The Price of Pleasing Diddy: Recapping Week Four - Trial By Jury: Diddy - Podcast on CNN Audio

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Trial By Jury: Diddy

After thirty years in the media spotlight, there are no cameras at the trial of Sean "Diddy" Combs. So, let CNN anchor and chief legal analyst Laura Coates take you inside the courtroom. On Trial by Jury: Diddy, she'll shine a light on every move that matters in Diddy's trial for racketeering conspiracy, sex trafficking and transportation to engage in prostitution.

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The Price of Pleasing Diddy: Recapping Week Four
Trial By Jury: Diddy
Jun 7, 2025

If Cassie’s turn on the stand was shocking, the marathon testimony we heard from the witness known only as "Jane" in week four of the trial of Sean "Diddy" Combs was jaw-dropping. Laura and CNN Entertainment Correspondent Elizabeth Wagmeister break down major moments and walk us through how the prosecution is mounting their racketeering and sex trafficking case, from accusations of drugs in checked luggage, a "love contract," and emotional and graphic text exchanges.

Episode Transcript
Laura Coates
00:00:03
I'm Laura Coates, and this is Trial by Jury. We are now four weeks in, a whole month into the trial of Sean Diddy Combs. A lot has happened, a lot more is gonna happen, and this week was no exception. We heard explosive and graphic testimony from another alleged victim just this week. Here to break it all down for us, and what is frankly to come, is none other than my partner in the courtroom, Elizabeth Wagmeister. She, of course, is our CNN entertainment correspondent. Elizabeth, this was quite a week.
Elizabeth Wagmeister
00:00:42
It really was, and I don't even know where to start, so let's just start with today, Laura, and then we can backtrack. You'll tell me what you wanna talk about, but we have to talk about Jane, who of course is testifying under a pseudonym, so that is not her real name. Now she got on the stand Thursday in the late afternoon, and she was on the stand all day Friday. She will continue to testify next week. In fact, prosecutors have said that this witness could be on the stand for a full week. That's longer than Cassie, to put that into perspective.
Laura Coates
00:01:14
Wait a minute, longer than who many believe was the government star witness, Cassie Ventura, this witness will testify longer, even for the direct? Wow.
Elizabeth Wagmeister
00:01:25
So that's what they've said. And look, you never know what's going to happen, of course, in a court of law. But they said that their direct will take around three days, and that they anticipate that the cross will take just as long, if not longer. So that could be six days. And we know that Cassie was four days. And I have to tell you, I think the reason why is because this is very complex, complicated testimony. So was Cassie's. So was Mia's. But this witness, it's complex to another level, and I think that's why they're being so detailed, Laura.
Laura Coates
00:01:59
The complexity of it, I mean, this case, you and I have talked about it, the quintessential sex, drugs, and rock and roll, and you add in the violence that's been alleged, the torment, the grueling testimony. This case has gone, I think, beyond what a lot of people thought the testimony would actually include, and yet there is still the burden of proof that has to be met by this prosecution team. Tell me about this witness and how her testimony compared, so to speak. I'm not comparing the trauma that's alleged, but just the details that came in through this witness as it might even compare to the earlier witnesses.
Elizabeth Wagmeister
00:02:40
'You know, it's a great question because, and as you said, we are not comparing the trauma of any alleged victim who is on the stand, but as we look at what the jury will be thinking in that deliberation room, it is fair to compare these three main government alleged victims. And the reason why is because Jane is more similar to Cassie in the sense that these are both former girlfriends, former romantic partners. Unlike Mia, who was not a former romantic partner. She was an employee. So to some jurors, that may be more cut and dry because there's always the defense when there is a former, romantic partner, why did you stay? Why did you say in this if you did not like what was going on? I'm not saying that that is fair or right or wrong, but that is always the defense in these cases. So Cassie endured some grueling cross-examination. I anticipate Jane's will be even more grueling giving her testimony. So big picture, Laura. Jane was dating Sean Combs from early 2021 through August or September, 2024. That is when Sean Combes was arrested and put into jail at the MDC. So that's pretty staggering, that this witness on the stand, she is not talking about ancient history here. She's not talking about 2009 like Cassie was. She is talking about something that is less than a year ago. And I have to tell you, Laura, the big bombshell that came out in court today, there was literally an audible gasp in this courthouse where I was sitting. Jane said, to this day, as she is testifying against Sean Combs, he is still paying for her rent. That was a shocking moment.
