The Rise and Fall of Diddy - Inside the Circle: 2

Episode Date: September 23, 2025

The government’s case against Sean Combs comes into sharp focus with Cassie Ventura at its center. From her raw, emotional testimony to chilling corroboration by a former bandmate, a best friend, her own mother, and one of Combs' employees, the courtroom fills with voices that say they saw the abuse, but stayed silent out of fear. But the defense pushes back -- casting doubt, blurring lines, and turning agency into ambiguity. Was this coercion? Or something else? Featuring interviews with Dave Aronberg, Elizabeth Millner, Matthew R. Lee, and Natalie Whittingham-Burrell.—-Host - Jesse WeberReporter - Elizabeth MillnerExecutive Producer - Jessica LowtherWriter and Producer - Cooper MollAssociate Producer - Tess Jagger-WellsEdit and Sound Design - Anna McClainGuest Booking - Diane Kaye & Alyssa FisherAdditional Production Support - Juliana Battaglia & Stefanie DoucetteLegal review - Elizabeth VulajKey art - Sean PanzeraSee Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

You're listening to a long crime series available exclusively on Wondery Plus. To listen to the remaining episodes, join Wondry Plus and enjoy ad-free listening to over 50,000 episodes, including more thrilling long-crime series like new episodes of Karen the retrial and sidebar with Jesse Weber. Join Wondry Plus in the Wondery app, Spotify, or Apple Podcasts. This podcast is a long crime production. It covers ongoing legal proceedings related to the federal charge. trial of Sean Diddy Combs. The content may include graphic descriptions of alleged sexual acts, violence, abuse, and drug use. These topics may be disturbing or triggering for some listeners. Listener discretion is strongly advised. The allegations discussed are based on court documents,

public testimony, and media reporting. Sean Combs is presumed innocent unless and until proving guilty in a court of law. The views expressed in this podcast are for informational and journalistic purposes only, and do not constitute legal advice or a judgment on the outcome of the case. The legal experts and attorneys interviewed are not actively involved in this case. It began quietly, a message, a wire transfer, a hotel room no one was supposed to walk into. In another case, these might have been background noise, fragments of a relationship, private and unremarkable. But here, in a federal courtroom in Manhattan, they became something else. entirely. Across six days of testimony, a story began to emerge, not all at once, but piece

by piece. Through voicemails and photographs, text threads and long pauses, witnesses who said they were afraid then and are still afraid now. Cassie Ventura took the stand first. Her account was raw, exhausting, a relationship defined by control, then rewritten with gifts and silence. but hers wasn't the only voice. A best friend who said she watched the violence, a former bandmate who said she was threatened to keep quiet, a mother pulled into the chaos by a single demand, and an assistant who said he saw it all and kept going.

This wasn't just about what happened behind closed doors. It was about the people who were there, the ones who stayed, the ones who left, and the ones who were finally ready to speak. I'm Jesse Weber, And this is the rise and fall of Diddy, the federal trial. If the prosecution's case was a constellation of abuse, control, and criminal enterprise, then Cassie Ventura was the star at its center.

She wasn't just a victim or an accuser. She was the narrative thread tying everything together. Dave Aaronberg, former Florida state prosecutor, put it simply. She is the linchpin for the government's case. She connects all the dots. She is the key witness. And if the jurors believe her, the human trafficking case is over. The prosecution couldn't distance her from the center of the case.

They needed her now, vulnerable and irreplaceable. She is the narrator of this story about what happened. And sometimes you use as a narrator someone else who's not the key witness in the case because the narrator is just someone who has all the information who can walk the jury through it, who may not be subject to a withering cross-examination. But the prosecution had no other choice. They needed Cassie to be on the stand to connect all the dots, and they needed her to be on the stand ASAP because she's eight months pregnant.

And when it came time for cross-examination, the defense moved carefully. They went easy on her on the cross-examination. She is the key government witness, and they used a woman smartly to cross-examine her, and they did not badger her. Defense attorney Anna Esteveo didn't deny what Cassie said. She dissected it, bit by bit. She pressed on timing, on drugs, on memory. Estabello's tone was calm, methodical, no fireworks, just a steady, deliberate effort to unwind the government's narrative. If the prosecution had

painted Cassie as a victim trapped in a system of coercion, the defense now aimed to introduce something messier. Agency, ambiguity, contradiction. The question started with language. Estaveo returned to the 2016 incident at the Intercontinental Hotel in Los Angeles, one of the more violent episodes Cassia described. Cassia testified that Combs attacked her in a drug and alcohol-fueled rage. But in an earlier interview, she'd said Combs had, quote, blacked out. Estabello seized on that. If Combs was blacked out, how would he remember threatening Cassie? Cassie didn't flinch, citing that everyone has a different interpretation of blacked out, and that doesn't mean he didn't remember.

