Law&Crime Sidebar - P. Diddy on Trial: Bruises, Bombshells, and Blackmail

Episode Date: May 15, 2025

Casandra Ventura, better known as Cassie, was back on the stand in federal court to undergo cross examination from her ex’s attorneys. Sean “Diddy” Combs is accused of forcing Cassie to participate in wild sex parties called “Freak Offs.” But Combs’ team has maintained that while the two had a toxic relationship, there's no proof of sex trafficking or racketeering. Law&Crime’s Chris Stewart chats with correspondent Elizabeth Millner about what happened in court Wednesday.PLEASE SUPPORT THE SHOW: Check out Odoo for a true customer-centric tool for your sales needs with a free 15-day trial today at https://www.odoo.com/sidebarcrmHOST:Jesse Weber: https://twitter.com/jessecordweberLAW&CRIME SIDEBAR PRODUCTION:YouTube Management - Bobby SzokeVideo Editing - Michael Deininger, Christina O'Shea & Jay CruzScript Writing & Producing - Savannah Williamson & Juliana BattagliaGuest Booking - Alyssa Fisher & Diane KayeSocial Media Management - Vanessa BeinSTAY UP-TO-DATE WITH THE LAW&CRIME NETWORK:Watch Law&Crime Network on YouTubeTV: https://bit.ly/3td2e3yWhere To Watch Law&Crime Network: https://bit.ly/3akxLK5Sign Up For Law&Crime's Daily Newsletter: https://bit.ly/LawandCrimeNewsletterRead Fascinating Articles From Law&Crime Network: https://bit.ly/3td2IqoLAW&CRIME NETWORK SOCIAL MEDIA:Instagram: https://www.instagram.com/lawandcrime/Twitter: https://twitter.com/LawCrimeNetworkFacebook: https://www.facebook.com/lawandcrimeTwitch: https://www.twitch.tv/lawandcrimenetworkTikTok: https://www.tiktok.com/@lawandcrimeSee Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

Wondery Plus subscribers can binge all episodes of this Law and Crimes series ad-free right now. Join Wondry Plus in the Wondery app, Apple Podcasts, or Spotify. The third day of the explosive sex trafficking trial of fallen music mogul Sean Diddy Combs and it delivered even more bombshell revelations as one of the government's key witnesses. Cassandra Ventura, better known as Cassie, Diddy's former girlfriend and protege, remained on the witness stand. She detailed years of alleged abuse, coercion, and the dark reality behind the so-called freak-off parties and visual evidence is being shown to jurors. How did Did he react to testimony in court today? What were the emotions of the courtroom and what could

a cross-examination of Cassie look like? Welcome to this special edition of Sidebar presented by law and crime. I'm Chris Stewart and for Jesse Weber. We know it's being reported on from the outside, but to help us get an inside look at everything that is happening inside the courtroom in the southern district of New York, I want to bring in our law and crime reporter Elizabeth Milner, who was in the courtroom once again today. Elizabeth, thanks for taking time as court just wrapped. Just first up, what was the mood in there today, day two of Cassie being on the stand? Well, definitely the mood was just, again, kind of like it was for day one of. Cassie's testimony. A lot of people were anticipating what is going to happen today. What more is our prosecutor is going to go over with Cassie. And really today was just kind of a summation of her entire 11-year relationship with Diddy, who she refers to as Sean, whenever she's testifying. But as far as today, the mood kind of, it was a little different inside that courtroom.

It was, you know, part two of her direct examination. We thought that there would be a point where we would get to the cross-examination at some point today. That's not happening. It's going to be happening first thing tomorrow morning. But as far as just the mood in general, you know, Cassie comes in today. She's wearing a long gray dress. She did something similar that she did yesterday where she just walked directly to the witness stand. Her family was there to support her. Those family members included her mother, her brother, and her husband, Alex Fine.

Meanwhile, on the other side of the courtroom, you have Diddy's children. Now, it was a little different than it was yesterday in that his daughters weren't present. And I was actually told by a source that they weren't present for a reason that, you know, it's a reason for a lot of kids. there for graduation. They have prom coming up. And so that is why they are not in the courtroom. And that is why they're no longer in the city, actually, because they're flying back home to attend to those types of activities. But so for the most part, those who were there to support Diddy today were one of his associates, his sons, that included Quincy Brown, that included

Justin Combs. It included Christian Combs as well, too, as well as Diddy's own mother, Janice Combs, who was inside that courtroom. So really, it was, you had on one side, Diddy's family, you on the other side, Cassie's family, who was accompanied by Cassie's attorney as well, too. And so that was kind of the mood that was set today. Now, even when Cassie had walked inside that courtroom, did he, for the most part, from what I saw, kept his eyes on her, saw her when she had first entered the courtroom, saw her as she walked up to the witness stand. Meanwhile, Cassie, from what I could see of her, didn't really pay much mind to the defendant or the defendant's family. Again, she just made kind of a beeline to the witness stand. And again,

she was back under oath. And so, you know, for the most part, she definitely kept her composure. There were emotional points throughout her testimony. I'm sure we'll talk about more in depth than just the second. But for the most part, that was just the general mood of the court, thinking that we were going to get to the cross, but it was still another day of direct examination. And at this point, it seems that Cassie won't even be off the stand until the end of the week. I want to thank Odu for sponsoring sidebar. Odu is an incredible all-in-one business management software that offers you a range of applications. One of my favorite Odo applications is their sales tool.

The Conbon Pipeline Game Changer, whether you're working with leads or full-blown opportunities, you can visually track every stage of your sales process. Just drag and drop to move deals forward. It is fast and honestly kind of satisfying. And when it's time to send a quote, it's literally a couple of clicks. And the reporting? Super clear.

