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Is on Trial, a special series from DATELINE True Crime Weekly bringing you daily coverage from the Sean Combs racketeering trial. He has pleaded not guilty to all the charges against him. I'm Andrea Canning and it's Thursday, June 5th. Just a heads up. In this episode, we're going to be talking about some graphic details and harrowing subject matter today. The prosecution's last key witness began her testimony. The judge has allowed her to testify under a pseudonym to avoid harassment. She is being called Jane in the courtroom and the judge has asked the press to be very careful about revealing her identity. So we are not going to describe her. What we can tell you is that the government's third superseding indictment against Sean Combs lists her as victim number two. The prosecution alleges that Combs recruited her and used force for fraud and coercion to get her to engage in commercial sex acts. They're alleging that Combs replaced Cassie Ventura in freak offs with Jane and some of those happened as recently as last year. NBC News correspondent Chloe Meloss has been in the courthouse this afternoon and she stepped out to bring us the latest. Hey Chloe.
Chloe Meloss
Hey Andrea.
Andrea Canning
It's been an intense day in downtown Manhattan. Even before Jane took the stand, there was some drama with Sean Combs himself. Tell us about it.
Chloe Meloss
So the judge told Diddy, if you continue to look at the jury and make faces, any sort of expression at all, I'm going to kick you out of the courtroom and you're not going to be able to be here. And Diddy just said, yes, Judge, I understand. So during testimony of Brianna Bongalin, I guess Diddy was nodding and really shaking his head and making eye contact with.
Andrea Canning
The jury, who claims that Combs dangled her over a balcony.
Chloe Meloss
Yes. And her testimony really had a lot of holes today on cross examination. Andrea. It's what a ton of journalists were buzzing about outside of the courthouse, that it was a big day for the defense.
Andrea Canning
Okay, is this the first time, Chloe, that Combs has been scolded for doing something like this by the judge?
Chloe Meloss
I've been in the courtroom most days, and I have never seen anything like this happen. But I do want to give you the perspective of somebody that's literally had their eyes glued to him the entire time. And that's court artist Jane Rosenberg. She's the one that one of the individuals that draws all of those court sketches that you see. She's had her eyes and binoculars on him for over a month. And she told NBC News that Diddy has been making facial expressions both affirmatively and negatively, depending on the testimony. Now, I've seen that. I mean, I've seen him look directly at the jury. I've seen him nod his head. I've seen. I'm not sure exactly what happened that was escalated things so much.
Andrea Canning
Combs's defense attorney told the judge he would make sure that that did not happen again. So, Chloe, after lunch, Jane, victim number two, according to the prosecution, finally took the stand. What did you learn about her? And of course, we already told you off the top, we have to be careful about not revealing too much about this woman.
Chloe Meloss
Right. So I'm not going to describe what she looks like. I know who she is. I know her backstory. But that's because I've been covering all of this for a couple of years now. She dated Diddy from 2021 up until his arrest in 2024. And she seemed really nervous, and she actually started to cry at some points.
Andrea Canning
You learned that they apparently had goofy nicknames for each other.
Chloe Meloss
Yes. So she testified that she met Diddy in Miami because her friend was actually dating him and that they exchanged numbers on the DL and that they decided to have nicknames for each other and they came up with Bert and Ernie.
Andrea Canning
Interesting.
Chloe Meloss
And Maureen Comey, the prosecutor, who is very serious, is like. You mean like Sesame Street? Yeah, it was like this sort of light, funny moment for a split second.
Andrea Canning
Yeah. Who doesn't know Bert Nurney? And so. So she said that on the stand, that their first date in Miami lasted five days.
Chloe Meloss
So according to Jane's testimony, they continued to text each other and FaceTime each other and talk on the phone in the weeks after she first met him, and that her friend actually was seeing other people during the same time and got engaged and moved overseas quite quickly. And that's when Jane felt like it was safe to start dating Diddy. So she tells Diddy that she's going to be in Miami for an event. He pays for her hotel, and she ends up meeting up with him, and they have sex on the first night, and they end up having sex for the next five days. And it's interspersed with dinners, beach walks. And she says that she's really falling head over heels for him.
Andrea Canning
The prosecutor asked Jane to describe the next three months of their relationship.
Chloe Meloss
She said that they did a lot of drugs, that they went on a trip shortly after that five day first date. They went to Turks and Caicos, then they went to the Bahamas. And she testified that she did everything from ecstasy to molly with Diddy, and that she did so much ecstasy that at one point she lost her sense of self on the beach. But she said that she continued to take ecstasy every 12 hours.