It was a small moment, but telling. The defense wasn't trying to argue that the abuse didn't happen, not directly. Instead, they were asking the jury to look closer, to see inconsistencies, to question reliability. Then came the text messages. Displayed on courtroom monitors, they showed the jagged texture of Cassie and Combs' relationship, sometimes angry, sometimes flirtatious. Elizabeth Milner, law and crime reporter, was in the room. It felt like they were trying to just throw all of her messages back at her face,

maybe possibly confused the jury at some points, to kind of throw this back in her face that she was the one who willingly participated in these at some points. But the goal wasn't confusion. it was context. Was this sex trafficking, or was this a toxic relationship that didn't meet the legal threshold? Matthew Russell Lee, courtroom journalist, put the defense's framing like this. They admitted in their opening that he's guilty of domestic abuse, but they're going to try to say this is not sex trafficking. This is just terrible relationship. To reinforce that line, the defense pointed to Cassie's own behavior, her continued contact with Combs, and her

role in arranging escorts. Legal analyst and public defender Natalie Winningham Burrell says it was an attempt to blur lines between consent and coercion. The number one thing that they're pointing out is Cassie's motivation to lie. Should we believe the extent of her allegations because she had a financial motivation to make up these allegations. And that's the defense's best case in order to receive a multi-million dollar settlement. They also pointed out how she got a settlement from the intercontinental hotel who basically allowed Diddy to buy the video of him assaulting her and that she had text messages that were contemporaneous to the freakoffs that would have indicated some level of participation that was voluntary, right?

And so that's what they do. They chip away at her credibility because really she makes up the majority of the case because not only was she either voluntary or involuntarily participating in these freakoffs, she was observing him doing the things, which are the predicates for the RICO offenses. So everything for the defense has to rely on them not allowing the jury to believe her. And at the heart of that strategy was contradiction. She said that there were times in her relationship that she didn't want to do it. And there were times that, for example, text messages would be brought up where,

Cassie was being the one to kind of initiate the freak off, and she would have to explain that. The cross-examination pressed on her continued contact with him, the time it took to report, the emotional gray areas. However, an inconsistency does not necessarily mean a lie, and the defense had to contend with that. Relationships are complicated, and you can say that you consent at the beginning, and then withdraw your consent later on,

and then you could not report it to police until much of the way. later. You could remain friends with the person until much later. It's just real life. This is what happens. It doesn't mean it didn't occur. On May 15th, the defense didn't dismantle Cassie's account. Instead, they leaned into ambiguity, highlighting her agency, her choices, the blurred line between control and consent. But in the courtroom, Matthew R. Lee says that strategy landed unevenly. They didn't really do much on Cross with Cassie. Maybe you couldn't. But I think that they may have put themselves in an irredeemable hole there. Hello, I'm John Robbins,

comedian and host of Wondery's How Do You Coke Podcast? I'm also, plot twist, an alcoholic. I've written a book, Thirst, 12 drinks that changed my life, published by Penguin. Thirst is a book about alcohol. It's mystery, it's terror, it's havoc, it's strange meditations. But John, I hear you cry. Isn't that a rather odd book to write for a sober man who more than anything wants to stop thinking about alcohol?

well, yes, but I had to go back to find out why the one thing I know will kill me still calls out across the night. It's the story of what alcohol did for me and what alcohol did to me. If that's of interest to you or someone you know, thirst, 12 drinks that changed my life, is available to pre-order now, online and from all good bookshops. By the time court resumed the next morning, the tone had shifted. The legal wrangling before the jury even entered was. thick with evidentiary fights over text chains, bruised legs, grainy videos, and metadata.

But the deeper battle was over meaning. And behind it all was one voice, one witness. The defense zeroed in on the aftermath on what Cassie said and did after the alleged assaults. They showed jurors messages that sounded tender, a rehab video where she smiled, a selfie sent with a kiss emoji. And the jury wasn't just being asked to decide what happened. they were being asked to decide what it meant. They showed a message where Cassie described planning burning man with combs.

