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Sean Diddy Combs' Criminal Trial; Cassie Ventura's Cross- Examination. Aired 2:30-3p ET

Aired May 15, 2025 - 14:30   ET

THIS IS A RUSH TRANSCRIPT. THIS COPY MAY NOT BE IN ITS FINAL FORM AND MAY BE UPDATED.

[14:30:00]

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BRIANNA KEILAR, CNN ANCHOR: And we're back now with our breaking coverage of Sean Diddy Combs' criminal trial in New York. We should note that on the left side of your screen, you are going to be seeing a play by play of what is happening in federal court because cameras are not allowed inside. But we do have a team of reporters who are watching the proceedings and sharing what they hear.

BORIS SANCHEZ, CNN NEW DAY WEEKEND ANCHOR: Sean Combs is facing charges of racketeering and sex trafficking, and right now the prosecution's star witness Combs' ex-girlfriend, Cassie Ventura, is on the stand under cross-examination. We understand that just a short time ago, the jury was dismissed for a short break. We do have our panel of experts alongside us.

I wonder though, Areva, when it comes to a sensitive cross-examination like this, how the defense goes about putting someone on the stand who has already settled a case with the defendant and is accusing that person of sexual assault of all of these salacious things, they have to walk a fine line between pressing her to try to make their argument that there was no coercion, that this was something consensual. But at the same time, she's a sympathetic witness, right, for the jury.

AREVA MARTIN, ATTORNEY AND LEGAL AFFAIRS COMMENTATOR: Not only is she sympathetic, Boris, she is eight months pregnant, and we know that the defense wanted the judge to have her already seated when the jury enters the courtroom so they wouldn't see her very visible pregnant belly, and the judge refused that.

So, she's walked into that courtroom every day and taken that witness stand, walking past the jurors, showing her visible stomach. That has to have an impact on these juries. And you're right, that settlement for a lot of jurors, they're going to be asking, my goodness, if you didn't do anything wrong, why would you pay $20 million?

Now, lots of folks understand this. Lawsuits are settled for lots of reasons, but that has to be one of the questions that these jurors will ask themselves. And going after her aggressively could definitely alienate jurors. You can't bully her. You can't be too aggressive because she is the victim even if you don't believe the charges against Diddy are legitimate. They have seen enough evidence of her being violently beaten by this man, so she is a victim. There are no two ways about that. And yes, handling her very delicately takes a lot of skill on the part of a defense attorney and it takes a lot of discernment. And from what we're hearing from the reports inside the courtroom is that the defense is being very delicate in their questioning of her.

KEILAR: Let's talk about a moment that we're just learning about, which is that Ventura testified that Combs introduced her to rapper Kid Cudi around 2011 so they could work on music together. We've heard a lot about Kid Cudi here in the last day or so. Ventura said she began dating him while she was on a break with Combs. She testified that she got a burner phone to communicate with him because she didn't want Combs to find out about the relationship. She said she thought it would be way too dangerous to tell him about that.

But then this is really an interesting part, and Imran, if you can maybe talk a little about -- bit about this. Ventura said, Combs eventually found out about the relationship when he went through her phone during a freak off. She said that she was still having these freak offs, these sexual encounters with Combs while she was on a break from him because it was a job. That's a refrain we've heard her say now for days.

She said Ven -- that Combs lunged at her when he found out, but he didn't make contact with her. What do you think about this line of questioning and the fact that she was still having these encounters with him while she was dating someone else? How is the jury potentially receiving this? What's the defense trying to do?

IMRAN ANSARI, FORMER PROSECUTOR AND CRIMINAL DEFENSE ATTORNEY: So, from a defense standpoint, I think they have to bring this out. This was brought out by the prosecution on direct, this relationship with Kid Cudi, and then also the sort of circumstantial testimony there that Combs said he wanted to blow up his car. And then ultimately, Kid Cudi's car blows up.

So, the defense has to handle this in some way. But I believe the way they are bringing out this testimony right now from Ventura is adding to what we've talked about, about painting this picture of a complicated relationship between Ventura and Combs.

[14:35:00]

And ultimately with the building blocks on the defense standpoint, bringing it away from the actual charges that the prosecution has brought, the sex trafficking charges, the conspiracy -- racketeering conspiracy charges. And then arguing to the jury that this was a complicated relationship. Yes, there was abuse. Yes, there was domestic violence. But -- and there was certain sexual things that the jury may find that is not palatable. But it wasn't those charges. The elements of those crimes were not met on the prosecution's case.