Andrea Canning
Wow. And at times, I mean, this testimony reads like a tawdry sex novel. She's talking about their sexual encounters and the details involved with that.
Chloe Meloss
So on one hand, Jane is testifying that she's falling in love with him, but they're having a lot of sex, watching a lot of pornography, and that Diddy wants her in very scandalous lingerie in what she called stripper heels. And that once, while they were watching pornography over the next couple of months, he would start to get more bold with her. And she testified that he started to say, can you imagine yourself with one of these men? Would you ever want to have sex with another man? I'd love to watch you with another man.
Andrea Canning
Sounds like the beginning of a freak off.
Chloe Meloss
Exactly.
Andrea Canning
Tell us about where that went, him introducing this idea of more people.
Chloe Meloss
So it was actually at this moment in her testimony, Andrea, that Jane began to cry. And she paused for several long seconds and took a tissue to her eyes and looked down at the floor and testified that when she was watching pornography while having sex with Diddy that he said to her, you know, can you imagine yourself with one of these men? Would you ever want to do this? And she said that. She just said, okay, because this was a man that she loved. She could tell he was getting turned on, and she wanted to make him happy. And Jane testified that she went into the bathroom. When she came out, Diddy was wearing a robe and intensely looking at his cell phone. And then within the next few hours, they went to a hotel in Miami and an escort showed up by the name of Don from a company called Cowboys for Angels.
Andrea Canning
Jane testified that the next day she felt excited, you know, that it was something she'd never done before. But she also testified that she thought this was a one time thing.
Chloe Meloss
Right? So also, I just want to point out that during her testimony, she said she had already been up for about 24 hours at this point, that she agreed to have sex with somebody else. And she testified that she was on drugs, she was high, and they went to this hotel. And when she and Diddy got to that hotel, she testified that she saw assistance there, but she couldn't remember their names. Setting up the baby oil, making sure that there were beverages in the room. She didn't talk about lighting or cameras or drugs. But again, this is that part of the RICO conspiracy charge, because the prosecutors want you to believe that. That Diddy was telling his minions, right, the people that worked for him, his employees, to go and set up these hotel rooms for freak offs. You know, that they were aware of the escorts, you know, that they were a part of this illegal activity, and they have to get him on multiple predicate crimes to prove RICO conspiracy, which we've talked about a lot.
Andrea Canning
And Jane testified that she tried to tell Combs she didn't want to do any more free coughs.
Chloe Meloss
Yes. So she testified that it was like opening Pandora's box, that that set the tone for the rest of the relationship. And it was a door that she could never shut, but she wanted to. 90% of her relationship over the next few years centered around these encounters with escorts and that she told him repeatedly, both verbally and in writing, whatever that means, that she didn't want to do it.
Andrea Canning
She says he threatened her.
Chloe Meloss
Yes. So she testified that Diddy was paying for her rent and that when she told him, you know, do we have to keep doing this? I don't really want to do this anymore, that he said to her, okay, well, how many more months of rent do you need? Because I'm not going to pay for somebody's Rent that isn't my girlfriend and isn't doing these things. And then Maureen Comey, the prosecutor, said, well, were you trying to break up with Diddy? And she said no, that she just wanted to have sex with just Diddy. She didn't want to have sex with these escorts. But he was holding the rent over her head, which goes to sex trafficking. You're talking about force, fraud, coercion. He's coercing her into these freak offs because he's holding the rent over her.
Andrea Canning
Yeah. This is the prosecution's argument. It seems like the key here is like, is it coercion or did she feel obligated? You know, is there a difference there? I mean, one's pretty serious.
Chloe Meloss
I saw some different journalists turning around in the overflow and they were whispering to each other and they were mouthing the phrase, this is really muddy. So it is muddy. There's a lot of gray in this entire case. But what sort of text messages, what sort of emails does she have to back up that she didn't want to participate? I do find it interesting that she was still with him up until his arrest. So it's a big question for me as somebody who's been covering this for so many years now. What made her want to be a witness for the prosecution? What changed? So we expect her to take the stand tomorrow and for several days next week. And we've been told that there are a lot of exceptions, explicit text messages, photos and videos.
Andrea Canning
And the defense clearly will get their shot at cross examining her. And I'm sure they are eager to do that. Chloe. When we come back on our weekly show, Dateline True Crime Weekly, the episode that came out this morning, we played my interview with one of the courtroom sketch artists from Combs trial. We're going to play you a bit more from that interview, how she sketches anonymous witnesses.
