Sean Combs: Kid Cudi takes the stand.

Summary

Dateline: True Crime Weekly - Episode: "Sean Combs: Kid Cudi Takes the Stand"

Release Date: May 23, 2025

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Overview

In this gripping episode of Dateline: True Crime Weekly, hosted by Andrea Canning of NBC News, listeners are immersed in the high-stakes racketeering trial of music mogul Sean Combs, also known as Diddy. The episode delves deep into conflicting testimonies that paint a complex picture of Combs, featuring accounts from long-time employees and famous collaborators. Central to today's discussion is the dramatic testimony of acclaimed musician and actor Scott "Kid Cudi" Mescudi, whose revelation on the stand has sent shockwaves through the courtroom and beyond.

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Testimony of George Kaplan: The Admiring Employee

Timestamp: [02:09] - [04:19]

Andrea Canning opens the episode by introducing George Kaplan, Sean Combs's executive assistant of ten years. Kaplan's testimony presents a dual narrative of admiration and unsettling behavior.

• Admiration for Combs: Kaplan describes Combs as "a person that was larger than life" and praises the executive team, stating, "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" ([02:55]).

• Witnessing Violence: Contrarily, Kaplan recounts a disturbing incident on an airplane where he observed Combs engaging violently with model Cassie Ventura. He describes the scene: "Cassi crouched on the ground and Combs holding a glass in one of his hands up in the air" ([02:27]). This violent outburst prompted Kaplan to question his position, ultimately leading to his resignation.

• Reporting the Incident: Kaplan confesses to reporting the altercation to Christina Karam, Combs's chief of staff. However, his account of not receiving a visible reaction from Karam raises questions about the internal handling of such incidents ([03:15]).

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Chloe Melas Reports: Inside the Courthouse

Chloe Melas, NBC News correspondent, provides live updates from the courthouse, capturing the tension and anticipation surrounding the testimonies. She highlights the stark contrast between Kaplan's reverence for Combs and the violent incidents he witnessed, emphasizing the complexity of Combs's character as portrayed in court.

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Kid Cudi's Explosive Testimony

Timestamp: [07:27] - [11:20]

The episode takes a dramatic turn with the testimony of Scott "Kid Cudi" Mescudi, a multi-platinum artist and one-time romantic interest of Cassie Ventura.

• Initial Confrontation: Kid Cudi recounts a pivotal moment in December 2011 when Cassie alerted him that Combs was aware of their relationship: "Diddy knows about us. He knows that we're dating" ([07:27]). This revelation leads to a series of alarming events, including a mysterious visit to his home and the discovery of a Molotov cocktail in his car.

• Meeting with Combs: Determined to address the threats, Kid Cudi arranges a meeting with Combs at Soho House. He describes Combs's demeanor during the encounter: "looked like a Marvel supervillain" ([07:27]). Despite the intense situation, Kid Cudi portrays the meeting as calm, yet Combs denies any knowledge of the incidents: "what are you going to do about my car?" Combs responds, "what are you talking about?" ([09:52]).

• Aftermath and Defense Strategy: The defense team exploits the lack of concrete evidence supporting Kid Cudi's claims, questioning the absence of DNA evidence, fingerprints, or eyewitnesses linking Combs to the arson attempt ([11:24]). They also aim to undermine Cassie's credibility by suggesting she maintained dual relationships, thereby portraying her as manipulative ([12:03]).

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Defense’s Counterarguments and Strategy

Timestamp: [04:34] - [12:23]

The defense systematically dismantles the prosecution's case by:

• Legitimizing Combs's Business Practices: They emphasize that Combs ran a legitimate, global business and that his demanding nature was standard within the industry. When discussing Combs's temper, the defense notes, "his temper...didn't help his business...it hurt his business" ([05:04]).

• Challenging Witness Credibility: By highlighting the absence of tangible evidence against Combs and pointing out the lack of a direct threat in Kid Cudi's testimony, the defense casts doubt on the severity and legitimacy of the allegations ([11:12]).

• Discrediting Cassie Ventura: The defense insinuates that Cassie had agency in her relationships, suggesting that her dating Kid Cudi alongside Combs undermines claims of her being trapped in a dangerous association ([12:03]).

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Implications for Key Individuals

• Christina Karam’s Involvement: Christina Karam, Combs's chief of staff, faces scrutiny as Kaplan disclosed the airplane incident to her. She has publicly denied involvement, stating, "these false allegations of my involvement are causing irreparable and incalculable damage to my reputation..." ([03:54]).

• Cassie Ventura’s Position: Cassie's interactions with both Combs and Kid Cudi reveal complexities in her personal life, potentially impacting the jury's perception of her role and relationships within the trial.

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Looking Ahead: Upcoming Testimonies

Timestamp: [12:36] - [12:53]

As the trial progresses, the next scheduled witness is Capricorn Clark, expected to testify on Tuesday. With the court closing over Memorial Day, anticipation builds around the revelations Clark might bring forth. The judge has instructed the jury to avoid external media influences, humorously advising them to "watch the Knicks" instead ([12:53]).

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Conclusion

This episode of Dateline: True Crime Weekly masterfully navigates the intricate layers of Sean Combs's trial, juxtaposing laudatory accounts with harrowing allegations. Through the compelling testimonies of George Kaplan and Kid Cudi, Andrea Canning and Chloe Melas provide listeners with a nuanced understanding of the case, highlighting the tensions between personal admiration and potential misconduct within Combs's inner circle. As the trial unfolds, the impending testimonies promise to further unravel the truth behind the charges, keeping true crime enthusiasts on the edge of their seats.

