting together this picture that these kids were, like, fast, you know, that they.

[Alaina]

Put themselves in these positions.

[Ash]

Exactly.

[Alaina]

This is very much a victim blaming strategy.

[Ash]

Yes.

[Alaina]

Of. Well, what did you expect?

[Ash]

And it's not only coming from the defense, but, like, the press, everybody. Yeah.

[Alaina]

Yeah.

[Ash]

The emphasis on the expensive and out of control lives of these, you know, Manhattan's elite teenagers reinforced a growing class divide, too, across the city and confirmed what a lot of people outside of that social class believed, that there was one set of rules for rich people and another one for everyone else.

[Alaina]

Yeah.

[Ash]

So immediately everybody's polarized of Course. And that became even more apparent within days of Robert's arrest when he started getting an outpouring of support from wealthy friends and family, and also even influential figures like Archbishop Theodore Edgar McCarrick of New Jersey, who wrote a letter of support in favor for bail.

[Alaina]

No comment.

[Ash]

That was a mouthful.

[Alaina]

Yeah.

[Ash]

Yeah. There was also a noticeably gendered tone to the ways people talked about the victim versus the suspect.

[Alaina]

I'm shocked.

[Ash]

When discussing Jennifer. Many reports seem to have taken a tip from Jack Lippman, and rather than focus on the fact that she was straight up murdered, they discussed her, quote, sexual aggressiveness.

[Alaina]

Yeah, that's a cool thing to do when somebody is dead and can't defend themselves.

[Ash]

Also, how do you know? Yeah, how do you know?

[Alaina]

Well, you don't. And she's dead, so she can't defend herself.

[Ash]

And this is.

[Alaina]

That's the strategy.

[Ash]

One instance where one person is saying this about her who's also the last person that saw her alive. So, like, are we really gonna.

[Alaina]

Maybe you should question that a little bit.

[Ash]

Yeah. Okay. But Robert Chambers, on the other hand, was described in very sympathetic terms. Friends and acquaintances insisted that he was, quote, not the violent type and were shocked that he had, quote, found himself in such a situation.

[Alaina]

Oh, I love the passive use of found himself.

[Ash]

I just found myself sitting across Central Park.

[Alaina]

He just found himself.

[Ash]

I just looked around, and suddenly I was.

[Alaina]

What a nice way to say that.

[Ash]

Yeah. One headline read, friends call Robert a reluctant Romeo. Shy with girls.

[Alaina]

I hate it here.

[Ash]

Gross.

[Alaina]

I hate it here. Yeah. That is so yucky.

[Ash]

Well, and also, which one is it? Is he a reluctant Romeo, or, like your defense attorney was just saying that he doesn't have to chase girls.

[Alaina]

Yeah, that girl. Yeah.

[Ash]

And now he's a reluctant Romeo.

[Alaina]

Yeah.

[Ash]

You can't have it both ways.

[Alaina]

That. That's very much like the. The Brock Turner effect, where it's like he. You know, he lost everything. He could have been. This kid could have been, like, an amazing athlete. And it's like. I'm sorry, are we talking about. Who are we talking about here? Yeah.

[Ash]

Who lost everything?

[Alaina]

What part, victim or aggressor are we talking about? Oh, that leads me. It's very much talking about it. Like, one, this happened to him.

[Ash]

He. He just found himself in these circumstances. He didn't do it.

[Alaina]

This happened to him. And two, let's talk about his losses. Him and his losses. And what's like. What?

[Ash]

It's like he took it away from himself. In that case, one friend from Dorian said, we have to fight for Robert's rights. There's nothing we can do for Jennifer now. That's an instance of I'm.

[Alaina]

I'm gonna. I'm ahead out.

[Ash]

We think before.

[Alaina]

Yeah, we listen. Head out.

[Ash]

We listen and we judge.

[Alaina]

Yeah, I listened, and I am judging harshly.