You can get a live view of your pipeline, conversions, and what's working, on closing, not guessing. So right now, you can get a free 15-day trial of Odu's all-in-one business solution and see how it can make your life easier. Check it out at Odu.com slash sidebar CRM. Now before we get to that testimony involving Cassie today, Elizabeth, I understand there's a little bit of some drama between the prosecution and the defense. What happened? So there were actually arguments outside the presence of the jury before the testimony restarted this morning. So even outside of the presence of the jury, Cassie is not on the

witness and her family wasn't in the courtroom when these arguments were happening. But essentially from the defense's point of view, they wanted no communication between Cassie and her attorney whenever she would be under cross-examine witnesses to do. So essentially, the defense from their point of view said that it's not an issue about emotional support, whereas the government in their argument was saying that the witness should be able to kind of consult with her attorney under the assertion of privilege, a lot of legal jargon, a lot of legalese there. But from the defense's perspective, they were just concerned about Cassie and her lawyer being able to consult with one another on the testimony and kind of how that would even happen is, you know,

she is a government witness. They were concerned that the government would tell Cassie's lawyer or something. Cassie's lawyer would refer it to them while she were under a cross-examination. And so they were just a little worried about that. Now, as from the government standpoint and Marine Comey was making this argument today, she essentially said, you know, whenever she is talking with the attorneys, the attorneys of the prospective witnesses, that they're really just kind of talking about logistics. They're not talking about testimony. They're talking about transportation. They're talking about security. They're talking about, you know, when Cassie presumably can leave the courtroom, who will follow her out of the courtroom, security and logistics. And so those were

one portion of the arguments. Another big argument that was made this morning prior to Cassie restarting her testimony were just marked exhibits from the defense. From the government's point of view, they said that the defense was not producing their new exhibits. They thought that these exhibits would be shared all the way back in April, which was just a few weeks ago, and said that their goal is not trial by ambush, whereas the defense says, you know, they are marking a tremendous amount of exhibits.

Some of these exhibits, even, you know, in the government's possession. And so these, the category about these exhibits were pretty much text messages between Sean Combs and Cassie. And the defense was saying it was pretty much unfair if the government can prepare a witness with these text messages. They said, you know, marking exhibits in response to direct testimony. They can hand over the exhibits essentially around the time cross-examination starts, whereas the government was making the point that they wanted these exhibits now.

They wanted them pretty much ASAP, again, them pointing back to the fact that these had to be turned in by April and we're already, you know, in trial right now, we're in testimony right now. And even from the judge's response, he was kind of a little like, why are you just bringing this up now while we're in trial if this was an issue and you didn't have them before the start of trial why didn't you raise that issue before and then we could have handled in this matter so that way we're not holding up the jury and so that way we can get the day started so that took about a good 30 minutes of just back and forth between you know the defense and the government

and essentially the conclusion was just that these exhibits would be turned in around the cross-examination time so a time that we soon or the government could soon be getting these exhibits so that way they can market, possibly re-ask these types of questions under redirect. And that's why, you know, this testimony is taking a little bit of time because there's just so much intricate pieces, you know, from both sides that, you know, they just want to make sure, again, all their ducks are in a row for the most part. But it seems like the, from the defense's point of view, they'll hand over the exhibits, just not when the government initially wanted to. And another person involved with Cassandra Ventura, Alex Fine, who's her husband,

father of her children. And first off, you just think of what it must be like for him, listening to the testimony that we'll talk about in just a moment of what his wife is saying on the stand about her relationship with Sean Diddy Combs. But what possibility is there that Alex Fine could actually testify at this trial? From the defense's perspective, it seems like it was kind of a strong possibility. And I say the defense, because the defense plans to call him as a way, witness to kind of impeach his own wife's testimony, which is something that you don't really see

every day. So this argument was first brought up just yesterday. And essentially, this kind of was about the time frame around, you know, 2018 time. So essentially from the defense's perspective, these arguments were brought up yesterday. And this was just about the testimony that was going to be brought in something that was even talked about today. And this was about an alleged rape that happened in 2018. And essentially, from their point of view, they were saying that Alex Fine allegedly threatened Diddy, for the most part. They said that Diddy, or excuse me, that Alex Fine threatened Diddy about Cassie demanding this $30 million, threatened to beat the F out of Diddy. Those were the words that were used in court yesterday.

And the defense says that they want to call Alex Fine as an impeachment witness. And the government said, you know, for the most part, that he should be allowed inside that courtroom while his wife is testifying, while his wife is there on the stand to provide emotional support. And I will even say, you know, sitting just a few rows back from him, you could kind of feel the tension just between him and Sean Combs, not from Sean Combs' perspective, but more so from Alex Fine, to Sean Combs where he looked visibly upset, in my opinion. He looked like, you know, that he was just, you know, reliving this testimony and going through this testimony in the extreme graphic detail. It just seemed like he was very upset of, you know, why did you do this to my wife?

This is somebody that I love and I want to protect her. It definitely seemed like it was kind of a protection mechanism, or maybe it was just, you know, his, you know, natural reaction, but you could kind of feel just during some of that testimony today that there were some tense moments, but back to these arguments outside of the presence of the jury that happened yesterday. So the defense says, you know, they wanted to, they wanted to exclude him and get an outside of the courtroom when this alleged rape was in 2018, it was talked about during her testimony. So for the most part, during the duration of her being on the witness stand, He did stay in that courtroom as well as her brother, as well as her mother and her attorney as well, too.

But then when it came to this testimony about the 2018 party that had happened at Cassie's brother's house, and then we're talking about the alleged rape that had happened also in that same year. And that's a big year, too, because that was the year that Cassie called it off with Diddy, as she had said. But so when they were starting to get into that 2018 timeframe, I did see Alex get up out of the courtroom, walk out of the doors. and he didn't come back for the rest of her testimony, mainly because of these arguments that happened outside of the presence of the jury yesterday. I know how emotional it was yesterday in the courtroom for day one of Cassie's testimony. What more did we learn in day two of Cassandra Ventura on the stand being questioned by prosecutors?

