← The Rise and Fall of Diddy
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- [00:01]
Jesse Weber
You're listening to a law and crime series available exclusively on Wondery. To listen to the remaining episodes, join wondery 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 Wondery in the Wondery app, Spotify.
- [00:21]
Natalie Whittingham Burrell
Or Apple Podcasts this podcast is a long crime production. It covers ongoing legal proceedings related to the federal trial of Sean Diddy Combs. The content may include graphic descriptions of.
- [00:35]
Elizabeth Milner
Alleged sexual acts, violence, abuse and drug use. These topics may be disturbing or triggering for some listeners.
- [00:42]
Natalie Whittingham Burrell
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.
- [00:52]
Elizabeth Milner
Until proven guilty in a court of law.
- [00:55]
Natalie Whittingham Burrell
The views expressed in this podcast are for informational and journalistic purposes only and do not constitute legal advice or a.
- [01:02]
Elizabeth Milner
Judgment on the outcome of the case.
- [01:04]
Natalie Whittingham Burrell
The legal experts and attorneys interviewed are.
- [01:06]
Elizabeth Milner
Not actively involved in this case.
- [01:11]
Jesse Weber
In the first three episodes of this series, we told you the full story of the life of Sean Diddy Combs. His humble beginnings, his personal tragedies, his thirst for success. For decades he was untouchable. A mogul, a visionary, a king of hip hop. He built an empire from the ground up. He became the man he set his sights on being. But Combs legal troubles began with a lawsuit filed by his ex girlfriend, Cassandra Ventura, and escalated significantly when a federal indictment was handed down in September 2024.
- [01:46]
Elizabeth Milner
Sean Combs, aka Diddy, aka Puff Daddy, aka P Diddy Diddy PD love all the different names that he has. He's been accused by a federal grand jury of five different counts. Count one being racketeering conspiracy. Count two being sex trafficking. And that pertains to alleged victim who we now know to be Cassandra Ventura, AKA Cassie. Count three, transportation to engage in prostitution. Count four, also federal sex trafficking. And that has to do with alleged victim number two, we only know as Jane Doe. And then there's another count of transportation to engage in prostitution. So five counts overall.
- [02:23]
Jesse Weber
These are the allegations federal prosecutors made against Sean Combs and they say that crimes span decades. Now, as his much anticipated trial commences, witnesses, or rather alleged victims will finally have a chance to speak out. How far will Diddy fall? Or will he walk free with a reputation in ruins? Federal courtrooms don't allow cameras or audio recordings. That means only those inside the room witness not just what's said and who says it, but but how it said. The tone, the rhythm, the body language.
- [03:01]
Natalie Whittingham Burrell
We are relying on people in the courtroom to accurately report what they're hearing and seeing.
- [03:07]
Jesse Weber
This podcast is made possible by daily court transcripts obtained by Law and Crime along with on the ground reporting from our very own Elizabeth Milner. Embedded in the courtroom. Together, they help us bring to life what can't be captured from text alone. I'm Jesse Weber, and this is the rise and fall of Diddy, the federal trial. It's one of the most explosive celebrity trials in recent memory. The federal case against Sean Diddy Combs. Opening statements began on Monday, May 12, 2025, inside the Daniel Patrick Moynihan Courthouse, the federal heart of the Southern District of New York. What started as A pool of 600 prospective jurors was narrowed down to 1812 jurors and six alternates, all sworn to remain impartial, all scrutinized by both sides. Here's Elizabeth Milner.
- [04:03]
Elizabeth Milner
The entire process was more than a week long. It started on Monday, May 5, and the final jury wasn't even selected until the same day as opening statements. And so they were asked a lot of questions because this is a very high profile case. This defendant was a high powered person. He was a mogul, and a lot of people knew who he was. And even more importantly, a lot of people have even seen that surveillance video of the brutal physical assault that happened at the Intercontinental Hotel of Diddy and Cassie in 2016. But as far as just jury selection goes, prospective jurors at the time were asked a number of questions. They were asked questions about their relationship with law enforcement. They were asked questions about their views on prosecutors and law enforcement. Have they ever been involved in legal issues, that being lawsuits or even crimes, criminal cases? They were asked, have they been a victim of a crime or do they have particular feelings about law enforcement, hip hop, artists, witnesses testifying under immunity, witnesses testifying under a pseudonym?