[Ash]

There's nothing you can do for Jennifer now. I'd say there's actually a lot you could do for Jennifer now.

[Alaina]

Imagine if everybody. Imagine if everybody thought that way. When somebody gets murdered, it's just like, well, nothing we can do now. That's it.

[Ash]

Oh, that's nice.

[Alaina]

Oh, cool. Yeah, sure. Let's just move on.

[Ash]

Sure. That was great for her family.

[Alaina]

Yeah, let's blow by that. That literal life that was stopped in its prime.

[Ash]

You can't be there for her family now. No, you gotta be there for. Oh, no, you have to be there for Robert.

[Alaina]

Yeah.

[Ash]

Interesting. I don't think I get it. So the picture of Robert Chambers as this gentle giant who would never act violently or hurt anybody was just one aspect of Jack Lippmann's defense strategy. Just one day after his arraignment, Lippman also told reporters that he was now weighing an insanity plea. Huh. That's a completely different route, sir.

[Alaina]

That's interesting.

[Ash]

He said, it appears that the state of mind of Robert Chambers that led to this tragedy was completely out of character for him, and therefore an insanity plea is possible.

[Alaina]

Huh. Okay.

[Ash]

I just feel like you're arguing two very different points at the same time.

[Alaina]

Yeah, I would say that.

[Ash]

And what the press didn't know was that this characterization of Robert as innocent was completely at odds with the statements that he had given himself to police. Before giving his statement where he confessed to accidentally causing Jennifer's death, he actually denied having been there at all, which proves.

[Alaina]

Oops.

[Ash]

That he knew he was wrong. And he claimed that those scratches on his face came from his cat. Oh, I have three cats. I have three precious baby cats. First of all, they've never scratched my face. Secondly, they don't cause that deep of scratches. Like, I know cat scratches can be deep, but he has scratches all over his face.

[Alaina]

Yeah, I mean, if you look at the scratches, I wasn't there. So I can't tell you if a cat made those or not, but I would be shocked if a cat made those.

[Ash]

Yeah, same.

[Alaina]

I can tell you that.

[Ash]

Yeah.

[Alaina]

Yeah.

[Ash]

Interesting. Well, later, he deviated from that story and said, yeah, it was Jennifer, but it was like a.

[Alaina]

It's just so he even later is like, no, it actually was her.

[Ash]

Yeah, like One night, the first story, the original story, like the chronologically the first story I told.

[Alaina]

Yeah. But after he, like, later. Okay.

[Ash]

He changed his story a million times. So I just.

[Alaina]

I said one of them that's even wilder. That, like, where he's. He moved, like, from the cat to actually know it was her.

[Ash]

Yeah.

[Alaina]

Like you were really gonna try to lie about that.

[Ash]

Oh, yeah. Well, he was gonna say he wasn't even there. And then he was like, actually, I was. And I watched the entire aftermath play out as well.

[Alaina]

Like, damn. Those are two very different things.

[Ash]

Yeah, they sure are. That's a theme in this case.

[Alaina]

Yeah.

[Ash]

But a month later, in late September, Robert Chambers did plead not guilty to one charge of second degree murder and one charge of murder under circumstances evincing a depraved indifference to human life. In his statement to the press, Manhattan District Attorney Robert. I think it's Morgan Thou told reporters, we believe that either one or both of these occurred and that the autopsy showed, quote, a substantial amount of pressure had been applied to Jennifer's neck, which justified the charges.

[Alaina]

Wow.

[Ash]

On October 1, 1986, Robert Chambers was finally released from jail on $150,000 bond, which is crazy. Yeah. And that was on the condition that he report daily to Monsieur Thomas Leonard, a former teacher at the Church of the Incarceration. No incarnation, is it?

[Alaina]

Like, Monsignor.

[Ash]

Monsignor. Monsignor.

[Alaina]

Monsignor. There it is.

