Dateline NBC - Sean Combs: The jury watches more Freak Off videos.

Episode Date: June 24, 2025

In the last days of the trial, the prosecution played more videos of the sexual encounters at the center of the case. Their summary witness also introduced texts and voice notes in which Combs's staff arranges travel for his girlfriends and Combs himself haggles over the price of escorts. In the morning, the defense announced it won't be calling any witnesses at all.If you want to read NBC's coverage of the trial, check out our newsletter, “Diddy On Trial”: NBCNews.com/Diddy 

This is On Trial, a special series from Dateline True Crime Weekly, bringing you daily coverage from the Sean Combs racketeering trial. He is pleaded not guilty to all the charges against him. I'm Andrea Canning and it's Monday, June 23rd. Just a heads up, in this episode we're going to be talking about some graphic details and harrowing subject matter. At the federal courthouse in downtown New York, the prosecution is winding down its case.

Today, a Homeland Security agent was on the stand, introducing new text messages, videos and voicemails prosecutors want in evidence. The jurors, of course, watched and listened to these videos and voice notes, some of which were explicit. NBC News correspondent Chloe Maloss was in the courtroom watching their reactions. And now, rather than standing on the sidewalk in the middle of a heat wave, Chloe is in an air conditioned office

to tell us why this could potentially backfire for the prosecution. Hey Chloe, hey Andrea. Okay, so at this point in the trial, it seems that the jurors should understand what a freak off is or a hotel night or a wild king night. What argument is the prosecution making by playing more video from these nights?

Well, when you talk to one of our legal analysts, Danny Savalos, he would say that this is typical. This is prosecutorial overload. They want to really hammer home their points, especially when it comes to several of these charges, the two sex trafficking counts that he faces, as well as the transportation to engage in prostitution. And what better way to do that than show you more freak off videos. But how does that backfire though by continuing to hammer at home, if you will? From what I've been told by lawyers like Danny, it's that the jury can feel like this is overkill

They can also feel as though these women like Jane or Cassie Ventura do not look like they were being Forced or coerced into these drug-fueled sex parties that actually they look like they're having a good time and that there's consent there So again, we haven't seen these videos There was a four day period in December of 2021 that Combs filmed actually 50 different freak off videos and the jury saw some of those today. So we don't know what's on them. Yeah. And you're saying that because they're not allowing people in the courtroom to see the videos, just the jurors.

Right. They're under seal, Andrea. And this is something that just the jury and the defense and prosecutors get to see. This is to protect the anonymity of someone like Jane. This is to also protect the identities of some of these escorts. I just want to point out that while these videos are being played, Combs' mother, Mama Combs, that's her nickname, was staring straight at the jury looking for their reaction. Combs was kind of looking around. He doesn't seem as stressed today as he has in previous weeks.

And you were also watching the faces of the jury. We know that it's a bad idea, obviously, to try to read jurors' faces because you just never know what they're thinking. And Joe Tecapina told us that on Friday. What were you seeing though? What were their expressions regardless of what's going on in their brain? Some look uncomfortable watching the videos while others seem to be paying close attention and taking notes.

In the past, we've seen some jurors even wince. They've already seen freak off videos, but I don't think you can ever get used to seeing these. And so everybody has a different tolerance. And I think that that's what's really going to happen during these jury deliberations is there's also an age divide here. And what are different people's opinions of consent and of this type of what Combs's team would say is just a kinky lifestyle. This federal agent, he brought up other evidence as well. Was there anything impactful or interesting in the text messages that were brought up,

Chloe? Well, we heard a lot about Christina Karam, also known as KK today. We saw that she was across many text messages with Coombs and she was also in touch with a travel agent named Jessica Ruiz to set up these hotel nights. She saw what credit cards were being used, and she really was Combs's right hand. But again, remember, she put out that statement, vigorously denying any sort of criminal involvement and that she had nothing to do with anyone being sex trafficked.

But it's interesting, right? The government's last witness is this Homeland Security investigator. We don't see KK on the stand. Chloe, there's a moment in one of these voicemails where Combs realizes he's run out of baby oil. It's another one of those audio text messages, right? Also known as voice notes for all the hip people out there. But Combs, he really loved voice notes and he would send a lot of them, whether it was to Jane, his former girlfriend,

or whether it was to KK. And in one of those that you're referencing, he sounds out of breath and very concerned that he's run out of these seven bottles of baby oil and he thought that that was enough. And KK's like, I got you. She responds in a text message. And then he miraculously has baby oil show up at his hotel room door, assuming it's an assistant brought it there. Yeah. So how does this fit into the Rico conspiracy charge?

