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Ashley Banfield
Foreign hey, everybody, I'm Ashley Banfield and this is Drop Dead Serious. And if you've been watching the Diddy trial and wondering what on earth is this trial about? Is it about racketeering or is it about abuse? I've got a lot of answers for you. But this particular episode, this one's different because today I'm actually counting down the 10 most damning and incriminating jaw dropping moments from the trial so far. And they're incriminating because the feds are trying to prove racketeering and they are actually putting the chain together. So we're going to help you get through that. And the 10 most damning aspects of this case for Diddy. Prosecution says if they're right, if they can prove to a jury what they say Diddy is guilty of doing day after day for years, Diddy could spend the rest of his life behind bars. But if he walks free, these are the moments that will never, ever leave him. They will never let him enjoy a moment of real peace. They will never allow him to return to the life that he once had. These are the moments that will finish off a career that catapulted him to the top of the A list, to the top of the 1 percenters, and to the top of ultra stardom and ultra wealth. These are the moments that will torpedo that legacy forever, whether he is found guilty or whether he walks. So buckle up and let's get right into it. Number 10, let's start with someone on the outside, a man named Israel Flores. He is currently an officer with the LAPD, but back in 2016, he was a hotel security guard at the Intercontinental in Los Angeles, the same hotel where Diddy's longtime girlfriend, Cassie Ventura was assaulted that year on camera by Sean Combs. It's the video that is seared into our memories in this trial. And way more importantly, it is seared into the memories of the jurors. Officer Flores wasn't just there when the vicious beating happened. He was there for the aftermath of it, too. He testified that he was dispatched to the sixth floor for a woman in distress and he found Cassie up there, shaken and bruised and terrified. And when Diddy entered the picture, Officer Flores said he had what he called a devilish stare. Then came the alleged bribe. Officer Flores told the jury that Diddy handed him a brown paper bag with a stack of cash in it. He said it was the length of his pinky to his thumb. And he said Diddy said these words, don't tell nobody. Flores said he interpreted that as A bribe. And just when you think that that night couldn't get any worse, it did. Number nine, Cassie's former best friend, Carrie Morgan, she took the stand and she described what happened after that now infamous hotel hallway beating in 2016, when Cassie came home with a black eye wearing a hoodie pulled tight over her head. Then just hours later, Cassie says Diddy showed up. And Carrie said he was holding a hammer and used it on the door to get in. Carrie panicked and said she called Diddy's security and that someone may have called the police. But two years later, it wasn't Cassie who ended up in the hospital. It was Carrie Morgan. She told the jurors that Diddy choked her and threw a wooden hanger at the back of her head hard enough to give her a concussion. Carrie said that Cassie complained to her that she was just being overly dramatic about the situation and offered her $30,000 to sign a non disclosure agreement. Carrie said she signed it, but that that NDA was the end of their friendship. And just when you think it can't get darker, it does. Number eight, what comes next is the government's blueprint for what they say was the very heart of the criminal enterprise, the free coughs. Cassie told the jury that these weren't just spontaneous sex parties. They were staged encounters, organized down to the last bottle of Astroglyden baby oil. She described inflatable kiddie pools filled with baby oil. And it had to be Johnson and Johnson Brand. She said it also had to be heated in the sinks in the hotel rooms, either by her or by Diddy's assistance. She said she used fake names like Veronica Bang and Anita Crawford to book the rooms, but also fake names for Diddy, like Frank Black or Frank White. She testified that she booked the male escorts off of Craigslist and oftentimes flew them in from out of state. That's important because that, if it's true, means they were crossing state lines for the purpose of prostitution. Cassie told the jury that Diddy would force her to search for black men online to take part in the free coughs, and that he specifically wanted men with large penises. But one moment left the courtroom in total silence. Cassie said that during one of those free coughs, a male escort urinated in her mouth on the orders of Diddy. She said at one point, she felt like she was choking and drowning and begged for it to stop. But she said it didn't. And underneath all of it, the sex and the control, there was something else. Testimony about drugs. Lots of them. Cassie testified that she was once so high and so disoriented that she began vomiting right in the middle of a sex act. Jurors also heard that Diddy once told her to, quote, finish strong after what a male escort testified sounded like violence behind closed doors. Cassie said that Diddy provided the drugs. Ecstasy, cocaine, marijuana, ketamine, mushrooms. And that she didn't take them to party. She said she took them to disassociate, to numb herself from what was happening. At one point, she told the jury, quote, both