Dateline NBC - Sean Combs: Kid Cudi takes the stand.

Episode Date: May 23, 2025

The artist and onetime romantic rival of Combs testified that after Combs found out he'd been dating Cassie Ventura, he broke into his house and unwrapped his Christmas presents. A few weeks later, someone dropped a Molotov cocktail through the roof of Kid Cudi's car. Combs has denied involvement in both incidents.To get caught up on the Combs trial and stay on top of news from the courtroom, listen to our daily episodes at Dateline: True Crime Weekly.And if you want to read NBC's coverage, 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. Episodes drop in the Dateline True Crime Weekly feed. This is On Trial, a special series from Dateline True Crime Weekly, bringing you daily coverage from the Sean Combs' racketeering trial. He has pleaded not guilty to all the charges against him. I'm Andrea Canning and it's Thursday, May 22nd.

Just a heads up, in this episode, we're going to be talking about some graphic details and harrowing subject matter. Today in court, two witnesses offered the jury two very different versions of Sean Combs. A man who worked for him 10 years ago said being Combs' employee and learning about the entertainment business from him was like going to Harvard. But musician and actor Scott Mascotti, aka Kid Cudi, compares Combs to a Marvel villain and described a couple of incidents that sound like something out of The Godfather. NBC News correspondent Chloe Malas is outside the courthouse in lower Manhattan and is here to tell us what she heard. Hey, Chloe. Hey, Andrea. All right. Let's start with Combs's

employee. We're talking about an executive assistant by the name of George Kaplan. He's another reluctant witness, right? He had to be subpoenaed and offered immunity. Yeah, this is not the first time that we've seen this. And one of the things that he said was, quote, I desperately did not want to be here. 100% would rather not be here. What do we know about his testimony that's so incriminating that he could have been

in legal danger if he hadn't have gotten this immunity? That's really unclear, Andrea, because he didn't really incriminate himself in any way that I could see. He did talk about an incident that took place on an airplane in which he saw Combs getting violent with Cassie Ventura, in which he heard glasses smashing. And when he went back to look,

he saw Cassie crouched on the ground and Combs holding a glass in one of his hands up in the air. And he said that it was those things that made him really second guess why he was working for Combs and he ultimately quit. But he also said how much he admired Combs, the businessman. Yeah, he did. He said, you know, this is a person that was larger than life.

He had the world at his fingertips and that he learned a lot and that this executive team that he worked for was really the best of the best in the industry and that he still has respect for Combs. These violent episodes that he says he witnessed, did he tell anybody about that at the time? He said that he told a woman named Christina Karam, and she is Combs' chief of staff, or was, up until recently, and that

he told her about what happened on the airplane and that she was the first person that he told that he was going to be quitting. And he said that, you know, he didn't really get any sort of visible reaction back from her that he can remember. Do you think that we will see the chief of staff, Christina, get called to the stand? It's very unclear. Her name has been mentioned multiple times.

You would think that if the government wants to hear from her, they will. Has Christina, the chief of staff, has she released any kind of statement? She has talked about this. She released a statement to Rolling Stone, and I'll read part of it. She said, for months, horrific accusations have been made about me regarding my former boss, meaning Sean Combs. She goes on to say, these false allegations of my involvement are causing irreparable and incalculable damage to my reputation and the emotional wellbeing of myself and my family.

And then she calls it all disturbing and unthinkable. So George Kaplan was Combs' executive assistant and then we had on the personal assistant who took the stand earlier this week, two different roles, but the defense is saying that these roles all add up to a legitimate business that Combs was running. Right. So what we're seeing is when the defense has the opportunity to cross examine these witnesses, they are pointing out that Diddy really was running these massive global businesses and that this was a happy environment, that people were learning a lot and that although these

were grueling hours, that's pretty standard in the industry. All right. So the defense team seemed to land a punch when they got the executive assistant to talk about Combs' anger in the context of his business. The defense team seemed to land a punch when they got the executive assistant to talk about Combs' anger in the context of his business. The defense has admitted that Diddy had a temper. Remember his nickname is Puffy and how did he get that nickname? Because as a kid, he would huff and he would puff.

It's no secret. At one point, Mark Agnifilo said, from your perspective, his temper, from what you saw, it didn't help his business. And he said, no, it didn't. And Agnifilo says it hurt his business, right? And he goes, yes, it did. And so what they're trying to say is that his anger wasn't keeping people working for him out of fear,

that actually it elicited people to leave. So this idea that he was coercive and forcing people to stay in his company and carry out illegal activity, the defense team is like, well wait, they're trying to say that people had free will. When we come back, we'll talk about a multi-platinum artist and one-time romantic rival of Sean Combs, who finally takes the stand.