So, I think bringing in this aspect of Kid Cudi is, again, to show a complicated relationship between Combs and Ventura. And then ultimately taking it away from the charges the prosecutions have brought and arguing that, yes, there was domestic violence. It was a complicated relationship but those crimes were not committed.

KEILAR: All right. Everyone, if you can stand by for us, we do have more to discuss. We're getting in more information about some of these recent moments in this trial. And our extensive coverage of the Sean Diddy Combs criminal trial will continue here in just a moment.

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[14:40:00]

SANCHEZ: We are continuing to follow the latest details in the Sean Diddy Combs trial. Court is in a short break right now, and this is at least the second break that Combs' ex-girlfriend, Cassie Ventura, has asked for today while under a cross-examination.

KEILAR: That's right. And our panel is now back to discuss. And let's discuss something, this came out before the break, but Dave, maybe you can speak to what the defense is trying to do here. They are bringing out a message that shows Cassie Ventura was frustrated about not being able to spend time with Combs and his children.

She said, I've been at the edge of tears this whole week. I don't think that you sympathize with my feelings. I understand you feeling like you need to protect your children, but after a while, it's like for what? They've never known you and Kim, meaning Porter, to be together unless there's something that I just don't know about. They were babies when we started dating.

What does this illustrate the defense is hoping for the jury?

DAVE ARONBERG, FORMER STATE ATTORNEY, PALM BEACH COUNTY, FLORIDA: The relationship is complicated. It was back and forth. She was in love with him, and this doesn't sound like to the defense that this is someone who's being held against her will and doing things she didn't want to do when she wants to get even closer to Diddy. In the midst of all this, she wants to get closer to him and his family. And so, I think that's part of it.

But you know, this is all pointing things in context. The prosecution will come back and will say, yes, you could feel this way. At the same time, you could be the victim of force fraud and coercion. You can still be consensual, perhaps at some part at the beginning, and then revoke your consent later and say, no. No more.

So, this is just part of the context. They're going to have to keep going back and forth with these messages and see which version of the story the jury believes.

SANCHEZ: We should note, Ventura is now back on the stand. And during the break we understand that Combs -- or actually during the previous break, we understand that Combs had shared something with the attorney that's handling the cross-examination.

And as the questioning was going on, he was apparently writing on orange sticky notes and passing one after another to the attorney sitting beside him. It's fascinating to sort of get that color and hear the reaction within the room to Ventura's testimony.

I wonder, Jem, we've been discussing the context of this relationship that Ventura had with rapper Kid Cudi when she was on a break from dating Combs. I'm not sure a lot of folks, at least personally I wasn't familiar with that relationship, and further the details of the story that Combs apparently had told Cassie that he wanted to blow up Kid Cudi's car in front of his friends or so that his friends could find out about it. And then not long after that, Kid Cudi's car actually blew up. That was a stunning part of testimony even though it's not central to this case.

JEM ASWAD, EXECUTIVE MUSIC EDITOR, VARIETY: Yes. You know, Kid Cudi is a reasonably popular rapper. He's not top level. The relationship was public, you know, or public enough for him to -- for Diddy to find out about it. The car blowing up, I mean, I don't even remember what the speculation about that was at the time.

I think there was some implication that Diddy could have been involved, and quite honestly, it would not be extremely out of character for something like that to happen. I feel like something that gets overlooked in a lot of these situations is they tend to think that people are just one thing, and clearly, they're not. You know, all of us contain multitudes, as they say.

But I've met Diddy on a few occasions, interviewed him I think three times. One time he had -- it was a video interview. He had his sunglasses on. He was very direct, not warm at all, you know, just like very distant. Only answering the questions. It was about his album, ironically called Love, funny enough, his most recent album.

Before that I was interviewing him about his late mentor, a man named Andre Harrell, who he -- you know, who basically brought him up. They fell out. Andre fired him. And, you know, but Diddy went on to say that that was one of the best things that ever happened to him because he went on to get his own record deal.

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During that interview, he was enthusiastic, he was excited, he was laughing, he was fun, he was charming. And people can be both, especially people on that level. And if you do the wrong thing, it can go the opposite direction very quickly.

KEILAR: He'd see two sides even in the course of your work. Richard, so far, what are you just making of how the defense has approached this?