Laura Coates
00:04:29
Really? Now, I have to say, I'm shocked for a number of reasons. One reason I'm shock is because obviously, if you are the prosecution, you want to ensure that there is nothing intimidating or that a witness is beholden to a defendant in a case because it could sway your testimony. That's the clear fear of anyone who thinks they might be under any kind of thumb of a defendant. On the other hand, if you're the defendant, you might want to use that information to suggest that this person has some ulterior motive or bias, and I'm trying to grapple with the nuance and how to interpret that. That's stunning.
Elizabeth Wagmeister
00:05:13
'It is, and that's why I say this is so complex. So Jane says that in this three-year relationship that she really was in love with Sean Combs. She fell fast for him. She did not use this word, but you know how people use the term love bombing? That is essentially what she was describing, that from the first month when they met, he took her on a trip to Turks and Caicos, everything was beautiful, he showered her in gifts. He started paying her, giving her monetary cash gifts after that trip on the first month. She said that she did not ask for it, that he gave it to her on his own accord.
Laura Coates
00:05:52
Because the time away from her occupation, he wanted to sort of supplement in some way.
Elizabeth Wagmeister
00:05:58
'That's what she said, that was her explanation. Well then, after a few months of them dating when it was just the two of them, she then said that Sean Combs introduced his fantasy. And his fantasy was bringing other men into their sex life. And she said that the first time that she was very nervous, but she tried it. She actually said that she felt exhilarated after it because she felt like it was something, she used the word taboo, crazy, sexy, something that brought her closer to her partner because it was so out of the norm for her. But she never thought it would happen again. And then Laura, she said 90% of the sex that she had with Sean Combs, who she loved, was with other men. And she says that she told him on numerous occasions she did not want to have sex with other men. And this is not just her word, we saw text. The jury was shown dozens of text messages. They listened to voice notes. She did tell him that she did not want to have sex with other men, she is seen putting a big effort to showcase that to him. And he always kind of brushed it off. And she, in all fairness, she said that she would then go along with it because she wanted to make him happy. And then where the payment comes in with the rent. She said that in their relationship, in early 2023, that Sean Combs presented the idea of a love contract. That's the word that she used. And I'm looking at my notes from court right now. She says that the love contract was a monthly allowance and that she asked for $15,000, he ended up giving her $10,000 a month. She said that she rented a new place, a pretty big home for her and her young son to live in. And she said that the reason why she agreed to this is because she felt that the first two years of their relationship, she was giving in to what he wanted, which was these freak-offs, or as she said, these hotel nights. She says she did not want to have sex with other men. So she felt, since she did that for two years, that he could give her this two-year contract which he proposed according to her testimony, to pay her monthly. That is when she said, and she was asked by the prosecution, again, getting ahead of what certainly would come up at cross-examination, that's when the prosecutor, Maureen Comey, said, does he still pay her rent today? And she said yes, he does.
Laura Coates
00:08:11
This is so interesting because on the one hand, there is some analogy that can be drawn to the testimony of Cassie Ventura, the idea of the love bombing, the idea that introducing in other partners in these sexual nights at these hotels. The divide comes from the manner in which either expressed their displeasure with wanting to participate in them. But then you come back to this point surrounding financial dependence and how the prosecution could view that as a mechanism of coercion or force for trafficking. You have to wonder what the jury is thinking when, much like the earlier testimony, and you and I have talked about this, of other witnesses, there seems to be this mixed motive as to why somebody has chosen or by default remained in a relationship or under the employment of Sean Diddy Combs. And I do wonder if the jury hears these different ideas as to the why, whether it's love, whether it is lust, whether it financial dependence, whether it fear, which they'll actually credit for the witness.