The timing was crucial after the last alleged freakoff. It didn't fit the prosecution's clean arc of trauma and escape. I think the defense was starting off really kind of slow, just building it up that this was a relationship of love and that this was a relationship where she was the one at times that would initiate the freakoffs and that there were at times where she agreed to do them. But I think that's the whole point is that, yes, you can agree to do these sex acts.

You can agree to participate in. That is consensual. That's not the problem. The problem came when Cassie no longer wanted to do this. And when the defense tried to suggest that her continued participation meant consent, Cassie held the line. She, according to her, felt forced to do this, felt compelled to do this. Still, the defense kept pressing. if she had agency, if she stayed, if she scheduled the escorts, was this really trafficking?

Or was it something darker, but legally distinct? I think he's going to try to say like, hey, it may look to you like a terrible relationship, but the fact that she often bought the supplies, that she arranged for the escort to go, that she sort of liked some escorts more than others, it's a terrible thing to say, but he's going to say that this was a toxic relationship, but it's not sex trafficking. But that line came with risk. I thought the cross was very well done by the defense. They scored some points which were necessary for them to score.

But the narrative that the defense is trying to say that somehow this is all generated by Cassie falls flat a bit. Because in a RICO case, the question isn't whether the witness is clean. It's whether they were part of a criminal enterprise and who was really calling the shots. What a RICO is about, and if we think about when the RICO statutes were initially promulgated in the 70s and 80s to take down the mob is with the understanding that the middleman who is doing the activity of buying the drugs or working directly with the prostitutes is not the mob boss, right? It's to go after the mob boss. And so what you do is either by flipping them, so you offer them immunity or you offer them a plea deal. that's very, very sweet. Or you just say, we're never going to prosecute this person.

We don't see them as someone we want to prosecute. You put them on the stand and they testify against the boss. That's what happened here. Cassie wasn't just a victim. She was also a participant. But in the government's telling, she was executing orders, not giving them. So they were in this dual relationship where not only was Cassie being directed, but she was directing. But her, I guess, defense to that was that she was directing, for example, which prostitutes, male prostitutes, or escorts to pick based on what Diddy told her and what he directed her to do.

She was directing which drugs to take based on what Diddy wanted. And she received these resources through Diddy in exchange for her doing those things for him because she created a cover for him. I think a jury is sophisticated enough and the prosecution team is sophisticated. enough to see through that, and the prosecution would argue that this is all at the behest of Diddy. The defense tried to neutralize that, painting Combs is equally compromised. They did try to say that Diddy was equally on drugs. He was equally addicted to opiates, and so he didn't quite understand what he was doing

any more than Cassie did. But once again, given his image as this music mogul, multiple millionaire, it's going to be very hard to say that he wasn't in control of things. his faculties. In the end, the government didn't need Cassie to be blameless, just position beneath the boss. That's the logic at the heart of every RICO case. So, yes, it is a defense argument that Cassie was more hands-on, but Cassie was the middleman.

And so that is exactly what RICO was for. It's to get to the person that is at the top directing all of the criminal activity. It was a case built on contradictions on a relationship that was both intimate and violent, both glamorous and abusive. And now the defense was asking the jury to walk that tightrope. I think what the defense was trying to do was essentially show that this wasn't forced fraud or coercion when it comes to the sex trafficking charge. I think what the defense is trying to do is that Cassie wasn't a kept woman. She wasn't held against her will. that she was free to do whatever she wanted.

The defense was definitely trying to be like, well, you stayed and you came back over and over again for an 11-year period. And whether or not the jury either questioned that or maybe possibly resonated with that, that's still kind of up for debate. But the government was betting the jurors didn't need the victim to be perfect, just honest.

It's just real life. This is what happens. It doesn't mean it didn't occur. And so I think that's going to be the crux of the case here, whether or not the jury understands that. And if the jury does understand that, the federal government's going to get a conviction. The government's case doesn't depend on Cassie being perfect. It rests on the idea that coercion doesn't always look like handcuffs or threats yelled across a room.

Sometimes it's a gift, a flight, a lingering promise, a quiet implication that leaving would cost more than staying. But it was still very, I think, good for the defense to bring out moments in which it's seemed as though it was advantageous to her to remain in a relationship with him. Those moments complicated the story on purpose, because the defense wasn't just challenging Cassie's truth. They were highlighting the contradictions in how she lived it. Be that as it may, I don't know that that overcomes how horrific she describes the abusive portion of their relationship. It wasn't a clean narrative. She wasn't always passive. and she didn't try to hide that.