Welcome back. Okay, Chloe, Scott Mascotti, aka Kid Cudi, took the stand to tell the story of what happened between him and Sean Combs over a two-month period in late 2011, early 2012. Tell us what he said today. Kid Cudi says that in December of 2011, he got a phone call from Cassie and it was at 5.30, 6 a.m. and she was freaking out. She was completely stressed. And she said, did he knows about us? He knows that we're dating. And Kudkudy said he was totally confused

because why would that be a big deal? He and Cassie had been together for about a year and he had no idea that she was still romantically involved with Combs or that it would even be an issue. And so he gets in his car, races to pick up Cassie and takes her to a hotel. And then that's when they got a call from one of her friends whose name is Capricorn.

And Capricorn said, Cuddy, I'm in front of your house. Diddy forced me to get in the car and go to your house, and he's inside with somebody else. So Kid Cuddy says that he is furious. He's so mad to think that Combs has broken into his house. He calls 911 and he's worried that he might be walking into a violent situation. So he gets to his house.

There's no signs of forced entry. He goes into his kitchen to see some of his Christmas presents for his family unwrapped, but Diddy's nowhere to be found. Kid Cudi claims that Diddy was threatening him and then he finds out his car has had a Molotov cocktail thrown into it? Yeah, I mean, it's such a wild story. Shortly after Christmas, he and Cassie decide that they're not going to date anymore

because Combs' presence is just looming over the relationship now. One morning in early January 2012, he gets a phone call from his dog sitter who says, your car is on fire in the driveway. And the top of his convertible looks like somebody had slashed it. And a Molotov cocktail was found in the driver's seat. And for anybody that doesn't know what that is, it's a bottle with flammable liquid inside and a rag. Basically like a homemade bomb.

Combs has denied being involved in this incident. He's absolutely denied being involved in this incident. Okay, so Chloe, it's interesting because Arson is actually one of the crimes listed in the indictment against Combs. Do we know if this is the incident that they're talking about? We are pretty certain.

Cuddy says on the stand that he ends up meeting with Sean Combs because he's suspicious about what happened with his car. How does that go? So after this incident with the car, Kid Cuddy testified that he was like, enough is enough. I want to go meet up with Combs in person. And Combs had actually been reaching out to him wanting to meet up. So they agreed to meet at Soho House, which is this very famous, exclusive members only club. And this is actually a moment that got a lot of laughs

in the courtroom today, believe it or not, despite the sobering testimony. Kid Cudi walks into this conference room and Diddy is staring out the window with his hands behind his back, his back to the door. And Kid Cudi said that he looked like a Marvel super villain. But he says that he and Combs spoke and that he was very calm. There were no threats.

They both talked about how they didn't realize that the other one was dating Cassie. And they shook hands and he said, what are you gonna do about my car? And looked him straight in the eyes and Diddy looked back at him and said, what are you talking about? The prosecutor asked Kid Cudi about this exchange. And they said, what was your understanding

when Sean Combs said, I don't know what you're talking about. And Kid Cudi said that he was lying. So a couple of years later, Kid Cudi actually ran into Combs again at Soho House. And he said that Combs approached him and said, man, I just want to apologize for all that bullshit. The apology Kid Cudi took as an apology for the car and everything else, but it sounds like there's really

no proof other than his word. Right. How did the defense approach that on cross? We know that the authorities led an investigation and they collected DNA evidence, fingerprints, and we heard Ryan Steele saying, you know, what proof do you have that Combs left this Molotov cocktail in your car

or told somebody to do it or that he had even been in your house. Where's the surveillance footage? Were there any eyewitnesses? And, you know, Kid Cudi couldn't demonstrate any of that. Lowy, it seems like the defense was also through Kid Cudi trying to maybe discredit Cassie. You know, she's living these two lives. They say she's playing two men, even though she's not on the stand at this moment. She kind of is in a way. lives. They say she's playing two men. Even though she's not on the stand at this moment, she kind of is in a way.

Absolutely. They have to prove the prosecutors that Cassie was in a violent relationship, that she couldn't leave and she didn't leave. But this year, dating Kid Cudi shows that maybe she was able to date who she wanted when she wanted and that she was able to freely be in and out of the relationship. Yeah. Well, there was, as you said, a lot going on, Chloe. Court is closed tomorrow and on Monday for Memorial Day. What do we

expect for next week? Who do you think is going to take the stand, Chloe? So we're expecting on Tuesday Capricorn Clark. So the jury is going to have a long weekend. And the judge said, I'm ordering you not to talk. If you see something on TV, change the channel. Go for a walk. Go on a bike ride. He said, watch the Knicks. Oh, that's a good one.

Chloe, thank you and enjoy your weekend. Thank you everyone for listening. We'll be back with a new episode as promised Tuesday. Have a good weekend. Thank you everyone for listening. We'll be back with a new episode as promised Tuesday. Have a good weekend. 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 the help of the Dateline True Crime Weekly

team. Our senior producers are Alison Orr and Liz Brown-Kuruloff, Original Music by Jesse McGinty, Paul Ryan as executive producer, and Liz Cole as senior executive producer of Dateline.