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cover of episode 176. Jennifer Levin - Looks That Killed

176. Jennifer Levin - Looks That Killed

2023/8/7
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Murder With My Husband

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Jennifer Levin meets Robert Chambers at Dorian's Red Hand Bar, a popular spot for the young and wealthy. Despite warnings about his bad boy reputation, Jennifer is intrigued by Robert.

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Hey everybody, welcome back to our podcast. This is Murder With My Husband. I'm Peyton Moreland. And I'm Garrett Moreland. And he's the husband. I'm the husband. Seems like the consensus was they don't want us to change the intro. We would never. And the consensus was they want me to have a 10 seconds. We'll agree to disagree on that one. Well, speaking of 10 seconds, I think it's your turn.

It is. I also, real quick, just wanted to remind everybody that we have a newsletter that goes out every single week, every Wednesday. We put some fun things in there, some fun random facts, some true crime stuff, some reminders, updates, everything. So if you're curious, there's going to be a link on YouTube, podcasts, anywhere you listen, and subscribe. It's free. Good 10 seconds. My turn? Just kidding. No. Did it not count as my 10 seconds? I don't got anything crazy today. I spent...

Probably four hours this morning. I woke up early because I was having some stomach issues, if you know what I'm saying. So I woke up early, dealt with that really early. And then I said, you know what? Let's go clean out the garage. So I went to the garage, cleaned everything out, threw all the trash in the driveway, called one of those companies that comes and picks up junk.

I called one of them. They came over. They grabbed all the junk. And now the garage is clean. And we put one of our cars in it. Finally. Yeah, finally. We haven't been able to put a car in the garage. That makes it sound like it was really bad. It wasn't. It's a small garage. Yeah, it's really small. Yeah, it's a pretty small garage. It's also our storage space. Yeah.

Yeah, we definitely couldn't get two cars in there. Even if it was clean, like two cars wouldn't fit. No, I'm just happy to have a garage. Me too. When I was growing up in Idaho, I had to park my car outside because, you know, there wasn't enough garage space. And, whoo!

That sucked in the winter. I bet. The first time that I went to Utah and dealt with that, I was like, get me out of this place. Yeah. It's awful. It was horrible. And if you're watching on YouTube, I currently am wearing golf clothes. It's just not like an everyday attire for me. I don't just walk around in golf clothes. Yes, he does. I do not. I'm going to play nine holes after this, so. He said. Yeah.

He said yesterday he was in his golf clothes again. Oh, wait, no, no, no. Okay, let me explain it. No, let me explain it. Let me explain it. Okay, go. Let me explain it. Okay, okay. So yesterday, okay, fine, you can explain it. Real quick, and then we got to jump into it. Okay, so yesterday he's in his golf clothes, and we get out of the car, and dead serious, he looks me in the eyes and goes, you think if you just saw me randomly, you didn't know who I was, you would think I was a professional golfer? Dead serious.

I was just thinking about it. I was walking around, you know, I was like, oh, I'm looking pretty good right now. Like I have a nice polo on, I have a nice hat, I got some nice shorts. And I was like, I wonder if like I was just walking around like, you know, like if someone goes, oh, that could be a pro golfer. Like you never know these days. Yeah. You know what I'm saying? So funny. Oh man. The consensus was no on that, by the way. My wife said no.

I said you look like you just got done working in the office. You look like you just came home from the office. Okay, great. Even better. All right, let's hop into it. Our sources this week are Wasted, Inside the Robert Chambers, Jennifer Levin Murder, By Linda Wolfe, Vulture, AETV, Good Housekeeping, Inside Edition, Hollywood Reporter, People Magazine, Ranker, History.com, The New York Times, UPI.com, ThePeopleHistory.com, and Oxygen.com. Okay, so...

You have to admit, there is nothing like young love.

Being a teenager, having a crush on someone, it makes you feel like anything is possible. Your heart has never been broken, so you just jump off. You go in full force. And when that person reciprocates, it feels like almost invincible. And this was the high that 18-year-old Jennifer Levin was riding back when she met the handsome, charming 19-year-old Robert Chambers in 1986.