[Ash]

But it was during this time that the District Attorney announced that Robert Chambers was also under investigation for several burglaries that had occurred around the city, and that charges would also be added in the near future. For those, or could be. At the very least, there were a lot of delays in bringing the case to court. But finally, In January of 1988, Robert Chambers finally went to trial for the murder of Jennifer Levin. In the time between the discovery of the body and the trial, a ton of information and misinformation had been spread through the media, which unfortunately, very much worked to the benefit of the defense, for sure. Since he'd confessed to having played a role in Jennifer's death, though, it was obviously impossible for him to deny that he had killed her.

[Alaina]

Yeah.

[Ash]

So instead, Jack Lippmann's strategy was to obscure various facts about the case in the courtroom and convince the jury that Jennifer's death was the result of his client defending himself against an assault on Jennifer's part.

[Alaina]

Huh.

[Ash]

Which is just bonkers.

[Alaina]

That's truly bonkers.

[Ash]

And just, like, really up.

[Alaina]

Damn.

[Ash]

Yeah.

[Alaina]

Yeah.

[Ash]

In the courtroom, the jury witnessed the Entire videotaped confession that Robert made to the police the day he was arrested. But the problem was, it was clear that the evidence discovered during the investigation didn't support his claims entirely. For instance, the position of Jennifer's body found when she was discovered, the dirt coverage, the extent of her injuries, they were all inconsistent with Robert's claim that he had wrapped his arm around her throat in order to move her off of him.

[Alaina]

Yeah.

[Ash]

Like, again, consistent pressure had been applied to her neck.

[Alaina]

Oh, yeah.

[Ash]

It wasn't a quick move.

[Alaina]

No, it was definitely not that quick. Like, oops.

[Ash]

No. In order to defend against the obvious inconsistencies, though, Jack Lippman told the jury the tape was the unvarnished truth, but that it contained a number of obvious silly lies that one could expect from a scared teenager just adducing his client to a scared teenager.

[Alaina]

Yeah.

[Ash]

The prosecutor, Linder Linda Fairstein, on the other hand, explained that the facts made Robert Chambers account of assault almost entirely impossible. She pointed out that if the death was an accident and like I said earlier, why didn't he just go for help?

[Alaina]

Yeah, that's the thing. Why don't.

[Ash]

Years later, when she was asked about the case, she returned to that point on the Today show in 2016. She said, said he sat on the wall behind the Metropolitan Museum and watched as her body was found and as her body was taken away from the park in a body bag. And he never went over to the police and said, this is my friend. This was an accident. I know who she is. It's like they were. Like they had a history together. They very much knew each other. They were friendly, of course, to just watch and know that whatever the circumstances were, you caused that death. And he was watching.

[Alaina]

He's a. He's a white man. A rich. Well, I shouldn't say rich, but he is a. He was wealthy and he's socially in a higher echelon. White man.

[Ash]

Yup.

[Alaina]

You could have said, you know what I mean? Like, you're, You're. You're not in a position where it's scary for you to. To say that an accident happened. You know what I mean? Where some other people it may be.

[Ash]

Yeah. Like marginalized.

[Alaina]

Genuinely scary to say it because you're just not gonna be believed or immediately. It's like you are the one of the only people, you know, one of the only kinds of people that can say that was an accident. You will at the very least be considered to be believable.

[Ash]

You're so right.

[Alaina]

You know what I mean?

[Ash]

Really. Valid point.

[Alaina]

Like the. The innocent until proven guilty. It's like, that's really only the case for certain people.

[Ash]

Yep.

[Alaina]

He happens to be part of that. That kind of people.

[Ash]

Yeah.

[Alaina]

You know, so it's like the whole, like. Like, I'm like, so why didn't you. You know, like, you really. Like, that's weird. It's weird. This is. And again, this isn't even like a. This isn't even like a stranger, which would. That would be weird enough. This is somebody like, you genuinely know and cared about. Spent a lot of time with many.

[Ash]

Yeah. Many instances dated. Yeah.

[Alaina]

Like, why wouldn't. I don't know. It's just very strange to me. It's.