Chloe Meloss
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Andrea Canning
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Willie Geist
Hey guys, Willie Geist here reminding you to check out the Sunday sit Down podcast. On this week's episode, I get together with Ina Garten in front of a live studio audience for the second ever Sunday Sit down live event. We talked about her rise from home cook to culinary icon with some hosting tips and a proper dessert tray mixed in, too. You can get our conversation for free wherever you download your podcasts.
Josh Mankiewicz
I'm Josh Mankiewicz and I hope you'll join us for season four of dateline Missing in America. In each episode of dateline's award winning series, we will focus on one missing persons case and hear from the families, the friends and the investigators, all desperate to find them. You will want to listen closely. Maybe you could help investigators solve a mystery. DATELINE Missing in America Follow now to listen to the first episode. Tuesday, June 10th.
Andrea Canning
Welcome back, everybody. This is Christine Cornell.
Christine Cornell
People are fascinating. The stories are fascinating. It's always a challenge. And when you're lucky, you make art.
Andrea Canning
And this is a piece of our interview, a little more about her experience drawing Sean Combs federal trial over the past month. When you're drawing them, are you just trying to get it right, like as close as you can, or are you trying to capture like more of a feeling or what, you know, is it can you describe that?
Christine Cornell
It's both things. You know, you want to have an accurate drawing that really resembles them and you want to capture a little bit of the dynamic of the courtroom. You know, you can't help but feel that there was a tension between P. Diddy and, you know, Cassie. I could see it on her, you know, Cause, you know, she held her own, but she wept a little. And Diddy, of course, is fighting for his life. So, you know, he's in warrior mode.
Andrea Canning
Yeah. So you're trying to capture also some personality there then as well. State of mind.
Christine Cornell
Sure.
Andrea Canning
You know, not only are you drawing the defendant, but you're also capturing other things in the courtroom as well. The judge or there's the lawyers or the juror. Obviously you can't show the jury, but, you know, you can't draw them. You just don't.
Christine Cornell
In any detail?
Andrea Canning
In any detail. Okay.
Christine Cornell
You know, I did one yesterday because I've been asked a lot, how's the jury reacting?
Andrea Canning
Yeah.
Christine Cornell
And I think they were incredibly pained by Steele's cross examination of Mia because she was shrunk into herself. She kept her head down. I've never seen a witness not make eye contact with anybody in the courtroom.
Andrea Canning
Given that Mia is her not her real name, pseudonym, were you allowed to are you allowed to shoot even, even her, like bent over or not?
Christine Cornell
You know, she, I drew, you know, a triangle that was the color of her skin with her hair falling across her face.
Andrea Canning
This is all fascinating. You know, there are times where we know that sketch artists get critical feedback.
Christine Cornell
Sometimes for the most part. I get a lot of affirmation, you know, puffy combs. Mom is sitting behind me and she tapped me on the shoulder and gave me a thumbs up. She likes the way I'm drawing her son. Really? And I said, well, ma' am, do you mind if I draw you? And she right away started posing for me.
Andrea Canning
Oh, my goodness. Well, thank you so much for doing this interview.
Christine Cornell
You're a sweetheart. Thank you.
Andrea Canning
Thanks. Just super interesting. If you want to take a look at some of Christine's sketches, you can find them on our website@dateline truecrimeweekly.com Chloe, back with you. Thank you so much as always for bringing us all your color from the courthouse and the courtroom.
Chloe Meloss
Thanks, Andrea.
Andrea Canning
Thank you for listening, everyone. We'll be back with a new episode tomorrow. If you want to read the latest developments and analysis from inside the courtroom, check out the NBC newsletter. Diddy on trial go to nbcnews.com diddy to find that. On Trial is produced by Franny Kelly with help from the Dateline True Crime Weekly Team Radio. Our senior producers are Alison Orr and Liz Brown Karloff original Music by Jesse McGinty. Paul Ryan is executive producer and Liz Cole is senior executive producer of dateline. Pass it on.
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Dateline NBC Podcast Summary: Sean Combs - "Jane" Takes the Stand
Release Date: June 6, 2025
In this gripping episode of Dateline NBC, NBC News delves deep into the high-profile racketeering trial of Sean Combs, also known as Diddy. Titled "Jane Takes the Stand," the episode provides an in-depth analysis of the courtroom proceedings, focusing on the testimony of a key witness, pseudonymously referred to as Jane. The episode navigates through the complexities of the case, presenting both prosecution and defense strategies, and offers listeners a comprehensive understanding of the unfolding legal drama.