What she never could have anticipated, though, was that summer crush would cost her her life.

So for today's case, I want to transport us back to the year 1986. This is where our story begins. Imagine you're passing a newsstand or catching a glimpse of the 7 o'clock news. Some of the headlines you'll see are, this space shuttle Challenger explodes just a minute after takeoff. A mishandled safety test at the Chernobyl nuclear power plant leads to disaster.

A Pan Am flight carrying 394 passengers has been hijacked heading for the United States. So a pretty big yet grim year. And amongst all the glitz and glamour of the Big Apple, things are looking just as bleak. Crime is getting worse in New York City, rising 8% that year. All eyes are on the U.S. Attorney for the Southern District of New York, who's cracking down hard on organized crime.

But no one is expecting a threat to come from a wealthy 19-year-old living in the Upper East Side. And Jennifer Levin, the girl in our story, certainly isn't. The 18-year-old Jennifer was born in Long Island, New York. But in the last few years, she'd moved to the blossoming, artsy neighborhood of Soho with her father, a prominent real estate agent. Wait, this is hilarious because I was just looking at places in New York today. I don't know why. Just, you know, it's like, oh, what if we...

move to new york never gonna happen but um soho is one of the ones that came up yeah um anyways it was like one of the top 10 places to to live in new york so jennifer attended the baldwin school which was a prestigious all-girls school in the chelsea neighborhood of manhattan and to say jennifer was popular there would have been an understatement she had dozens of friends and plenty of admirers she was bubbly outgoing even voted best looking in her graduating class

But by the spring of 1986, Jennifer was ready to get out of New York City and start her next chapter at Chamberlain Junior College in Boston in the fall. In the meantime, though, she and her friends have been spending their nights drinking and recounting old memories at a place called Dorian's Red Hand Bar, just a few blocks from Central Park on the Upper East Side. And if you are keeping track, yes, she's not of drinking age, but I...

I think if you've watched Gossip Girl, it's safe to say that most Upper East Side kids aren't of drinking age and are still drinking. - That's funny. - So Dorian's was a cozy, old-fashioned little spot that on cold nights always had wood burning in the fireplace, but it was sophisticated.

Girls came in with their best mink coats, men in their khakis and button downs. It was a place to see and be seen, particularly if you were young, beautiful, and wealthy. So over the course of 1986, Jennifer and her friends became regulars at Dorian's, getting to know many of the other people who came and went from the place. Then one evening, Jennifer spotted a young man sitting at the bar, a guy she hadn't seen at Dorian's before.

She asked her friend, who's that? He's gorgeous. His name was Robert. But Jennifer's friend sort of warns her about the guy. I guess people were always gossiping about him. Apparently he'd stolen money from some friends, broken into people's apartments, had gotten mixed up with drugs. But to Jennifer, that made him somewhat more appealing. If it were true, it meant he was a bad boy. And so she wanted to know more.

His full name was Robert Emmett Chambers, and he was 19 years old, so just a year older than her. He was 6'5", about 220 pounds of muscle with piercing blue eyes. Like Jennifer, Robert had attended fancy prep schools throughout the city. But unlike Jennifer, most of his schooling was paid for by scholarships since his mother couldn't quite afford to pay his tuition on a nurse's salary.

His mother, an immigrant from Ireland, worked hard to give Robert the life that she'd always dreamed of. With little cash she had, she spent on nice clothes for him so he could feel like he fit in at school. But Robert felt he needed more than clothes to play the part.

Oftentimes, he felt like he didn't belong at these prep schools. He thought he stood out like a sore thumb. As a result, many found him to be sort of antisocial. However, Robert's mother knew how to climb the ranks of New York's elite. And over time, she worked her way into some of the city's wealthiest families, working as a private nurse for people like John F. Kennedy Jr. and Millicent Hearst, the newspaper mogul's wife.