[Ash]

It's a very removed position to be.

[Alaina]

It. It feels that way. Yeah.

[D]

Hi, weirdos. I'm Candice DeLong, retired FBI criminal profiler and the host of Killer Psyche. If you enjoyed Morbid's coverage of the tragic murder of Jennifer Levin, known as the Preppy Killer case, you should check out my episode of Killer Psyche, where I dive deep into the psychology of Robert Chambers. I explore his troubling behavior, privileged background, and the psychological factors that led to this devastating crime. On Killer Psyche, I used my decades of experience to uncover the why behind some of the most shocking crimes in history. If you are fascinated by what drives people to commit such heinous acts, join me for a closer look into the twisted minds behind them. Follow Killer Psyche on the Wondery app or wherever you get your podcast. Wondery plus subscribers can listen early and ad free. Start your free trial in the Wondery App, Apple podcasts, or Spotify today.

[Ash]

Well, the trial dragged on for 13 weeks. And during that 13 weeks, very intimate details of Jennifer's life and sexual experiences were put on display.

[Alaina]

Which really sucks.

[Ash]

Which is ridiculous. And that was obviously primarily by the defense in order to portray Robert as the innocent victim in some terrible tragedy.

[Alaina]

Yeah.

[Ash]

And by obscuring the facts of the case and painting a picture of Jennifer Levin as sexually aggressive and assertive, Litman hoped that he could convince at least a few jurors, because that's all you need, that Jennifer's death truly was an accident, that she had attacked Robert, forced him to have rough sex, and he was just protecting himself. Ellen Levin, Jennifer's mother, said later when it happened, how she was being portrayed, how it suddenly became her fault. He was blatantly playing the victim.

[Alaina]

Yeah.

[Ash]

I can't imagine having to stand by.

[Alaina]

And that again, that it became her fault. Like, that's wild.

[Ash]

It made it. It's like, she's on trial all of a sudden. In the end, though, the defense's strategy worked. The jury deliberated for nine days before reporting to the judge that they were hopelessly deadlocked. Talked. There was only four jurors convinced of Robert Chambers guilt, and the rest were in favor of an acquittal. Wow. Yeah.

[Alaina]

That's really shocking.

[Ash]

It is like it is. Ellen Levin said, I can't imagine that there was someone on that jury that thought he was a clean cut young man who would never do anything like this.

[Alaina]

Damn.

[Ash]

In their note to the judge, the foreman indicated that there was actually three jurors who, quote, could not go on because of the mental and emotional strain. And another juror indicated that, quote, votes in the jury room had swayed violently back and forth. So at least there was like, they were very clearly considering there was some.

[Alaina]

Like, passion behind, you know.

[Ash]

Yeah, they were considering both sides.

[Alaina]

Yeah.

[Ash]

But. But ultimately came to a very interesting decision.

[Alaina]

Yeah.

[Ash]

So whatever the case, the deadlock jury is usually always. And was in this case a bad sign for the prosecution. They weren't hopeful that a retrial would produce a different outcome. Them. So in late March of 1988, they offered Robert a plea deal. He would plead guilty to one charge of first degree manslaughter in an exchange for a sentence of five to 15 years in prison.

[Alaina]

Wow.

[Ash]

Just like nothing. But he had no better options, so he accepted the deal. And before accepting the plea agreement, the judge asked Robert Chambers whether he, quote, intended to cause serious physical injury to Jennifer Levin on the morning of her death. Death. And in response, Chamber said, looking back on everything, I'd have to say yes. But he insisted that, quote, in his heart, he still had not intended to injure. Injure Ms. Levin physically.

[Alaina]

Huh.

[Ash]

So he said yes, but no.

[Alaina]

Yeah, but no.

[Ash]

Yeah, like what? But not really. Looking back, I'd have to say yes, but, like, not in my heart.

[Alaina]

But not in my heart. Like, okay, well, that doesn't really help us here.

