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Inside Diddy's World: What His Assistant Saw - Trial By Jury: Diddy - Podcast on CNN Audio

Published 14 hours ago19 minute read

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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 assault to engage in prostitution.

Inside Diddy’s World: What His Assistant Saw

Trial By Jury: Diddy

May 21, 2025

As week two of the RICO and sex trafficking trial against Sean "Diddy" Combs continues, Laura Coates sits down with Suzi Siegel, one of Combs’ former assistants, to hear more about what went down in Diddy’s world behind the scenes. Plus, we learn from CNN’s Elizabeth Wagmeister about a key piece of testimony from Cassie Ventura’s mother.

'I'm Laura Coates, and this is Trial by Jury. So it's week two now of the racketeering, otherwise known as RICO, sex trafficking trial against Sean "Diddy" Combs. And you know, prosecutors, they have called many more witnesses to take the stand: friends and family of Cassie Ventura, you got former employees of Sean "Diddy" Combs, you even have people who participated in these freak-offs who took the stand. We've got an update now from Elizabeth Wagmeister, our CNN Entertainment correspondent who was in the courtroom with me today, Wagmeister, tell me everything.

Elizabeth Wagmeister

00:00:40

'So Laura, Cassie Ventura's mother was called to the stand today as a witness. This was a witness that I was really, you know, had my eye on because she's a very important person to hear from, right? Her daughter is the star witness in this case, and she is alleged a decade plus of very violent domestic and sexual abuse. Well, it turns out she was on the stand for a very brief moment, in fact, so brief that the defense did not even cross-examine her. This is the first time that the defense has opted not to question a prosecution witness throughout this trial. They simply got up and Combs's attorney essentially said good afternoon and I don't have any questions for you. It's very clear that the prosecution only wanted her on the stand to corroborate some very specific instances. So let me walk you through one of those. You remember that Cassie had testified last week that back in December 2011, she went home to Connecticut for the holidays to visit her family and stay at her parents' home. Well, this is when she was dating Kid Cudi because it was during a rough patch, she said, with her relationship with Combs. And we all know from her testimony, she alleges Diddy was very jealous of Kid Cudi and obviously things went downhill from there. Well, there was an email that was shown to the jury today. It had been previously shown during Cassie's testimony, but I want to read it because it is a powerful piece of evidence. So here's an email that Cassie wrote to her mother and also Capricorn Clark, who was one of Diddy's employees. Here's what Cassie wrote, this is verbatim, I'm reading it to you: the threats that have been made towards me by Sean "Puffy" Combs are that, he is going to release two explicit sex tapes of me. One on Christmas day, maybe before or right after and another one sometime soon after that. He has also said that he will be having someone hurt me and Scott Mescudi physically. He made a point that it wouldn't be by his hands. He actually said he'd be out of the country when it happened. Now the Scott Mescudi that she refers to there is Kid Cudi. Now this email Cassie's mom said on the stand made her feel sick. She said she got physically sick when she read this, but nevertheless, after Diddy allegedly threatened her daughter, as we see in this email, then she and her husband, so Cassie's parents, took out a home equity loan on their house to send Diddy twenty thousand dollars, which he had demanded. This is according to her mom's testimony. Diddy, of course, you know, he's a billionaire, at this time maybe not, but worth hundreds of millions. Obviously, the juxtaposition there that he was asking for $20,000 because he was upset with Cassie for dating another man. Her mom testified to the fact that, you know, she said he wanted the $20 thousand because he said that he spent $20 thousands on expenses for Cassie. So he ended up accepting the money, but then the mom said that he wired back the funds a few days later. So this was just one instance that she testified to, but since I brought up Kid Cudi, I do want to tell you, he is going to testify. We could see him take the stand, Laura, as soon as tomorrow, but definitely this week, according to prosecutors.

