Sean Combs: "Jane" sobs through her testimony.
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Visit gcu.edu. This 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 Friday, June 6th.

Just a heads up, in this episode, we're going to be talking about some graphic details and harrowing subject matter. This morning, the prosecution witness who was testifying under the pseudonym Jane to protect her identity took the stand again. By 9.30, she was sobbing. She told the jury that Sean Combs had a fantasy, watching her have sex with other men, and that she obliged him on a weekly basis for about a year.

She wept as she tried to explain why she kept doing it, even though she testified that she didn't want to.

NBC News correspondent Chloe Malas has been in the courtroom today, and she's stepped out to give us an update. Hey, Chloe. Hey, Andrea. So the testimony was pretty rough to listen to, almost a repeat of Cassie Ventura's testimony. I would say it was just as emotional. Jane was crying from almost the moment that she got on the stand. She held this Kleenex the whole time and cried.

Sean Combs just stared at her as she walked down the aisle of the courtroom and made her way to the stand. He just really did not take his eyes off of her. So she gives this description of, I realize she's not using the term freak-offs, but it sounds similar to freak-offs. And she talks about how Sean is kind of directing these sexual encounters with her and other men.

So they are freak-offs. It's just a different name for them. On a short night, it would be a 12-hour hotel night. And then at the longest, it was three and a half days. And she testified that this would go on with no sleep. And she was taking copious amounts of drugs and mainly ecstasy to keep her awake. Hmm.

So what was different about how she describes these sexual encounters versus what we heard from Cassie? There would be multiple escorts on one night that Combs would have escort after escort, just this revolving door show up. And she testified that sometimes she would break down and cry because it was just so difficult and she would be so tired and her body would be incredibly sore. Hmm.

When Cassie Ventura was testifying...

I vividly remember her talking about specific escorts from this company called Cowboys for Angels. And that's what we heard during Jane's testimony today as well, that it was the same site that they would get these escorts from. Am I getting this right? Cowboys for Angels? Is that what it's called? Yes. So Cowboys for Angels is a website. I just looked up, just curious, Cowboys for Angels, and that's the number for that.

Elite straight male companionship for the discerning woman. Luxurious, professional, discreet, operating nationwide since 2008. It's really unbelievable, though, when you think about it, because other than, I believe, two counties, Andrea, in all of the United States, prostitution is illegal. In my opinion today, the prosecution has...

without a doubt, met the bar of transportation to engage in prostitution. Combs faces two of those counts. They have had escorts take the stand, and now they have Jane's testimony of these escorts traveling all across the country, even internationally. So if the jury didn't believe Cassie, I think that Jane really drove that home for the prosecution. Mm-hmm.

The prosecution asked Jane about a 2023 text she sent to Combs, and it's reminiscent of Cassie's texts and testimony. It is. She read this while she was on the stand. I wish we could take this back to when we first started dating. One night of fun just turned into the entirety of our relationship. My heart is breaking. And this is one of many text messages that have been put forth recently.

as evidence today by the prosecution. Also in that 2023 text, Jane states pretty clearly that she doesn't want to keep taking part in these encounters. It's incredibly strong. So I'll read you what we've written down. You know, we're taking this all shorthand, you know, like we're taking notes during her testimony. So, you know, it's not until later that we get the transcripts, but

Essentially, it says that she finds it all dark and sleazy and makes her feel disgusted with herself and that

She says, it's the only reason you have me around and why you pay for my house. I don't want to feel obligated to perform and fear losing you. I don't want to feel like that anymore. I just want to talk like adults and figure out where we go from here. It really sounds like part of her probably wants to be with him and she loves him. And then part of her also doesn't want to lose sort of the perks, right? That go along with him. Is that fair? That is fair. And this, I think,

Andrea is one of the more complicated parts that the jury is going to have to wrestle with because you have Jane testifying that she actually liked the majority of these escorts. She found them cute. She found them charming. She found them handsome. There were even ones that she picked out herself and hired. But on the other hand,

She says that she didn't want to do it, that she only performed in these hotel nights because she wanted to please Combs. But that the second that they left, she would be so happy to cuddle with Combs, lay with him. She would cook for him. She would put on his favorite show and she would just sort of like flip back to being in this

loving relationship that she wanted. And I think it might be hard for some of the jurors to be able to understand how she could compartmentalize these horrors and just immediately go back into a relationship with him.