[Ash]

That doesn't make any sense to anyone. But in reality, it was revealed in a press conference later that day that Robert Chambers statement was a prerequisite of the agreement. Of course, a spokesperson for the Levin family said one of the big things was hearing him say that he had intent. Still, the plea was a disappointment to the rest of the family, who not only lost a daughter, but also had to watch as she was slandered during the trial. Her grandfather, Arnold Dominic, I believe, said, I can sum up my feelings in eight words. Robert Chambers has literally gotten away with murder. Murder. Wow. Yeah. As far as the family was concerned, the inability to secure a murder conviction was the result of Jack Lippmann's strategy. It absolutely was.

[Alaina]

Yeah.

[Ash]

Her grandfather said Lippman predictably tried his case in the press in which he aimed to malign and character assassinate the victim, reaching the depth of degradation by terming a young girl's simple date book as a sex diary.

[Alaina]

That's all. I. I understand, again, that this is like a job. I understand the whole thing, but, like, that tactic, to me, it's shitty. Is like dirty pool. Like, that is just. I don't know. Like, I don't see the integrity in that.

[Ash]

No.

[Alaina]

As a strategy. I just don't. If you can. If your case is strong, you shouldn't have to malign somebody who's dead's dating history. Yeah.

[Ash]

I completely.

[Alaina]

You shouldn't have to and like to do that. I just. This is just. Me personally, I think it's yucky.

[Ash]

I do, too. Because again, there's.

[Alaina]

If you can win the case. Win the case.

[Ash]

There's a lot of routes to go down.

[Alaina]

Yeah.

[Ash]

And he himself, clearly, he had two routes that he could have gone down, but he picked one.

[Alaina]

I just think it's yucky. And especially when somebody can't be there to defend themselves.

[Ash]

Exactly.

[Alaina]

Like, I don't. I don't know.

[Ash]

And when that person was murdered.

[Alaina]

Yeah.

[Ash]

No matter what, that person was murdered.

[Alaina]

Exactly. That's the thing.

[Ash]

It's up. And that's due to the family. It puts the family through a whole other layer of trauma. And one.

[Alaina]

No one's private life like that should be splashed around for their family to hear.

[Ash]

No.

[Alaina]

When they've been murdered.

[Ash]

Right.

[Alaina]

They have had the ultimate injustice done to them. And now you're adding on to it. Yeah.

[Ash]

It's injury.

[Alaina]

Like, I. I don't know. Like that. Just like having. I don't know. I don't get it. I think it's. I. I understand it's a tactic. I understand that defense attorneys have to do things, but, like, of course. And I understand it's a job and it's a valid job and all that. Don't worry about it. But that particular tactic just doesn't do it for me. I don't get it. I just think if you can win your case, win it some other way.

[Ash]

Agreed. Agreed.

[Alaina]

If it's a good case, you'll win it some other way.

[Ash]

Agreed. Completely.

[Alaina]

Without having to make, like, slut shame a dead girl.

[Ash]

Yeah. Well, in April, Robert Chambers went before the judge for Sentencing. And when asked whether he had anything to say, he told the judge to Jennifer, nothing I can do or say will ever bring her back. And I'm sorry. The Levin family has gone through hell because of my actions. And I'm sorry. For two years, I've not been able to say I'm sorry, and I wish to have my feelings known. The judge sentenced Robert Chambers to 15 years in prison for manslaughter with a minimum of five years and another sentence of 15 years for those burglary charges, with those sentences to run concurrently.

[Alaina]

Damn. Yeah.

[Ash]

So I. The judge was like, I got you. Yeah.

[Alaina]

He was like, okay.

[Ash]

Robert Chambers started his sentence at the Shawagung, I think is how you say it, correctional facility in Ulster County, New York. And it didn't take long, unfortunately, before his addiction issues returned. When he came up for parole in 1993 and 1994, the parole board flat out rejected his bid for parole, and they cited unsatisfactory behavior in prison, including his involvement with drugs.