Well, we learned a lot, and a lot, Chris, and I say that because I used up pretty much half of this notepad, just taking notes. of pretty much, what, seven hours of testimony today? And so when Cassie was brought back onto the stand, she was handed over two drives. These drives had messages, photos from her devices. Even one of these devices had enhanced images, more photos, more messages. Then they started kind of talking about her aliases

that she had used when she was either booking escorts or booking hotel rooms, such as Jackie Starr, such as Veronica Bang, such as Mia Crawford. Then, you know, they kind of touched base a little bit about Shug Knight. Why was Shook Knight brought into this testimony today, mainly because there was a point where she had said, she being Cassie, had said that Diddy Security Guards and Diddy himself packed up some guns from a safe and tried to find Shook Knight, who apparently was just down the hill from them. So that was the first start of it. Then they had touched base

about, you know, the escorts and confirming that they weren't police officers or cops. And Cassie would essentially lead, you know, with the fact that she wasn't a cop to make the escorts feel more comfortable. And she said that Diddy had told her to essentially say that. A big point of her testimony initially this morning was just about the Intercontinental Hotel Surveillance Video and, you know, the whole fighting back and the concept of why she didn't fight back in this particular incident. So she said that she fought back early in their relationship, but she said it was worse for herself when she did fight back. She said that when she did fight back, that Diddy would be actually surprised that she would fight back. They were shown the surveillance video from the Intercontinental Hotel again, that from 2016, you know, we were seeing it again. The prosecution asked her what Sean Combs was holding in his hand.

She said nothing at first. Then there's a point where he kind of goes off camera, but you can see him through the reflection of the surveillance video. Because initially we just thought that was the, we just thought that was a portion of the hallway when really, It was a mirror showing the reflection of what was really kind of happening. And so he had grabbed her phone. He had walked towards the room where there was actually an escort waiting because they were leaving a freak off, or that she was actually leaving a freak off. And that's why Diddy had run outside of that hotel room with a towel on.

You see Diddy through this mirror reflection, throwing a vase at her. She said she didn't get hit by this vase. It just hit a wall instead. And she says she can't necessarily recall the exact words he was saying to her when he had thrown the vase at her, when he was essentially viciously beating her. in this hotel. And I will say this about Cassie's testimony today. You know, if there was something that she didn't remember, she just flat out said that. She didn't try to, you know, make up words or try to put words necessarily in his mouth from what I could tell under her direct examination.

But, you know, she says she didn't remember what he had said to her during this time. You could see her picking up a hotel phone to call somebody downstairs. Then next thing you know, she's putting her arms up to keep him away from her. She, there was a point where we saw that security video of Officer Israel Flores, who now works for the LAPD, but at the time he was working security for the hotel. You see him back inside the surveillance video. You see Cassie walk to the opposite side away from the hotel room that they were in. You see, Diddy walking towards that hotel room? And then she is seen walking back towards that hotel room, not because she wanted to go back to this freakoff or anything like that from her testimony today. It was essentially because she just

wanted to get herself so she could leave. And she said, that Diddy didn't want her to leave. He wanted her to stay, but she did leave. She went back to her apartment. She ended up taking an Uber. Then we saw some text exhibits from, for example, these were the texts from Diddy, who and these text messages was going by Pop Pop. And again, that was a name that he liked him. He liked her to call him. And this was actually a nickname she even gave her grandfather. This was something we had learned yesterday. So these text messages said from Diddy to Cassie, call me. He also said, yo, please call me i got six kids please call me yo please i'm surrounded call me my kids um help and then cassie said

put a robe on and that was because he was running around in a towel something we had all saw through this surveillance video ditty's texting her back call me call me now cassie said i went and checked everything as long as you don't disturb the guests you're good the guests being the other ones in the hotel room um and then we had learned who this mysterious escort was who was inside that hotel room and it was this man named jules somebody that they used often during these freak-offs. He was an escort, and he was somebody that we saw an exhibit photo of him. He is a light-skinned man. He appears muscular, couldn't really tell necessarily. He has a bald head. And then she says she doesn't remember the conversation she had with Jules specifically after this

incident had happened until actually another freak-off. And so we saw another exhibit photo, this of Cassie. She's wearing sunglasses. It's a selfie photo. And it's a selfie photo. And it's a selfie photo of her with a busted lip or a fat lip, as she had called it in court today. And this was taken actually in the Uber after she had left the Intercontinental Hotel in Los Angeles. She had a black eye as well. I mentioned the sunglasses. The sunglasses were covering the black eye, but you could see the black eye just peeking out through the sunglasses. Meanwhile, at this point, Did he still text messaging her saying, call me, call me now, call me. The cops are here. You're going to abandon me now. And Cassie says she wasn't aware the cops even came to the hotel. She had responded,

have a premiere Monday, and I'm kind of paraphrasing here because it was a lot of messages going back and forth, so I had to make sure I had to write everything down. She said, you are sick for thinking it's okay what you've done. And she said, stay away from me. He said, he being diddy responded, call me. I'm about to be arrested. If you don't pick up, you'll never hear my voice again. Please, I'm getting arrested. And then Cassie responded, plugging my phone in and going to bed, you should do the same. Kind of, and for the most part, insinuating that he might have been telling a story or just using this to over exaggerate. And she had brought up another person who the government has said might be a witness in this case,

and that being Carrie Morgan, somebody that Cassie was friends with for a number of years, 17 years, according to her testimony. And she had said that her friend, her best friend at the time, Carrie Morgan, was upset after seeing Cassie's black eye. She was at her home. She saw this black guy before she had known that Diddy was physically abusive towards her before. And Carrie was actually somebody who had called the cops on Cassie's behalf. Cassie said once the cops did arrive and spoke to her, she didn't say who did this to her, did this by being physically violent.

I mean, she said she wouldn't disclose it because she still wanted to protect him. And Chris, I just got to point out here, you know, I think there's a lot of always conversation about why do people stay in these abusive relationships? Why do people keep going back? Why do people return? And just hearing Cassie's testimony from her own mouth today, from her own words. just hearing her tone because throughout most of her testimony yesterday and even today, she's very soft-spoken. And I don't know if it's nerves.