She did not deny where she was seeking Diddy out, where she was upset that he was cheating on her, where she wanted to initiate sexual contact with him. But even as she acknowledged the messiness, she drew a line again and again. And then she was also very forceful when she spoke about the things he did to her that she did not want to be done to her

and that she told him she did not like. Her credibility, Natalie argues, didn't come from consistency. It came from conviction, owning the parts that were hard to explain and refusing to soften the ones that weren't. I think when witnesses waffle back and forth and they refuse to answer the defense questions and they pretend like they didn't say things that they clearly said, it makes them less credible.

But she never did that. She was answering their questions and admitting where it was that people could find fault with her. She'd never, ever backed away from, I did not want to do these things. He crossed the line. He disrespected me and abused my body and my mind. The prosecution didn't need the jury to believe that Cassie had done everything right, only that she hadn't been free.

But even as she exited the courtroom, her story wasn't finished. Because what prosecutors argued next wasn't just about what Cassie endured. It was about what others saw. And so they called their next witness, someone who had. once stood beside Cassie on stage, backstage, on tour buses, and in dressing rooms, a woman who had been part of the brand, the machine, the image. She was a pop star once, a familiar face on red carpets, music videos, on stage besides Sean Combs himself.

Don Richard was a member of Danity Kane, which was a all-girl group that did he put together, extremely talented singer. But when Dawn Rashard entered the federal courtroom on May 16, 2025, she was there as a witness. Their relationship goes back for decades because we know Don Rashard was on making the ban, and then she later went on to be a part of the ban, and that turned into Danity Kane, and then after Danity Kane disbanded, then she went on to work for Diddy's dirty money, and that was just kind of a group with Diddy, with Kalina Harper, and with Don Rashard. And this group was together for just a couple of years.

from 2009 to 2011. And so during that time frame of 2009 to 2011, Cassie was dating Diddy. Dawn wasn't just on the periphery of their relationship. She saw its dark underbelly firsthand. Dawn Richard witnessed Diddy strike Cassie with a skillet filled with eggs. She witnessed a physical confrontation and the abuse between them. That skillet incident, she said, took place during a brunch at Combs. home in 2009. Did he took this pan or this skillet and attempted to try to hit Cassie in the head.

It's a hot pan and she was just making eggs and apparently he tried to use this in a way as a weapon against his own girlfriend. Don Rashard described Cassie falling into this fetal position and it's interesting she said the fetal position because according to a lot of witness testimony, this was a position that she would just, she being Cassie, would just naturally get in because these happen so often. These physical assaults to her happen so often. Cassie didn't even fight back during this incident. She just fell to the ground and then Diddy was punching her in the head. He dragged her by the head.

And then all of a sudden, Don just heard glass breaking and she heard yelling. And maybe just as haunting, what didn't happen next? She said she didn't even call the cops because she said she never saw anything like that before. And she thought that because Diddy was doing this to someone that he supposed to, loved. She only worried about what could have happened to her if she were to intervene or if she were to report this to police. Fear seemed to be the center of it all. Fear of combs, fear of retaliation, fear of more abuse. And the skillet incident wasn't the only time she said she saw him strike Cassie. She said that she continued to see Cassie even after the ex-skillet incident. She said

She saw Cassie at hotels in the studio at Diddy's homes and that she saw Diddy be violent with Cassie also frequently. Don Richard had explained that there was a moment in 2009 where Cassie was attacked by Diddy. Did he had come down the stairs. He was screaming and he had beat her in front of Don Richard and demanded Cassie just get him food. And Don Richard recalled Diddy frequently beating Cassie would happen in their Los Angeles home or in the recording studio. So while Dirty Money was recording, she even recalled another instance where Diddy had hit Cassie over at Central Park while they were about to perform in that Cassie had a black eye and had to cover it with sunglasses. But what made her testimony so damning was how ordinary the violence seemed to become. There were just a lot of moments and points where Don did recall Cassie being physically assaulted.

And I think another sticking point is that most often no one would intervene. mean to help Cassie in these situations. Richard's direct testimony also supported one of the most disturbing threads of Cassie Ventura's story, the coercion and control surrounding so-called freak-offs. Her testimony is quite significant because what it shows is that he was flagrant about his abuse of Cassie, but also it bolsters Cassie's allegations that these freakoffs were not consensual, that they were abusive or they were not all consensual. But her time on the stand wasn't all that smooth.