Elizabeth Wagmeister
00:09:22
'It's so true, and that is why this is so complicated. And again, I keep saying, I think more complicated than Cassie. We're seeing a pattern here that, like Cassie, that both Jane and Cassie said that they did not want to participate in these freak-offs, that Sean Combs gave them drugs, that there were employees around them who were helping set up these freak-offs who were complicit, allegedly, in Sean Combes' behavior, which prosecutors say is criminal behavior. But what's more complicated is Cassie was signed to Bad Boy when she was 19 years old and they quickly started dating. Her career was on the line. That is what she explained. Jane, she was an older, not older woman, but older than Cassie at 19. She was older, this was more recent. You know, she did have many things in her life paid by him. So I think you're absolutely right, Laura, that there's many schools of thought to look at this, but you could see one juror saying. Wow, he used this financial dependence over her. He dangled it over her head. This is sex trafficking by coercion. You could see another juror saying, these things sound horrific and maybe she didn't want it, but why didn't she leave? Did she want the money? And you have to assume that that is where the defense is going, but I have to tell you, there were so many horrific allegations that she expressed when she was on the stand. At times, Laura, she was sobbing. I mean, sobbing. She had to collect herself. The prosecutor asked her numerous times, do you need to take a break? She kept pushing through. She didn't take a break, but she was crying for so much of it. And I just, I wonder when the jury's listening to this, even if there is that gray area, and it's so confusing with him paying for her rent still to day? Are they thinking, wow, these things sound so cruel. And, you know, I mean, one of the examples was, during one of these hotel nights, she said that she was not on drugs, Sean Combs was, but she didn't want to do drugs. She was trying to stop him from doing drugs. So she didn't take drugs. And she said, that she couldn't stand this freak-off, that she usually was on drugs which made it feel less real. When she wasn't on drugs, Sean Combs had her have sex with two men. She said that she went to the bathroom in this hotel suite. She threw up. And Sean Combs came up to her and he said, Oh, good, you're throwing up, you'll feel better. Come out. There's a third man here. And then she had sex with three men. So these details are just so sordid and so graphic that again, every juror, we have no idea what they're thinking. But you can imagine the different thoughts going through each person's head.
Laura Coates
00:12:02
And again, the timeline is gonna be so important here because this is not something that's even close in time, perhaps even to the end of his relationship with Cassie Ventura. And the idea that this was somebody that he was involved with almost up to the time of his arrest suggests that there was already a federal raid in the midst of their relationship as well. We remember that moment when there was almost the simultaneous dispatch of federal agents to different estates owned by Sean Diddy Combs, not the least of which included that Star Island home, which we saw the different pictures of and different contents taken out of. You know, the way in which the prosecution has unfolded their case is a bit of a case study in chronology. We always assume as a prosecutor and as you're unfolding your case, that you wanna adhere to this notion of primacy and recency, right? You want to have the very first thing a juror hears be the biggest value, and the last thing they hear be the biggest value. And things that might be not as helpful to your case or things that could lessen the credibility of a witness in the middle. Here we have almost a rolling hills effect, right? You've got Cassie Ventura almost to start it out. Then you've got different personal assistants. You've surveillance video. And forensic examiners, now you've got this other witness who I'm sure is captivating this jury. Do you have a sense that the prosecution is explicit and connecting the dots to RICO? Do you get the sense, if you were a juror, and obviously we're all speculating here, but when I'm in that courtroom listening to what's happening, the prosecution's not, you know, beating the jurors over the head with obvious details. They are weaving a tale that they will then, at closing, bring back together.
Elizabeth Wagmeister
00:13:56
'You know, it's so interesting to hear you say that they'll bring it back together at closing because I have actually been sitting there some days wondering why aren't they connecting the dots in a more clear way? You know? Why aren't they spoon feeding this to the jury? Now, I'm not an attorney, but you as a former prosecutor, you basically just answered my question, which is they'll likely do it in their closing and they'll connect all those dots. But I do think that they made some great headway today with that racketeering charge in regards to Jane. Like, for example, there was one instance where Jane on the stand, she said, Sean Combs essentially made her out to be a drug mule that on two separate occasions that he said to her, go to my house in Beverly Hills and pick up a package. What was in that package? Drugs. Jane said that she saw the drugs with her own two eyes when he unpacked them. And he said, Pick up the package and bring it to me in Miami. Go to my house, security will have it for you. So she contacts Kristina Khorram, who is Diddy's chief of staff and very close right-hand woman.
