Dateline NBC - Sean Combs: Cassie Ventura takes the stand.

Episode Date: May 14, 2025

On day two of testimony, the defense cross-examines a man who took part in "freak offs" and the prosecution calls their star witness.Description: In emotional and sometimes graphic testimony, Cassie Ventura tells the jury about her relationship with Sean Combs, who she says was abusive, violent and controlling. Chloe Melas describes how Combs -- who has denied all the allegations against him -- reacted in court.To get future daily episodes of Sean Combs "On Trial" follow Dateline True Crime Weekly: https://podcasts.apple.com/us/podcast/dateline-true-crime-weekly/id1745566056For more NBC coverage of the trial check out our newsletter, “Diddy On Trial”: NBCNews.com/Diddy

Hey everyone, Andrea Canning here with a bonus drop from the Dateline True Crime Weekly team. For the next eight weeks or so, we'll be bringing you daily updates from the trial of Sean Diddy Combs. I'll be talking to NBC News correspondent Chloe Maloss every day after court about what she's seeing inside, the witnesses, the evidence, and what it all means. Starting tomorrow, episodes will drop in the Dateline True Crime Weekly feed. This is On Trial, a special podcast from Dateline True Crime Weekly, bringing you daily coverage from the Sean Combs trial. I'm Andrea Canning. Today is May 13th.

In this episode, we're going to be talking about some graphic details and harrowing subject matter. Sean Combs is facing charges of racketeering, sex trafficking, and transportation for the purposes of prostitution, all of which he has denied. The second day of testimony began with his defense team's vigorous cross-examination of a man who says that he was paid to have sex with Combs's then-girlfriend, Cassie Ventura, and that he also saw Combs behave violently toward Cassie. Then, just after 11 a.m., the prosecution called Cassie Ventura herself. She is their star witness, and NBC News correspondent Chloe Maloss

was in the courtroom when Cassie made her way to the stand. She joins me now from just outside the courthouse to tell us what happened next. She's eight months pregnant and walks into this courtroom wearing this fitted brown dress, this long brown overcoat. Her husband was sitting right in front of me and you could hear a pin drop.

This has been the most anticipated testimony for over a year. Before we get to Cassie's actual testimony, let's talk about this other witness who started the day off. He is the man who says that in 2012 and 2013, he met Cassie and Shawn Combs at hotels around New York City and at both of their homes. This was for sex with Cassie.

He testified yesterday and again today on cross that he witnessed Combs being violent with Cassie on at least two occasions and it made him very uncomfortable, but yet he decided not to say anything. He is a bit of a conundrum. During his testimony, he talked about having participated in these freak offs and that he developed a friendship with Cassie or so he thought. On cross examination, one of Combs' attorneys, Xavier Donaldson, really picked apart his

testimony and said, look, some of the things that you're saying are not what you told investigators in the lead-up to this trial. And I know that this witness, he apparently said that he had thought about going to police, but didn't want to because he enjoyed being part of this world that he was in with these celebrities. On one hand, he says, I was so afraid for my life. I did not know what Sean Combs was capable of, which is why I didn't go to the police, which is why I didn't physically intervene.

But then there's a text exchange between himself and Cassie Ventura after this incident where he claims he saw Combs be violent with Cassie, where he says, I just love y'all. That's paraphrasing the text message. And when Xavier Donaldson on cross-examination said, well, if you were so scared for your life or you were so disgusted by what you had seen, why did you write that? And he actually says, oh, well, I didn't mean what I texted. I just did that debate Cassie because I wanted her to ask me to participate in another freak-off

so that I could go see her in person and make sure that she was emotionally and physically okay because I was worried about her. But is that something that the jury's really gonna buy? Combs' children were in court. How did they handle this? Did they stay for the entirety or, I mean, it's a lot. You know, at one point, prosecutors introduced a photo as evidence just to establish the

fact that Cassie was dating Combs and it was early on in their relationship. And in the photo, it's Cassie, Sean Combs, someone else, and Kim Porter. Reportedly, the love of Combs' someone else, and Kim Porter. Reportedly the love of Combs' life died of pneumonia several years ago and her children were in that courtroom. And I looked over at them and I thought that I was gonna see tears but they remained strong and very stoic. One of Combs' ex-partners was also there today, the mother of his son Justin. Her name is Misa Hilton and what was interesting about her presence is that

