Sean Combs: Listen to Combs’s messages to “Jane.”

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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 Monday, June 9th. Just a heads up, in this episode, we're going to be talking about some graphic details and harrowing subject matter.

The start to week five of testimony was overshadowed by a dramatic defense motion over the weekend. The defense accused the prosecution of misconduct and asked for a mistrial.

But the judge allowed testimony to continue while he waits for the prosecution's response.

Back on the stand for her third day of testimony was Jane, the second woman prosecutors allege was a victim of sex trafficking at the hands of Sean Combs.

The prosecution has been asking Jane to read aloud text messages she and Combs sent each other during their three-year relationship.

They've also played voice notes Combs sent to her, and we will play some of them for you on the podcast.

NBC News correspondent Chloe Malas joins us now to tell us what it was like to hear Sean Combs' voice in the courtroom. Hey, Chloe.
Hey, Andrea. Chloe, a lot of Jane's testimony is tough to listen to.

These text messages that she's reading and voice notes, you know, between her and Sean Combs that the prosecution is playing, they reveal a very toxic relationship. There are multiple text exchanges.

Jane was on the stand today reading between her and Combs, in which she she says she doesn't want to do this anymore. She's feeling used.
She doesn't want to take part in these hotel nights anymore.

And at one point during her testimony, she's reading a text exchange in which he's calling her crazy and really diminishing her concerns and her feelings.

But I mean, we all, well, I won't say all, but I've had boyfriends that have made me feel crazy. And I know that this probably strikes a chord with many women out there.
Yeah.

I mean, the question is, you know, what is illegal and legal, you know, when you're talking about a bad boyfriend?

And we've asked MSNBC legal correspondent Lisa Rubin to join us a little bit later to answer our questions about that. But Chloe, first, let's talk about these Combs voice notes.

They were entered into evidence so we can actually play them for our listeners. Girl, girl, girl.
I don't sent you flowers already. Anybody talk about that in the past? That's what I'm talking about.

You don't know how to just move on. How can somebody like have a relationship with you even as a friend and you don't know how to move on you go to

like it just goes crazy just just stop I'm saying let's move on and my tone is like this I'm just waking up Sean Combs's tone seems non-threatening at one point he says he sounds like that because he just woke up and he says he sent her flowers

Right, so he actually doesn't sound too intense. And when you're hearing that juxtapose to Jane's testimony on the stand, I mean, she sounds incredibly emotional.

It definitely could raise some questions with the jurors because there are several instances, whether it's a text exchange or a voice note, in which he's like, okay, fine.

You know, you don't have to participate in anything that you don't want to. This was all mutual.
You know, we both signed up for some freaky stuff. I think he called it kinky.

And that that's all this was. This was not sex trafficking.

There was another voice note chloe that was played that uh speaks to these what jane calls hotel nights others have called freak offs ain't nobody threatening you and i don't ain't trying to go back and forth with no woman where my life is at right now i don't have no time for no gangs baby girl me and you could be mad i could have a spat we could have whatever then after that you better get on your job that's really that's that's that's that's all it is so as you can hear in that voice note combs is saying you better get on your job right and i mean it makes it very transactional.

And I'll leave the legal analysis to Lisa later in the episode. Chloe, I just have a question.

When he says, you better get on your job, at that point, does the prosecution say he's referring to her doing these hotel nights? Like, that's her job? Yes.

Because she has to uphold her part of the deal, right?

So they had this thing called a love contract, where if she participated in these hotel nights, he was going to pay for two years of her rent of her home in Los Angeles.

This feels now more like it's, you know, getting to the heart of the charges. Absolutely.

The last voice note that we're going to play you is Holmes talking about her really being upset that, you know, he's with other women, even though they're in an open relationship. Let's take a listen.

I'm not going to be explaining this to you. It don't matter if I just got finished with her the other day.
I'm single I could do whatever the f ⁇ I want to, but I didn't.