Her direct testimony had been emotional, detailed. But under cross-examination on May 19th, the tone shifted. The defense didn't raise their voice, but they highlighted their focus, pushing for cracks in her account. The cross-examination of Don Richard was very intense. I wouldn't necessarily describe it as a great. But it did feel very intense to the point where I think Don got a little tripped up on her answers. Dawn's cross became an indictment of her motives, her memory, and her credibility. She was asked about Diddy's drug use and that even after witnessing Diddy being physically abusive to Cassie and witnessing everything that she had gone through, essentially, that Don Rashard even tried to continue working with Diddy, even to the point that she had reached out as,

late as 2020, 2021, because they were doing this reboot of making the ban and Don wanted to be a part of it. There was just a lot of kind of back and forth as the defense was really trying to poke holes into her testimony. They leaned on one familiar tactic. Why didn't she go to the police? So the defense is right to point out where there's a lack of contemporaneous reporting to law enforcement. That is always going to undermine the credibility of witnesses. But that's not an undermining that can't be overcome, right? It's almost like a rebuttable presumption. If you witness this crime, you would have called the police. Since you didn't call the police, you must not have witnessed this crime. But as we all know, many people do not want to involve law

enforcement in their lives. Many people do not want to get involved in people's romantic relationships. And they may have their own personal reasons for why they're apprehensive about reaching out to law enforcement. That is outside of the context. That's just real world, general every day, you know, what people do. The government knew that would be a line of attack, but they also knew why Richard and others stayed silent. This is a special circumstance in which you're dealing with someone, Sean P. Diddy Combs, who has such excess power and control

over the people that are around him. She testified that after one assault, Combs threatened her life directly. She recalled that on the next day, that dirty money, the group that she was a part of at the time, was called to record at Diddy's home, and that Diddy gave Don and Kalina Harper flowers and told them that this was kind of a passionate spat between a boyfriend and a girlfriend,

and that being Cassie and Diddy, and warned Don and Kalina not to say anything because he wanted to take this group with dirty money to the next level and wanted to take them to the top, and said something along the lines of people go missing, if they were to say something against him. And when those words came out in court, everything stopped.

A sidebar was called and there was discussion that was had amongst both parties because the defense did not want this statement to be in. They didn't want this statement to continue. And so they really just didn't like that there was this insinuation that Diddy was threatening to have someone killed or that people go missing. And Don took that to be a death record. She said that she was shocked and she was scared after hearing this threat made to her. And when she considered leaving bad boy records,

she said Combs associates told her she could if she stayed quiet. Of course, no one is going to want to go to the police because they would be afraid. And so for that reason, I think that the prosecution can overcome that argument that's coming from the defense that because they didn't go to the police, they must not be telling the truth. But that doesn't mean that there might not be a juror out there somewhere that thinks to themselves, I can't believe any of these things happen because no one called the police. It's still a possibility that there are people on that jury that that's where they're going to swing with this. But as time will tell, the more threats they hear, the pattern remains the same.

No police, no record, only fear. You're also hearing evidence of what a powerful man this is. Cassie testified that he threw her friend onto some patio furniture that was on a balcony. We heard evidence that he blew up a car. You have the evidence of him threatening people. You have the evidence of him assaulting people of him committing arson on their property and affecting people's careers and sidelining them and all types of things like that. When Dawn Rashard took the stand, she wasn't just a witness.

She was also a plaintiff with a pending lawsuit against Sean Combs, alleging sexual assault, verbal abuse, and exploitative working conditions during their time in Dan and E. Cain and Diddy Dirty Money. The defense seized on that. Nicole Westmoreland, another of Diddy's deep bench of defense attorneys, pressed her not only on what she claimed to have seen, but on when she said it and how her lawsuit might have shaped those details. Nicole Westmoreland was bringing Don's lawsuit to kind of use against her. She was asked about previous statement she had made to the government where in March of 2025, so just a couple months before trial, she didn't tell prosecutors the whole people go missing comment.

And Don said that she was trying to answer the questions as best as she could. Then they brought up her April 2025 interview with the government where she did speak about the egg incident with prosecutors again. And they had claimed that Don didn't even mention this people go missing aspect to her recollection of things until May 10th. So that was just a couple of days before. for trial. She pushed further, questioning whether Richard had actually witnessed certain assaults or simply pieced them together afterward. Really just trying to hone in on how this

chain of events really happened, whether or not Diddy was trying to hit Cassie, attempting to hit Cassie, whether or not he actually hit Cassie, whether or not Don actually saw it, or whether or not she just heard all the commotion and just made assumptions on what was really happening. Then came the high-profile dinner incident, where Cassie was allegedly punched in front of a room full of celebrities. Usher was there, Jimmy Hyveen was there, Neo was there. She was asked why no one intervened or why she didn't even mention that these celebrities were there.