- [05:01]
Jesse Weber
The panel skews educated. Every juror has at least some college degree. They range in age from 30 to 74, with eight men and four women seated in the box.
- [05:11]
Elizabeth Milner
They are a very diverse group. They come from different walks of life. They all come from just different parts of New York City.
- [05:19]
Jesse Weber
Some admitted they'd heard of the case. A few had even seen the video surveillance footage from 2016 released by CNN in 2024 showing Combs assaulting Cassie Ventura in a Los Angeles hotel elevator bank, a key piece of the government's evidence. And in a controversial move, the jury won't be sequestered. That decision raised eyebrows. In a case this high profile, why wouldn't you isolate the jury from outside influence, from headlines, so social media, even friends and family. Public defender and legal analyst Natalie Whittingham Burrell says there's rationale behind the decision.
- [05:57]
Natalie Whittingham Burrell
There are many high profile cases in which the juries are not sequestered. It is very rare for a jury to be sequestered, especially because you have to think about the fact that these people are already being massively inconvenienced. They can't go pick up their kids from school, they can't go to work, they can't have their normal lives and they have to live in basic anonymity. And then to say, okay, we're also going to remove you from the world and all of your devices, that is just a recipe for disaster. A lot of times you get more issues sequestering a jury than not sequestering a jury.
- [06:30]
Jesse Weber
As for who's presiding over the case.
- [06:32]
Elizabeth Milner
Of the century, Judge Arun Subrahmanian. He is a very fair and level headed judge. As far as his rulings, they seem pretty fair and across the board. He listens to both sides and I think he's the perfect person to be on this case.
- [06:48]
Jesse Weber
In each of their opening statements, the government and the defense painted two very different pictures of the man behind the music empire. Let's start with the prosecution.
- [06:57]
Natalie Whittingham Burrell
The federal prosecutors have a bit of a reputation for being dogged, thorough and lining up all of their ducks in a row before they proceed with the prosecution. We know most people know that they have a conviction rate in the 80 to 90% range.
- [07:14]
Jesse Weber
At trial, Assistant U.S. attorney Emily Johnson stood before the jury and described Sean Combs not just as a music mogul, but as the mastermind behind a sprawling criminal enterprise.
- [07:27]
Elizabeth Milner
She said the defendant's crimes go back as far as 20 years. Even in the indictment, they allege from at least in or around 2004 up until 2024. She had started off with her statement saying that this is Sean Combs, a cultural icon, a businessman larger than life. Then she kind of peels back some of the layers of this case, that being that these crimes went back 20 years. They involve kidnapping, arson, drugs, sex crimes, obstruction.
- [07:54]
Jesse Weber
According to the government, Combs allegedly used a network of loyal employees, bodyguards, assistants, executives, not just to run his companies, but to help him commit and cover up crimes.
- [08:07]
Natalie Whittingham Burrell
Once the prosecution's arguments started, they alleged that Diddy was using his business as a criminal enterprise and he was doing that in order to cover up the various crimes that he was committing. And this is what a RICO is and why it's hard for the general public to wrap their head around it. And so I think that their job in the opening statement was to say these various crimes were being committed under the guise of him being the CEO of Bad Boy Records, to further his own goals and aims as the CEO. He directed people to commit these crimes who were in his employ. And those crimes included things like arson, sex trafficking, bribery, and things like that. How he would violently force his girlfriends into doing sexual acts that they did not want to do, which we know is sexual assault. And so he's using his organization in order to commit these separate and disparate crimes. The crimes themselves don't even have to be related in a RICO prosecution, however, if they're all being committed to further the aims and goals of the organization, it becomes a RICO.
- [09:23]
Jesse Weber
Asa Johnson described how Combs allegedly forced two women, Cassie Ventura, his girlfriend of nearly 12 years and and another woman with the pseudonym Jane, into what prosecutors called freak offs. Coerced sexual encounters with male escorts arranged by Combs and filmed for his pleasure.
