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Trial By Jury: Diddy

After thirty years in the media spotlight, there are no cameras at the trial of Sean "Diddy" Combs. So, let CNN anchor and chief legal analyst Laura Coates take you inside the courtroom. On Trial by Jury: Diddy, she'll shine a light on every move that matters in Diddy's trial for racketeering conspiracy, sex trafficking and transportation to engage in prostitution.

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Blown-Up Cars and Backstage Secrets
Trial By Jury: Diddy
May 23, 2025

As the second week of Sean “Diddy” Combs’s racketeering trial came to an end, all eyes turned to another entertainer, Scott “Kid Cudi” Mescudi, whose explosive testimony about Diddy included allegations of a burned-out Porsche and a frightened dog. CNN entertainment correspondent Elizabeth Wagmeister joins Laura Coates to break it all down, and we revisit a conversation with Diddy’s former makeup artist, Mylah Morales, which was referenced in today’s testimony. 

Episode Transcript
Laura Coates
00:00:04
'We're wrapping up the second week of testimony in what will be an eight to 10 week trial for racketeering and sex trafficking against Sean "Diddy" Combs. Today, the jurors heard from one of the most high profile witnesses yet. I'm talking about the musician, the actor, Scott Mescudi, otherwise known as Kid Cudi. Kid Cudi and Cassie Ventura briefly dated back in 2011 during a time when they were in an on-again, off-again relationship. Although it came out in testimony, perhaps Cassie and Diddy were more on than off to the surprise of Kid Cudi. And on the stand today, he would go on to testify to what it was like to find himself in the alleged crosshairs of an angry and jealous Sean "Diddy" Combs. Or shall I say, what it like for his car to be in the alleged crosshairs of Sean "Diddy" Combs.
Laura Coates
00:01:01
'I'm Laura Coates. And this is Trial by Jury. Before we dive into this unbelievable testimony of Kid Cudi, I've got to take a step back because there was the continuing testimony of George Kaplan. Now remember, he was the executive assistant of Sean "Diddy" Combs. Why I found him so interesting is because he was two things at once, completely professionally enamored with Sean "Diddy" Combs, called him a god among men, said that he really helped him become the man he is today, and that in some respects, he still relies on and shares and uses the lessons of what he called an opportunity of a lifetime to work for this icon. But then, he also described why he left this plum employment position. He said it's because he witnessed too much violence against the women in Sean Diddy's life. First, Cassie Ventura, where he witnessed a airplane incident, where she was in the back of the private plane, on her back, legs in the air, distancing herself from Sean "Diddy" Combs, who was lording over her after having shattered glass. And she apparently screams out to the security and everyone else who was also on that plane, Isn't anybody seeing this? He said he looked away. Another instance he describes a woman by the name of Gina. Diddy was apparently throwing decorative green apples at very hard and a commotion later on as well near the gate for that two-star island lavish house in Miami Beach. Now these two moments that were described, this completely professionally enamored and awestruck 23-year-old, now much older, and then the person who, as the defense counsel said had such a moral compass that he was forced to leave. It really painted a very distinct picture for these jurors. I wonder which one they will believe is the real Sean "Diddy" Combs? We had somebody else who really had a different viewpoint of Sean "Diddy" Combs completely, and that was Kid Cudi. Joining me now is my partner in court, CNN entertainment correspondent Elizabeth Wagmeister. Look, you and I were sitting in that courtroom, and we were watching Kid Cudi not only walk in, but testify, and this whole dynamic and vibe was very apparent. Remember, this is the person who was dating Cassie Ventura, and Diddy apparently found out about it. And we learned this because Diddy and Cudi seemingly were both blindsided they were dating the same woman at the same time. There was only a phone call from Cassie Ventura where she said, he's found out about us, and Cudi said he was confused because he didn't know they were even still involved.
