Dateline: True Crime Weekly
Sean Combs: Cross-examination of Cassie Ventura begins.
Fri, 16 May 2025
The defense showed Combs's ex-girlfriend texts where she appeared to be a willing participant in drug-fueled sex acts. She testified that in the early days of their relationship she wanted to make him happy, but later feared his anger if she said no. Ventura also admitted to jealousy over other women Combs was dating during their 11 years together, but said Combs's jealous rage turned into violence, such as when he found out she was dating musician and actor Kid Cudi. Allegedly he kicked her in the back and later blew up Kid Cudi's car.If you want to read NBC's coverage of the trial, check out our newsletter, “Diddy On Trial”: NBCNews.com/Diddy
Chapter 1: What is the Sean Combs trial about?
This is On Trial, a special series from Dateline True Crime Weekly, bringing you daily coverage from the Sean Combs trial. I'm Andrea Canning. Today is May 15th. In this episode, we're going to be talking about some graphic details and harrowing subject matter. Sean Combs is facing five charges, including racketeering and sex trafficking. He's pleaded not guilty to all of them.
Chapter 2: Who is Cassie Ventura and why is she important to the case?
Today, the defense began its cross-examination of Cassie Ventura, Combs' ex-girlfriend, and the centerpiece of the prosecution's case against him. During a grueling day on the witness stand, they confronted Cassie with her own texts and emails, some of them explicit, challenging the portrait she painted of Combs, the abuser and predator.
Instead, the defense presented a love story for the jury that they say might have been toxic but was not criminal. Tensions are high at the federal courthouse, and NBC News correspondent Chloe Malas was inside.
Chapter 3: How did the defense portray the relationship between Sean Combs and Cassie Ventura?
Chloe, it's been quite a day. It has. And one of the reasons, Andrea, is because Ventura is about to give birth and they want cross-examination to wrap up as soon as possible because they think that she could go into labor this weekend.
How did she do being cross-examined? I mean, this day could not have been easy for her.
Chapter 4: What challenges did Cassie face during cross-examination?
It has not. She is reserved. We haven't seen her crying like the days before. She's been very soft-spoken, sometimes giving one-word answers, but she's being cooperative. And I have to say that Combs' defense attorney, who is leading the cross-examination, is being very respectful, even at one point calling her charming and beautiful.
One of the defense attorney's first questions to Cassie was, you and Sean Combs were in love for 11 years. I hear a lot of activity in the background.
There are a lot of characters down here. There are all sorts of people, some that support Ventura, some that support Combs, and others who just have something to say that might not even have to do with the trial, as you just heard a moment ago. It's something that happens all day.
OK, so back to the question at hand, Chloe, one of the defense attorney's first questions to Cassie was you and Sean Combs were in love for 11 years. What point are they trying to make?
Chapter 5: What evidence did the defense present about the couple's relationship?
They're showing emails and text messages from the course of their 11 year relationship, and they're trying to show that it wasn't all bad, that this was somebody who was in love with Combs. and who made it known that she even wanted to have his child, that she wanted to marry him.
And so they're trying to establish that Ventura was not forced to be in this relationship with Combs and that she freely came and went during this on-and-off relationship.
One of the things, Chloe, that seemed really powerful to me from the defense today was when they showed Cassie texts about Freak Offs, texts that she wrote, she seemed like this willing participant.
In 2009, Sean Combs wrote, to Cassie that he cannot wait in reference to a freak-off. And she responds, I can't wait either. The defense confronted her with another text message, this one from 2017, which said, I love our FOs. And Cassie says that those were just words. But again, those words are being used against her. Interesting to see if it will sway the jury at all.
And clearly the defense can say, you know, that going by these texts, that these freak-offs were a part of the swinger lifestyle that Cassie and Combs were living. All consensual.
So Cassie has pushed back, saying that she took part in the freak-offs because she wanted to make Combs happy. She was afraid of him. And because these freak-offs were most of the time filmed, that he actually used them as blackmail, right, forcing her to stay in this relationship.