Laura Coates
00:14:59
Essentially. Who by the way has been mentioned throughout the trial but has not been charged criminally with anything and she has repeatedly denied ever having any criminal involvement.
Elizabeth Wagmeister
00:15:09
'Yeah, she's brought up a lot. She's brought a lot, and this week, Laura, the prosecutors, for the first time ever, they actually called her a co-conspirator, which was, they had been alluding to it, but it was the first they said that, but it is important, as you said, to note that she has denied any wrongdoing.
Laura Coates
00:15:25
'And then the co-conspirative notion of it, I think there's some hearsay rationale behind in terms of what you can bring in if somebody is an alleged co-conspirator, their statements can come in differently than say they were not. But I am curious, and I want you to finish your point, I am curious, to the extent to which the jurors are hearing her name, are they wondering, will they hear from her?
Elizabeth Wagmeister
00:15:51
I would be.
Laura Coates
00:15:51
But go ahead.
Elizabeth Wagmeister
00:15:53
'I would, right? If I'm on the jury, I'm thinking, when are we going to hear from this woman herself? Anyway, so back to this incident that Jane testified to, where she had said on two occasions that Diddy asked her to get drugs from his home in LA, travel with them to Miami. Jane Doe said that she contacts Kristina Khorram, and she says, is this safe? Like, I'm very nervous about this. And that Kristina Khorram's response was, it's fine, I do it all the time, just throw it in your checked luggage. So that's bringing her in as the racketeering charge. You know, Jane, just like many other witnesses, spoke about the fact that assistants were setting up these hotel nights, otherwise known as freak-offs. So these staff members have been woven through her testimony and I do think that they're making headway. On that racketeering charge as it pertains to Jane, it's probably even maybe more clear on that charge than the sex trafficking given all this gray area and complexity that we've discussed with Jane.
Laura Coates
00:16:59
You know, it's important as you're describing why the different names of people who are employees of the overall corporations and different entities that are led by Sean Diddy Combs, what the prosecution is trying to convince the jury of is that they all are a part of an inner circle that is synonymous with an enterprise or a racket. That's part of the element to actually prove racketeering and RICO. And one of the things that in the first several weeks of trial, you heard sort of murmuring in the courtrooms about was, well, are you suggesting that all of these employees of these different entities, their sole function was to facilitate Diddy's sex life and his personal affairs and relationships? And it left a lot of people scratching their heads as to whether they'd be able to link these things. I am still curious as to how the prosecution will put a fine point on this aspect of it and who might testify, you know, and I think it's interesting as well, when you think about this, is the prevalence of the conversations around drug use. You know I had interviewed a great friend of Diddy, who's outside the courthouse most days, you know, with the sort of Free Puff shirt as a part of our show. And he said to me that the family was surprised by Diddy's drug use, they were unaware.
Elizabeth Wagmeister
00:18:26
Meaning Sean Combs' family.
Laura Coates
00:18:27
Sean Combes' drug use, which I thought was pretty surprising given the prevalence of how much we're hearing about it and the fluency everyone who has described using drugs on that stand has talked about their reaction to and his use of the drug component in an earlier witness this week. Her name was Bryanna. She was somebody who I think the prosecution called because she had alleged he had dangled her over a 17 story building and then thrown her allegedly into furniture on the patio. The defense spent a great deal of time trying to deconstruct her credibility, either through drug use or her provision of drugs to Cassie Ventura as part of her income, but also trying to show literal receipts that he, Diddy, and Cassie could not have been in two places at once, namely that he was not at the location where she alleged he threw her into that furniture. So I bring her up because some people believe, in fact, many who were listening thought that she had undermined the prosecution's case. You believe that this latest witness moved needle yet again for the prosecution?