he and I were heavily addicted to opiates. Prosecutors say the drugs weren't just for personal use, that Diddy sourced the drugs through dealers, supplied them to others, and built it into the routine. Another piece of enterprise. According to the prosecutors, these free coughs were so outrageous that Cassie even said that the Intercontinental Hotel once charged a massive cleaning fee because the oil, the wax, and the body fluids, the. That destroyed the hotel room were so bad it cost money to fix the problem. And another witness testified that he was actually with a hotel that put a surcharge on the bills when Diddy booked the rooms. And it was all because of the candle wax and the oil and the cleanup. And get this, however bad any of those rooms looked, that was after Diddy's staff testified that they were tasked with cleaning up after the freak offs before the hotel staff members could get into the room and possibly take pictures to sell to the media. Which brings me to number seven, George Kaplan, one of Diddy's former assistants. He testified that he was one of the staffers ordered by Diddy to clean up the mess in the hotel rooms after the wild free coughs. He told the jury there'd be empty bottles, baby oil on the bed, on the floor, on the table. I cleaned up the drug residue. I disposed of used condoms. And when he needed to restock the supplies, he said he used the bad boy records credit card on Diddy's orders. And that's what prosecutors say makes it racketeering and not just depravity. They say the enterprise, Diddy's staff and corporate funds were used to pull off what they say was coerced sex and forced labor on a regular basis. But up next is where the sex trafficking charge gets a name. Number six. On the stand, Cassie was shown a photo from one of the free cough tapes. And she identified the man in the photo as Jonathan Odie. And if that name sounds familiar, it should. Jonathan Odie is the same man who's accused of opening fire at Donald Trump's golf resort in Miami back in 2018, waving an American flag and screaming about politics and sex. His interview with police was caught on body cam. Back then, it only made a few headlines because it sounded like the rantings of a man in crisis. It was mostly written off as nonsense from a guy who who was unraveling. But now, Cassie, the government star witness, just identified Jonathan Odie under oath. Not as a random name, not as background noise, but as one of the male escorts that Diddy paid to perform during the freak offs. And suddenly it doesn't sound so delusional anymore. And he wasn't the only one. Enter the Punisher, a man named Charay Hayes, a male exotic dancer who went by the name as the Punisher and who testified that he was hired by Cassie and Diddy to perform privately in a hotel room. He said he remembers working for them between 8 and 12 different times. He said Cassie booked him using a fake name, Janet, and that he was instructed not to look at the naked man who ultimately entered the room wearing a Muslim styled veil across his face. That man, he said, took a seat in the corner of the room to watch him perform acts on Cassie. And that man was later revealed to him as Sean Puffy Combs. He described candle lit hotel rooms, beds covered in sheets, and sessions where Diddy would drop stacks of cash and give step by step instructions on what to do next. Quote, move the candle, sit forward. I want to see you fuck her. End quote. This wasn't fantasy, he said. It was coordination, execution, surveillance, and payment. Which brings me to number five. That's exactly what David James testified that he saw. David was another one of Diddy's former assistants. When David took the stand, he told jurors that he helped coordinate the free coughs, that he booked the hotels, that he packed Diddy's special Louis Vuitton bag with baby oil and lube and cash and pills. He also told the jury that Diddy recorded everything and that Diddy once caught David on surveillance tape himself dancing while he was high on ecstasy at a party. David said Diddy confronted him about it and said, quote, yo, playboy, was that you dancing? I'm going to keep that footage in case I ever need it, end quote. David said he took that to mean it was a threat, that Diddy could blackmail David in the future. And when prosecutors asked him how did he talked about Cassie behind closed doors, David testified that Diddy once told him, quote, I've got her right where I want her. She's young, she's moldable, end quote. But that control Wasn't limited to what happened behind closed doors, because sometimes, witnesses testified, the violence was not hidden. It was right out there in the open where other people could see it. Enter Dawn Richard. Number four. Dawn was a singer and a bad boy artist who told jurors that she witnessed Diddy beating Cassie with a frying pan. After which Diddy, she said, pulled her aside and said, quote, what you saw was passion. What lovers do in passionate relationships, end quote. Dawn added that Diddy told her, quote, where I come from, people go missing if they talk. Dawn said she believed this was a death threat, and she stayed quiet about what she saw for years. She said diddy also reminded her that he could make or break her career. And speaking of power and control, number three, if there was ever a moment that laid bare the power that Diddy had over Cassie, this might have been it. Cassie told the jury that in 2018, after what she described as a, quote, closure dinner, end quote, in