I think a lot of the evidence that we've seen today and on Friday from this special agent is that Combs also set up these hotel nights and hired these escorts all on his own. He interfaced with the travel agent. He was very aware where these escorts were flying from and that he would sometimes talk to these escorts himself over text message. In one instance, you have Sean Combs talking to this woman named Bridget, who runs Cowboys for Angels, this escort service, and he actually writes to her over a text message saying, Stop raising my rate. I am a long timer. And he says he couldn't even perform.

Chloe, you're saying that this escort couldn't make it happen, so to speak? Chloe, you're saying that this escort couldn't make it happen, so to speak? Yeah, it sounds like this escort could not perform the sexual duties required. And these are the text messages now on the back end between Combs and this woman, Bridget from Cowboys for Angels saying that like, regardless of what happens, that's not our problem. You still have to pay them for their time and their companionship. This is very clear that Combs knew that he was hiring escorts. And again, that goes towards transportation to engage in prostitution.

And this also goes towards the RICO conspiracy charge because one of the predicate crimes is sex trafficking. Lauren Henry Was the defense able to undermine any of this on cross-examination? Lauren Henry There were some text messages between Jane and a particular escort, Cabral, in which she is booking his travel for him, in which she seems very excited about having him come. She says she wants him to FaceTime her right now, but when she took the stand, she said that a lot of those FaceTimes, Combs was with her and that he would get turned on by watching her have

sexy conversations with these escorts. So again, she has maintained that she was forced, even though these text messages seem really loving and willing in nature. SONIA DARA Okay, thank you, Chloe. When we come back, the federal agent testifying today is what's called a summary witness. We've asked NBC News legal analyst Danny Savalos to join us to explain what that is and to talk to us about some breaking defense news. Danny, thank you for joining us again. Thanks for having me.

You're going to do us right and you're going to make explaining a summary witness interesting, right? I don't know if I can do that, but I can explain what they do. Please do. So, oftentimes when you have documents, records, and data, you need a witness to essentially organize information for the jury, but they have to take the stand and explain what they did to organize it so that the jury can understand why and it's admissible as evidence. And it can be really, really dry, but it's quietly the most important part of the case. Why is it so important?

Because in a case like this, text messages, hotels, any of this data that comes in is critical because it's more reliable than just somebody getting on the stand. And are they also confirming kind of what the prosecution has said, confirming that it's accurate and that this is backing up everything you've heard? Oh, sure. I mean, that's what they have to do. I mean, if you didn't have these summary witnesses, the jury would have to comb through

all of this information and summarize it themselves. So the prosecution has called a couple of these summary witnesses. Their testimony, of course, has been less dramatic than, you know, say, Kid Cuddy or Cassie. Why would a prosecutor want to close their case, you know, with the testimony of people who are somewhat removed from the story? Because the people themselves are not what we call percipient witnesses. So an employee of the government, obviously he wasn't

at the freak-offs, he or she, and they can't testify as eyewitnesses. But they're testifying about facts and data and information that really may not lie in the same way that a witness and eyewitness to something that happened may misremember or lie or fabricate. And also kind of wrapping everything up, right? Sure, yeah, yeah, and exactly. And you know, the government has a tough decision to make in terms of do they want the flashier witnesses at the end or do they want these sort of drier

witnesses? And it could be that the strategy as well, since this is the information that we think is the most important, even if it's a little less sensational than Kid Cudi and his burning car, then we will put it at the end. This morning before the jury was even sworn in, defense attorney Mark Agnifilo dropped some big news. What was it? Yeah, that the defense wouldn't be calling any witnesses.

And candidly, to defense attorneys everywhere, this really isn't a surprise for a couple different reasons. Number one, the government has the burden of proof to the highest degree beyond a reasonable doubt. So for that reason, it's very common, including in my cases, to call no witnesses at all and simply make your entire defense case about pointing out reasonable doubt in the government's case. Because if you start calling witnesses that you don't absolutely need,

you can snatch defeat from the jaws of victory. It is a huge risk because of that burden of proof. Nobody wants to be the cautionary tale of the defense attorney who had a pre-good case going and then started calling witnesses who torpedoed his own case. So the defense's case is really through cross-examination. Oh, definitely. And in my opinion, this is just my experience, but that's not that uncommon in these federal

cases where the government just has a ton of evidence. And if you call one or two witnesses, that almost looks worse than calling zero witnesses. And for those people wondering, well, why pay these high-priced lawyers if they weren't going to call any witnesses? That's not really the measure. The measure is what gives you the best chance to raise reasonable doubt as to the government's case. And by the way, I would say the only part that is no surprise whatsoever is that they were never going to call Combs. Yeah. Danny, you always do make it interesting. You came through. Thank you so much for that.

Thank you. Thanks for that. Thank you. Thanks for listening. 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 slash Diddy to find that. On Trial is produced by Franny Kelly with help from the Dateline True Crime Weekly team. Our senior producers are Allison Orr and Liz Brown-Kurloff. Original music by Jesse McIntee.

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