- [09:44]
Elizabeth Milner
So a number one thing that they were talking about from the indictment, from the time Diddy was arrested, from the time Cassie filed her lawsuit, was these freak offs. And these freak offs were hours long, even days long sexual sessions where Diddy and Cassie would bring an escort and they would have these sexual encounters at hotels and homes and just different places in the country and even outside of the country. And so Emily Johnson really drove home the point that this case is not about a celebrity and their private sexual preferences, because I think that was something that definitely the defense was making it out to be that the government was attacking his alternative lifestyle, his swinger lifestyle, and that sort of. So then she kind of laid out that these were called freak offs, but they were also called wild king nights. They were also called hotel nights. And so then we started to learn more just about staff setting up these rooms in advance. The lighting that went into this, the extras that were a part of this, such as lube and cash for escorts, baby oil, drugs for both women and Diddy. Women had to dress a specific way, such as being in lingerie. They had to have their nails done a certain way. They had to have tall heels, and that the women would partake in drugs such as mdma, so that way they could stay awake for these hours and days long sessions.
- [11:01]
Jesse Weber
Prosecutors also said they'll show how Combs attempted to keep these stories buried, Paying off a hotel security guard for surveillance footage, pressuring victims to stay silent, and using his wealth and power to maintain control. Their message this wasn't about fame or bad behavior.
- [11:19]
Elizabeth Milner
The government alleges that he didn't act alone, that he needed the help of employees and staff in order to continue allegedly building this enterprise that they say is criminal.
- [11:30]
Jesse Weber
They say this was organized crime hiding in plain sight.
- [11:37]
Natalie Whittingham Burrell
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- [12:22]
Jesse Weber
Case, the defense seized the stage, led by Tenny Garagos. If that last name rings a bell, you probably followed your fair share of headline making trials. Tenney is the daughter of famed defense attorney Mark Garagos, who's represented everyone from Michael Jackson to Scott Peterson and most recently, the Menendez brothers. But make no mistake, Tenny Garagos isn't riding coattails. She's built her own reputation as a fierce and formidable attorney, and now she's stepping into the spotlight, taking on the biggest case of her career in one of the most closely watched trials of the decade. She got right into it, admitting some of Diddy's bad behavior but attempting to reframe it because when the facts are tough, the strategy's acknowledge what you can't deny and shift the focus. In her opening statement, defense attorney Tenny Garagos wasted no time reframing the government's case not as a criminal conspiracy, but but is something much more familiar. A troubled relationship.
- [13:23]
Elizabeth Milner
Kenny Garagos presented the opening statements for the defense and she had to kind of admit while she was giving her opening statement and presenting this to the jury that Sean Combs is a complicated man. But she had said that this isn't a complicated case. She said that this is a case about real life relationships that the government is turning into this RICO conspiracy and turning this into sex trafficking. She says this case isn't what we had heard about on the news and that Essentially, Diddy's story will be told over the next two months.
- [13:53]
Jesse Weber
She also reminded jurors of who Sean Combs is. Not just the man in handcuffs, but a music mogul whose influence shaped the generation.
- [14:02]
Elizabeth Milner
She had kind of talked about how Diddy contributed to the culture and had a lot of great music, which drew a lot of people to him specifically, and that a lot of people just wanted to be around him because he would give them opportunities.
- [14:15]
Jesse Weber
And then came a calculated moment of theater.
- [14:18]
Elizabeth Milner
There was this moment during the defense opening statements where Diddy kind of stands up, Tinney introduces him to the jury, and mind you, when he's inside the court for his trial, he looks completely different than we've seen him in press photos, on red carpets, on even social media. He is kind of a little more toned down. He appears a lot grayer. He's wearing a sweater. He's wearing something slack, something that he might not wear if he wasn't detained in MDC Brooklyn or anything like that. But as far as just the picture that people may have of him in their minds, not necessarily the case that we're seeing inside that courtroom every day.
- [14:55]
Jesse Weber
Then Garagos turned to the government's claims of coercion and abuse, not to deny them, but to defang them and to.
- [15:03]
Elizabeth Milner
Answer to what the government had alleged. In their opening statement, Tenny Garrigo says that the government has no place in his bedroom, he being Diddy. And that the defense admits Diddy did have a temper, especially when he drinks, and sometimes he would get so angry. And they admitted that he did lie to his girlfriends. He was kind of mean to his girlfriends. But he's not charged with being mean. He's again charged with RICO and sex trafficking and transportation to engage in prostitution.