Sean Combs stands accused on multiple charges related to racketeering, fraud, and coercion. The prosecution alleges that Combs orchestrated a scheme to recruit individuals into engaging in commercial sex acts, replacing former associate Cassie Ventura with Jane and others in orchestrated "freak offs." The case hinges on demonstrating a pattern of criminal behavior to fulfill the requirements of a RICO (Racketeer Influenced and Corrupt Organizations) conspiracy.
At [01:29], Andrea Canning introduces Jane as the prosecution's third superseding indictment witness. To protect her identity, the judge has mandated that she remain anonymous, referred to only as Jane in court. Despite these restrictions, Chloe Meloss provides context about Jane's background from her previous encounters with Sean Combs.
Jane testified that her relationship with Combs began in Miami, where they exchanged contact through mutual acquaintances. "We decided to have nicknames for each other and we came up with Bert and Ernie," Jane shared during her testimony ([05:02]). This seemingly innocent detail provided a glimpse into the personal dynamics of their relationship.
Over the next three months, Jane described a relationship marked by intensive drug use and sexual encounters. She stated, "We did a lot of drugs, that they went on a trip shortly after that five-day first date. They went to Turks and Caicos, then they went to the Bahamas" ([06:25]). Jane's account included the use of substances like ecstasy and molly, which she claimed led to a loss of self-awareness on some occasions.
A pivotal moment in Jane's testimony occurred when Combs allegedly introduced the idea of involving others in their sexual activities. "Can you imagine yourself with one of these men? Would you ever want to have sex with another man? I'd love to watch you with another man," Combs reportedly asked ([07:03]). This led to the introduction of an escort, Don from "Cowboys for Angels," into their relationship ([07:39]).
Jane testified that Combs exerted control over her by tying financial support to her participation in these activities. "When I told him, 'Do we have to keep doing this? I don't really want to do this anymore,' he said, 'How many more months of rent do you need? Because I'm not going to pay for somebody's rent that isn't my girlfriend and isn't doing these things'" ([10:00]). The prosecution interprets this as coercion, alleging that Combs forced Jane into continued participation under the threat of financial withdrawal.
Throughout the proceedings, Sean Combs displayed noticeable reactions to the testimony. At [02:49], Chloe Meloss reports that the judge warned Combs about making facial expressions toward the jury. Despite the warning, Combs nodded and shook his head during testimony, prompting concerns about potential courtroom decorum violations. "I've been in the courtroom most days, and I have never seen anything like this happen," Meloss noted ([03:39]).
The defense faces significant challenges in dismantling Jane's testimony, which is central to the prosecution's case. However, Jane's account has been met with skepticism due to perceived inconsistencies and the emotional strain visible during her testimony. The defense intends to cross-examine Jane rigorously to expose any weaknesses or contradictions in her narrative.
Moreover, the legitimacy of the RICO charges hinges on proving a pattern of criminal activity orchestrated by Combs. "They were trying to get him on multiple predicate crimes to prove RICO conspiracy," Meloss explains ([08:43]). This approach requires substantial evidence linking Combs directly to the alleged coercive activities.
An exclusive segment features Christine Cornell, a court artist who has been documenting the trial through sketches. Cornell provides a unique perspective on the emotional undercurrents within the courtroom. "There was tension between P. Diddy and, you know, Cassie. I could see it on her, you know, 'Cause, you know, she held her own, but she wept a little," she observes ([14:47]). Her sketches capture the palpable stress and the confrontational atmosphere as the trial progresses.
The episode concludes by highlighting the complexity of Sean Combs' trial, emphasizing the delicate balance between credible testimony and prosecutorial ambitions. With Jane's forthcoming testimony expected to continue shaping the narrative, the case remains fraught with legal and ethical considerations. As the trial advances, Dateline NBC promises to keep listeners informed with real-time updates and in-depth analysis.
Jane on Relationship Dynamics:
"We decided to have nicknames for each other and we came up with Bert and Ernie." ([05:02])
Jane on Coercion:
"I'm not going to pay for somebody's rent that isn't my girlfriend and isn't doing these things." ([10:00])
Court Artist Christine Cornell on Courtroom Tension:
"I could see it on her, you know, 'Cause, you know, she held her own, but she wept a little." ([14:47])
For listeners seeking more detailed accounts and visual representations from the trial, visit Dateline True Crime Weekly to view Christine Cornell's courtroom sketches and access exclusive content.