'All right, we're starting to learn more about this inner circle or whatever the circle looks like. Well, how about somebody who also was a part of this world, at least the orbit. I want to talk to somebody who was actually a former assistant of Sean Combs. I'm talking about Suzi Siegel, who worked for him for less than a year, but has a lot of insight into what that whole world was like and I want unpack and really get an understanding of what it was like behind the scenes. Let me talk to her right now. Suzi, I've got to tell you, everyone is completely captivated, not only with this trial, but specifically what it was like to work for Sean "Diddy" Combs. They want to know what the day-to-day tasks would be that if you work for him, you might be assigned. Tell us what you had to do.

Okay, so I was his EA, which is his executive assistant. So that's different than a PA, which I think you heard from today during the trial. So I didn't move with Puffy very much. I was in the office being his secretary basically, his EA answering calls. There was a ton of logistics around booking planes. He flew private, he flew NetJets. So making sure that his whole team moved, security, everybody. He could never be in one place alone, standing alone, because he would get flocked. So the idea was that he had security, he had his driver, and we were always moving him as quickly and as seamlessly as we could to events in his car with his driver. Sometimes of course, abroad or on a plane. So it was a lot of logistics and planning, but also I sat in his office outside of his door.

So it sounds like, especially given how famous Diddy is, him having security guards around was just sort of the standard MO. It wasn't necessarily because he wanted to bring sort of, the figuritive "big guns" everywhere.

I mean, I think because of what happened with Biggie and Tupac, that was just always right here. And, you know, he was beefing with various record industry people like Suge Knight, which we heard about at the trial today. So I don't think he ever felt like he could let his guard down or that he was safe. There was that element. And then, of course, there was just the regular being a celebrity, and he was recognized everywhere that he went. So for all of those reasons, he never was without security.

So you worked for him for less than a year, right? You were fired by Diddy. What was your relationship like with him when you did work for him?

You know, I'm realizing now that there was two circles of staff, right? I mean, I knew I wasn't in the inner circle of trust. I mean that was clear. You know I didn't know him, I came in through a reality show. So I always knew that there were probably some things I was privy to and some things that I wasn't and probably the staff that traveled him and the people who were seriously loyal to him and had been with him throughout this whole journey. So I did have this sort of transparent access into his calendar and his, you know, his calls, I would listen in on some of them if they were business calls, but now it's very clear to me that there were two circles of trust. I knew that I was not in the trusted circle, but I had no idea what the trusted circle was seeing.

Do you have any idea, any idea what that other circle, I don't know if it was concentric or not, because obviously at the core of it, getting into math here, but any sense of what the other circle was assigned to do and how it was different from what you were supposed to be doing?

Yeah, I mean there was only one time that these two circles sort of overlapped. So those were the people that if he was at a hotel one night would be picking him up from the hotel in the morning, right? So you know, he did have a place in Manhattan and a place, you know New Jersey and a place all over the place, Fisher Island. But sometimes he would stay in hotels and do whatever he was doing. So, I was not privy to that, but I could be sort of at command central control, making sure that the driver, the PA would come. But however, there was something very strange. I had one, only one time I was asked by a couple of his assistants to accompany on one of these pickups at the hotel, um, and there was this big Louis Vuitton bag, which was mentioned at trial today as something that was always, he always had it with him.

The med bag, they're calling it a trial.

'I remember that he always has a Louis Vuitton bag and there was this sort of thing like, make Suzi carry it, you know, and it was really heavy and you know I'm like sort of a smallish woman but I remember being like, okay if that's what my use is here I'll pick up this bag. I had no idea what was in that bag and it seems like there was a lot of contraband and a lot things that he used in his freak-offs, but I didn't know. I assumed that some type of sexual activity was obviously happening in a hotel room. I did not know with who, but I think so that was the sort of stuff that the inner circle and the PAs were clearly knowing what was happening in those hotel circles. But that's the closest I ever got to what was potentially a freak-off, and that was in probably late 2008 or early 2009. So according to the testimony, this stuff was already happening, even though obviously I didn't know. And you know, I don't blame P-Diddy for not wanting me to know what was going on.