- [15:33]
Jesse Weber
It was a deliberate strategy. Acknowledge the bad behavior, but draw a hard line between moral failings and a federal crime.
- [15:42]
Elizabeth Milner
And so the defense says that the jury will see this possibly as a domestic violence case, as opposed to sex trafficking case, and even surprisingly, admitted that Diddy had a certain love for a certain product, and that product being baby oil, something that they've essentially talked about every single day of trial. But according to Tenney, Garagos, it's not a federal crime to have this love for baby oil. And says that the victims were capable, strong women, that they were adult women. They were free to make their own choices. And those choices came with pros and cons.
- [16:15]
Jesse Weber
But with the infamous Intercontinental Hotel video on deck, the defense knew they had to get out ahead of what jurors were about to see.
- [16:23]
Elizabeth Milner
They knew that a big piece of evidence was going to be introduced coming up, and that was going to be the really long played out version of a CNN video that we had seen nearly a year prior and that being at the intercontinental Hotel in 2016. But the defense really kind of had to drive home the point that Diddy is a flawed man, and they had to own up to that, because if they didn't own up to it and then the jurors would see this domestic violence at the hotel, then that could possibly ruin the case for the defense if they weren't forthcoming in their opening statement.
- [16:53]
Jesse Weber
But legal observers say this opening wasn't just a narrative pivot, it was a technical one. Garagos wasn't simply trying to humanize Sean Combs. She was trying to dismantle the government's entire legal framework piece by piece. Natalie Whittingham Burrell explains.
- [17:10]
Natalie Whittingham Burrell
They did the thing that almost all defense attorneys do. When you have bad facts that you can't overcome, you admit them and you minimize them.
- [17:18]
Jesse Weber
The defense concedes Combs may have been controlling, violent even, but they argue it was personal, not organized dysfunction, not conspiracy, private conduct, not enterprise level crime.
- [17:32]
Natalie Whittingham Burrell
They said that everything that the girlfriends, including Cassie, was doing was consensual and that it had nothing to do with Bad Boy. It was all about Diddy personally and his personal toxic relationships, but that it had nothing to do with the actual organization of Bad Boy records and therefore is not rico. Personal proclivities may make you, as an individual, liable for things like rape, liable for things like the solicitation of prostitution, but it doesn't necessarily mean that it's rico. You need that organization there in order to say that it's a corrupt organization committing multiple crimes. And so that's the distinction that they're making.
- [18:17]
Jesse Weber
And it's that distinction between personal wrongdoing and organizational corruption that will define the defense's case moving forward.
- [18:25]
Natalie Whittingham Burrell
What they're asking the jury to do. The defense set aside his personal proclivities, set aside that you may not agree with his lifestyle, and look and see whether or not these are are individual failings or an organizational corruption.
- [18:45]
Jesse Weber
So the defense had drawn its battle lines. Admit what you must, minimize the rest and cast the crimes as personal failures, not federal ones. But now it was the government's turn to start proving otherwise. The prosecution's first witness wasn't a celebrity or a former insider. It was someone from the outside looking in. Someone who had no connection to Diddy's empire, but who saw firsthand the aftermath of one of its most disturbing alleged incidents.
- [19:15]
Elizabeth Milner
So the first person who was called to the witness stand was Officer Israel Flores. Now he's a police officer for the Los Angeles Police Department, AKA the lapd. He had been working for LAPD for seven years, but he also was an army reservist. So I was kind of wondering, where is he going to go with this testimony? How does this relate to the case?
- [19:33]
Jesse Weber
His relevance was soon made clear.
- [19:36]
Elizabeth Milner
He had talked about another job that he had previously had, and that was working security. Once he had said security, I was like, oh, he must have worked for the Intercontinental Hotel in Los Angeles, where we had all seen that video of Diddy brutally beating Cassie Ventura after she was trying to leave a freak off.
- [19:55]
Jesse Weber
Flores wasn't there to speculate. He was there to explain what the footage couldn't. What happened just before the camera turned on.
- [20:03]
Elizabeth Milner
And we learned a lot more of kind of everything that happened after the video was cut off.