In legal terms, her credibility may be debated. There were times where, quite frankly, it was very hard to watch it sometimes because you could tell that it was uncomfortable, that testifying in front of a group of people, in front of jury, in front of Diddy, were really tough for Don. And I think by the time she got off the witness stand, And I think maybe the damage might have been done. But in the government story, Dawn Richard's role was clear, not just a witness to abuse, but a witness to silence

and to a world built around protecting one man no matter the cost. He's this all-powerful, all-knowing, all-controlling, all-consuming personality. And I think that Don's testimony really bore that out. Dawn Richard's testimony left the courtroom with a chilling, sense of proximity. This wasn't just a story told by a woman at the center of the relationship. This was someone just close enough to see the violence and just far enough to be warned not to talk about it. Her words added weight to Cassie Ventura's account, but the government wasn't finished building its wall of corroboration because their next witness had seen things from yet

another angle. So Carrie met Cassie in 2001 and the two were best friends. However, around 2018, The two no longer spoke to one another, in part because of Diddy. Carrie Morgan wasn't a bandmate. She wasn't in the industry. She was something more personal. Cassie's best friend for nearly two decades. Morgan told the court their friendship ended abruptly because Sean Combs attacked her. They were over at Cassie's house in the Hollywood Hills and Diddy assaulted Carrie this time.

Carrie had explained that Cassie locked herself in the bathroom and Diddy began choking Carrie. boomerangued a wooden hanger at her. It hit Carrie in the right ear, and Diddy was doing this because he wanted to know who Cassie was cheating on him with. Carrie was going to file a lawsuit, and what ended up happening is that Cassie kind of played middleman here and essentially just negotiated kind of an off-the-book settlement for $30,000, and that $30,000 went to Carrie after the assault. And the reason for their falling out is because, according to Carrie, Cassie,

told Carrie that she was milking this assault and I guess just making more of a deal out of it than it actually was. And so what ended up happening was that Carrie signed a non-disclosure agreement or an NDA. And Carrie explained that she hasn't spoken to Cassie or Diddy since. And that as of now, Carrie has no pending lawsuit or any civil claim against Diddy. And so that was the biggest reason for the two falling out, was that Diddy had turned his rage and his temperament onto Carrie. And Carrie Morgan didn't come to court willingly. She said that she was subpoenaed to testify, and she didn't want to testify, mainly because she had moved on with her life, and that life was no longer what she was about.

Her reluctance set the tone for what followed, an account shaped by distance, but anchored in memory. Her testimony gave jurors an intimate view of how the relationship. between Cassie Ventura and Sean Combs wore down not only Cassie, but those around her. She recalled that Diddy would have some mood swings. He would yell. He would get mad. And that Cassie actually lost her confidence while she was in a relationship with Diddy. Carrie recalled hearing Diddy talk down to Cassie a number of times. He criticized her looks, how she behaved, who she talked to, and that there were times where Cassie wasn't answering the phone that Diddy would call Carrie to look for Cassie.

Morgan described herself not just as a friend on the outside looking in, but as someone who at times was pulled directly into the violence. She kind of spoke a little bit about the 2016 March 6 incident, and that being the incident that happened at the Intercontinental Hotel. Cassie came home and she had a hoodie on. She dropped her bags and didn't say anything to carry. Carrie was over at Cassie's place around that time. Cassie had pulled her hood back or her hoodie back.

She revealed that she had a black eye. Carrie explained that 30 minutes later, Diddy came over with a hammer. And Carrie was terrified and Cassie was just so numb to what had happened that Carrie even said, I don't think she even cared if he had killed her. And there was another time in 2013 where they all went to Jamaica together. It was Carrie's friends, Diddy and Cassie. Diddy came kind of halfway through this vacation. Then Carrie all of a sudden heard Cassie screaming and it was just this terrifying scream.