[Alaina]

Wow.

[Ash]

Because people say all the time there's more on the inside than there even is on the outside.

[Alaina]

Yeah. Which is wild to think about.

[Ash]

Yeah. Two years later, after being transferred to Greenhaven Prison, Chambers was again denied parole due to, quote, the nature of his offense and poor disciplinary record. Oh, so he was not doing well.

[Alaina]

Damn.

[Ash]

After repeatedly being denied parole, Robert Chambers gave an interview to the press where he described himself as a political pawn and a victim of a state administration that was determined to keep him in prison. Which is like, No, I think if you just, like, maybe tried good behavior, it could work out for you.

[Alaina]

Yeah. It's like, I don't. I don't know about that.

[Ash]

But he wasn't about that life.

[Alaina]

No, not about that.

[Ash]

In 1997, he told the parole board. To be honest with you, I wasn't even going to come in today. I'm at a point where I'd rather just have you tell me, listen, you're gonna max out in 2003.

[Alaina]

Whoa.

[Ash]

Like, why did you go, whoa? As it turned out, he was right. He was never granted parole, and he was released in February 2003 after having served his entire full sentence.

[Alaina]

I. I mean, in part, I'm sure. Not. Not at all. From that attitude that he came in.

[Ash]

Oh. Because if I'm on the parole board and you say that, I. Yeah.

[Alaina]

I'm gonna be like, you're sitting there.

[Ash]

Cool. That's basic. Consider that a request that I am now granting.

[Alaina]

That's wild.

[Ash]

But his release was obviously unwelcome. News to Ellen Levin. She said, my concern is that from the minute he gets out of prison, he will be treated like a slave celebrity. In his own statement, Robert Chambers expressed his regret and again apologized to the Levin family. He said, there's not been a day since Jennifer's death that I have not regretted my actions on that day. I know that the Len family continues to suffer her loss and I am deeply sorry for the grief that I have caused them.

[Alaina]

Wow.

[Ash]

Yeah. I mean, I mean, nothing you could say can bring someone back.

[Alaina]

I was going to say, nothing you can say can bring someone back. And that is just a. That case is like, what happened that night is so brutal.

[Ash]

Yeah.

[Alaina]

And it's like, I don't, I don't understand how you reconcile that later.

[Ash]

I just don't understand. I like, I don't understand what happened that night. And I don't think we ever.

[Alaina]

I don't understand this.

[Ash]

There's too many stories and I don't believe any of them.

[Alaina]

Yeah.

[Ash]

I have an idea. I have my own idea, obviously, that I'm not going to share because I. We don't need to get into like, opinions here, but. Yeah, but who knows?

[Alaina]

Because, you know, people, you know, people are walking around here. We don't need to insert our.

[Ash]

Well, as it turned out, Robert's freedom was to be short lived then.

[Alaina]

Oh, oh, no.

[Ash]

And people are walking around, though. In 2005, just two years after his release from prison, he was sent back after pleading guilty to possession of heroin. He was released in 2008, only to be arrested yet again, this time for purchasing 246 grams of cocaine from an undercover police officer.

[Alaina]

Yikes.

[Ash]

Yikes.

[Alaina]

Oh, no. Have not been learned.

[Ash]

You always wonder how that hits someone.

[Alaina]

Yeah.

[Ash]

When they're like, hey, by the way, you're under arrest after selling you 246 grams of cocaine.

[Alaina]

That's got a. That's a bad day.

[Ash]

That's a lot of cocaine, dude.

[Alaina]

Bad day.

[Ash]

Yeah.

[Alaina]

Wow.

[Ash]

Yeah. Well, after initially intending to go to trial, which I'm like, what were you, what? Robert and his lawyer, they all changed their minds and they accepted a plea deal from the prosecution, where he pleaded guilty in exchange for a sentence of 19 years and four months in prison with five years probation to follow. Awesome. And on July 25, 2023, Robert Chambers was again released from prison after serving 15 years of his 19 year sentence. And he continues to claim that Jennifer's death was accidental and the result of him trying to defend himself during quote, unquote, rough sex.