Elizabeth Wagmeister
00:04:07
'That's right and you know what I was thinking back to was Cassie's testimony because of course Kid Cudi isn't the first one to talk about these a few days of what they allege happened. Cassie spoke about this and remember from her perspective, she said that her and Sean Combs were in a rough patch, that they were on a break and she obviously wanted to date other people. Now what she has conveyed what the prosecutors are hoping that the jury gets away from her testimony is that she was not able to freely date other people. But then you get to Kid Cudi's testimony today and as you said, Laura, he said, I was confused. You know, she told me that they were on a break. So he was confused even why Sean Combs was upset. And that was an interesting moment because what the defense did, and I would love to hear your take, Laura, as a former prosecutor, but I thought that the defense was quite effective in their cross-examination, where they almost related to Kid Cudi in saying, well, you are confused, and so was our client, so was Sean Combs, because you were both being played. That's the word that they used.
Laura Coates
00:05:21
'This double life or that she was leading two very different lives. And why this is important for the overall trial is that Kid Cudi is alleging that upon learning that Diddy had found out about his relationship with Cassie, Diddy went to his home, allegedly broke into his home brought an assistant with him, somebody by the name of Capricorn, who Cudi and Cassie often would hang out with and knew quite well. And so we're likely to hear a little bit more about that scenario of somebody being forced to come along to witness a alleged break-in while Diddy was waiting for Cudi to have this discussion in his home. Cudi then races to his home to figure out why somebody is, as he calls it, crossing the line by not calling him but instead waiting for him in his own home. And then days later, they actually go to Cassie's home for Christmas. He spends time with her family. He is deeply involved with her, but then returns at some point later to find that his car is on fire. Now, of course, this timeline was very much pointed out and the order of things, a highlight of the trial, but ultimately, it painted a picture of a very jealous and unhinged Sean "Diddy" Combs, who would speak to him in a very calm manner trying to work this out. On the other hand, Cudi attributed the violence and the arson to him.
Elizabeth Wagmeister
00:06:52
'Yes, and you know, that word calm, he kept bringing that up. And the reason why is when Kid Cudi was asked what was Sean Combs's demeanor, he kept saying, eerily calm. You know, like, it was weird to Kid Cudi that Sean Combs, after he believed broke into his home and after he believed set his car on fire, that he would be approaching this in such a calm manner. Now, I want to go back to that Marvel supervillain moment, Laura. So Kid Cudi, he explained the situation where after his home was broken into and after his car was set on fire with a Molotov cocktail, that's what he testified to. He said that he finally thought, you know what, I am going to talk to Sean Combs. Because during that Christmas vacation, when Kid Cusi went to Cassie's family's home in Connecticut, he testified that Sean Combs was repeatedly texting him and he was thinking, Why would I get back to you? You just broke into my home. You messed with my dog. That was exactly what he said because he alleged when Sean Combs broke into his home that he then locked his dog behind a door in the bathroom, which got Kid Cudi very shaken. He said the dog was very frazzled after that. So, back to Connecticut. Sean Combs is texting him. He's not responding. But then fast forward to January 2012 after the car is blown up. Kid Cudi says to himself, I've got to talk to him. This is getting out of hand. This drama is a lot. Let's just talk man-to-man. So they arrange this meeting at Soho House in LA. And Kid Cudi was asked by the prosecutor, what do you remember about when you arrived about Sean Combs's demeanor? And he said, he's looking out this window with his hands behind his back, looking like a Marvel super villain. And that was just one of those moments. I always say courtroom theatrics. But I think those things really matter to a jury.
Laura Coates
00:08:54
Oh yeah, you can hear some sort of laughter. Even the attorney questioning had to chuckle a little bit at that reference point because it was one of those rare moments of levity that really painted the picture of what this drinking with martinis James Bond moment, or in this case Marvel super villain moment would have looked like. But he also learned later that when Cassie joined on in this meeting, Cudi was surprised to know that she had gone back to him. And that made some statement along the lines of, well, we're in love, and you know, things happen. And that was a moment that I thought people were reacting to because here is where this opening for the defense, as you say, to come in and to cross, to talk a little bit about, well, who exactly was Cassie Ventura? Was she somebody who was trapped and victimized and helpless? Or strategic and cunning? And able to have other relationships? This is the dynamic that the defense wants to create, but the prosecution really wanted to make sure people understood the violence associated with Diddy, the controlling nature and the jealousy as another data point.
