Sean Combs: Cassie Ventura's cross examination wraps up.

Summary

Dateline: True Crime Weekly – Episode Summary
Title: Sean Combs: Cassie Ventura's Cross Examination Wraps Up
Release Date: May 17, 2025
Host: Andrea Canning
Produced by: NBC News

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Introduction to the Trial

Andrea Canning opens the episode by introducing a special series titled "ON Trial," which offers daily coverage of Sean Combs' sex trafficking trial. Combs has pleaded not guilty to all charges. Andrea sets the stage for today's focus: the recent cross-examination of Cassie Ventura, Combs' ex-girlfriend, highlighting the tension and drama unfolding in the courtroom.

Andrea Canning [01:03]:
"Today is Friday, May 16th. Just a heads up, in this episode, we're going to be talking about some graphic details and harrowing subject matter."

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Cassie Ventura's Testimony Under Scrutiny

Cassie Ventura took the stand while eight and a half months pregnant, displaying signs of exhaustion but maintaining composure throughout her testimony. She faced intense pressure from Combs' defense team, which aimed to challenge her credibility and portrayal of events.

Chloe Meloss [02:00]:
"She kept her composure. She did rub her belly at multiple points. And she did seem to be a bit fidgety."

The defense was on a tight schedule due to Cassie's impending childbirth, leading to frequent breaks during the cross-examination.

Andrea Canning [02:13]:
"And the defense was essentially on a deadline. They were told, you have to wrap this up."

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Playback of Explosive Audio Recording

A pivotal moment in today's proceedings was the defense's presentation of an audio recording featuring Cassie confronting a man. This tape revealed a side of Cassie characterized by anger and threats, contrasting her typically soft-spoken demeanor.

Andrea Canning [02:32]:
"Let's talk about this explosive tape that the defense played... It is a different side of her."

Chloe Meloss [03:12]:
"Remember, she's up there soft spoken, demure, and you hear the defense saying that there was physical abuse on both sides."

The defense aimed to depict mutual abuse and instability in Cassie's relationship with Combs, introducing complexity to her character and motivations.

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Drug Use and Credibility Attacks

The defense delved into Cassie's admitted drug use, seeking to undermine her credibility. Cassie acknowledged her addiction to opiates, which she used to cope with the emotional and physical toll of her experiences.

Andrea Canning [03:28]:
"Why does the defense find that to be relevant information for the jury?"

Chloe Meloss [03:28]:
"Because they're trying to attack her credibility. They're trying to challenge her."

Cassie explained that her drug use was a means to disassociate during intense moments, allowing her to participate in drug-fueled encounters she otherwise wished to avoid.

Chloe Meloss [03:42]:
"So it was this vicious cycle. And at one point she says that she even went to rehab to try and recover."

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Defense's Portrayal of Sean Combs' Behavior

The defense also focused on Sean Combs' alleged drug and alcohol use, particularly referencing a 2016 incident where Cassie claimed Combs assaulted her while "blacked out."

Chloe Meloss [04:16]:
"They're trying to say that that wasn't actually the real Combs perpetrating those acts of violence."

By highlighting Combs' substance abuse, the defense contended that any violent behavior was a result of his impaired state, attempting to distance him from orchestrating a broader criminal enterprise.

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Allegations of Rape and Defense Counterarguments

A highly emotional segment involved Cassie's allegations of being raped by Combs in 2018 following their breakup dinner. Combs has denied these claims and was not charged with rape.

Chloe Meloss [05:21]:
"What they showed is that although Cassie Claims that they broke up in 2018... the defense is saying... the very next day, you sent loving text messages."

The defense questioned the consistency of Cassie's accounts and pointed to subsequent affectionate communications as evidence of a complex and possibly manipulative relationship dynamic.

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Sean Combs' Courtroom Demeanor

Throughout Cassie's cross-examination, Sean Combs remained notably detached, focusing intently on his legal team without displaying visible emotion. Observers noted a lack of alignment among the defense attorneys, suggesting internal discord.

Chloe Meloss [06:07]:
"He is so engaged, but he doesn't show any sort of visible emotion."

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Final Defense Strategies and Prosecution's Response

In the concluding moments of the defense's cross-examination, they presented an email exchange from 2019, showcasing cordial communication from Combs post-crisis, contrasting with Cassie's assertion of ongoing control over their tumultuous relationship.

Andrea Canning [08:19]:
"Cassie's testimony is finally complete... he said that he's so proud of Cassie and her bravery."

On redirect, the prosecution emphasized proving racketeering by linking Combs' business operations to illegal activities, introducing his employees as intermediaries involved in the alleged sex trafficking enterprise.