RICHARD GABRIEL, TRIAL CONSULTANT: Well, I think they're obviously creating these building blocks where they're really trying to, basically, very little -- first of all, they want to make it about the individual relationship. They obviously want to make it about the complications there.

The Kid Cudi thing, I think is a really interesting. One, because I think from the prosecution standpoint it's actually kind of trying -- they have to build a case for racketeering, which has to do with a pattern of conduct that doesn't just have to do with Cassie Ventura, but has to do with numerous people and the influence over a variety of individuals that are going to further the enterprise of this.

And so, the Kid Cudi thing, and the thing -- I think is maybe impliedly, but also is going to make sort of this mafioso connection to the jurors to say, hey, does this conduct, even though it may not be proved that he had anything to do with the car blowing up, it does sound a little bit more like an organized crime thing, which is obviously where the racketeering charges came from.

All of this though, comes from the point to really, jurors want to fill in the blanks. They want to find out who are these people, and obviously the defense is doing a good job of kind of creating this more nuanced picture of the relationship.

But ultimately, they're going to have to grapple with as they come up with how does the rest of the testimony actually comport with the two different stories that these sides are saying about what this relationship is, whether it's an individual relationship and a dysfunctional one, or whether it really is this power dynamic where he is completely in control of this whole situation and is coercing her into this -- these situations.

SANCHEZ: Everyone please stand by. We are eagerly awaiting a new update from our reporters. You see those three dots that are flashing on the red bar there, that means that something is getting typed up. So, we are awaiting an update from inside the courtroom where obviously cameras are not allowed. Cassie Ventura's testimony has resumed in the courtroom. Obviously, we're covering every detail of this trial. We have more of our analysis after a quick break.

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[14:50:00]

KEILAR: We are following some new testimony in the sex trafficking trial of Sean Diddy Combs. Cassie Ventura, his ex-girlfriend, still under cross-examination by the defense.

SANCHEZ: Yes. The judge, just a short time ago, told defense lawyers that he wants them to wrap up their questioning of Ventura by lunchtime tomorrow. Let's bring back our panel of experts right now. Dave Aronberg, Imran Ansari, Richard Gabriel, Jem Aswad, and Areva Martin.

Dave, I want to go back to you and just get your thoughts on what comes next, because obviously you have the prosecution trying to point out that Cassie Ventura says that she was coerced into these acts. The defense is trying to essentially say that she was trying to please him, that all of it was consensual. And then you have, as we've alluded to in previous parts of the conversation, these expert witnesses that are expected to come up and supplement this testimony. How do you see that playing out?

ARONBERG: Corroboration is key, Boris, because Cassie has been a great witness, and as Areva correctly said, she's been a sympathetic one, eight months pregnant. But the jury wants to see corroboration. There are other people out there who are coerced into this. Apparently, there's one witness who is not showing up, so they have two others who are apparently going to be very key in showing that this was not a consensual activity.

Right now, it's a he said, she said but it will get a lot better for the prosecution once Cassie's story is buttressed by other witnesses, other proof, other corroboration.

KEILAR: And Areva, as you're looking at how the defense has navigated this. Are there any things they have brought up that you think are going to be addressed when the prosecution is doing redirect?

MARTIN: I think they're going to redirect on this timeline because essentially a lot of these messages about being in love and wanting to participate in the freak off happened at a certain point in time, and I think the prosecution needs to take the jury back to those points in times when Cassie Ventura was clearly saying, I don't want to participate in this. I'm fearful of being blackmailed. I'm fearful of the violence that I may suffer if I refuse to participate in the freak offs.

So, I think that's what the prosecution's job on redirect is to acknowledge that there was a period when she may have been in love, she may have been sending these nice messages about getting close to his family, meeting his children. All of that happened, but consent can happen and as one of the other panelists has said can be revoked.

And the prosecution has to get the jury focused on that time period when Cassie Ventura was clearly not willingly participating or consenting in these activities. And then we'll see these other witnesses that will come forward to corroborate her revoking of any consent to the extent it existed at any point in time.

KEILAR: Yes, such a good point. She might be OK with something at one point and then not be at another time, and we'll see how the jury responds to that.

[14:55:00]

Thank you all to our panel for weighing in such great expertise on this. And ahead next hour we have more of our extensive coverage of the Sean Diddy Combs' criminal trial.

And attention Walmart shoppers, prices are about to go up. This is "CNN News Central."

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