Eventually, this afforded her and Robert the lifestyle she always wanted. They moved from Queens to a brownstone on 90th Street on the Upper East Side. But this didn't help to solve Robert's problems. If anything, some of his bad habits became worse over time. By the time he was 13, he was sneaking into bars, drinking steadily, and using marijuana heavily. Robert was often invited to parties and seen fraternizing with girls who flocked to his handsome good looks and charm.

When he couldn't weasel his way into public watering holes, Robert found a few secret corners of Central Park to sneak drinks and do cocaine. By the time he left for his freshman year at Boston University, Robert had been accused of stealing credit cards from a friend and a teacher, as well as a few other instances of petty theft.

Perhaps not surprisingly, Robert only lasted one semester at Boston University. He was caught with marijuana in his dorm room and this time had stolen his roommate's credit card. So by the spring of 1986, Robert was back home with his parents. And that bad boy reputation Jennifer was hearing about seemed to be pretty true. She just didn't know the full extent of it yet.

In May 1986, Jennifer received her diploma, and on the night of her graduation, she and a few friends went out to celebrate, and of course, their destination of choice was Dorian's. Ever since Jennifer had laid eyes on Robert, she hadn't been able to get him out of her mind. Part of her hoped, or rather expected, to see him at Dorian's that evening, and she got lucky. She and her friend Betsy spotted him sitting at a table almost right away.

This time, Betsy, who happened to know Robert, took a seat next to him while Jennifer played it cool at the bar. When Betsy returned, she had some good news for Jennifer. Robert had told her that Jennifer was one of the best-looking girls he'd ever seen. He wanted to get to know her more, but not inside the bar. He had other girlfriends there who'd get jealous if they saw him chatting. Could she meet him outside in 20 minutes so they could talk in private?

And Jennifer was elated. By the time she came back from her first conversation with Robert, she was glowing. Just a few days later, they went on a date and had sex for the first time. At first, Jennifer worried it was just going to be like a one night stand. But after going to Boston for her college orientation in July, she returned home to a slew of voicemails from Robert begging her to call him back.

The two met up again for another date before Jennifer went on a trip to Los Angeles a few weeks later. But while Jennifer was away, Robert didn't hold out for her. He kept seeing other women. He was even spotted in Central Park with a beautiful new 16-year-old blonde also from the Upper East Side. Oh, wait. Isn't he like 20? He's 19.

When Jennifer returned to the city on August 25th, she hadn't heard much from Robert, but she knew where she could find him. So she and her friends made a point to stop by Dorian's around midnight.

This is August 26th. The bar was packed that evening when Jennifer scanned the room for Robert. After wading through the crowd of familiar faces, Jennifer made her way to the back enclosed porch area. That's when she spotted him. Those piercing blue eyes, the charming smile, sitting with a group of people that Jennifer didn't know. Rather than approach Robert directly, Jennifer sat down and introduced herself to the others at the table, talking about her trip to Los Angeles.

Meanwhile, Robert acted cold as if he didn't know her. As she talked, he just scowled and made faces at her from across the table. Jennifer could tell something was off with Robert. And after a few moments, she left him and his friends to continue their conversation without her. But about an hour later, Jennifer spotted Robert standing near the back bar alone. She figured this was her opportunity to confront him about his childish behavior, why he hadn't called her and why he pretended he didn't know her.

As they were chatting, Robert's new girlfriend, the young 16-year-old blonde, walked over and interrupted their conversation. Then she threw a bag full of condoms at Robert and yelled, you can use these with someone else. Jennifer couldn't help but laugh at the awkwardness of the situation. What?

Clearly, Robert had been playing them both, but he'd been caught in the act and now half the bar was watching. Robert was visibly embarrassed and angry, particularly at Jennifer for laughing along with everyone. So he turned a cold shoulder and didn't speak to her for much of the night.

By 2.30 a.m., some of Jennifer's friends were ready to head out, but Robert was still at the bar, and Jennifer felt there was still time to clear the air between the two of them. She wanted answers about their status one way or another. She deserved them.