And Diddy essentially said that Cassie was taking too long in the bathroom. And so Diddy, on this trip to Jamaica, druged Cassie by her hair. Cassie was later pushed. She hit her head. Carrie explained that Cassie didn't move and was in the fetal position, a position that a lot of witnesses, again, have testified that Cassie gets into as kind of a defensive mechanism. And so Carrie thought initially that Cassie was knocked out when she had hit her head. But when Carrie and Diddy began arguing, that's when Cassie just took off.

She ran over into the woods. Carrie then went to go look for her. Carrie found her. And the two crouched in a ditch in order to just get away from Diddy, just another instance of her trying to escape just ditty's wrath, essentially. Carrie explained that Cassie didn't receive medical attention during this incident. And the two just went on after that. The prosecution had called Morgan to corroborate. but the defense saw an opening to complicate.

Mark Agnifalo also raised the question of bias, that perhaps Morgan was angry about the end of the friendship, that she might be emotionally invested in framing Combs as the villain. But Morgan didn't take the bait. She said her testimony wasn't about revenge. It was about truth, about saying under oath what she said she had seen and lived through. Then they pivoted, not by attacking her directly, but by shifting focus to Cassie's emotional.

state. The defense asked Carrie if Cassie was jealous of Kim Porter. Again, Kim Porter being the mother of some of Diddy's children, Carrie had responded yes because Cassie was never allowed to go to the New Year's Eve parties, which was this big family events with all the kids there and Kim Porter there. I feel like what the defense was trying to do is butter up Carrie in a way to paint this picture that there was just a lot more layers to this than maybe what the prosecution was saying.

Morgan's account stayed consistent. and her tone stayed composed, something the prosecution was likely counting on to sustain its narrative spine. She made for a very compelling witness because she really kind of, one, verified a lot of Cassie's claims, but also was just very honest on the stand. It didn't seem like it was falling apart like we've seen in other cross-examinations. When Morgan left the stand, she didn't just confirm what Cassie had already alleged. She expanded the scope. She added a firsthand account of violence, a falling out, a hush payment,

and a silence that lasted years now broken. By the end of her testimony, Morgan had done something powerful. She didn't just echo Cassie's story. She filled in its shadows. She showed what it looked like when abuse was witnessed, when fear didn't belong just to the victim, but to the people who loved her. And in that way, Carrie Morgan wasn't just another voice.

She was evidence of the silence that surrounded Sean Combs and the cost of breaking it. Carrie Morgan had given the jury a glimpse of what it meant to be close to Cassie and just close enough to danger. Her testimony, like the others, was emotional and raw. But the prosecution wasn't only building a case on personal memory. They were constructing something broader, a map of how control worked inside Sean Combs' world, not just behind closed doors, but in hotel bookings, in daily routines, and employees trained not to question, but to enable.

And that brought them to their next witness. David James, Combs' former personal assistant. On May 20th, James walked jurors through what his role actually meant. He testified under a grant of immunity that was made clear at the outset. The government wasn't shielding a criminal. They were extracting testimony from a man who had witnessed too much, and some might say possibly enabled it too. James described an entire system of logistics, arranging hotel stays under fake names,

stocking rooms with sex toys and marijuana, preparing Molly and water bottles with the tops removed. There were NDA binders in the drawer, a Polaroid camera by the bed, and an explicit understanding that when women arrived, they were to hand over their phones and remain inside until Combs said otherwise. There was also cash.

Lots of it. Thousands of dollars, often in brown envelopes. James said it was used for tips, for expenses and for silence. All this corroboration just shows how much of a nefarious actor did he is. I mean, why would you pay in cash all the time and have to give people lie detector tests and use fake names? I mean, I know that you're a celebrity and celebrities use fake names to avoid the paparazzi, but this seems a lot worse than that.

This seems to be a whole intentional business relating to making sure. the boss gets to have his perverse sexual desires satisfied and they're going to use force, they're going to use fraud, they're going to use coercion, they're going to use drugs, intimidation, everything possible to make this happen. I mean, every bit of it from the lie detectors to the fake names to the coverups, the hotel rooms, and the cash, all that is used for people to think this is one dirty dude. And if you muck up the defendant enough, then jurors may say, I don't know all the details about racketeering, but he did something wrong here.