[Alaina]

Wow.

[Ash]

Which I disagree with that.

[Alaina]

I. I have my own thoughts about that, but. Okay. Wow.

[Ash]

That is something.

[Alaina]

That's an unsettling one. On a different level, it is because, like, I. It kills me that, like, we will not know what happened.

[Ash]

Yeah. And it's really awful for her family.

[Alaina]

That's what kills me is like, for her family to not have any real idea of what happened except that she was brutally murdered.

[Ash]

Yeah. And they know the details. They sat through the trial. And we always say your mind fills in those blanks, of course. And it's probably worse than anything that could ever even occur.

[Alaina]

That's what's. That's what I feel so bad about is like.

[Ash]

And she was so young.

[Alaina]

Yeah.

[Ash]

She was really just about to leave the city. Like, this was her last night out on the town like that. It's just really sad. It's really sad that somebody who was working on their future was taken away by somebody who was very much not.

[Alaina]

That's the thing. I'm like, are you. Like, you're not clean here? That's the thing.

[Ash]

Like, I know it's not that simple. Like, as far as addiction goes, I'm.

[Alaina]

Not going to claim to know that.

[Ash]

Put the work in, you know, but like, especially. But all those years you have to yourself in prison to work on things.

[Alaina]

Well. And like, he did. Like, one thing you can say is, like, he was just. He's an entitled. He was an entitled guy. He's an entitled teenager. He was an entitled or absolute friend.

[Ash]

Said that like.

[Alaina]

Like, that's the thing. And it's like. And whatever happened that night, something awful happened to her. And whether it was an accident or not, it was brutal as fuck. And I just can't see.

[Ash]

I mean, remember, like, one of her eyes was swollen near shut.

[Alaina]

She had blood on her nose.

[Ash]

Her tooth was loose. She had dirt and blood cake to the side of her mouth.

[Alaina]

Her bra was pulled up around her neck. Like, this doesn't. Like, you're gonna have to explain to me more like how. Like, I don't get it. I don't understand it. My brain is not. Is not putting this onto that side of the.

[Ash]

But at the end of the day, it's on. The book says manslaughter.

[Alaina]

It's manslaughter. Wow.

[Ash]

Which must just. If I can't imagine somebody doing that to my family member and having to sit with that.

[Alaina]

That's the thing. Like, just.

[Ash]

And then to watch that person get out of prison time and time again.

[Alaina]

Well, that's. That's the worst Part like that. It's just watching someone be able to go live their life. Life.

[Ash]

Yeah. And then also on like such a silly note, having him be named the Preppy Killer.

[Alaina]

Well, that's the other thing.

[Ash]

Come on.

[Alaina]

It's like when you said that name, I was like, what? Yeah, like, you gotta be me. And weirdly, I. I didn't know this case.

[Ash]

I didn't know it either, actually. It was a Dave suggestion.

[Alaina]

Yeah, that was a. That was strange. But I. I hate when they give those kind of nicknames, like the Preppy Killer. Like, that's.

[Ash]

It's very tasteless.

[Alaina]

It is, but because it also. That's also a way of taking away some of the sting of the reality of it.

[Ash]

He's just a preppy guy. He just loves Vineyard.

[Alaina]

High society guy, you know?

[Ash]

Totally. Yeah. He's caught in the wrong place.

[Alaina]

Hate that a lot.

[Ash]

I do too.

[Alaina]

Hate that a lot.

[Ash]

Hate it.

[Alaina]

And I feel really bad for Jennifer and really bad for those who care about her.

[Ash]

I know.

[Alaina]

I agree. I hope. I hope they feel like they got some kind of justice at some point, but.

[Ash]

Hope so.

[Alaina]

But it's a little upsetting. It is, yeah.

[Ash]

Yeah. Big time.