By about 4:00 AM, the bar was emptying out and getting ready to close. Finally, Robert approached Jennifer and asked if she'd be interested in leaving with him. Jennifer knew she should stay strong, that she should tell him no after the way that he treated her all evening, especially after knowing that he'd been two-timing her over the last couple of weeks. She had a crush, a big one, and she only had a few more days left in New York before she'd be leaving for Boston for college.

which meant only a few more days to spend with Robert. Against her better judgment, Jennifer said yes. She threw her jean jacket over her shoulder and flipped her hair as Robert opened the door for her to leave. I think it's safe to say in the 80s, people in New York, teenagers in New York were doing it a little different than the rest of us. I also think that like while you were talking about everything, it's just so, I mean, the 80s, I mean, I guess it is kind of long ago now, 40 years ago, but-

It's just weird to think that, right? You can just call someone on a cell phone. Oh, let me call them on my iPhone. Let me see what they're doing. Let me go check their Instagram. Yeah. Right? A dating was so different. Yeah. I don't know. It's just, we didn't never live through that or experienced it. No. So it's just so interesting to... She had to get home, check her voicemails. Exactly. He hadn't called. She hears he's a grapevine. He's been running around with a blonde thing. Yep. She goes to the bar.

Like there's a confrontation. It's just different. It's like it's not that long, but it is long, but it's just foreign to us because we didn't grow up in the 80s. Did you know today is a great day to warranty? Well, actually, every day is a great day when you're not worrying about your appliances and home systems. And that's what you get with an American Home Shield warranty. With an American Home Shield warranty, unexpected breakdowns like a leaky faucet or a faulty water heater won't break the bank because covered repairs and replacements are taken care of just like that.

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So over New York City's Central Park, the sun was starting to rise the next morning around 6.15 a.m. A female cyclist riding behind the Metropolitan Museum of Art spotted something under the trees. It looked like a woman, possibly asleep. But something gave the cyclist a pit in her stomach, a feeling that she needed to get a closer look just to be sure. She got off her bike and moved towards the body. When she was about 40 feet away, her fears were confirmed.

This wasn't an unhoused New Yorker snoozing in the grass. It was a young woman, naked, aside from the clothes that had been bunched up along her neck and waist. The woman ran back to her bicycle, hopped back on, and rushed to a payphone to call the New York Police Department. By 6.21 a.m., the radios of two police officers went off with the phrase, "'Woman down at 81st and East Drive.'"

Sergeant Anthony McCulloch was one of the first to arrive at the crime scene. He approached the body, wondering if he could maybe still help her. Her neck was covered in blood, red bruises, as though she had been strangled. But McCulloch checked her pulse anyway. There was nothing.

Jeez, man.

McCulloch's gut reaction, this wasn't just a murder, it was also a rape. Meanwhile, a crowd had already begun to gather, which is so heartbreaking. Like no one should have to see, well, no one should see a victim in that scenario. I don't think I'd stop.

Like how there's a crowd gathering, I'd be like, okay, like this is not my place to be, time to be. Yeah. McCulloch couldn't think of anything else to do but grab a sheet of brown wrapping paper and drape it over the woman until other investigators arrived, which is what exactly I was just saying. Moments later, detectives from the crime scene unit secured the scene and began collecting photographs, fingerprints, hairs, fluids, and anything else that might offer up a sign of her killer. They

They also located the woman's underwear about 50 yards away from the scene. And a jean jacket lying next to the body helped confirm her identity. Inside was an expensive wallet with passes to fancy nightclubs and a learner's permit. It belonged to Jennifer Levin. As the crowd grew, watching the detectives comb the scene for clues, one familiar face stood amongst the onlookers.

A jogger, who we'll call Barbara, and her friend passed the group and stopped to see what all the commotion was about. Barbara turned to a young man, no older than 20, and asked what was going on. He said he didn't know, but the police looked like they'd found a body. Barbara couldn't help but find the young man strange. His face was covered in scratch marks. When she asked him if he'd gotten any closer to see who it was, he said he hadn't. He was worried the police would shoo him away.

