Sean Combs: "Jane" takes the stand.

0:00This 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.

0:36so 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, 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 Malas has been in the courthouse this afternoon, and she's stepped out to bring us the latest. Hey, Chloe. Hey, Andrea. It's been an intense day in downtown Manhattan.

1:14Even before Jane took the stand, there was some drama with Sean Combs himself. Tell us about it. 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 Breonna Bongolin, I guess Diddy was nodding and really shaking his head and making eye contact with the jury. Breonna, who claims that Combs dangled her over a balcony. Yes. And her testimony really had a lot of holes today on cross-examination, Andrea.

1:56It's what a ton of journalists were buzzing about outside of the courthouse, that it was a big day for the defense. Okay. Is this the first time, Chloe, that Combs has been scolded for doing something like this by the judge? 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.

2:30And 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'm not sure exactly what happened that escalated things so much. Combs' 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.

3:05Right. 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. You learned that they apparently had goofy nicknames for each other? 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 Burt and Ernie.

3:48Interesting. 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. Yeah, who doesn't know Burt and Ernie? And so she said on the stand that their first date in Miami lasted five days. 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.

4:32So 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. The prosecutor asked Jane to describe the next three months of their relationship. She said that they did a lot of drugs. 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.

5:24Wow. 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. 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 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? You know, would you ever want to have sex with another man?

6:05I'd love to watch you with another man. Sounds like the beginning of a freak off. Exactly. Tell us about, you know, where that went, him introducing this idea of more people. 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.

6:51She 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. 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. Right. So also, I just want to point out that during her testimony, she said she had already been up for about 24 hours.

7:31At this point, 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 assistants 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 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.

8:26And Jane testified that she tried to tell Combs she didn't want to do any more freak-offs. 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. She says he threatened her. 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?

9:08I don't really want to do this anymore. That he said to her, OK, 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.

9:48Yeah, 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. 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.

10:33What 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 explicit text messages, photos and videos. 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.

11:22Welcome back, everybody. This is Christine Cornell. People are fascinating. The stories are fascinating. It's always a challenge. And when you're lucky, you make art. 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 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.

12:05Diddy and Cassie. I could see it on her, because she held her own, but she wept a little. And Diddy, of course, is fighting for his life. So he's in warrior mode. Yeah. So you're trying to capture also some personality there then as well, state of mind. Sure. 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 jury. Obviously, you can't show the jury, but, you know. You can draw them. You just don't draw them in any detail. In any detail. Okay. You know, I did one yesterday because I've been asked a lot, how's the jury reacting?

12:46Yeah. 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. Given that Mia is her, not her real name, pseudonym, were you allowed to, were you allowed to shoot even her bent over? You know, I drew a triangle that was the color of her skin with her hair falling across her face. This is all fascinating. You know, there are times where we know that sketch artists get critical feedback sometimes. For the most part, I get a lot of affirmation.

13:29You 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. Oh, my goodness. Well, thank you so much for doing this interview. You're a sweetheart. Thank you. Oh, thanks. Just super interesting. If you want to take a look at some of Christine's sketches, you can find them on our website at datelinetruecrimeweekly.com. Chloe, back with you. Thank you so much, as always, for bringing us all your color from the courthouse and the courtroom.

14:09Thanks, Andrea. Thank you for listening. Everyone will 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 slash Diddy to find that. On Trial is produced by Frannie Kelly with help from the Dateline True Crime Weekly team. Our senior producers are Alison Orr and Liz Brown-Kurloff. Original music by Jesse McGinty. Paul Ryan is executive producer and Liz Cole is senior executive producer of Dateline.