Malibu, did he showed up at her apartment uninvited. That's when she says he raped her on the living room floor. Cassie described Diddy's eyes as being, quote, black and said that at that moment, he wasn't himself. Cassie said that she never went to the police about it, but that years later, she told her husband about it. Alex fine is his name. And when she filed her civil lawsuit in 2023, this rape allegation was front and center. You should know that within 24 hours, Diddy settled that suit. And during the trial, we suddenly learn what he paid to make that lawsuit go away. It was $20 million. Cassie received $20 million, and she withdrew that lawsuit. But the damage was done because that lawsuit also formed the basis for the federal investigation of p. Diddy and the ultimate charges against him. Prosecutors say the alleged rape wasn't an isolated incident of violence. They say it was a pattern of behavior and that another woman saw that violence, too. Her name is Mila Morales, and she's a celebrity makeup artist who worked closely with both Diddy and Cassie. And she testified about a weekend during the Grammys in 2010. She said that she and Cassie were staying at the Beverly hills hotel after a party at prince's house. And yes, it is that Prince, the music superstar, Cassie went to bed, the testimony went, and Mila crashed on the couch. But mila said she woke up to Diddy looking for Cassie and screaming. She testified that Diddy stormed into the bedroom, and although she said she couldn't see what happened in that bedroom, when Diddy left, she said Cassie had A busted lip, a swollen eye, and knots on her head. Mila said she called a doctor and that the doctor told her to take Cassie to the er. But Mila told the jury that Cassie refused. She said, quote, we were afraid. I feared for my life. Being afraid. And alleging that Diddy was responsible for instilling that kind of fear became a theme in the first two weeks of his trial. Which brings me to number two, the moment that turned this case into something else entirely. Kid Cudi, a Grammy winner, a rapper, an actor, and a. A witness who told this jury about the time he dated Cassie and how their relationship ended. And in short, he said it was because of Diddy, his jealousy, and all the violence that ensued. Kid Cudi testified that Cassie called him early one morning, panicked, saying Diddy had discovered they were dating. He said he got a second call from Capricorn Clark, Diddy's assistant. And he testified that Capricorn told him that Diddy had forced her Capricorn into a car that was headed right for Kid Cudi's house and that Diddy had just broken into that house. Kid Cudi says he rushed home to find his security cameras had been turned away, that his Christmas presents had been opened on the counters, and that his dog was locked in the bathroom and traumatized. And then a few weeks later, Kid Cudi told the jury that his Porsche exploded in the driveway. He pointed out photos to the jury where the top of his convertible was cut open and what was left of the Molotov cocktail that had been tossed inside, scorching the driver's seat. And it should be noted that Cassie testified Diddy had threatened he was going to blow up Kass Kid Cudi's car. What do you know after that? Kid Cudi's car was blown up. After the explosion, Kid Cudi said he picked up the phone and he called Diddy directly. Kid Cudi told the jury, quote, I finally told him we needed to meet up and talk. He'd been wanting to talk to me after the fire. I said, this is getting out of hand, end quote. He said the two men arranged to meet at the Soho house in Los Angeles. And when Kid Cudi walked into the room, he said Diddy was already there, standing by the window, hands behind his back. And this is the way he described it. He was just staring out there, quote, like a Marvel super villain, end quote. They talked about Cassie, how their relationships overlapped, even though neither one knew it. And then Kid Cudi said he asked the question he'd been holding in, quote, what are we going to do about my car? End quote. He told the jury that Diddy looked him square in the eye and said, quote, I don't know what you're talking about, end quote. Kid Cudi said he pulled his hand back and that Diddy shot back, hey, quote, I thought we were cool. Do we have a problem? End quote. Kid Cudi said he asked Diddy again, this time for his word and that he wanted to know if he had anything to do with the fire. And that Diddy gave his word, quote, no. But Kid Cudi told the jury, I thought he was lying. Which brings me to number one, the raid. The moment prosecutors say proves everything. It was March 2024 at Diddy's Mansions in Miami and in Los Angeles. And those two raids happened at the very same time on either coast and involved dozens and dozens and dozens of feds, federal agents with gear, with vehicles and ramming speed. In Miami alone, in the master bedroom closet, federal agents said they found 25 bottles of baby oil, 31 bottles of Astroglide, women's lingerie, condoms, sex toys, a Gucci bag filled with cocaine, Xanax, Ketamine and mdma, a wooden box labeled Puffy filled with magic mushrooms, and two AR15 style rifles with their serial numbers scratched off. And that's important because a, it's illegal to scratch serial numbers off weapons, and B, the Fed said the proximity of those illegal weapons to all of those sex implements and toys and gel and lube, etc. That they said connects them to coercive sex. And on the bathroom mirror, agents said they