He needs to go down for something. That was the prosecution's theory, that this wasn't chaos. It was infrastructure, and James was a cog in the machine. But on cross-examination, the defense sought to twist that frame. They painted James as someone

who had everything to gain by exaggerating, a man who stayed quiet for years, who only told the government what it wanted to hear once immunity was on the table. They pressed him on inconsistencies. Why hadn't he said more sooner? was this really about truth or survival? James didn't recant, but his image, like everything else in this case, depended on where you stood. To prosecutors, he was a witness to a sprawling

coercive operation. To the defense, he was an opportunist. Still, for jurors, his testimony did something important. It made the logistics real. It took the idea of control out of abstraction and anchored it in detail. And what came next moved the story outside the wall? of Combs' homes and hotels and into the family tree. Regina Ventura didn't work for Diddy. She didn't live with her daughter. She wasn't part of the

world of handlers, contracts, or hotels. But when she stepped into the witness box on May 20th, she did something that none of the other witnesses could do. She brought the story home. She described herself as a protective mother, someone who saw her

daughter pulling away, growing more frightened, more isolated. She recalled Cassie calling her in December 2011 panicked. She said Combs had discovered her relationship with rapper Kid Cuddy, and he had erupted. There were threats against Cassie's life against Cuddies. And then there was a demand. She testified that Combs said, wire me $20,000 or I'm going to release a sex tape of your daughter.

She went to great lengths to meet the demand. She claimed she got a home equity loan and wired the money. She said she believed it was the only way to protect. her daughter. To ask the mother of your girlfriend for $20,000 and then she had to take out a home equity loan, I feel like that was really just kind of a shocking moment. And it really played into a little bit of what the government was alleging as far as there were been allegations of blackmail and there have been allegations of retribution if you didn't abide by what did he wanted or did he's rules. He ended up returning it, but that's extortion. I feel pretty clearly

that's the extortion referred to as a predicate act in count one. But her time on the stand wasn't spent just talking about the money. Ventura described the moment she saw Cassie bruised and battered. She said she tried to confront Combs, tried to go after him, but was held back. That image of a mother trying and failing to protect her daughter may have spoken louder than any forensic expert or industry insider. It makes her more sympathetic, Cassie, that her mother's on the stand saying that I was so upset the way he treated my daughter that I tried to hit him. I tried to attack him, but I couldn't get to him. And I think other mothers in the jury will relate to her. For all her emotion, there were limits to what Regina Ventura could

actually confirm. She wasn't in the room when it happened. She couldn't speak to every allegation firsthand. It could have gone to her lack of knowledge. That's really what happened. I mean, all the knowledge that she has is like secondhand. Did she ever see? Did he abuse her daughter in front of her? But the defense didn't go there. They didn't even cross-examiner. They didn't ask a single question. It may have been strategy, an effort to avoid alienating the jury, or it may have been something else. The recognition that this witness, standing with a trembling voice and a bruise memory, was simply untouchable. I can see why you wouldn't want to cross-examine the victim's mother, but if you don't cross-examine, you're basically confessing.

Up next, witnesses from seemingly opposite worlds take the stand. one from inside the empire, the other from far beyond it. But in the courtroom, their stories pointed in the same direction. Mr. Combs finds out about the relationship between Ms. Ventura and Kentucky. Diddy comes over to Capricorn Clark's home, essentially banging out on the door, saying, why the F didn't you tell me about this? And so we're going to go kill this expletive. Capricorn Clark says, no, I don't want to go.

I don't want to do this. And he's like, you're coming with me. I don't give an F what you want. Together, their testimony did more than corroborate. It connected the abuse to motive and the motive to retaliation. She calls Ms. Ventura to let her know or let Cutty know that they were in his home and that she was in fear of Mr. Cutty's life. Next week, we break it all down. The witnesses who didn't just back up Cassie's story, they added fuel to the fire.

And if the jury believes them, that fire wasn't just personal. It was criminal. This has been a long crime production. I'm your host, Jesse Weber. Our executive producer is Jessica Louther. Our writer and producer is Cooper Mall. Our associate producer is Test Jagger Wells. Edit and sound design by Anna McLean.

Guest booking by Diane Kay and Alyssa Fisher. Additional production support from Giuliana Bataglia and Stephanie Doucette. Legal review by Elizabeth Vuli. Key art design by Sean Panzera. and special thanks to Elizabeth Milner for her in-depth reporting on this case. Follow Law and Crimes, The Rise and Fall of Diddy, the Federal Trial, on the Wondery app. You can listen to more episodes exclusively and ad-free right now on Wondery Plus. Join Wondery Plus in the Wondery app, Spotify, or Apple Podcasts, and get ad-free access to more thrilling

long-crime series like new episodes of Karen the retrial and sidebar with Jesse Weber. Start your free trial today.