The defense got Cassie to admit there had been jealousy in the relationship. I know the actor Michael B. Jordan was brought up at one point.
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Chapter 6: How did the defense address allegations of coercion and blackmail?
So Cassie dated Michael B. Jordan during a brief breakup between she and Combs. But remember, I mean, this appears to have been an open relationship. Combs was with Kim Porter, the mother of several of his children. He had other girlfriends.
How does that help the defense by bringing up jealousy?
Well, they're trying to say that Cassie was so jealous that she at times initiated violence in the relationship. They're trying to poke holes in this idea that she was forced into this relationship, forced into these freak offs. How are you trapped and can't get out if you're actually publicly dating other well-known celebrities?
The defense zeroed in on Cassie's relationship with Kid Cudi.
Yeah. So at one point she was dating Kid Cudi and Combs allegedly was so upset over this that he actually blew up Kid Cudi's car. Cassie actually said that Combs kicked her in the back at his house after finding out that she was cheating on him.
Were there any ever any charges or any proof that Sean Combs blew up Kid Cudi's car?
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Chapter 7: What role did jealousy and other relationships play in the defense's argument?
No, there hasn't been anything yet. But Kid Cudi did speak out to The New York Times after Cassie filed her explosive 2023 civil suit in which she talked about a car exploding in a driveway of someone she was dating. And Kid Cudi said, yep, that was me.
Wow, that's crazy. And I'm sure Sean Combs... has or would deny blowing up his car? They have.
His legal team has said that that didn't happen. But again, we're expecting Kid Cudi to potentially testify and that to play out over the next several weeks.
The defense is saying that Cassie filed this lawsuit against Sean Combs to ruin his career.
At one point, the attorney says, did you realize after you filed this suit that it ruined his career? And she said, I could see that. But we've also learned how much she was paid as part of that settlement, which was a secret up until yesterday afternoon. She was paid $20 million.
That is a lot of money. A lot of money. Is the defense trying to say that Cassie, you know, did all this to get back at him? Or are they saying that she, you know, did it to make money or both? His defense team has always said that this was a money grab. It sounds like there are a lot of stops and starts today. Cassie's pregnant. Also, a lot of objections. Was it... Did it feel like that?
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Chapter 8: What incidents involving Kid Cudi were discussed during cross-examination?
I hate to ruin it for everybody, but it's not like the movies. There are sidebars. There are objections. And Ventura is asking for breaks. And I don't know if it's because she needs to sort of reorganize her thoughts. Perhaps she has to pee because she's about to give birth. I've had two kids. I know what that's like. It is moving slowly.
And you actually can see some of the jurors at times falling asleep. But that's not to say, though, that there haven't been these explosive moments. It ebbs and it flows.
When we come back, Cassie's husband is becoming a point of focus for the defense and the media. How is he involved in the case? Welcome back, everyone. And Chloe, a lot of back and forth happening between the lawyers and the judge when the jury isn't in the room and things got heated today.
Yes, it did. So according to the prosecution, they got the list of defense exhibits late last night, about 400 exhibits around 3 a.m. And they claim that it was messy, inefficient, putting them behind the eight ball.
And it wasn't just the prosecution. Cassie's lawyer also is complaining, right?
There's a lot of questions as to what sorts of text messages or email exchanges between Cassie and Diddy is admissible. And the judge is having to rule in the moment. And so although they only have a day and a half to get this done, there's a lot of stopping and starting. I mean, this is cutthroat. They are really not agreeing on anything.
Let's talk about Cassie's husband, Alex Fine. He knows Sean Combs as well. And he's been coming up in discussions with the attorneys.
So Cassie actually met Alex Fine through Diddy because he used to be Diddy's personal trainer. Then he actually ended up training Cassie. And so they fell in love. And it actually appears that there is some overlap between... Her relationship with Alex Fine and the end of her relationship with Diddy.
Cameras are following her husband, too, when he goes in and out of court. This is all part of the spectacle, right?
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