You're straight flipping out on me. And I told you that you had one more time to do this.
You're nuts. So be sad, go crazy, do whatever you want to do.

So I find this to be incredibly interesting, right? Because jurors could actually take that in a positive way, being like, you know, he's telling her straight, he's not hiding anything.

But on the flip side, you could say, well, maybe he's lying and he's gaslighting her and he's making her feel crazy. So there are two ways to look at this.

And it's fascinating to get this inside glimpse into what was going on. A big moment in court today was when the prosecution asked Jane what her reaction was to Cassie Ventura's civil lawsuit.

To remind people, Jane and Combs were together from 2021 until he was arrested in September 2024. Cassie filed her lawsuit with the allegations of free coughs in November of 2023.

Jane got really emotional talking about it. She did, Andrea.
And during her testimony, she said that she almost fainted. In fact, I think I did, is what she said

when she saw Cassie Ventura's civil suit. She testified that she couldn't sleep, that reading those pages felt like a, quote, nightmare, that she had empathy.

for Cassie and it was at that point that there was an objection and then ultimately a sidebar between prosecutors and Combs's legal team.

And then when they came back to her, she testified that she couldn't believe that she was reading her own story.

so it was an incredibly powerful moment jane testified that she sent combs a text about her reaction to the lawsuit which she read aloud today yeah so i'll read you some of that text message So Jane writes, I feel like I'm reading my own sexual trauma.

I'm sick. It's exactly word for word, drug-filled days and nights.
She goes on to say, you made me feel crazy about the sex. Trauma is what I was feeling.
I feel very violated.

This was sexual exploitation. I immediately looked over at the jurors.
Some were feverishly writing notes.

Others seemed, you know, a bit disinterested. The prosecution asked Jane if she told anyone about how she felt, and she said no.

So Maureen Comey specifically asked her, were you considering a lawsuit or reporting to law enforcement? And Jane testified, no.

I was feeling manipulated and violated, and he was the only person I could vent to because I didn't tell anybody about what we had going on because it was a shameful, dark secret of mine.

And that is similar to other testimony that we've heard so far during this trial, Andrea, from individuals saying that they were too scared to tell their friends or family or even go to law enforcement.

Something that happened in court today really gives you a glimpse into Sean Combs' inner circle during a very difficult time.

The prosecution asked Jane about that hotel hallway video that's come up so much with Cassie.

And Jane testified that she was with Sean Combs and his team in Miami when the video aired on CNN last spring. What does she say? It is fascinating.

So she testified that it was a very eerie day that she saw Combs huddled with his team and his family. And ultimately, they invited her to join this sort of power session with the team.

And they were trying to come up with a sincere apology post. So this is before he posted that Instagram apology video.
Her behavior on that video is inexcusable.

Jane testified that Sean Combs had something to say about what happened in that hallway. That's right.

So she testified that he told her that this was the only time that he had had physical violence like that with Cassie. He said that they had some issues, that Cassie would hit him.

And when asked by the prosecution, did he say he would hit her? Jane testified, I think so, yes. What a morning.

When we come back, Chloe and I will be joined by Lisa Rubin. She's an MSNBC legal correspondent, and we wanted to talk to her about the case the prosecution is trying to make.
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Welcome back, everybody. Hey, Lisa, thank you for joining us.
Hi, guys. Let's talk about the prosecution's case so far.
Last week, Chloe used the words muddy and gray.

You, Lisa, have been following this case very closely as well.

We're hoping you can help us understand if you agreed. You know, does the testimony look kind of muddy from a legal perspective?

It looks less muddy from a legal perspective when you think about what the elements of some of the crimes are here.

And I'm going to put aside the racketeering charge, Andrea, for a second and focus on the sex trafficking charge.

And I think it's important that we like sort of identify what it is that it takes to prove sex trafficking.

So the crime of sex trafficking has like three elements according to the jury instructions that the government has proposed.