I don't know if it's just because reliving this and even her being emotional throughout her testimony that, you know, this is, you could tell this was a very difficult process for her, her having to relive this entire experience, her having to tell the entire world essentially just everything that she had gone through through her 11-year on and off relationship with Sean Combs, you know, you could just kind of feel the emotions, kind of going through her, something that I don't think necessarily translates that well through the transcript. But hearing through her, she appeared on it. She appeared very truthful. She appeared very credible in my eyes. And so she had said, you know, she just wanted to protect him. And there

was something that she had said a lot of times during her testimony is that she loved him. She thought that this was what love was. And she just essentially never wanted him to get in trouble or anything. And so that's why she kind of protected him as much as she did. She said even after the 2016 hotel incident that he had come to her apartment. She was on the 17th floor of this apartment, and this is an important part because we'll talk more about the testimony of why the 17th floor is so important in this. But, you know, she had said that Diddy try to get into her apartment? He was banging on her door, yelling at her front door. She even heard from Diddy's, one of his primary assistants, that being Christina Corum, somebody who's been

named in some of the civil lawsuits against him. She said that she had heard from Christina a quorum that day, someone she refers to as KK. And she even spoke with a man named D. Rock, who worked security for Sean Combs. She said she even went to D. Rock's house that day, said D. Rock and his wife were there for her, somebody that she even considered a friend. And she said the next time she actually saw Sean Combs was at D. Rock's house. And she had went there to Sean's house, or excuse me, she was at D. Rock's house. And then she had later gone to Sean Combs's house, mainly because she had a movie fitting. because this is also another important part of this testimony is that she had a movie premiere

very shortly after this entire incident. And for the most part, she said she didn't even want to do this particular freakoff. She mainly did these freakoffs to appease Diddy to make him happy. But she said she didn't even want to do this particular freak off because she didn't want to pump herself with a whole bunch of drugs, because she didn't want to be tired or slouch. This was something that she had worked hard for. And she wanted to kind of enjoy this moment for herself. So she didn't want to do this freak off, so it wouldn't ruin her premiere.

But she went to Sean Combs' house for a movie fitting. Then we in the gallery and the jurors as well to saw an exhibit of Cassie and a gold gown. She had sunglasses on while she's doing this fitting picture. And then she said it was to cover up a black eye that she had had. And so the photo was taken in Diddy's bedroom. She said she even had to cover up the bruises from this beating by using makeup. She had to cover, she had to use a whole bunch of makeup even on her face to cover her black eye. And then we had seen another photo from that red carpet from that premiere where, you know, if you really

zoom into it, you could see bruises kind of on her backside. And then we saw another photo, this of Cassie in a green dress. He said this was a dress that she had changed into during this premiere in a popcorn closet of all places at the movie theater. And she had gone to an after party with Diddy. So we saw an exhibit of Diddy on her arm. and they were sitting together at this after party, and you could see a bruise on her leg. She said she had a bruise on her right shin. Joshua said she had bruises on her thighs, and so we really got an in-depth picture of, one,

what had happened at the Intercontinental Hotel from her perspective, but also even the aftermath of just having to kind of cover everything up, emotionally, physically with makeup, and then just go off and act like everything was picture perfect. And so, you know, it was a stark difference from seeing that surveillance video and then seeing a red carpet photo of the two of them together, a photo that we and ourselves even have in house and just seeing that she appeared happy, but knowing that on her body, a bunch of bruises

given to her by her boyfriend at the time. And as all of this is playing out in the courtroom and you have very emotional testimony from Cassie, you have these images, selfies that she took, like with a busted lip. And I know it can be tough to tell, but how does it seem to be playing the jury well from the jury's perspective from what i could see because it's really kind of hard to see them at all points but from where i was sitting today i will say they've kept pretty

stone cold throughout this entire testimony and that's kind of hard to tell mainly because you know i don't know what their reactions are going on inside their head even us in the gallery you know for the most part we're kind of you know stone face and then when we get outside of the courtroom and then we're just like oh my god that was a lot so you really don't know what was kind of going through their head. But I will say, you know, from my perspective, from what I could see, I didn't necessarily see anybody getting emotional or wiping away tears. But you definitely could tell that the jurors were laser focused on Cassie and just the line of questioning. There were some glances at Diddy as well, too, throughout this testimony. But for the most part, you couldn't really tell

their emotion. So no idea what's actually going on through their heads while they're listening to all of this. And today, there was a lot of talk about the escorts that Cassie says, was involved in these freak-off parties and there were several names that were brought up. What stood out to you with those names that were brought up in court? Yes, so we saw a lot of photos, a lot of these escorts. And so, for example, we saw just a bunch of back-to-back exhibits, one from a man named Ash, who was hired through this escort service called Cowboys for Angels through this man named Garin.

and this was someone they would fly out to Las Vegas, to Ibiza. There was an escort who she didn't know the second name, but she remembered that he was hired by Cowboys for Angels, saw him in New York. There was an escort named Islander, somebody who was hired mostly in Las Vegas, in Los Angeles. There was a man named Tommy also hired through Cowboys for Angels. This man was used in Miami,

another escort whose name she couldn't remember used in Los Angeles, an escort named Skyler hired also by Cowboys for Angels. used in Los Angeles. There is another escort through Cowboys for Angels named Jake used in Los Angeles as well, too. Couldn't remember another escort's name. Also booked through Cowboys for Angels used in Los Angeles. There was a man named Greg used in Miami. She didn't remember how he was hired if he was hired through Craigslist or Backpage.