Why was I fired? You know, it's interesting. I really wanted that job and thought it was a big opportunity for me. And I didn't want to lose it. I actually cried when I got let go. Um, but I think that I was a little bit of a squeaky wheel there. Like, I don't think I was that brave and speaking out about things, but I negotiated over my salary. Nobody did that, you know? Like, Puffy didn't want to pay anybody. I came to work for him through a reality show, so it was very odd. It was VH1. I Want to Work for Diddy early days, so I "won" this show, no money. And I sort of just, you know, yeah, I have to be quiet. I won. And then I arrived the first day and. You know, I'm sitting in HR like any normal first day hire and the number on the contract was like less than I had made sort of out of college. So I was like, oh, this is how Puffy worked, right? He's trying to like get people for as cheap as he can. And I didn't sign it. So I said, I have to have my lawyer look at this. And I was, like, Oh my God, I couldn't even pay the basic bills of my life as a New Yorker, you know on the salary when it's supposed to be such an important job. So I think I was a little bit lippy, not, I don't think that much, but I did speak up. Like I thought that we should. We were working around the clock. I definitely made some noise with some of the staffers that we should be getting real time and a half and real overtime. And I remember saying it and people's eyes opened up, like, is this woman crazy right now? Like, she's just talking about things that, you know, an unhappy employee would talk about, but it was so not done, Laura, that it was clear that, like, what are you doing? Like, you can't say anything, you know? Take the money. Take the zero money. We're all like, nobody could have a life. You know, you were sleeping with your Blackberry at the time under your pillow, rolling to two in the morning, up at a, you had no life. You were booking jets. The phone was there all the time. You were taking care of his family, right? You were taking care of some of the women in his life. So it was just like his barber, right, getting his doctors, right? it's like nothing, it never stopped. I didn't get fired, I'm sure, for my performance, but when they let me go, they said you know, restructuring or whatever corporate jargon it is. And I was, you know, led out the door by two giant security guys crying with my bag of shoes from under my desk and being like, oh my God, I cannot believe that I just got let go.

I mean, just thinking about all that was tasked of you, and you're but one of the circles. And after the reality show talking about, and you talked about the women, one of them was Cassie Ventura, right? That you knew that he was involved with in some way. Obviously, a lot of the testimony has been about violence towards her. And we've seen that hotel surveillance video, we've heard more than one person testify about either witnessing or hearing violence. Cassie herself did. Did you ever see it?

I did not see any violence. I can't, again, this man did not get away with this for as long as he did by sort of showing his true colors in front of people who weren't in the inner circle. I think he knew exactly who he had power over and who he didn't, right? But what I do know from seeing the inner circles of we were basically working for Cassie, too, in many ways, because she was with him all the time. He was managing her career. They were dating. They were staying together most nights. They were going to parties together. They were gonna premieres together. I know, like, our stylist was styling her, right? Makeup, all this stuff was intertwined. So, like, if something happened and she had a mark on her face, like what we saw from trial today, like somebody in our inner team would have seen it either because she was out and exposed all the time. She was a star, right? And she was dating one of the most famous people in the world. So if there were marks on her face, which clearly there were. I'm like, somebody was doing makeup or covering it up, but I never saw any of that.

Do you think that the violence that was alleged, does it surprise you? When you read that indictment and you heard about this case, obviously you used to work for him. Did it surprise some of these allegations?

You know, like I've said, I never saw any of this. This is horrifying, but not surprised.

'Not surprised, like women's instinct, really, like, I trust my instincts, I have good ones, you know, I grew up in the Bronx, like I really do have to trust, you know I don't always get it right, but like, the first time I looked into this man's eyes, I was kind of like, what's, something's missing there. Like, yeah, I never felt like unsafe around him, but I felt like this man doesn't see humans as humans. It was so clear to me, Laura, that his entire way of dealing with everybody was this transactional, I'm going to get you for the most I can get you for. This was clear, just working for him, right? This like, sort of late-stage capitalism, like gone awry, also combined with. You're so lucky you worked for me. I'm the most famous person, you know, sort of in this part of the world, and in hip hop and beyond and luxury, I think he really knew who he could get away with this stuff with, and he acted differently with different people depending on where the power was. Now I'm like, oh, I think, this is conjecture, obviously, but I'm, like, there was a reason why he chose, or we hear the word grooming a lot, and I'm like. I think he groomed this young up this beautiful starlet.