Elizabeth Wagmeister
00:10:15
'Absolutely, and it's really, it's a tale of two Cassies, right? The prosecution is saying this is an abused woman who was threatened and coerced into these freak-offs against her will. She only did them because she was placating him, because she was so concerned for her safety and for her life because he was physically violent. And then the defense says she's no victim. She's a cheater. She is a strong woman and she's a cheater. So that is the persona that the defense is trying to portray Cassie Ventura with. Now, I will tell you that after cross-examination, on redirect, when the prosecution got backed up, they then questioned Cudi again, and they got him to reiterate, yes, Sean Combs is a violent man. Cassie had told me about that. Kid Cudi said that he was concerned not only for her safety, but for his safety. And that was his response when he was asked, how did this relationship end? And he said, you know, I was concerned about her safety and my safety. He knows that Sean Combs is a violent man. That's what he testified to. And he also called him a liar because he said that during that meeting at Soho House, when he called him, a Marvel super villain, he said that when they shook hands after the meeting, he said to him, what are we going to do about my car? And Sean Combs said, what do you mean? I don't know what you're talking about. And when Kid Cudi was asked on redirect, which remember is the final word that the jury heard during his testimony, he was asked, what was your interpretation of that? And he said, my interpretation is that he's lying. So it's interesting because I thought Kid Cudi was incredibly honest as a witness where he did say, I was confused with Cassie. I thought she was broken up. I felt played by her. I was hurt, but he also said, I was worried for her safety. Sean Combs was violent, and I believe that he broke into my house and blew up my car.
Laura Coates
00:12:11
He also, I mean, he was asked a series of attributes of whether he agreed with them as applicable to Cassie Ventura. Smart, strong, a strong personality, talented, interesting. He agreed to all of those things. But he was also in love with her and also described her as carefree, as far as he could tell, and that Combs never interrupted their time together, which the jury is going to be balancing those statements against her testimony of being constantly surveilled. Constantly bombarded with messaging and communications from Sean "Diddy" Combs, and then found and searched for by his security detail and otherwise if she dared not to respond. But then there was, I want to just point out, there was a moment when Kid Cudi was asked about the intimate relationship between himself and Cassie Ventura, whether they were involved in consensual sex together. The prosecution immediately objected and they ended up having a sidebar. And I want to just give people a little bit of background context of this because a case involves sexual misconduct. There's a rule called 412 when it comes to sex offense related cases and you cannot offer evidence to prove a victim engaged in other sexual behavior or evidence offered to show that there is some predisposition that is sexual for a victim, because it is essentially trying to negate and victim blaming and negate the notion that, oh, well, if the person is having sex, well, then there must've been consent in every instance. If she was having sex with anyone, then there was to have been consent in all interactions. And so, he did have that moment when he was prevented from talking about their intimacy, but he did say that he never heard from Cassie Ventura that she had been sexually abused by Sean "Diddy" Combs. And that just harkens back to yesterday's testimony with that psychologist who said, look, oftentimes victims of sexual abuse or this level of degradation as has been alleged, sometimes, Elizabeth, they won't tell anyone because the shame and fear of judgment is too great and the disassociation as well.
Elizabeth Wagmeister
00:14:27
You know, Laura, we had the same exact thought, because right when Kid Cudi testified that she told me about the physical abuse but not the sexual abuse, I thought the same thing as you. It's humiliating, they're full of shame, they don't even want to think about it themselves, let alone tell someone else, and this expert witness testified to the fact that that's why they often go back to their abusers, because in this weird, twisted, backwards way, they can't tell anyone else, but their abusers. So they keep going back to them. So it's really interesting that we both had that same thought because if the jury had that the same thought, then that means that the expert witness was quite effective for the prosecution.