And for the most part, if she could remember, it was through Cowboys for Angels. She said that it was through Cowboys for Angels. Another escort whose name she didn't remember but remembered him from Free Gov's, an escort named Brian hired as an escort in New York. He was booked through Craigslist. A man named Ben was hired through Cowboys for Angels as well, too, through the man named Garrett. He was booked in Los Angeles, Las Vegas. And I say all these different cities, mainly because that's how frequent they were. She said she did hundreds of these freaks, but there was one particular escort that stood out to me. And that's because he's a familiar face. Not because I know

this personally, but because we, this is somebody we've covered so many times. here at law and crime. And this was an escort named Jonathan. Obviously, I know Jonathan's last name to be Audie. We saw his photo. I remember his face. And he's a big name. Maybe somebody that people didn't kind of click right off the bat, but I definitely did. This was an escort that definitely stood out to me. Why? Because he did an interrogation after he was in another incident. I don't think it had anything to do with sex crimes or anything like that. It actually had to do with Trump. And when he was interrogated, he was pretty much saying that he was a sex slave for Sean Combs and Cassie, and nobody at the time believed him. Nobody, everyone thought that this man

was just going on a wild, crazy tangent, that he was just saying things out of his behind. But Cassie confirmed today that he was an escort that they had used in these freakoffs. So it seems like from, you know, Jonathan's perspective that he was telling the truth the entire time and that, you know, while the claims were made years before this case even went to trial years before Cassie had even filed her lawsuit, people didn't say. take him seriously. But Cassie herself confirmed today that Jonathan Addy was definitely an escort that they had used previously and said that she had seen him several times, specifically in Miami. And so that was definitely a name that was brought up that stood out to me. But,

you know, this is just some of the escorts that they had booked for these freakoffs. And Cassie said she had booked them again through services like Backpage, through Craigslist, through Cowboys for Angels and these escorts, essentially, especially the ones that they were more comfortable with, were flown to different places, kind of making this argument, you know, for counts three and five, transportation to engage in prostitution. And so that was one, again, definitely a name that stood out to me. But again, that was just some of the escorts that Cassie and Sean Combs had used during their freak-offs in their freak-off sessions. Yeah, and to your point, I mean, it just seems like there were so many names.

just today and locations that were being that were already being laid out in this testimony that she's having with the prosecution. What is it like to be in the courtroom? The video from the Intercontinental Hotel in Los Angeles, we have all seen it. There's few people I feel like in the world that haven't seen that video at this point, but what's it like to be in the room as Sean Combs is there and that video is being played? So this was a video that we have seen for a while now that even being you know going back as far as just um last year but then even for jurors they've been seeing this video essentially every single day since trial and it's only wednesday and so from what i could see um just of ditty's reaction while this video is being played you know

it seems like this is kind of a point where you know anything that had to do with physical abuse you could kind of tell and i say kind of like that mainly because again i don't want to make assumptions of what's really going on in his mind but i feel like you could kind of tell this is something that he's ashamed of. Definitely. I think there are points where he kind of, even in between breaks, you know, when the jury's out and stuff like that, he kind of looked at his sons and he had looked at his associates or friends in the courtroom and just kind of was just like, like kind of reassuring them that, you know, are they okay? Is he okay? That type of thing. But again, this is a video that he's seen a number of times. And so he didn't

have a big emotional reaction to seeing this video played out again in court. But, you know, never know necessarily what is 100% going on in his mind as this video is being played and now as all of these allegations and everything is being displayed again out in open court. And you're one of the few people who have seen Sean Combs since he's been arrested because he's transported to the courthouse. He's in prison or in jail, excuse me, for the moment. And just what mannerisms have stood out to you?

Because we all know the mogul. We all know Sean Combs and Diddy and all of this. But to see him in this position as a defendant, what mannerisms have stood out to you so far in this trial? Just watching how Sean Combs interacts with his attorneys and sits there at the table. Well, as he's sitting at the table, he looks very differently than when I was covering him during those pretrial hearings in that he's not in a jumpsuit anymore. He's not in that MDC issue tan jumpsuit. He's in kind of more. of a toned down look. Even from when he was, even prior to when he was arrested, you know, normally prior to his arrest, we see him in designer clothes. We see him in sunglasses, but now it's completely different. We see him very much toned down in neutral colors. For example, today, he was wearing a cream sweater, a white undershirt. He had gray slacks on the previous day. We have seen him in gray sweater, gray slacks. And even before that, we were seeing him in a Navy sweater and navy slacks. And so for the most part, his mannerisms in the courtroom, he is very much

participating in his own defense. He is intently listening to all the testimony that's been given. So far, it's just been Officer Israel Flores, as well as Daniel Phillip, one of the escorts, and then Cassie herself. And for the most part, he is just jotting down notes, handing them on to his attorney, asking questions. There was moments that photos were shown inside the courtroom. He's looking at these photos. He's looking at these exhibits. So from the mannerisms, I could tell of him, he's very much so participating in his defense. You know, even during the pretrial hearings, I would notice he would look often into the gallery. He's not doing that this time around.

He is very much focused on what is going on with this court case as, again, taking those notes down. But I will say one thing that also stands out to me is that he looks at all the jury members each and every time that they come into this court room, which, you know, from my perspective, I can only imagine how intimidating that might feel from theirs. But they don't know Sean Combs to the full extent that maybe we do because we've been covering this case so often and so much. But, you know, Diddy, for the most part, from the mannerisms I could see of him, he definitely is not taking this very lightly. He is definitely paying attention. He's taking this process very seriously. And it seems that, you know, we can expect a lot with this cross-examination of Cassie, possibly off of some of the notes that Diddy himself had said, because from the defense's perspective, they have been chalking this up as kind of a toxic relationship, a domestic violence issue, that this isn't necessarily sex trafficking or. Rico or transportation to engage in prostitution. Obviously, their defense attorneys, they're

defending their client. But for the most part, you know, we kind of know essentially what the defense is, something that Mark Agnifalo had even said, that they're kind of, you know, have had the defense on their shoulders this entire time. They kind of let everybody know their strategy, essentially, and that's discrediting the witnesses, chalking this up to being a domestic violence, bad, and nothing criminal, and that these freaks were consensual, that Cassie wanted to be there, that she didn't necessarily say no. But there were points. her testimony today where it was clear that she had said no to some things. And I'm sure we'll talk about that in a second. Yes, absolutely. I mean, let's talk about the freakoffs because

some visual evidence is starting to be presented in in the courtroom. What did what were you able to see today? What was shown? Yeah, so the freakoffs were definitely a major point and a major sticking point throughout her testimony. You know, drugs were talked about during these free calls because she essentially did enough drugs to disassociate from her testimony today. She did things such as ketamine and the initial part of their relationship. She said she even did opioid. She did volume and Xanax and GHB and cocaine and marijuana. She drank alcohol. She was taken to sex clubs with Diddy. And essentially, you know, she said there was a lot of times where she just felt objectified, that freakoffs were all that she was good for.