after the video of Cassie being beaten at the hotel in LA came out, she posted something on Instagram about it. Yeah, I was actually surprised to see her in the courtroom. About a year ago, that's when she wrote, My Heart Goes Out to her, meeting Cassie, saying, I know how she feels, also saying that Sean needs help. But she is sitting right there on Combs' side of the courtroom. When we come back, Cassie Ventura takes the stand. How did Sean Combs look when Cassie walked into that courtroom? He turned around and he watched her walk down the aisle of the courtroom and go up to the

witness stand. And he really stared at her during her entire testimony, his face expressionless. I saw him looking over into the jury box multiple times. But when there was one of the breaks, everybody left the courtroom, and then when we all came back in, as Combs walked back in, he looked over at his family sitting behind him,

and he opened his eyes really wide, and you could see him let out this big exhale. You can tell he's stressed. And this is very different than the Sean Combs that we've seen at all the pre- hearings where he's smiling and he's even yesterday Blowing a kiss to his family. He looks tense Maybe that's because this is the first time that he's seen Cassie since they broke up several years ago And also I mean because let's be honest he faces up to life in prison and and you can argue that this whole thing is happening

right now possibly because of her. Oh absolutely there will be other witnesses there are other alleged victims but Cassie is the star witness. So Cassie gave some insight into how she met Sean about this age gap between them. He's seeing somebody else at the time let us know kind of what she said about how this all started. So Cassie's an artist, right, who had a couple of hits very early on in her career. And she described being introduced to Combs because she was hoping to sign with Bad Boy Records. And she ultimately did land this 10 album deal with his company.

And she said she knew him as this serial entrepreneur, he was a kingmaker, and she was just excited to be in his presence. And in the beginning of their relationship, he was really looking out for her. She had a couple of bad performances, and she said that he always had her back. But then she says that it was her 21st birthday,

and she celebrated it in Las Vegas and that is the night that Combs kissed her for the first time. And she actually said in her testimony today that she ran out crying because she was so taken aback by the fact that he was showing interest in her, he's essentially her boss, and she was really confused. And she described herself as just being just really naive when it came to relationships. But then she said shortly thereafter, their situation became romantic, and that she started to fall in love with him. And that's when they became intimate, and then they ended up staying together on and off for 11 years. Yeah, I mean, it was a long time.

And when you look at those pictures of them on red carpets, they look so perfect together. And what's also really interesting is that she said, she thought that they were in this monogamous relationship, but it turned out that Combs had, quote, many girlfriends in his life, right? And she said on the stand today that she was jealous of that.

And so that is something that we heard in Combs' defense's opening statement yesterday that this, all of this rage was fueled by jealousy on both sides. So we heard the so-called escort talk about the Free Coughs. What was Cassie's version of them in court? Cassie said that early on in the relationship, he introduced the idea of having threesomes. And ultimately, they had a threesome with an escort. And she said that she didn't want to do it, but that she didn't really vocalize it because she wanted to make Sean happy. And she said that once they did it, it just kept going.

And that at one point, these freak-offs were happening weekly and some of these freak-offs would last days. At a certain point, she said Sean was essentially controlling most of her life. I mean, she said that, look, I mean, he was the head of Bad Boy. He controlled her career. He told her what to wear, allegedly. She said that she was the one that was instructed by Combs to go and hire these escorts. Sometimes she would book the hotels,

she would pay the escorts, and that she would even bring candles and baby oil and help really arrange the hotel room before these freak-offs happened. Cassie got emotional at times, Chloe? Yeah, so pretty early on in her testimony, you saw her holding a Kleenex, and she was wiping her nose and kind of wiping her eyes.

And then when she started talking about how she really felt forced into these freak-offs and that she really was in love with combs and really just wanted to make him happy, that's when she broke down crying. So it was a very emotional day. Cassie will be back on the stand tomorrow, and the defense will have their

turned-across exam and at some point, Chloe, thank you so much for taking the time to talk to us. Yeah, thanks so much. Thanks for listening. Remember, starting tomorrow you'll only be able to find our in-depth coverage in the Dateline True Crime Weekly feed, so make sure to follow us there. And 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 producer is Liz Brown-Kurloff, original music by Jesse McGinty, Paul Ryan as executive producer, and Liz Cole as senior executive producer of Dateline.