Barbara and her friend continued strolling on, but her friend was also alarmed. She turned to Barbara and said, did you see the scratches on that guy's face? He looked like he'd been attacked by a machine. Eventually, the police asked the onlookers to clear the area, including that young man, who, unbeknownst to them, happened to be their number one suspect, Robert Chambers. Of course it was. Which again, I find it so strange when somebody kills someone, which I'm assuming he did.

That they go to the scene of the crime, right? Or they involve themselves in the crime. I mean, I assume it's to try to make themselves look not guilty. But, I mean, I don't know. I just think it's the opposite. It can also be like, okay, I'm not obviously a professional. But I've heard it could be a psychological obsession. For sure. This need to keep feeling that high that they got when they killed them originally. Like, oh, that was me and blah, blah, blah. Yeah. Yeah.

So he'd been lurking in the shadows for hours, waiting to see how the scene unfolded. Finally, Robert went back to his apartment to clean up his face and go to sleep, but it didn't take long for police to catch up with him.

Police quickly learned that the last place Jennifer had been spotted mere hours before her attack was Dorian's red hand and the person she'd been seen leaving with was none other than Robert Chambers. So he's their first stop on the suspect tour and when police arrived at Chambers' mother's apartment where he was still living there was one thing they couldn't help but notice. Those horrible scratch marks all over his face. When police asked how he got him he said it was from his cat. He

He was playing with it, tossing it up in the air and catching it, and it got scared and attacked him on the way down. Already, police were finding this story a bit unlikely, even more so when they learned later that the family cat had been declawed. But at this point, they were willing to let it go. They asked Robert if he knew Jennifer Levin. He said, yes, he did. Then police asked if he'd be willing to come down to the police station for further questioning. That's so funny. Do you know her? Yeah, I mean, I guess so. I just spent...

The last night with her before she died. Yeah, it was the last person to see her. Yeah, but I guess I kind of know her. Well, strangely enough, Robert happily agreed. He's like, yeah, I'll come down with you. After reading Robert his rights down at the precinct, a detective, Mickey McEntee, began the interrogation. He asked Robert more about his relationship with Jennifer. Robert admitted they had sex earlier in the summer. And yes, he'd seen her at Doreen's the night before.

but they hadn't spent much time together last night, and he certainly didn't leave with Jennifer. He claimed Jennifer had told him she was going across the street to a Korean deli to buy some cigarettes and then was maybe going to meet up with an old fling. Meanwhile, Robert said he went to a donut shop on 86th and Lexington and then went home and watched The Price is Right.

It's around now that police notice. Not only did Robert have scratches on his face, but his hands were totally cut up too. When they asked him how that happened, he said he was doing some work on a neighbor's apartment with a sander. The tool got away from him and ended up destroying his hands. Man, some bad luck. First the cat attacks his face, now the sander Fs up his hands. Well, and we like always see this. It's like how many...

I know I was last to see her, but I actually wasn't. She went and met up with another fling. Oh, I know I have scratches, but that was the sander. Oh, I know, but that was my cat. It's like... So many people don't get attorneys or lawyers. I know. It's kind of crazy to me how many people...

Well, I guess I would say it is a lot more talked about now, though. I don't know how much had this kid already gotten away with. Yeah. I mean, look at what they were already getting away with. So obviously the detective is pretty sure this guy is lying to him. But Robert didn't seem even the least bit nervous. So McKente is worried that even if Robert did kill Jennifer, he's never going to get a confession out of this guy. He's going to be a tough nut to crack.

By 7 o'clock, Robert had been at the station for four hours, and the entire time, he'd stuck to his original story. The police knew it was time to apply more pressure, which is why they brought in one of their hardest detectives, Mike Sheehan. At around 8 p.m., Mike Sheehan dropped his files down on the table in front of Robert, pulled the chair back, and took a seat across from him. His first question was, how'd you get those scratches?

When Robert stuck to his guns on the cat story, Sheehan scoffed and asked, what kind of cat do you have, a mountain lion? Now Robert's realized he's in trouble. This is the first detective to come in and kind of call his bluff. And when Robert also insisted that, no, no, no, I left the bar alone, I promise, Sheehan called his bluff again. He said some of Jennifer's friends saw you guys leave the bar together. How do you explain that?