- [20:10]
Jesse Weber
According to Flores, a call came into the hotel's security office. A woman was in distress on the sixth floor. When he got there, the hallway was in disarray, flowers scattered on the floor, a dent in the wall, and Cassie Ventura, visibly shaken, standing outside the elevator bank. He testified that surveillance footage, although motion, triggered an incomplete captured combs dragging Cassie down the hallway. He documented the incident in a written report and took photos of the damage. His testimony may have seemed simple. A security call, a hotel hallway, a traumatized woman. But for prosecutors, it was crucial. It put jurors in the aftermath of alleged violence. It gave them a timestamp, a setting, and a witness with no personal stake in the outcome. But it also did something else. It gave jurors a physical scene, one that matched the emotional and graphic claims the government would lay out in the weeks ahead. While Flores didn't speak to racketeering or trafficking, he helped the government draw a through line from private violence to public consequence. And he offered something the defense couldn't easily explain away. Independent corroboration. Prosecutors would go on to call more personal, more graphic witnesses. But Flores presence on the stand sent a clear message early in the trial. This story doesn't just live in Cassie's words or Diddy's world. It lives in evidence.
- [21:39]
Elizabeth Milner
This message is sponsored by Greenlight. With school out, summer is the perfect time to teach our kids real world money skills they'll use forever. Greenlight is a debit card and the number one family finance and safety app used by millions of families helping kids learn how to save Invest and spend wisely. Parents can send their kids money and track their spending and saving while kids build money, confidence and skills in fun ways. Start your risk free Greenlight trial today@greenlight.com wondery that's greenlight.com wondery if Israel Flores.
- [22:12]
Jesse Weber
Helped jurors picture the aftermath, the prosecution's next witness took them deeper inside what the government says was a pattern of coercion masked as consent. Daniel Philip is a former male escort and manager of a New York City mail Review show. In 2012, he says he was booked for a private performance at the Gramercy Park Hotel. The request a black dancer for a client. None were available. So Philip, who's biracial, agreed he thought he was walking into a routine booking. What unfolded instead would become a central example in the government's effort to prove that what looked consensual on the surface masked something darker underneath.
- [22:52]
Elizabeth Milner
So he arrived to the Gramercy Park Hotel around nighttime. But when he arrived, a woman opened the door and it was only her. There was no bachelorette party. There was no other women expecting this dance from this male dancer.
- [23:06]
Jesse Weber
Philip had never met this woman before. What followed was a set of instructions and rituals that prosecutors say were consistent across multiple incidents.
- [23:17]
Elizabeth Milner
And so this woman, who we now know to be Cassie Ventura, Cassie had asked Daniel Philip to rub baby oil on her and give her a massage. She actually even referred to Cassie as C when Cassie opened the door. And when Daniel Phillip had met her in person, she was wearing lingerie, she had a red wig on, and she even had sunglasses on.
- [23:37]
Jesse Weber
Too soon, a third person entered the room. Philip hadn't been told to expect him.
- [23:43]
Elizabeth Milner
Then all of a sudden, a man in a white robe with a bandana over his nose, over his mouth and wearing a hat comes in. And Cassie had referred to this man in the room as baby. And Daniel Phillip knew it to be. Now, Sean Combs, AKA Diddy.
- [23:59]
Jesse Weber
Philip described what happened next in exacting detail. A physical encounter, money exchanged, and a silent observer.
- [24:09]
Elizabeth Milner
He said during this encounter that Diddy didn't say much and that he didn't say much to Diddy. But Diddy had said that he was working in importing and exporting, which I thought was kind of an interesting tidbit that he had said. But Daniel Phillip admitted that he and Cassie did have sex together. They rubbed baby oil on one another. And while this was happening, that did. Diddy was watching all of this and he was masturbating during it. That Daniel Phillip also wasn't wearing protection when he had had sex with Cassie and that Cassie afterwards gave him a few thousand dollars.
- [24:43]
Jesse Weber
Even in a courtroom braced for disturbing testimony, this moment caused a reaction.
- [24:49]
Elizabeth Milner
Diddy's daughters actually walk out of the courtroom during this testimony.
- [24:53]
Jesse Weber
Who could blame them? The encounter didn't end that night. Philip testified that it continued and that the pattern stayed consistent.