Now, I should also note that Sean Combs has his own set of jury instructions that he's proposed to the court. So the three elements are a person has to knowingly recruit or entice the victim.

That's pretty much amply met here, right? Nobody's questioning that Sean Combs knowingly enticed or recruited Cassie or Jane to be involved in these sexual encounters with him, right?

Let me go to the third part next because that's also relatively easy. You have to show that the defendants acts were what they call in or affecting interstate or foreign commerce.

And all that really means is that what they were doing was affecting the flow of money.

And here, the government's done a pretty good job of showing that there was absolutely an impact on the flow of money, right?

And a flow of things of value, not just cash itself to both Cassie and Jane.

But also, there's been testimony from people in and around Sean Combs' professional world who were involved in setting up the freak offs, cleaning up after the freak offs.

They were paid to, and they've testified that it was part and parcel of their jobs to be involved in those ways. It's the second piece here that's really the trickiest.

So you have to show that the defendant, meaning Sean Combs, knew or recklessly disregarded the fact that force, threats of force, fraud or coercion, or any combination of all of those things would be used to cause the victim here, Cassie or Jane, to engage in a commercial sex act.

And I think the really interesting thing here turns on what it means to coerce somebody,

because

the way that the government describes coercion is it doesn't just mean coercion, like somebody would believe that they would be caused physical harm.

it means you had a scheme or a plan intended to cause them to believe that if they didn't do a particular act there would be serious harm to them and yes maybe he told her at one point do your job, but will the jury believe that she was coerced into performing particular sex acts with him?

Because if she didn't, she would suffer psychological, financial, reputational harm that is sufficiently serious that a reasonable person in the same situation would do the same thing or continue to do the same thing.

Yeah, probably. It feels like this is the kind of case that does not have a smoking gun.

It doesn't, although I will say that what is the smoking gun here may be the cumulative nature of the commercial sex acts.

Because for example, again, I'm referring to the government's proposed jury instructions.

If the jury has been shown that somebody was repeatedly, physically, verbally, or emotionally abused by the defendant, that can rise to the sort of serious harm that they thought they would suffer or that they feared if they didn't continue to perform the sex acts.

In the indictment, the prosecutors alleged that Combs knew he was forcing Cassie Ventura and Jane to have sex with these other men, or at the very least, he was recklessly disregarding the fact that they felt forced.

What exactly did they mean by that? Reckless disregard is like literally putting your head in the sand like an ostrich and just not caring what the impact is.

So I'll give you one example of what could be the reckless disregard here.

Each of these women has testified that at points in time during what Jane calls the hotel stays and what Cassie called the freak offs, they're up for like 30 to 40 hours at a time.

That's not human, right? And they are being given ridiculous amounts of drugs to keep them in a state where they can continue to perform for Sean Combs.

That's the kind of stuff that the government is saying. You couldn't have possibly thought that somebody would have consented to that under the circumstances in which it transpired.

It seems to me what you're saying is that what the prosecution is going for is all the little pieces coming together to create a story for the jury.

Yeah, and I think the combination of the different kinds of harms, I think the government is sort of building it up together so that you don't have to find any one of those things individually, but it's that totality of circumstances that a jury can walk away saying, yeah, these people did feel coerced to participate in the freak offs with him because if they didn't, here's the panoply of different harms they might suffer.

Yeah, these jury instructions are going to be really important. They're going to be huge.
Complicated. Very complicated.
Thank you, Lisa, for your insight and expertise. All right, guys.
Thanks.

And thank you, Chloe. We will see you tomorrow.
See you tomorrow.

Tomorrow, we'll have more of the recordings played during Jane's testimony, including their phone calls right after she read Cassie Ventura's 2023 lawsuit. Thanks for listening.

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 Kurloff.
Original music by Jesse McGinty.

Paul Ryan is executive producer and Liz Cole is senior executive producer of Dateline.

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