And here's where Robert started to crack a bit. He changed his tune, claiming, okay, yeah, I did leave the bar with her. And after a little more pressure from detectives on those scratch marks, Robert finally gave in. He said, okay, yeah, these scratch marks, they're also from Jennifer. Which, right there, right? It's just like open and shut. Right. You lied. I don't know.

And that's when Robert's entire narrative shifted. So here's his new story or his second story. All right, let's hear it. After the bar closed that night, he and Jennifer walked toward 86th street. Then they decided to take a stroll through central park. He claimed they took a seat on a park bench where Robert broke things off with Jennifer said he didn't want to see her anymore. And

And that's when Jennifer started scratching up his face. He said he got up to leave, but Jennifer asked him to stay and continue the conversation. Then he insisted Jennifer grabbed him from behind and attacked him. Then she tied his hands up with her underwear, tackled him to the ground, sat on his chest and began trying to sexually assault him.

Now, I want to pause just to remind you, Robert is 6'5 and about 200 pounds. Jennifer is more than a foot shorter than him at 5'1 and 110 pounds. Oh, my gosh. Okay. I'm not saying it's not a believable story. I'm not saying it doesn't happen. I'm just saying keep all of this in mind as you're listening. I mean, it's not a believable story.

Because Robert goes on to say that Jennifer was assaulting him so badly that he had to retaliate in self-defense, that it took all of his strength, but he finally worked an arm free and grabbed her around the neck.

He said he only had his hand around her throat for a second before tossing her off him. But after a few seconds of her not breathing, he realized he'd killed her. So Robert Chambers has just admitted to killing Jennifer Levin, but in self-defense. However, detectives knew there had to be more to the story. You don't just accidentally strangle someone to death like that.

That's hard. In order to cut off someone's air supply, you have to apply pressure for longer than just a few forgotten seconds, like he claimed. Still, he did confess, which is why they had enough to arrest Robert Chambers. By 2 a.m., he's taken on the walk, which is kind of like a police courtesy to the press where they get to snap a few photos of the accused before they're booked and thrown behind bars. And once the media saw what the handsome Robert Chambers from the Upper East Side actually looked like...

The preppy killer was born, racing the front page of tabloids for weeks, each day offering a juicier piece of information than the last. The day after Robert's arrest, his family had already hired one of the most ruthless defense attorneys in the city. His name was Jack Littman. Littman was notorious for doing whatever was necessary to prove a client's innocence and

And he often got their sentences reduced or just completely squashed. For example, he'd recently represented a 17-year-old boy who'd been charged with beating his girlfriend to death with a rock. But instead, Lippman successfully convinced the jury that the boy had pushed the girl off of him. She slipped and fell and hit her head on the rock.

that the whole thing was just an accident. And he convinced them that. So Littman knew what it took to make a male defendant look like a powerless victim. And Robert Chambers' case was no different.

Littman's other specialty was leaving no stones unturned. With him representing Robert, it was clear that any incriminating detail from Jennifer's past might be used against her in order to back Robert's claims. Ultimately, the facts would have to speak for themselves. And the autopsy proved that some of what Robert said in his confession appeared to be true.

There was no semen found in or on Jennifer's body, which led the pathologist to believe Robert hadn't raped her after all. There were, however, other details that were inconsistent with his story. After analyzing Jennifer's face, the pathologist found hemorrhaging on the side of her head, suggesting she was repeatedly punched in the face before she died. So the cause of death didn't appear to be solely strangulation, but also aggravated assault.

Lippman didn't seem to think these findings would be a problem, though. At Robert's arraignment, they pled not guilty. Lippman argued this wasn't any ordinary self-defense case, but instead Robert had defended himself in reaction to a violent sex crime.

But a prosecutor brought up the autopsy in that first court appearance. They claimed there were not just reports of hemorrhaging and bruising, but also bite marks all over Jennifer's body. Jeez, man. They argued she was the one who'd been under attack that night. It was clear to the judge at this point this was not going to be an open and shut case. So the judge ordered that Robert be sent back to jail pending a grand jury hearing. Good.