- [25:03]
Elizabeth Milner
Cassie had messaged asking for a picture of Daniel's genitalia and asked him to come back. And he actually came back to the room for a few more hours. This was the second time, and it was the same similar situation that it was during the first time where Diddy was off to the corner. He was masturbating the whole time during the second encounter.
- [25:22]
Jesse Weber
Only later did Philip come to understand who Cassie was and who had really been watching.
- [25:28]
Elizabeth Milner
He had learned later on who Cassie was because his boss had looked her up. And so every time he met Cassie, it was essentially just to have sex with her in front of her then boyfriend. And that then boyfriend being Diddy. And he said he did this up until around 2013-2014. So a pretty long time.
- [25:47]
Jesse Weber
Daniel Phillips testimony wasn't just graphic. It was strategic. For prosecutors, he offered more than a story. He offered structure, a way to frame what might seem like personal behavior as part of something organized, commercial and criminal. And in a federal RICO case, former Florida state attorney Dave Aronberg says that distinction is everything. You've got to show at least two predicate crimes to show that this is a criminal enterprise set up like an illegal operation, set up to do bad things. And so that's racketeering. Then you have human trafficking. Human trafficking is commercial sex acts where there is force, fraud, or coercion. So you have to show that there's a commercial sex act where people paid to engage in these sexual acts. And you heard of all these prostitutes and all this money floating around. The prosecution's theory is that Combs didn't act alone. He built a system. And Philip, they say, was one of many people brought into that system, Recruited, paid, and used in what they argue were transactional sex arrangements meant to serve Combs personal desires and expand his power.
- [26:58]
Natalie Whittingham Burrell
So what the prosecution is doing here is they're backing Diddy into a corner, essentially. And I think that's what Daniel Phillips testimony was more relevant to. He was hired by Diddy to perform in these freak offs. And the freak offs are relevant because they were the conduit by which Diddy was committing the predicate offenses for the RICO prosecution, which are the trafficking allegations. Also moving drugs and guns across state Lines and in multiple states and things of that nature. And hiring people for prostitution all across the country is what is going to get you into the RICO prosecution.
- [27:40]
Jesse Weber
It's not just about the act itself. It's about what that act connects to. A hotel, a payment, an interstate arrangement, and a powerful man watching from the corner. That's the architecture the government is trying to reveal. 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. So I do think that even if they can't satisfy all the elements of racketeering, they may win this case. Because when there's smoke, there's fire. If Daniel Phillips direct testimony painted a disturbing portrait of power and voyeurism, the defense worked quickly to reframe it. Not as criminal exploitation, but as consensual arrangement. They leaned into Philip's profession for framing him as someone who sees encounters through a commercial lens, not a moral one. If he was paid and went back, does that make him complicit, comfortable, or just unreliable? Jurors may be asking themselves, if Cassie initiated contact, if she paid him directly, if she invited him back, was Philip a witness to abuse or just a service provider caught in the middle of a toxic relationship? And then there's the demeanor factor. He gave explicit testimony but didn't show outrage. He described shocking details but kept emotional distance. That neutrality could land either way, as trustworthy or as cold and transactional. The defense's goal was to chip away at the story's impact without denying the events. But they couldn't erase the timeline, the money trail, or the unmistakable presence of combs in the room. So the jury's left with a character question. Is Daniel Phillip telling the truth? Does his account corroborate what Cassie and others have described? And perhaps most importantly, was what he witnessed part of a pattern or just a personal choice played out in private? Those are the questions the prosecution is banking on that Philip wasn't an outlier. He was a spoke in the wheel. If Daniel Philip provided the prosecution's blueprint, Cassie Ventura offered the lived experience. Hers was the most anticipated testimony of the trial. Not because she's famous, but because her story is the reason this trial's happening at all. The government star witness didn't come in quietly. She came in pregnant, more than eight months along and unmistakably poised for what would be the most emotionally charged testimony of the trial.
- [30:18]
Elizabeth Milner
It was a moment that a lot of us were just waiting for.
- [30:21]
Jesse Weber
And it came on just day two. The woman who once stood beside Sean Diddy, combs on red carpets, now sat across from him in federal court, calmly, quietly, prepared to speak.