Chloe Meloss [10:00]:
"They were really trying to prove racketeering... using his businesses to carry out illegal activity."

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Attorney's Statement and Next Steps

Cassie's attorney, Douglas Wigdor, affirmed her bravery and highlighted the complex dynamics of abusive relationships, suggesting that love and abuse can coexist, complicating the jury's perception.

Douglas Wigdor [11:06]:
"There are many women... who are abused by people who they love... she readily admitted that there were some good times in that relationship."

The trial continues with the prosecution aiming to solidify the connection between Combs' enterprise and the charges of sex trafficking, as the defense presents a narrative of mutual abuse and personal turmoil.

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Conclusion

Andrea Canning wraps up the episode by directing listeners to the NBC newsletter for ongoing updates and analysis, emphasizing the comprehensive coverage provided by the "ON Trial" series.

Andrea Canning [11:49]:
"If you want to read the latest developments and analysis from inside the courtroom, check out the NBC newsletter."

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This episode provided an in-depth look into the fraught courtroom dynamics of Sean Combs' trial, shedding light on Cassie Ventura's testimony, the defense's strategic maneuvers, and the overarching battle to establish or dismantle the charges of sex trafficking.

Transcript

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[Andrea Canning]

This is ON Trial, a special series from DATELINE True Crime Weekly bringing you daily coverage from the Sean Combs sex trafficking trial. He has pleaded not guilty to all the charges against him. I'm Andrea Canning. Today is Friday, May 16th. Just a heads up, in this episode, we're going to be talking about some graphic details and harrowing subject matter. Cassie Ventura, Sean Combs ex girlfriend, was back on the witness stand today under fire from Combs defense team. Once again, they confronted Cassie with her own words. But this time it wasn't just what she'd written in intimate texts and emails. Today the jury got to hear Cassie's voice on tape and she sounded angry. NBC News correspondent Chloe Meloss joins us now from outside the federal courthouse to tell us more. Hey, Chloe.

[Chloe Meloss]

Hey, Andrea.

[Andrea Canning]

So, Chloe, let's go back into the courtroom. Cassie took the stand this morning, eight and a half months pregnant. She must have been exhausted.

[Chloe Meloss]

She kept her composure. She did rub her belly at multiple points. And she did seem to be a bit fidgety. They would take breaks about every 90 minutes, which is completely understandable. They think she's gonna give birth over the weekend.

[Andrea Canning]

Wow. And the defense was essentially on a deadline. Right. Because of the pregnancy. They were told, you have to wrap this up.

[Chloe Meloss]

Yeah. I mean originally they were told yesterday that they only had five more hours to finish their cross examination. But then when they got in there this morning, the judge said that the prosecution had said that they could have until 4:30.

[Andrea Canning]

Let's talk about this explosive tape that the defense played. It's Cassie confronting a man. There's audio of it. She thought that this man had a video of one of the freak offs and she was quite angry.

[Chloe Meloss]

So, Andrea, in this audio recording, you hear her screaming at this man, she's saying, I'm gonna kill you. So she's freaking out and she wants to know where is the tape? And I think that the reason that they're playing it is to show a different side of her. Remember, she's up there soft spoken, demure, and you hear the defense saying that there was physical abuse on both sides. So again, you hear her screaming and making threats. It is a different side of her.

[Andrea Canning]

The defense also asked Cassie about her drug use, which she has fully admitted that she was using drugs, that she was addicted to opiates. Why does the defense find that to be relevant information for the jury?

[Chloe Meloss]

Because they're trying to attack her credibility. They're trying to challenge her. And one of the ways is by having her testify about her drug use.

[Andrea Canning]

Cassie actually said that she was using drugs to recover from the pain of the free coughs.

[Chloe Meloss]

So during her testimony this week, she's talked about taking drugs in an effort to disassociate during those freak offs so that she could actually participate in these drug fueled sex encounters that she says she didn't want to be a part of. On the other side of it, she would take drugs after the freak offs to try and come down off of other drugs. So it was this vicious cycle. And at one point she says that she even went to rehab to try and recover.

[Andrea Canning]

The defense also got Cassie to talk about Combs relationship to drugs. Why did they want to bring that in?

[Chloe Meloss]

So I thought that that was really interesting. At one point, Cassie actually described Combs as being blacked out on drugs and alcohol when he beat her up in 2016 in that video that we've all seen by now. And they talk a lot about his drug use. And what they're trying to say is that that wasn't actually the real Combs perpetrating those acts of violence. That it was because of these benders that they were mutually on.