Laura Coates
00:15:07
Certainly. And just thinking about how this will all be balanced out and and you know I often wonder about the order of witnesses because there's this rule, right? Primacy and recency, the first thing someone hears and the last thing they hear are going to be the most Impactful and you kind of bury things, maybe the bad facts, things you don't really like and help your case in between or moments that are not necessarily going to resonate as much in that jury deliberation room. But the order of things here I think was in many ways challenging for the prosecution thus far because they had a timeline associated with Cassie Ventura's pregnancy. And I wonder if they would have had her go so early as opposed to building up towards her testimony. Well, there's so much more ahead. And as you can imagine, everyone is completely transfixed by the pacing and the substance of this particular trial. Before you go... You saw Mylah Morales in court today. She is the makeup artist. I actually had a chance to interview her months ago now. She was somebody who...
Elizabeth Wagmeister
00:16:13
Wait, Laura, I'm sorry to interrupt, but I have to I'm going give you a little shameless plug. Your interview was actually called out in court. And let me tell you how it was called out. Because Mylah Morales was on the stand. And during cross examination, the defense was asking her about all of the media that she did because she testified to the fact that ever since this alleged incident happened where she said that she overheard Sean Combs beating Cassie Ventura. She said her and Cassie never talked about it. So then the defense said, but you did do a fair amount of media interviews. The first one being with CNN. And I was thinking, that's my girl Laura Coates. Because I remember, not to make light of this moment, but I just remember how impactful your interview was with her. Because this is someone who was very close to Sean Combs and Cassie for years. And I remember watching your interview and she was laying out these horrifying allegations, how she saw injuries on Cassie. After she heard what she thought was Sean Combs violently beating her, and that matched her testimony today. And I know that the jury is told every single day, do not watch the media, do not read the media. Do not pay attention to social media. Of course, during jury selection, they weeded them out. But this case in Sean Combs has been so prevalent, and your interview with her, Laura, was really such a major moment in the different beats of this story. I do wonder if some of the jurors remember seeing her and think, oh, that does sound familiar, because if so, her testimony matched up perfectly to what she told you during your interview.
Laura Coates
00:17:53
That's actually the perfect segue, Elizabeth, because after a break I'm going to bring you all my interview with that makeup artist when she was on our airwaves who says she was like a big sister to Cassie Ventura. And remember, the makeup artists were the ones who had to cover up these bruises that Cassie says were at the hands of Sean "Diddy" Combs. Elizabeth, I'll see you in court soon, okay?
Elizabeth Wagmeister
00:18:15
See you in court.
Laura Coates
00:18:15
We'll be right back.
Laura Coates
00:18:23
'Hey, welcome back, everyone. You know, today's testimony featured more than one music industry professional. Besides the rapper and actor Kid Cudi, the jury also heard from a makeup artist named Mylah Morales. And she worked for Sean Combs for about five years, from 2000 to 2005. And during that time, Morales testified that she met Cassie Ventura on a photo shoot when she was just 16 years old. And they had this big sister-little sister kind of relationship thereafter. What I'm going to do now is I'm going to play for you the very first media interview that she gave. It was actually on my show, Laura Coats Live, and it was in the immediate aftermath of the release of that now infamous video that shows Diddy abusing Cassie in a hotel hallway. I'm going to play for a portion of that interview because the story that she told me is also part of the testimony that the jurors heard today when she was in court.
Mylah Morales
00:19:24
Well, I have kept this secret for like 14 years. I mean, the first time I experienced it was 2010 and I was in the hotel room. Puff came in, and I had no idea Cassie left. And when I woke up, I just saw his presence come into the room. They went into the bedroom and shut the door, and all I could hear is screaming and yelling, and whatever was going on in there, I don't know. But all I could think of was to grab Cassie's things and start packing it up and just getting her out to safety. And bringing her to my house. So that's kind of like what transpired from that night. And once she came out of the room, she was badly beaten.
Laura Coates
00:20:22
Oh my God, what did her physical appearance look like?
Mylah Morales
00:20:27
I mean, it was knots on her head, black eye, busted lip, but a lot of knots all over her head. It's kind of a blur to me now because it's been 14 years.
Laura Coates
00:20:44
That must have left quite an indelible mark for you to have seen someone experience that.
Mylah Morales
00:20:51
Of course, of course.
00:20:52
Did she go to the police at that point or anything?