- [30:35]
Natalie Whittingham Burrell
Her body and her testimony is the evidence. It is the case because according to the government's best case, he used her body as an object onto which he placed these prostitutes, into which he put these drugs, to which he gave these money. He passed her a gun, he had his guard down around her. And so he was committing all of these crimes in furtherance of abusing her, and in so doing, allegedly by the prosecution, committed RICO violations. The way that I see it is that Cassie is the linchpin because of the duration of the relationship. But it's an allegory for the fact that bad boy is not really a record company, It's a RICO organization because all of his assistants, all of his bodyguards, record execs, everything that were supposed to be helping this woman put together an album were instead putting together these freak offs where they were doing this illegal activity.
- [31:39]
Jesse Weber
The courtroom shifted when she walked in and so did the defendant.
- [31:44]
Elizabeth Milner
When she walks inside the courtroom, we see Diddy kind of turn around from the defense table. He looked at her while she was taking the stand. She just didn't even look in his direction from what I could see of her. Just made kind of a beeline straight to the witness stand.
- [31:58]
Jesse Weber
Her voice was low, her demeanor polite, almost restrained, but what she said would land like a punch.
- [32:06]
Elizabeth Milner
She starts kind of peeling back just a little bit of their more than decade long relationship.
- [32:11]
Jesse Weber
She spoke of violence, of fear, of a relationship built around power and pain.
- [32:18]
Elizabeth Milner
She had admitted that they did have violent arguments, that there was physical abuse. She mentioned times where he would smash her head in and knock her over and drag her and kick her, and that these beatings would happen very frequently. And said at the end of these beatings that she would get knots in her head and bruises.
- [32:36]
Jesse Weber
Then, almost casually, she confirmed something many had speculated about the night in the hotel, captured on the Intercontinental Hotel surveillance footage later released by cnn.
- [32:49]
Elizabeth Milner
She was asked about the CNN video very quickly into her testimony, and she confirmed at that moment that she was leaving a freak off.
- [32:57]
Jesse Weber
The phrase freak off had already appeared in the government's indictment, but for the first time, jurors were hearing what that meant from someone who lived it.
- [33:07]
Elizabeth Milner
She said she had learned about freak offs within the first year of their relationship. And initially they just had called it voyeurism. And so as far as everything, a freak off entailed this really was first laid out in the government's indictment against Diddy. But hearing it from Cassie herself, who, for the most part, we hadn't heard her speak about these allegations beyond her lawsuit. And those were just written words. They were typed up, they were filed in federal court. And then obviously, we know it was settled the next day. But as far as just listening to her talk about this, again, she was very soft spoken, very forthcoming about this information, and said that as far as everything that entailed for the freak offs, that included hiring escorts, setting up these experiences.
- [33:50]
Jesse Weber
She talked about the fear about performing for him and how quickly it began to feel less like a relationship and more like work.
- [33:58]
Elizabeth Milner
She said it became like a job to her and that Diddy would tell her to do this. And she said she remembers her nerves from the first freak off that she ever had. And that first one happened when she was just 22 years old.
- [34:12]
Jesse Weber
What stunned observers most wasn't just the content of her testimony. It was the tone, the clarity, the lack of bitterness.
- [34:20]
Elizabeth Milner
She admitted that she did these freak off scenes to essentially make him happy because she was in love with him. I think an interesting point throughout her testimony is that despite these allegations and despite everything she had been through for this long period of time, she said she doesn't even hate Sean Combs. Despite everything that she has alleged in lawsuits and everything that she had talked about, especially with those physical beatings that she said she still didn't even hate him and had love for the better times. When the two were together.
- [34:57]
Jesse Weber
There were no theatrics, no tears, just a woman sitting in federal court describing the intimate details of her own dehumanization and the man she says made it happen. Her voice may have been quiet, but the details she shared weren't. Her accounts spanned more than a decade of alleged manipulation, violence, and sexual coercion. She described how something that began as a music mentorship spiraled into a relationship of extreme control. As she testified, jurors sat just feet away, hearing about everything from beatings to freak offs. Not from lawyers or secondhand accounts, but from the woman who lived it. And for Natalie Winningham Burrell, the emotional weight of that testimony wasn't just powerful, it was unforgettable.