Well that's the intimation from the prosecution it's not obviously explicit in an indictment and yet the intimation, especially from testimony we heard from a former assistant in a different you know level that you were, described Diddy claiming that Cassie was the word was "moldable" that was the word "moldable," which I think struck a a chord with people who were listening and trying to connect different dots. The prosecution, as you know, they've got to connect the dots. It's their burden of proof. He is presumed innocent and the defense is going to try to attack each and every instance of this. But I am really curious about, given all of his different business enterprises and all that you look at the sort of universe that Sean "Diddy" Combs was the head or at the helm of, was it really as fluid between his personal finances and business? Was it really such that everything that was coming into the operations as a whole were used for whatever?

'I mean, I didn't, I'm not his chief finance officer. He had a chief finance officer like a proper business. But like, I always assumed that there was the legitimate money that was coming in from deals with Estee Lauder and Ciroc and Kohl's and, right? These are like real businesses that are probably not messing around at all, right? But I also knew that he had like a slew of women. He was a rich person. And so there was always people around, I think, who we're trying to sort of get money off "The P-Diddy Tree," you know, so I can't imagine that all of that money was mixing, but I also don't feel that it was such a buttoned up enterprise. You know, I mean, there was probably a lot of cash floating around that I didn't know about and didn't see. So I can really speak to whether or not like there was money that was being co-funded, but it seemed really fluid to me between what was his personal life and what was his business life, but that is the case in many ways with many famous people, right? Anytime you're going out and doing something, you're writing it off, right? I mean this is what Corporate America does. So, very hard to say if the money was being accounted for and how, but I'm sure there had to be some secret side money to pay for obviously some of the things that the "freak-offs" required.

And we're hearing a lot about the items that were purchased with either cash or otherwise. Let me ask you his last question, because this has played a very big role in all the conversations. I mean, we're hearing, as much as we're hearing about violence in this trial, we're hear hearing about addiction. We're hearing about drug use. Did you ever see that? Was that as prevalent as it's being described in court?

I mean, I did not get the sense that he was a drug user. He was always rolling, he was always going, like I'm the same age as him and I could barely keep up with him. So I just assumed that that was his like make or break sort of like go for the billions type of energy. I did not see any drug use. He was a little bit of a hypochondriac. He had like 20 doctors and I was in charge at one point of trying to straighten out all these different doctors and now I'm wondering if maybe there were prescriptions that were potentially being used. I read somewhere in one of the transcripts that the name Frank Black was a name he was using. And you know what? He's in my phone under Frank Black. Like, that's what we booked every hotel.

Get out. Are you kidding, Suzi? Wow.

I am not kidding. So that code name was absolutely something we used to book him in hotels and stuff. So when I heard that it was on some of the prescription labels, I was like, hmm, interesting. He had a lot of doctors and he had a lot of people doing his bidding to get these drugs some of which were obviously street drugs and some of which prescription drugs. I didn't see any of it and I also think maybe he started using more heavily after I was done working for him because that amount of drug use from what they're alleging or saying seems to be a really, really serious addiction. I did not see any indication of opiate addiction or withdrawal, anything crazy like that.

Suzi Siegel, but what you've seen, I am so curious about. Thank you for relaying it here. It's crazy to think about this is what's happening right now and what may have been in the other circle, so to speak. Great to talk to you, my friend. We'll talk soon.

Make sure you're following Trial by Jury wherever you get your podcasts. We'll be back later this week with more updates. This episode was produced by Paola Ortiz, Dan Bloom, Graelyn Brashear, Alexandra Saddler, and Rachid Haoues. Our technical director is Dan Dzula, and the executive producer of CNN Audio is Steve Lickteig with support from Emily Williams, Kyra Dahring, Robert Mathers, Alex Manasseri, Lisa Namerow and Jamus Andrest. I'm Laura Coates, and I'm here for it.

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