Mylah Morales
00:20:57
No, we didn't know what to do at that point because, you know, Puffy is a very powerful person and we were quite terrified so I just brought her to my house and my friend, who is a doctor, I called her and she was, thank God she was in town because we didn t know what to and she treated her just to make sure she didn t have a concussion or anything like that. But it was really, it was painful to see Cassie like that because she's such a, you know, a beautiful human being and for a man to, for a man to just hurt any sort of woman or child or animal, it doesn't matter, but Cass is a good friend of mine and I just felt, you know, so I just didn't know what to do. I felt like I don't even know how to describe how I felt that night.
Laura Coates
00:21:52
Did she describe how she was feeling about having that happen? Did you get a sense that this was the first time?
Mylah Morales
00:22:01
It didn't feel like it, because it was almost like, you know, I feel like she might have been embarrassed that that happened in front of me. You know, it's like your family seeing you, you know, your boyfriend or your significant other beat you like that and your person who's close to you watch it happen and watch the aftermath it's kind of embarrassing, you know, I'm sure it is. Because I know that if that happened to me I would be embarrassed and wouldn't know what to say.
Laura Coates
00:22:41
You know, Mylah, and I think a lot of people likely do feel like that, but that's also heartbreaking to think, because if someone feels embarrassed, they are less likely to then go and seek help, because they are afraid that somehow what has happened to them is a reflection of who they are. And we know it's not.
Mylah Morales
00:23:03
Yes, and I can't speak for Cass, you know. Honestly, I can speak for her, but if it were me, I'm just saying if I were in her shoes, I would be embarrassed and ashamed, actually. And I feel like that's what survivors feel, and that's why they can't get out of these relationships.
Laura Coates
00:23:24
You mentioned not wanting to go to the police or even go to the hospital, having your friend treat her to see if there was any concussions or otherwise because of Diddy's perceived power. I mean, you are somebody who's in this industry. You have seen a lot of things happen behind the scenes that people don't want in front of the camera, that they want one particular image themselves maintained. What was it like having this be at the hands of somebody you perceived to be so powerful in an industry where you were working.
Mylah Morales
00:24:00
'Well, obviously, with somebody with that kind of power like Puff, it's really difficult because it's a very small industry and there's a lot of gatekeepers. It's a small industry in that we all know each other and I feel like people are afraid to speak up about it. The only reason why I am is because I'm a friend of Cass's and I really care about her very much so, and I'm outraged and very very like heartbroken about like how he's been treating her. It just it it breaks my heart and I just can't imagine like a man - a man treating a woman that way and not just a woman but a friend of mine that I've known since she was a teenager. So, you know, I've know Cassie before all of this so it's it's disgusts me and sadly I don't even know what sort of words to put.
Laura Coates
00:25:04
Well, it's hard to even put your, wrap your mind around it. And I can only imagine of all the women that you have worked with and people who are eager to be in the industry, what they are exposed to, how they could be exploited and abused in a variety of ways. And that's why the idea that not hearing so many more people speak up is is very frustrating and hurtful for so many people.
Mylah Morales
00:25:29
It is, it is. It is frustrating and hurtful, even for me, because I just, I watch, you know, I know what goes on behind the scenes and I just can't imagine why nobody's speaking up. I mean, everyone's just hush hush and quiet. I don't know, maybe they're scared.
Laura Coates
00:25:51
Well, the trial is off tomorrow, and so are we. Join us on the other side of Memorial Day weekend when we'll be following all those twists and all those turns in this trial for the ages of Sean "Diddy" Combs. Thanks for listening. Be sure to follow Trial by Jury wherever you get your podcasts. And while you're there, leave us a rating and a review. This episode was produced by Lori Galarreta, Emily Williams, Dan Bloom, Graelyn Brashear, Alexandra Saddler, and Rachid Haoues. Our technical director is Dan Dzula and executive of CNN Audio is Steve Lickteig. With support from Andrea Lewis, Hank Butler, Alex Manasseri, Robert Mathers and Lisa Namerow. I'm Laura Coates, and I'm here for it.