Yeah, I think it's also going to be hard for the jurors to differentiate between, you know, was Jane just trying to please Diddy or was she forced to do this? There were several times in which she testified to Maureen Comey, the lead prosecutor, that

She didn't know why she hired one of these escorts or why she sent a text message to one named Cabral inviting him to go on a trip with them. You know, she didn't have...

a good answer, right? And there are text exchanges she read on the stand during her testimony today, Andrea, in which she tells Combs, I don't want to do this anymore. You know, I don't want to do a hotel night tonight. And he just says, okay, cool. So it's how will the prosecution be able to prove sex trafficking with just her word? You know, because

One could argue, well, you weren't handcuffed physically. Couldn't you have walked out the door? So I think that we'll see a strong cross-examination by Combs' defense team. And you see them vigorously writing notes, Andrea. Yeah.

Are the jurors, you know, as you're telling me this story, it's all very interesting. But I'm thinking to myself, the jurors have been there for a long time now. They're hearing a lot of the same type of testimony. Are they getting fatigued at all? Several were yawning, which sounds horrible, but it's understandable. And, you know, some...

Over the last week or so, we're rolling their eyes during Mia's testimony. But really, during Jane's, it looks as though everyone's paying attention. Some are taking notes. Chloe, break it down for us as best you can about how Jane fits into this RICO conspiracy case, what her testimony could do to bolster the prosecution's case.

Sure. So she talks about several assistants, one of which is Brendan, another one named Frank, setting up those hotel rooms. That goes towards Rico conspiracy. She testified about Combs' chief of staff, KK, Christina Corum, who was having her go pick up drugs in California, which was a wild part of Jane's testimony today, that she was a drug mule and would bring ecstasy from California to Miami in her suitcase.

So that goes towards Rico conspiracy. You also have Jess. Who is Jess? She's some sort of a travel agent. Did she work in-house for any of Combs' enterprise? Was she a third party agent?

travel agent, you know, on Expedia who had no idea what who these people were or did she know. But you do have some of the people that worked for Combs being implicated here. Yeah. And to be clear, no one other than Combs has been charged with any crimes in connection to this case.

And Christina Coram gave a statement to Rolling Stone back in March saying, I have never condoned or aided and abetted the sexual assault of anyone, nor have I ever drugged anyone. Correct. When we come back, this afternoon, Jane's attorney asked to address the court. She said there are media outlets trying to discover and report her client's identity. What the judge had to say about that after the break.

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Welcome back, everybody.

Chloe, let's talk about people trying to figure out who the two anonymous victims are in this case. It's obvious that people are fascinated by Sean Combs' celebrity and lifestyle and the people around him. Is it a surprise that in this era of online sleuthing that people would be trying to pull back the curtain? It's not, but the judge is very aware in trying to decide whether

what he's going to do about it. This is always the risk. There are members of the public in the courthouse. It is their right. And then when you go to the overflow room, which is a courtroom on another floor with TVs, there's all sorts of people from homeless people who just want to have some air conditioning and a rest to

to other people that are fascinated by all of this, who flew in from other states. One guy's here from Canada just to listen. I mean, there is a lot of support for Combs on social.

of people that are following this trial, and several of the bloggers and streamers out here, you know, they're very skeptical of some of the individuals that are testifying. I think if we didn't have these restrictions on us as journalists, we could talk a lot more about Mia and about Jane, right? Because obviously as journalists, we know who they are, we know their backstory, and we could provide more context. And I think that context is important, and the jurors aren't going to get that.

Did the prosecution really think they could keep victims number two and four a secret, these alleged victims? I mean, with Mia...

Number four, both the prosecution and the defense asked her many questions about her Instagram account. And Combs has been fairly public about the women in his life over the years. I think it's easier to keep Jane's identity under wraps because Combs did date so many different women. And actually, some of the theories that have been thrown out to me, I couldn't believe how far off people were with their guesses. But when it came to Mia, that's more complicated because she worked with

At Combs' company. The judge has asked not only the press, but everybody in the courtroom and the overflow rooms to help protect these women. But, you know, what kind of enforcement power does the judge have? There's a lot of talk today of a potential gag order. But even if somebody does violate a gag order, some of these streamers who are revealing these women's identities don't even live here. They're not even going to this court.

courthouse. So how exactly will they be reprimanded? I also want to point out that the streamers that the judge said, you know, clear them out of the front of the courthouse, they're back. I'm staring at them right now. So clearly they're not deterred.

Okay, Chloe, thank you very much for this end of the week update. We're going to hear more from Jane on Monday. Is that correct? Absolutely. We could see her on the stand for three more days. All right. Enjoy your weekend to you and to everyone else. Have a good weekend. Thanks so much.

Thanks for listening. We'll be back with a new episode on Monday. 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 Allison Orr and Liz Brown-Koroloff. Original music by Jesse McGinty. Paul Ryan is executive producer and Liz Cole is senior executive producer of Dateline.

Thank you.

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