She had talked about an incident during her 29th birthday where she just wanted to have a dinner with her friend. She wanted to do karaoke, but Diddy wanted to do a freakoff, and she was pulled away from her friends, some friends that she actually wanted to be with, and she essentially gave up fighting Diddy and did this freak off, something that she didn't want to do. Blackmail was talked about, you know, sex videos of her, sexually explicit videos of her, freak off videos of her he would mention these to her when he was angry and she said that this was something that he commonly did she said that there was one time she dated someone else and did he had

threatened to put these videos out and he did this several times with her because even throughout their relationship together there were still points that these two were on and off away from each other but when she would date somebody else he said that or she said that did he would threaten to embarrass her and ruin her by putting out these images she said she feared for her career, for her family, and her family being her mother and her brother, she said it's horrible and it's disgusting, and she said that he would make her feel like an SLUT. She said she didn't even want to be recorded. There was a point talked about through text messages from July 22nd of 2013, where Cassie was saying, please delete any

video out of your phone. You have too many people who have access to your stuff. And she said, and Diddy said, I did, and no I cloud. And I'm paraphrasing here. He later on taking an ambient good night. As far as the videos themselves, she said that in 2014 that she was hosting a party and someone said that they saw a sexually explicit video of her. And so she had called Diddy. He had texted her, I called Pickup. When did he say he saw it? You're going to tell him that this is your life and this is serious. And then said, are you talking to him yet? this being the person who had told her about seeing these videos of her and said that they had a whole discussion at a restaurant with his security involved. And it was pretty much the security's role

in this whole scenario was to intimidate these people about why they were talking about the sexually explicit video. And she said that essentially everyone at this, this meetup was scared and confused about it. She said that Diddy's bodyguard uncle Polly was there. Her former manager James Cruz was there, someone who had worked with Diddy, she had talked about the recoveries of these freakoffs. But I will say there was a big discussion yesterday just about whether or not these videos or still images would be shown to the gallery, to the general public. So there was a whole issue just yesterday about whether or not we were, we being the public and we being the press that was inside that courtroom and those in the gallery would be

able to see these images of the freak-offs, whether they were still images or video images, the judge essentially ruled not to show them to the public, to the gallery, and something that will be under seal whenever they release all these exhibits. And it's mainly because that they didn't want to re-victimize the victims. And so from what the discussion was today, these images were still shown in court. However, they kind of made a big adjustment to doing that. And that, you know, when the jury was dismissed, they kind of turned the camera. or excuse me not the cameras the computer monitors where these jurors see these exhibits see these photographs they turned them a little bit in mainly so nobody could kind of peek at them through the gallery even for the attorneys themselves on both sides they were given a binder of these images instead of showing them on their computer screens just so that way nobody could see them but we got a description of what these photographs looked like just through Cassie's testimony and so she was asked you know do you recognize this individual and she said said that she had did. It was an exhibit of the escort, Jules, who was in that hotel room during

the intercontinental hotel incidents, an escort that they had frequently used during freakoffs, and it was a photo from a video of a freakoff. And then Cassie had said that she gave these images over to the government from broken devices that she had had, you know, and those included iPads, computers, former phones that she had used, but she had kept. And then I can, could see even just from sitting in the gallery, Did he looking at these images? He was looking over Anna Maria Estebeo's shoulders just to kind of take a peek at these images. I couldn't tell much of a reaction that he had just kind of sitting from where I was sitting after he saw these photos. But then there was another photo of Cassie and an escort named Dave in a freakoff.

There was another photo of Cassie and an escort named Greg in a freak off. There was another photo of Cassie on the couch. She had linens on her. The linens were on the floor. She was in high heels. She had water next to her and she had said that she had used water often during these freakoffs just because of how long these freakoffs were, how dehydrated she would get mainly from the drug use that she had had to have water near her just to stay hydrated through this. There was another photo shown with Cassie with oil all over her. There were candles around her. There were lube tops around her and those were just kind of the vivid descriptions that we had seen through her testimony. And again, we didn't see these images.

ourselves. They're going to be kept under seal. So only the jury and the respective parties are going to be able to see those. But those were just some of the images that they had brought up today as far as the freakoffs go. You know, Elizabeth, we talked about Cassie's husband being in the courtroom. There's another person who is a partner of Cassie once, who also came up today. That's a name that a lot of people know, and that's the rapper Kid Cuddy. Why did his name come up? How does that factor into this? Well, he was referred to as Scott Meskiddy in court today, and Cassie even referred to him as Scott throughout her testimony.

And so Kid Cutty was something that we had known about for a while, right? He was a name that was brought up in Cassie's civil lawsuit against a day that she filed in 2023 or towards the end of 2023 that was settled within the day of her filing. And we're going to talk a lot more about that in just a second. But Kid Cutty was brought up today in testimony, mainly because. there was a big issue surrounding just the conflicts that Kid Cuddy had had with Diddy, and the conflicts being that Diddy allegedly sent people to blow up his car. And so Cassie was testifying that they being Kid Cuddy and Cassie dated in 2011.

They first started off working together and they were just friends before they actually started dating. But then when Diddy found out, he actually found out during a freakoff, which was a very surprising part of today's testimony. He said that he was going through her phone and saw an email between Cassie and one of Diddy staff members named Capricorn Clark. This email was essentially about Cassie getting a toilet tree brag. But when Diddy found out about her dating kid Cutty, she had said that Diddy put a bottle, a wine bottle opener in his finger. So just picture that imagery. You have a kind of a swirly, pointy tip. It's in between.