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Notable Quotes:

• George Kaplan: "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." ([02:55])

• Kid Cudi: "Diddy knows about us. He knows that we're dating." ([07:27])

• Christina Karam: "These false allegations of my involvement are causing irreparable and incalculable damage to my reputation and the emotional well being of myself and my family." ([03:54])

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Stay informed with the latest developments and in-depth analysis by subscribing to Dateline: True Crime Weekly. For more details and updates on the Sean Combs trial, visit NBC News - Diddy on Trial.

Transcript

[Andrea Canning]

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[Chloe Melas]

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 Mascudi, 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 Meloss is outside the courthouse in lower Manhattan and is here to tell us what she heard. Hey, Chloe.

[Andrea Canning]

Hey, Andrea.

[Chloe Melas]

All right, let's start with Combs 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.

[Andrea Canning]

Yeah. This is not the first time that we've seen this. And one of the things that he said was, you know, quote, I desperately did not want to be here 100%, would rather not be here.

[Chloe Melas]

What do we know about his testimony that that's so incriminating that it could have, he could have been in legal danger if he hadn't have gotten this immunity.

[Andrea Canning]

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 get violent with Cassi 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.

[Chloe Melas]

But he also said how much he admired Combs, the businessman.

[Andrea Canning]

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.

[Chloe Melas]

These violent episodes that he says he witnessed, did he tell anybody about that at the time?

[Andrea Canning]

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.

[Chloe Melas]

Do you think that we will see the chief of staff, Christina get called to the stand?

[Andrea Canning]

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.

[Chloe Melas]

Has Christina, the chief of staff, has she released any kind of statement?

[Andrea Canning]

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 well being of myself and my family. And then she calls it all disturbing and unthinkable.

[Chloe Melas]

So George Kaplan was Combs executive assistant. And then we had on the personal assistant who took the stage 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.

[Andrea Canning]

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 stable standard in the industry.

[Chloe Melas]

All right. So the defense team seemed to land a punch when they got the executive assistant to talk about Combs's anger in the context of his business.

[Andrea Canning]

So the defense has admitted that diddy had a temper. I mean, remember his nickname is Puffy. And how did he get that nickname? Because as a kid he would huff and he would puff, right? So it's no secret. And at one point, Mark Agnifolo said, you know, from your perspective, his temper, from what you saw, it didn't help his business. And he said, no, it didn't. And Agnifolo 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.

[Chloe Melas]

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.

[Andrea Canning]

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[Chloe Melas]

Hey everyone, I'm Jenna Bush Hager from the Today show and I'm excited to share my podcast Open Book with Jenna. It is back for season two. Each week, celebrities, experts, friends and authors will share candid stories with me about their lives and new projects. Guests like Rebecca Yarros, Kristin Hannah, Ego Wodom, and more. Like a good book, you'll leave feeling inspired and entertained. Join me for my podcast Open Book with Jenna. Listen now on Apple Podcasts. Welcome back. Okay, Chloe Scott Mascudi, 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.

[Andrea Canning]

Kid Cudi says that In December of 2011 he got a phone call from Cassie and It was at 5:36am and she was freaking out. She was completely stressed and she said, Diddy knows about us. He knows that we're dating. And Kid Cudi 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 Cudi 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.

[Chloe Melas]

Kid Cudi claims that Diddy was threatening him, and then he finds out his car has had a Molotov cocktail thrown into it.

[Andrea Canning]

Yeah, I mean, it's such a wild story. Shortly after Christmas, he and Cassie decide that they're not gonna 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, you, 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.

[Chloe Melas]

Combs has denied being involved in this incident.

[Andrea Canning]

He's absolutely denied being involved in this incident.

[Chloe Melas]

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?

[Andrea Canning]

We are pretty certain.

[Chloe Melas]

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?

[Andrea Canning]

So after this incident with the car, Kid Cudi testified that he was like, enough is enough. I want to go meet up with Combs in person. And, you know, Combs had actually been reaching out to him when wanting to meet up. So they agree 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 supervillain, 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 going to 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.

[Chloe Melas]

The apology Kid Cudi took as an apology for the car and everything else, but sounds like there's really no proof other than his word.

[Andrea Canning]

Right?

[Chloe Melas]

How did the defense approach that on cross?

[Andrea Canning]

We know that the authorities led an investigation, and they collected DNA evidence, fingerprints, and we heard Brian 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.

[Chloe Melas]

Chloe, 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.

[Andrea Canning]

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.

[Chloe Melas]

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?

[Andrea Canning]

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.

[Chloe Melas]

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. 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 the help of the DATELINE True Crime Weekly team. Our senior producers are Alison Orr and Liz Brown Kurloff. Original Music by Jesse McGinty, Paul Ryan is executive producer and Liz Cole is senior executive producer of Dateline. Hey, guys, Willie Geist here reminding you to check out the Sunday Sit down podcast. On this week's episode, I get together with one of the biggest stars in the world, Gloria Estefan, on the extraordinary life story of a young Cuban exile who became a music icon. You can hear my conversation with Gloria.

[Andrea Canning]

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