Sean Combs: Cassie Ventura takes the stand.

Summary

Dateline: True Crime Weekly – Episode Summary

Title: Sean Combs: Cassie Ventura Takes the Stand
Host: Andrea Canning
Release Date: May 14, 2025

Introduction

In this gripping episode of Dateline: True Crime Weekly, host Andrea Canning delves into the high-stakes trial of Sean "Diddy" Combs, who faces serious charges including racketeering, sex trafficking, and transportation for the purposes of prostitution. Combs vehemently denies all allegations. The episode provides an in-depth look into the courtroom drama, featuring testimonies from key witnesses and exclusive insights from NBC News correspondent Chloe Meloss.

Trial Developments and Witness Testimonies

The episode opens with Andrea Canning setting the stage for the second day of Combs's trial. The defense team aggressively cross-examines a witness who claims he was paid to engage in sexual activities with Combs and his then-girlfriend, Cassie Ventura. Additionally, the witness alleges that Combs exhibited violent behavior towards Ventura, creating a tense atmosphere in the courtroom.

Notable Quote:

"He was honestly so scared for his life, he didn't know what Sean Combs was capable of."
— Chloe Meloss, [04:06]

Cassie Ventura's Anticipated Testimony

The prosecution calls Cassie Ventura to the stand, marking a pivotal moment in the trial. Ventura arrives at the courtroom visibly emotional, dressed in a fitted brown dress and overcoat, with her husband seated beside her. Her entrance is met with palpable tension, underscoring the significance of her testimony.

Notable Quote:

"This has been the most anticipated testimony for over a year."
— Chloe Meloss, [02:43]

Exploring the Relationship Dynamics

Andrea and Chloe discuss the complexities of Ventura's relationship with Combs. Ventura recounts how their professional relationship evolved into a romantic one, spanning over 11 turbulent years. She describes Combs as initially supportive, helping her navigate the music industry, but admits that underlying issues such as jealousy and infidelity eventually strained their bond.

Notable Quotes:

"On the stand today that she was jealous of that."
— Chloe Meloss, [10:39]

"He was the head of Bad Boy, he controlled her career. He told her what to wear."
— Chloe Meloss, [11:43]

The Defense's Position

The defense challenges the credibility of the witness by highlighting inconsistencies in his statements. They argue that his reluctance to come forward was driven by his enjoyment of the glamorous lifestyle rather than fear or coercion. This tactic aims to cast doubt on the prosecution's narrative of Combs's alleged misconduct.

Notable Quote:

"If you were so scared for your life or you were so disgusted by what you had seen, why did you write that?"
— Xavier Donaldson (Combs's Attorney), [04:06]

Emotional and Psychological Impact

Ventura's testimony reveals the emotional toll the relationship had on her. She describes feeling forced into sexual activities, including threesomes and regular sex parties, to please Combs. Her account suggests a pattern of control and manipulation, painting a harrowing picture of her personal struggles.

Notable Quotes:

"I really was in love with Combs and really just wanted to make him happy."
— Chloe Meloss, summarizing Ventura's testimony, [12:07]

"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."
— Chloe Meloss, [12:07]

Courtroom Observations

Chloe provides vivid details of Combs's demeanor in court. Unlike his typically charismatic public persona, he appears stressed and tense during Ventura's testimony. His interactions with the jury and his family display a side of vulnerability not seen in previous public appearances.

Notable Quotes:

"He really stared at her during her entire testimony, his face expressionless."
— Chloe Meloss, [07:50]

"He opened his eyes really wide and you could see him let out this big exhale. You can tell he's stressed."
— Chloe Meloss, [07:54]

Impact on Combs's Family and Public Perception

The presence of Combs's children and ex-partners in the courtroom adds another layer of complexity to the trial. Notably, Misa Hilton, the mother of Combs's son Justin, attends and shows a nuanced stance by expressing sympathy towards Ventura while remaining supportive of Combs. This dynamic hints at internal conflicts and the broader implications of Combs's personal life on his professional image.