[Andrea Canning]

So the defense is saying, you know, that essentially Combs might be a flawed man, but that behaving badly or taking drugs isn't the same as orchestrating a criminal enterprise or sex trafficking. And that is the bar for. Yes, the prosecution, exactly. Some of Cassie's testimony that was really hard to hear about was when she talked about her allegations that Combs raped her in 2018 after they had a breakup dinner. She got very emotional. Combs, you know, was never charged with rape and he has denied that allegation. But nonetheless it has come up. How did the defense handle that?

[Chloe Meloss]

What they showed is that although Cassie Claims that they broke up in 2018. Text exchanges show that they met up for dinner that fall in Malibu, California. And she claims that when he returned her to her apartment that he forced himself in and raped her. But what the defense is saying is, well, first of all, the date that you put in your civil suit is different from the date that you told prosecutors about that alleged incident. And also the very next day, you sent loving text messages, including a heart emoji. So obviously very complicated. It's going to be really interesting to see what does the jury take away from all of this.

[Andrea Canning]

How has Sean Combs been reacting to Cassie's cross examination?

[Chloe Meloss]

He is so engaged, but he doesn't show any sort of visible emotion. He's really focused on his own attorneys. He's constantly sending writing on post it notes and handing it to them. But again, this is just my opinion from sitting inside that courtroom today. There are a lot of attorneys, Andrea, and it almost seems like they're not all on the same page. I think there's a lot of cooks in the kitchen.

[Andrea Canning]

When we come back, the defense confronts Cassie with one last email. And what's next for the prosecution?

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[Andrea Canning]

Chloe after lunch, the defense wrapped pretty quickly. But before they did, they asked Cassie to go over an email exchange with Combs from 2019. Tell us about that exchange.

[Chloe Meloss]

And 2019 is a pivotal year to point out, Andrea, because this would have been after this alleged rape. This would have been after over a decade of freak offs. Combs writes, quote, I thank God for the time we had together. You are the greatest woman in the world. Don't ever forget that. Cassie responds, I don't hate you. I never have. Combs writes, one day I hope you can forgive me. I'm glad you found someone to love you and respect you. And he is referring to Alex. Fine. He is also referring to the fact that she had just announced that she was pregnant with her first child. Gosh.

[Andrea Canning]

Yeah, it sounds, after everything we've heard, that sounds so cordial. The defense left the jury with one last text about freak offs. It seems like they really wanted to leave them with the idea that Cassie was, she was the one in control.

[Chloe Meloss]

Combs defense has always maintained that, Andrea, because what they say is that the prosecution, the government, the way that they got these videos and these pictures are off Cassie's devices, not any devices that they got when they raided Combs homes last year. So in this final kind of mic drop moment today, the text from Cassie reads to Combs, I don't want to freak off for the last time. I want it to be the first time for the rest of our lives.

[Andrea Canning]

This is when you say complicated, man, this is complicated. What points did the prosecution make on redirect with Cassie?

[Chloe Meloss]

They were really trying to prove racketeering. And how do you prove racketeering? That he was running a criminal enterprise or using his businesses to carry out illegal activity. That's where you introduce the people that work for him, the personal assistants, the security. And that's where on redirect, you saw the prosecutors saying, who came to your apartment? Who did this for the freak offs? And they were talking about employees who would be his intermediaries.

[Andrea Canning]

I mean, it really comes down to that because they have to make that direct connection to their charges.

[Chloe Meloss]

Right.

[Andrea Canning]

So a bit of excitement outside of the courthouse. The Cassie's attorney, Douglas Wigdor just came out and actually spoke to all of you.

[Chloe Meloss]

Yes. So Cassie's testimony is finally complete and her attorney came out and spoke in front of the courthouse, addressing reporters, and he said that he's so proud of Cassie and her bravery. He also answered a quick question of mine. What about the moment in which she said on cross examination that she does not hate Mr. Combs and that when she looks back on their relationship, she still has some love for him for what they shared. Could you explain that dynamic?

[Douglas Wigdor]

It's a dynamic I think that will be explained further in this case, perhaps through the expert witness. I think we all know and can appreciate that there are many women, as I'm speaking here today, who are abused by people who they love. They had a 10 year relationship. I think she, she readily admitted that there were some good times in that relationship that does not obviously permit someone to do the things that she testified to.

[Andrea Canning]

Interesting. Okay, Chloe, thank you so much for bringing us all of this color from the courtroom.

[Chloe Meloss]

Of course.

[Andrea Canning]

Thanks for listening. We'll be back with a new episode Monday night. 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 producers are Alison Orr and 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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