- [35:47]
Natalie Whittingham Burrell
We saw the beating video of him beating her in the hallway. We read through the complaint of her lawsuit against him that settled in 24 hours. Yet still, the things that she said explicitly about the sores in her mouth, being urinated on, choking on urine, recurrent UTIs, those things were not as Salient and apparent at how horrific they were until she testified. And I think, especially as a woman, there was something that she said that was extremely visceral, which was being forced to participate in freak offs when she was menstruating. And I think many women can relate to not wanting to engage. Everyone is different, but most women, not wanting to engage in intercourse during that period of time, not wanting to engage in intercourse during a uti, not wanting to be urinated upon. To imply that any of this was consensual after a point, no matter what she said, would be laughable, because physically, the things that she talked about were viscerally painful to hear if you have female reproductive organs. And so I think that that would be hard to separate the visceral nature of that testimony and then look objectively at whether or not Diddy was participating in trafficking that would equal a predicate crime for rico, because that had such an emotional appeal to it.
- [37:17]
Jesse Weber
But Whittingham Burrell also flagged something more nuanced, something the defense could exploit.
- [37:23]
Natalie Whittingham Burrell
It was also apparent the complex nature of their relationship. You cannot escape the fact that towards the end of their relationship, after she alleges that he raped her, they had consensual sex. I think that's completely understandable within the cycle of domestic violence, and the jury is getting evidence from an expert about that. However, that's not an escapable fact, and it's very complex. That she texted him things that indicated that she wanted to have a freak off. Her testimony, I thought, was quite poignant, that she knew that's what kept him, and she didn't want to lose him, and she'd essentially been groomed by him without using that word. But it was still very, I think, good for the defense to bring out moments in which it seemed as though it was advantageous to her to remain in a relationship with him. Be that as it may, I don't know that that overcomes how horrific. She describes the abusive portion of their relationship.
- [38:25]
Jesse Weber
It's that emotional tightrope, the push and pull of power, love, and trauma that prosecutors say defines the entire case. Because the government isn't just trying to prove that Combs hurt Cassie. They're arguing he used her, that her body, her life, became a vessel for a wider criminal enterprise.
- [38:45]
Natalie Whittingham Burrell
If anyone's ever interacted with domestic violence or intimate partner violence, they will understand the buildup, the explosion, the reconciliation, the honeymoon period. The buildup, the explosion, the reconciliation, the honeymoon period. Right. It was credible to me what she had to say. 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. And then she was also very, 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, she never ever backed away from. I did not want to do these things. He crossed a line. He disrespected me and abused my body and my mind. And so I think that was touching, but I think it was also, it was horrific. The things that she described were absolutely horrific. If you think about the fact that when they met, she would have been 20, turning 21. He was 17 years older than her. She wanted to be break into the music industry. He was a music mogul. The power differential, the age differential, it's just very disturbing to think that was happening.
- [39:58]
Jesse Weber
Up next, the defense gets their turn. Cross examination and what they try to do with Cassie's credibility could determine how jurors weigh everything that came before.
- [40:10]
Natalie Whittingham Burrell
The number one thing that they're pointing out is Cassie's motivation to. To lie. Should we believe the extent of her allegations because she had a financial motivation to make up these allegations in order to receive a multi million dollar settlement. And that's the defense's best case. 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 freak offs, 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.
- [40:50]
Jesse Weber
They'll argue that Cassie isn't a victim. She's a partner who stayed for the money and is now testifying for revenge and a settlement. The trial of Sean Diddy Combs is expected to last eight weeks. We'll be there every step of the way. This has been a long crime production. I'm your host Jesse Weber. Our executive producer is Jessica Lowther. Our writer and producer is Cooper Maul. Our associate producer is Tess Jagger Wells. Edit and sound Design by Anna McLean. Guest booking by Diane Kay and Alyssa Fisher. Additional production support from Giuliana Battaglia and Stephanie Doucet. Legal review by Elizabeth Voulai. Key art design by Sean Penzera. And special thanks to Elizabeth Milner for her in depth reporting on this case. Follow law on 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. Join Wondery in the Wondery app, Spotify or Apple Podcasts and get ad free access to more thrilling long crime series like new episodes of the Retrial and Sidebar with Jesse Weber. Start your free trial today.