Meanwhile, headlines reading, Jenny killed in wild sex and sex got rough, monopolized the tabloids, regardless of whether the statements had any truth to them or not. Which, that sucks for the families. Yes. Horrible. And with those papers still hot off the press, Robert was getting transferred from his tiny courthouse jail to a cell on Rikers Island, which had a reputation for being one of the most dangerous prisons in the United States.

So many of the people who believed Robert was innocent fought for his release, hoping to gain his freedom before something went terribly wrong. Which is why, at the grand jury hearing, those who knew Robert testified emphatically on behalf of his character. They said things like, he's generous, he's considerate, he doesn't anger easily. Robert was portrayed as this reserved Upper East Sider, a former altar boy who could do no wrong. But the prosecutor, Linda Fairstein, knew the truth.

Robert's past was littered with petty offenses from burglary to credit card fraud. He'd had problems with drugs and alcohol abuse. Still, the defense painted Jennifer as promiscuous, someone who dated around, who dabbed in violent sexual fantasies, a pill that for anyone who knew Jennifer was impossible to swallow. That is so messed up for the families because they have to now sit through this and hear this when it's,

Not true. And it's quite literally the blame the victim defense that Jack Littman was famous for. It was a lie that was getting out of control. A lie that also sold papers. The public ate it up. Yeah. But it didn't stop Robert from being indicted on murder charges. Yet Robert wouldn't have to spend that time back at Rikers. He was released on bond where for the next two years...

He lived an ordinary life as the trial came together. Two years? And guess who paid his bail money? The owner of Dorian's Red Hand, Jack Dorian, whose son, Michael, happened to be a good friend of Robert's. Okay. So yeah, in the meantime, Robert's just out and about in New York City, shopping at Tiffany's, going to work, dating new women. The preppy killer was just out there on the loose. Oh, that would...

I don't know how you can do that without stressing out every single day you're going to jail for the rest of your life. I know.

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But come the fall of 1987, Lippman was working hard putting together the best defense he possibly could for his client, Robert. And he focused on getting one crucial piece of evidence he believed could help with the case. So in October 1987, Lippman sent a list over to Fairstein. It included a bunch of things he claimed he needed to adequately build his defense. And the biggest item on the list? Jennifer's private diary. Wow.

Littman had heard from Robert himself that it contained vivid descriptions of Jennifer's sexual encounters. Allegedly, it also contained a list of guys that she had dated in the past. And to Littman, that equated to other men he could call upon as character witnesses against Jennifer. Just proving that she has this sex diary and of course she tried to sexually assault my client. How would they get it? They'd have to steal it, correct? No, you can request it if it's in evidence.

Oh, you can? Mm-hmm. Unless it gets thrown out. Oh, man, that sucks. That sucks. Mm-hmm. Many felt it could be a critical tool in proving that Robert's account was true. But Fairstein insisted. The diary was nothing more than an appointment book. There was nothing regarding Jennifer's sexual encounters or anything incriminating against the 18-year-old in that diary. In fact, the diary had been discounted as evidence and handed back over to Jennifer's father for safekeeping.

If Lippmann wanted it, he'd have to subpoena it now from Mr. Levin. And if he did, Fairstein knew it would make Lippmann look like a chauvinistic monster asking for a victim's diary, hoping to prove she was sexually active and therefore must have been accountable for her own death. It would have been a lot easier to just get it from the prosecutor, but Lippmann didn't care. He subpoenaed the diary from the Levin's anyway, which made its way up to the judge handling the case.

But the judge ruled there was nothing in those pages that was relevant to the defendant's case. Oh, good, good, good. Littman's best shot at proving his hostile narrative against Jennifer was shot down. The one piece of evidence he thought could prove Jennifer's promiscuous reputation simply didn't exist. The defense was falling apart before the trial had even started.

Still, around the same time, jury selection began for Robert's case, and because this story had been one of the hottest gossip pieces in recent history, it was near impossible to find people who didn't have opinions about it before appearing in court.