You can kind of see the picture that's kind of painted there. he's she had said that he lunged at her and she just left this freak off and that was one of the few times she was actually able to um leave these freak offs because for the most part did he had made her stay according to her but she said after she had left this freak off she called kid cuddy from a burner phone he had picked her up um and she had had this burner phone just so that way and did he wouldn't even find out that she was speaking to kid cuddy in a romantic way or even um dating him and so um she said that diddy staff member capricorn Clark did not about their relationship And after Cassie met with Capricorn Clark, she went to Diddy's house and Diddy threatened to release freakoff videos of her and even threatened Kid Cuddy.

She said at this point that Diddy even kicked her in the back after that. And then we saw a photo of bruises just on her back from this kick that he had did according to her. She said after leaving and after this kick to the back, she just wanted to get her stuff from a hotel room and said that when she returned back to the hotel room, that it was completely destroyed. She said that there was even unflushed fecal matter. If you know what I'm talking about inside the toilet, she said it was essentially just a mess inside that hotel room. And then she had sent an email actually following up to Cassie's mother.

It was C-Ced on this email as well as Capricorn Clark, somebody that had worked for Diddy at around this time frame. So this was December 23rd of 2011. And if you kind of think about that time frame, that's around the holiday times, and she had sent this saying, and I'm paraphrasing here, threats have been made to me that he'll release two explicit videos of me. And she had said that threats were made to hurt her as well as Kid Cuddy and that Diddy wouldn't do it himself because he'd be out of the country, kind of insinuating that he had

other people to carry out this alleged crime instead. And she said when she went back home, she had shown her mom these bruises on her legs on her back. And we had seen, again, these photos through exhibits. And this was actually the first time that she had told her mother about the physical abuse she endured throughout her relationship. She didn't necessarily go into full detail about everything that she was enduring throughout her relationship with Diddy because she said that she was embarrassed to even kind of speak about these freakoffs. But she said that Kid Cuddy actually met her in Connecticut and stayed with her around three or four days around this time frame. And she actually broke it off with Kid Cuddy

during this time period, mainly because she was nervous just about the threats made by Sean Combs, according to her, to Kid Cuddy and herself, and was essentially saying that, you know, she broke things off, then nobody would get hurt. Nobody, nothing bad would happen to anybody. Even after this time frame where she broke things off with Kid Cuddy, she had went to Arizona to visit Sean Cone, something that she didn't even tell her family about because she thought it would disappoint them. And then even they had a whole meeting day being Kid Cuddy, Diddy, and Cassie herself. They all met together back at Soho House, back in Los Angeles. And Kid Cuddy asked about his car. And Diddy said, what car? And so essentially there was just, there was a meeting

that had happened. Diddy had essentially said what car kind of alluding to the fact that he had nothing to do with it, even though from Cassie's point of view and even from the text messages and email that we saw that there were threats that were made, especially after Diddy had found out about their relationship. And so Kid Cutty was a big focal point, especially during the afternoon, especially during that afternoon portion of her testimony where, again, we were seeing exhibits of physical abuse. We were seeing emails during this point. We were seeing text messages. And so that was a lot, or that took out a good chunk of today's testimony that kind of went on And maybe I would say maybe an hour or so.

And it seemed like from the updates we were getting on the outside that it was with each anecdote that she was giving, there was a picture that was provided in many cases, whether she had a busted lip or she had a black eye, just kind of detailing the physical abuse that she says that she went through in this relationship. We did learn a little bit about the breakup and how this relationship came to an end. What can you tell us about that? Yep. And so the breakup, as we know, occurred around 2018, so just a few years ago, honestly. And so around this time, Cassie was saying pretty much that she was abusing drugs during this time frame. She even sought out professional help around five or six different times while she was in her relationship with Diddy. And so she had essentially said the breakup was initially initiated when she said from her perspective that, She had known that Diddy was seeing somebody else throughout the duration of her relationship.

And she had said to Diddy that, you know, if I see that you're with this girl again or if you guys are going to continue doing this, I'm done. And she ended up actually seeing a photo of this unnamed woman and Diddy together. And so she said she was done with the relationship. And even around that time frame, so after she was done with the relationship, she even saw Diddy afterwards after that. She said that they had had a closure dinner around sometime in 2018. And by this time, she was dating someone out. She was dating Alex Fyn, somebody who is her now husband. And then I'm mentioning this specific dinner because she had said at the first, you know,

Diddy was nice during this dinner. They were having a good time. And then when they got back to her place, he had raped her in the living room, according to her testimony today. She said that she was crying throughout this experience. She said she was saying no. She said that Diddy's eyes essentially went black. And it was like that he wasn't even there during this and that he continued to rape her even though she was crying, even though she said no.

But still admits that the two were intimate again together, even after this alleged rape in 2018. She said that, you know, when she was asked, why did you continue seeing Sean Combs in a sexual manner after this rape, this alleged rape, I need to say, she said that she couldn't just turn her feelings off even after the rape. She said she still had a good vision of who Diddy was as a person said she couldn't even really hate him. She said that she even stayed in touch with everybody, including, you know, his assistance and security for a number of times. But then, you know, post-breakup, her and Diddy was still checking with one another for a period of time up until around 2019. And I bring up 2019 because Diddy sent a message to Cassie, a text message to her saying, I'll pull up and handle it face to face. no threats and facts that you'll not be threatening me. If I was you, I get me money. Get me my money. You have two iPads, too many iPads full of skeletons. And essentially what Cassie was

saying from this particular message was that Diddy was requesting a refund from her for Alex physically training her because, you know, this is something that we had known for a while now that Diddy had hired Alex Fine to train Cassie during this time. And essentially he just wanted his money back for that because they were dating around this time frame. Now the two are married. They have, you know, almost three beautiful children together. And then Cassie responded, do you want me to tell the truth because it's deeper than iPads? And so you could tell just by listening to this testimony that this pain goes back in years, at least to 2019, according to this text messages, where, you know, even there was another text message, this one from 2017, where