Notable Quotes:

"She is sitting right there on Combs's side of the courtroom."
— Chloe Meloss, [05:52]

"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..."
— Chloe Meloss, [07:50]

Emotional Breakdown and Testimony Highlights

Ventura becomes visibly emotional while discussing her coerced participation in Combs's sexual activities. Her breakdown underscores the psychological abuse she endured and highlights the severity of the allegations against Combs. This moment is pivotal in eliciting empathy from the jury and the audience.

Notable Quotes:

"That's when she broke down crying. So it was a very emotional day."
— Chloe Meloss, [12:07]

Anticipation for Upcoming Proceedings

Andrea Canning concludes the episode by previewing the continuation of Ventura's testimony and the defense's forthcoming cross-examination. Listeners are encouraged to follow the daily trial updates through the Dateline True Crime Weekly feed and the NBC newsletter for comprehensive coverage.

Conclusion

This episode of Dateline: True Crime Weekly offers a detailed and emotionally charged exploration of Sean Combs's trial, focusing on Cassie Ventura's impactful testimony and the intricate dynamics of their relationship. Through expert analysis and firsthand courtroom reporting, Andrea Canning and Chloe Meloss provide listeners with a nuanced understanding of the case's complexities and the profound personal ramifications for those involved.

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Produced by: Franny Kelly, Dateline True Crime Weekly Team
Senior Producer: Liz Brown Karloff
Original Music: Jesse McGinty
Executive Producer: Paul Ryan
Senior Executive Producer: Liz Cole

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For in-depth coverage and daily updates on the Sean Combs trial, follow the Dateline True Crime Weekly feed and subscribe to the NBC newsletter at nbcnews.com/diddyontrial.

Transcript

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[Andrea Canning]

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 Meloss 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, then girlfriend Cassie Ventura, and that he also saw Combs behave violently toward Cassie. Then just after 11am the prosecution called Cassie Ventura herself. She is their star witness. And NBC News correspondent Chloe Meloss 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.

[Chloe Meloss]

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.

[Andrea Canning]

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 Sean 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.

[Chloe Meloss]

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.

[Andrea Canning]

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.

[Chloe Meloss]

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 to bait Cassie because they 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?

[Andrea Canning]

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?

[Chloe Meloss]

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 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 going to see tears. But they remained strong and very stoic.

[Andrea Canning]

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.

[Chloe Meloss]

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.

[Andrea Canning]

When we come back, Cassie Ventura takes the stand.

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[Andrea Canning]

How did Sean Combs look when Cassie walked into that courtroom?

[Chloe Meloss]

He turned around and he watched her walk, 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 trial 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.

[Andrea Canning]

And you can argue that this whole thing is happening right now possibly because of her.

[Chloe Meloss]

Oh, absolutely. There will be other witnesses. There are other alleged victims, but Cassie is the star witness.

[Andrea Canning]

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.

[Chloe Meloss]

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, you know, serial entrepreneur. He was a king maker. And, you know, 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.

[Andrea Canning]

Yeah, I mean, it was a long time. And when you look at those pictures of them on red carpets, they look so perfect they together.

[Chloe Meloss]

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's defense's opening statement yesterday that this, all of this rage was fueled by jealousy on both sides.

[Andrea Canning]

So we heard the so called escort talk about the free coughs. What was Cassie's version of them in court?

[Chloe Meloss]

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 Shawn 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.

[Andrea Canning]

At a certain point she said Sean was essentially controlling most of her life.

[Chloe Meloss]

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.

[Andrea Canning]

Cassie got emotional at times.

[Chloe Meloss]

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.

[Andrea Canning]

Cassie will be back on the stand tomorrow and the defense will have their turn to cross examine at some point. Chloe, thank you so much for taking the time to talk to us.

[Chloe Meloss]

Yeah, thanks so much.

[Andrea Canning]

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 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 Karloff Original Music by Jesse McGinty Paul Ryan is executive producer and Liz Cole as senior executive producer of Dateline.

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