Three months of jury selection went by. The attorneys passed on hundreds of potential jurors. Finally, by January 4th, 1988, the trial was ready to proceed. Fairstein argued that in more than 8,000 cases of assault she'd seen over the last decade,

This was the first time she'd seen a male claim to be sexually attacked by a female. Not to say it was impossible, but Fairstein kept pointing back to their size differences. A 200-pound Robert versus a 110-pound Jennifer. That's what I was trying to say. Yeah.

No. She showed the jury photos that proved Jennifer hadn't been quickly strangled in self-defense. She'd been brutally beaten and dragged across the park. She also argued there hadn't been any sex that evening like Robert claimed, but there was a lot of violence caused by him.

Littman's defense was much weaker. He argued that the police could have mishandled her remains and caused the bruising on her face after they recovered her body. Littman called on very few witnesses to back his statements, and then he leaned heavily on the idea that, quote, the prosecution needed to prove its case beyond reasonable doubt before Robert could be convicted.

Mm-hmm.

One other sexist detail Fairstein pointed out that Jennifer's use of diet pills was able to be brought up and used against her in testimony. But Robert's history of cocaine wasn't admissible in court.

By March, the only thing left to do was offer their closing statements and let the jury deliberate. They left the box on March 17th. Eight days later, the jury still hadn't come to a decision. But they weren't just disagreeing. The members of the jury had been physically fighting while trying to come to a verdict. How can you not agree on this one?

By day nine, there was still no decision made. It had been the longest deliberation in New York history. Since they were leaning towards a hung jury, Littman and Fairstein decided to hammer out a plea deal for Robert. On March 25th, 1988, Robert and his counsel accepted the deal, pleading guilty to first-degree manslaughter. Robert was sentenced to five to 15 years in prison. No freaking way. That is it? No.

Mere weeks after Robert received his sentencing, one of the most incriminating pieces of evidence against him surfaced. It was a videotape of Robert at a party back around October 1987, right before the trial had begun. Robert was surrounded by a bunch of women in lingerie and he was playing with a doll. On the tape, he strangled the doll, then popped off its head before saying to the camera, Oops, I think I killed it.

Many felt this was Robert's strange way of admitting his intentions to kill Jennifer. But at that point, the decision regarding his fate had already been made. Robert ended up spending the full 15 years in prison. A little over four of those years were spent in solitary confinement because Robert had committed over 30 offenses during his sentencing, many of them drug-related. That's so crazy to me, yet he doesn't get life in prison.

In 1994, when he went in for his parole hearing, he told the board, Levin's family later sued Robert for $25 million in punitive damages for smearing their daughter's reputation. Robert didn't fight this. He was, however, released on February 14, 2003.

But about a year later, he found himself back behind bars, this time on drug charges. He was in and out of jail for the next several years. Then in 2008, he pleaded guilty to selling drugs out of his New York apartment. He is now serving another 19 years behind bars for that crime. Mind you, that's four more than he was sentenced to for killing Jennifer. That makes no sense to me. Never will. But listen.

The earliest Robert could be released is January 2024 for those drug charges. Okay. So it's coming up and we will keep you up to date on probably over on Rise and Crime to see if he gets released or not. Yeah. But that is the case of Jennifer Levin and the Preppy Killer. So one...

Horrible for Jennifer's family, too. I kind of feel... I don't feel bad for the... I don't want to say I want to feel bad. I don't know the best way to explain it. But it seems like Robert's mom worked so hard to try to give him a good life. And then he goes and kills someone and... Just screws it all up. And just selling drugs the rest of his life after she worked so hard for that, too. It's just...

Ah, whole thing sucks. I agree. I think we can definitely spend today thinking about Jennifer and her family because she really was not only victimized awfully in this crime, but also then just brutally dragged at trial and in the tabloids before getting to trial. And it's just, it's, it's disgusting. Yeah. Okay, you guys, that is our case for this week and we will see you next time with another episode. I love it. And I hate it. Goodbye.