Cassie sent to Diddy, I told you, I think this is all I'm used for. And this, she was referring to with Free Goss. She said, you know, I didn't leave you. I saved you from beating me up. Now let's fast forward to March of 2023. So just a couple years ago. But think about that time frame. That was a couple months before her lawsuit, the lawsuit that she had filed against

Sean Combs, and I'll get there in a second. But during this time frame in March of 2023, she had went to rehab for trauma therapy and her drug use. And she said, and this is where she started getting pretty emotional, is that she didn't want to be alive at that point. And that's a pretty interesting statement for her to make, because at this time, you know, us in the public, we had thought she had healed at that point. She was now married to Alex Fine. She already had children at this point, but for her to get on the stand today and say she didn't even want to be alive anymore, it was really gut-wrenching to hear. She said that around this time frame, she was even shooting a music video with an artist.

this artist was unnamed. She said that she had really bad flashbacks around this time frame. And to the point where she wanted to unalive herself, she had actually run into traffic and her husband Alex had to go and get her. And so it was just a very tough point. And it was a pretty hard testimony to listen to because she is visibly upset. She is crying on the witness stand at this point. But she's keeping her composure together as best as she could. Now after this suicide attempt. Then they started talking about the memoir. And this was something that the defense said

was essentially their argument that these allegations aren't real, that she had just wanted money. She was doing this for the rights of her book. But she had said that she had wrote down this book, mainly as trauma therapy for herself. And she said that this therapy for herself was in the form of the book. She said her

mom actually helps her with it as far as coming up with chapters. And the reason that she even wanted to write this book was so that Diddy's specific could read it so he could understand what he had done to her throughout the duration of their relationship because she didn't think that he'd ever realized necessarily what he had done to her and just how excruciating everything that she had went through from her perspective actually was to her um she said that she had carried the shame of doing these freakoffs for years at a

time um and she said she did everything for her ditty but you know she felt horrible about herself that she felt numb um because she chose to participate in this. And so this is when they get more into the weeds of the memoir where she had actually reached out to Diddy once again through the lawyer about the book. She even reached out to Christina Corum, one of Diddy's top assistants, someone she refers to as KK, and asked if Diddy had read the book. But Christina Corum's response, according to Cassie, was that no one took it seriously. And so she said she wanted to be compensated for her time and her pain. And this is what's interesting, Chris, is she said for the rights of her book,

she just threw out a number there. She said she threw out a number of $30 million. And she said that was a number. She just chose randomly because it was enough to essentially scare ditty. That is her motivation by putting that number figure down, which is a lot of money. I mean, $30 million, that is a lot of money. That would grab my attention.

It still grabs my attention. And I'm nowhere near any of that type of money in my banking account. That's for sure. But she said she didn't receive money for the book rights. However, when it came to the lawsuit, she did say this, and I think this is very big. There was always a discussion about how much she settled her lawsuit for, and she confirmed today it was for $20 million. So no, it wasn't that $30 million figure that, you know, she had used to essentially get Sean Combs' attention. But because of just how these allegations were and just even the reaction of when she had filed her lawsuit, you can understand why, from Diddy's perspective at the time, why he settled within the matter of 24 hours.

look at where we are today just because of that one lawsuit. And so, you know, she had said in court today, she had no other pending lawsuits with Sean or Sean Combs or any of his staff members. But she was asked, why are you testifying today? And she said still tearfully at this point, I can't carry this anymore, the shame and the guilt. What's right is right, what's wrong is wrong. I'm here to do the right thing. She was asked, you know, in the last bit of moments of her questioning, you know, how many freakoffs did you do? And she said hundreds. But then she said, you know, how many freakoffs did you do after the breakup? And she said none. So, you know, it was very hard testimony to listen to. I really, you know, just my perspective, just as a human

being, I really kind of felt for her during this testimony. I think a lot of people, for the most part, get caught up and just, you know, the baby oil and just things to them they perceive as funny in entertainment, but from her perspective, something that, again, doesn't translate the best in these transcripts where we just see words. She was very emotional just about recalling this excruciating time in her life. But thankfully, you know, she came out on top of this, and this is just me speaking candidly, you know, she has the support of her mother, she has the support of her brother and family, as well as her husband and, of course, her children. And, you know, she is within the third trimester of her pregnancy as well, too. So when she has

baby number three, you know, it seems that, you know, after everything that she's been through, that she is able to kind of just leave this in the past, you know, we don't know what cross-examination is going to look like, right? That is supposed to begin tomorrow morning. And we're kind of holding our breath a little bit because we don't know what to expect. Will they be aggressive with her? Will they be delicate with her? Because who wants to, like, you know, ask really assertive, really hard questions to someone who is visibly pregnant? How could that come across, especially to jurors, you know, where the defense doesn't want to seem like they're bullying her. So a lot of us are very much anticipating what could come out across, how they'll be able to kind of poke holes into her testimony or poke holes into her credibility as something that, you know, it seems like they're going to be going forward as far as their defense strategy goes.

But it's been a lot of her testimony within these last two days, a lot of things that have been divulged with this testimony. And so we're only kind of getting to the start of it, really, because now we still have the whole entire cross. to go into and so that is going to take assuming that she even gets off the sand by the end of this week you know her testimony can definitely carry all the way to Friday for sure yeah it'll be interesting to see how long the defense takes and to your point what approach do they take because based off everything we're hearing everything that that you're telling us I mean this was such emotional raw authentic it seems testimony that she's given to this point how do you handle that in a way where if you're a defense attorney,

you know, do you want to go scorched earth on somebody and really make the jury mad if they do feel for her? We'll see how it all plays out. I know we're battling the weather elements there outside the courthouse in the Southern District of New York in Manhattan. Law and Crimes Elizabeth Milner. Great job covering this case, as you will continue on, as this case continues on.

Thanks for joining us. Thanks, Chris. All right, everybody, thanks for joining us for Sidebar. Be sure to subscribe on Apple, YouTube, or wherever you get your podcast. I'm Chris Stewart, filling in for Jesse Weber. We'll see you next time.