Elizabeth Wagmeister
00:19:38
'I think that, let me put it this way, I think through my reporting, I think Bryanna's testimony, it doesn't matter who you talk to in that room, every person said there were some big wins for the defense there. I think now you have Jane on the stand, and again, it is complex. Some people on this jury may not understand why she would stay in this relationship if she didn't want to do these sexual acts, but she is a sympathetic character, she's crying on the stand, and she's echoing patterns that Cassie spoke to. And again, even if you are wondering, why would she stay? Why is she accepting payment from him? Why is he paying for her rent? These alleged incidents that she is describing during her testimony are just seemingly so cruel, Laura. I mean, there was one example that she gave and it's very graphic, so I want to warn your listeners. She said that her and Diddy, they got in a fight, not a physical fight, but they were fighting over text. And she had told him that she was feeling sick. She was, it was too much. She hit a wall, that's what she said, because of the drug use and the lack of sleep from these hotel nights, these freak-offs. So he wanted to do another freak-off and she said to him, I just really need a break. Like, I cannot, I've hit a wall, my body, I know my body and I've never felt this way before. I cannot do it. The drugs, the lack of sleep, I cannot do it. And she said that Diddy did not respond well to that. We saw these texts, by the way. And then she said to him, I'm getting my period tomorrow. And she actually sent him a photo of a tissue that showed the beginning of her period, and she sent it to him. And the prosecutor said, why did you send that? She basically said, I had to prove to him that I was not lying. You think of that, in any relationship, you have to send a picture to prove that you are on your period.
Laura Coates
00:21:41
Dehumanizing.
Elizabeth Wagmeister
00:21:42
Dehumanizing, and then he wrote back to her, quote, you have had your period so many times. He goes on to say, this shit is weird. Excuse my language, but these are his texts that were read in court. I don't believe you. You're playing with me. He goes onto say, Fucking weird, I'm done. So then she wrote back that she was sorry and that she loved him. And it just shows this pattern of this back and forth where she tries to tell him, I don't want to do this. Please, I don't want do this, and then he gets angry. And then she says, okay, I love you. And then they do it again. In fact, here is a direct quote that was played for the jury that they heard Sean Combs' own voice saying on a voice note. He said, quote, I'm going to disappear on you and you're about to have a rude awakening. And then Jane on the stand said that she realized it's true that at any moment he could cut her off. So again, this idea that the prosecution is hoping shows these financial threats, they hope will prove sex trafficking through threats. And by the way, she wrote back in a text, she said, quote, you've been transactional and it's super disheartening. She texted him, quote you keep threatening me. So again this is not just her saying from her memories. We are hearing voice notes and we are reading texts. between them that show a very, very complicated relationship. But I think no matter what your understanding is of trauma victims, I think anyone would agree that these are some very cruel conversations that are happening.
Laura Coates
00:23:14
Oh my goodness. We are now a month in to this trial, which was promising to be an eight to 10 week trial. And just when you thought it wasn't gonna get any more graphic, boom, more testimony comes in. She'll be on the stand for several more days, we know, and you can only imagine what might come up. And then of course, looking towards how the defense is going to try to undermine her credibility. And surely go back to what they said, even at their opening statements, the phrase was money grab. I'm curious to see what they will do next and you will be right in that courtroom bringing us the very latest as you always are. Gosh, thank you, Elizabeth.
Elizabeth Wagmeister
00:23:58
Thank you, Laura.
Laura Coates
00:24:02
We're gonna be back next week with the very latest on the trial. You know, this witness is gonna be on the stand for several more days. You gotta imagine yourself as a juror. How much have you written down in your notebook? At this point, what is sticking out to you? Don't you wish you could almost be the fly on the wall and see what is most important to these jurors? Because you better believe that is what is consuming most of the nights for the prosecution and the defense. Where are the holes? Are there seeds of reasonable doubt? Are there winds? Stay tuned everyone. This episode was produced by Graelyn Brashear, Eryn Mathewson, Alexandra Saddler, and Rachid Haoues. Our technical director is Dan Dzula, and the executive producer of CNN Audio is Steve Lickteig, with support from Emily Williams, Andrea Lewis, Mike Figliola, Hank Butler, Robert Mathers, Alex Manassari, and Lisa Namerow. I'm Laura Coates, and I'm here for it.