[Alaina]

Damn.

[Ash]

But yeah, that was quite an interesting case, to say the least.

[Alaina]

Very interesting and really sad.

[Ash]

Yeah. And we will be back next episode, I think, with Listener Tales. So it'll be a nice little palette cleanser.

[Alaina]

Nice little palate cleanser, if you will. Oh, and this is the end of the episode, so hopefully you're still here. Hi. If you are seeing on Spotify, we're just gonna start opening episodes with this and. And possibly closing with this as well. Honestly, if you are seeing a bonus episode designation on Spotify, we don't have. We don't have bonus episodes. We don't have anything behind a paywall like a bonus episode or anything like that. That's a Spotify issue. They did something like an update with their system or something like that. We have been begging to get that removed, but it's across the board, I guess, like an update that happens and they have yet to be able to remove it. We don't have any bonus episodes behind a paywall, nothing like that. What you are seeing as quote, unquote, bonus episodes that look like they're locked. I think it shows you like that it's locked or something like that. What those are, is they're showing our Wondery week early episodes as bonus episodes behind a paywall, which is not what they are. It's a very misleading thing. It's Very frustrating. We understand why that would be. Like, what the fuck? Like, where are these bonus episodes and why are they behind a paywall?

[Ash]

Just know that, like, they're not podcasts. I listen to have the same thing going on.

[Alaina]

Yeah, it's. It's across the board. It's not just our podcast.

[Ash]

You gotta scroll a little bit, find the available one, or listen on a different platform.

[Alaina]

Yeah. You know, if you. Wherever you. You know, this is. I think this is a Spotify issue only. So if you go to other platforms, you're not gonna. Like, I listen on Spotify too. So I don't like shitting on Spotify. But, like, but if it bothers you to see that the fake bonus episode that doesn't exist, like, you can go somewhere else to listen to it.

[Ash]

Go tell them. Because we know that. Yeah, let them know that.

[Alaina]

It's, like, really misleading because, like, we want it taken down as well. Because it's. We have been getting a lot of feedback that you guys think that we're, like, putting bonus episodes behind a paywall. And I promise you we're not. We will never do that. We're never gonna put bonus episodes behind a paywall.

[Ash]

No.

[Alaina]

Like, it's just not something we're gonna do where it, like, shows up in your feed as, like, oh, you wanna listen to this? Go pay money. Cause it's not in our real feed.

[Ash]

Like, not our vibe.

[Alaina]

That's not the vibe. So I promise you we'll reiterate this at the end, beginning of the next few episodes too. Just because I want everybody to know that, like, yeah, it's not. It's not a bonus episode by end of paywall. It's just not promise. So, yeah, with all that being said.

[Ash]

We hope you keep listening and we hope you keep it weird, but not so weird that you think that we do bonus episodes, because we don't even do bonus episodes. Those are not even locked by.

[Alaina]

A bonus episode would be free. Like Tobias's Toby Sa.

[Ash]

Foreign. If you like morbid, you can listen early and ad free right now by joining Wondery plus in the Wondery app or on Apple Podcasts. Prime members can listen ad free on Amazon Music. Before you go, tell us about yourself by filling out a short [e-mail] survey.

[E]

Some people get a wild haircut or book a spontaneous trip when life throws them a curveball. But Molly, well, she dove headfirst into a world of no strings attached sex, secret rendezvous, forbidden affairs, and unforgettable adventures. And together, we tell every juicy detail in Dying for Sex, Wondry's award winning podcast that's now streaming on a TV near you, starring Michelle Williams and Jenny Slate. And to top it off, we're dropping brand new bonus episodes where I sit down with the cast to spill all the spicy secrets, desire, friendship, self discovery and the ultimate bucket list of pleasure. This is a story that had everyone talking. Listen to the original Dying for Sex and brand new episodes on the Wondry app or wherever you get your podcasts. You can binge the original series before anyone else and completely ad free on wondryplus.