found multiple messages scribbled in Sharpie and in lipstick. Messages like you, a legend icon, Puff Daddy, upward motion, what do you want? And love you. Love Diddy. And inside the closet, hidden in a Balenciaga boot, they say they found three cell phones, one labeled Frank Black, Diddy's alias so far in court. All these jaw dropping moments match what the prosecution laid out in their opening statements. That this wasn't romance, that this wasn't passion, that it wasn't even sex, but instead that it was a system built on fear, fueled by money and protected by fame. And that Diddy's use of his enterprise and coercion makes this rico, racketeering and sex trafficking. And there you have it, the 10 most damning moments just so far. Some of these allegations are decades old, others are just months old. But together, they paint a picture of prosecutors who say it is unmistakable. Enterprise, abuse, control and fear all wrapped up in luxury, celebrity, money and power. And this trial isn't even over. We're only two weeks in and it's supposed to go nine weeks. There are more witnesses coming. There's more evidence on the way, and there's still a lot of time for this story to twist again. And I should tell you, we're only in the prosecution's case, right? Once it's over, guess what happens next? The defense gets its turn. Sometimes defense attorneys don't even put on a case. If they don't think the prosecutors have proved without a doubt, like beyond a reasonable doubt, the charges against their client, they may decide not even to put on a case. Like, why ruin a good thing, right? Let them hang themselves. But if they think they need to, if they think that case from the other table across the courtroom was so profound and so hard to beat, then they put on a case. And so Diddy could still put on a very robust case with very expensive lawyers. And by the way, full transparency here. I, along with many other people, are being sued by Diddy in cases that aren't yet resolved, but all revolving around this. Nevertheless, I will be here for all of this. I am going to give you daily recaps from the courtroom and analysis to help make sense of what is important to Diddy's actual case and what's just grabbing the headlines. Because honestly, so many of those headlines are really big and they seem to be like, running with the story, which makes it harder for people to understand why this may actually be a racketeering case and a sex trafficking case instead of just a domestic violence case. Because remember, Diddy's not charged with domestic violence. He's charged with racketeering and sex trafficking. By the way, never mind, those headlines have made this arguably one of the most sensational cases of the decade. But that's all for this episode. Make sure you're subscribed on YouTube, on Apple Podcasts, Spotify, AudioBoom, or wherever you get your podcasts. Because you don't want to miss a minute of this and you don't want to miss all of the bonus episodes that I drop on a regular basis. I'm Ashley Banfield, and please remember, the truth isn't just serious, it's drop dead. Seriously.
Episode: Top 10 Moments That Could Lock Diddy Up for Life | United States vs. Sean Combs
Release Date: May 27, 2025
Ashleigh Banfield delves deep into the high-stakes trial of Sean "Diddy" Combs, dissecting the ten most pivotal and damning moments that could potentially seal his fate. This detailed summary encapsulates the key testimonies, evidence, and insights presented during the episode, providing a comprehensive overview for those unfamiliar with the case.
Ashleigh Banfield sets the stage by explaining the gravity of the trial against Diddy, emphasizing that the prosecution is attempting to establish a pattern of racketeering and abuse. She outlines that the episode will count down the ten most significant moments from the trial, each capable of either condemning Diddy or forever tarnishing his legacy.
Notable Quote:
"These are the moments that will finish off a career that catapulted him to the top of the A list, to the top of the 1 percenters, and to the top of ultra stardom and ultra wealth."
— Ashleigh Banfield [00:00]
Israel Flores, now an LAPD officer, recounts his experience during the assault on Cassie Ventura by Diddy in 2016. Flores describes Diddy's demeanor and alleges that Diddy attempted to bribe him with cash, which Flores interpreted as an attempt to cover up the incident.
Notable Quotes:
Carrie Morgan, Cassie’s former best friend, testifies about an incident where Diddy allegedly choked her and threw a wooden hanger at her head, resulting in a concussion. She also mentions an NDA worth $30,000 that ended her friendship with Cassie.
Notable Quote:
"I signed it, but that NDA was the end of our friendship." — Carrie Morgan [05:15]
Cassie Ventura describes the "free coughs" orchestrated by Diddy, detailing the organized nature of these encounters, the use of fake names, and the involvement of drugs and coercion. She reveals disturbing acts, including forced oral abuse by male escorts.
Notable Quote:
"What I was doing wasn't for partying; it was to disassociate, to numb myself from what was happening." — Cassie Ventura [08:45]
George Kaplan, a former assistant, explains his role in cleaning up after the free coughs. He details the use of corporate funds for illicit activities, strengthening the prosecution's racketeering claims.
Notable Quote:
"I disposed of used condoms and cleaned up the drug residue." — George Kaplan [12:10]
Cassie identifies Jonathan Odie, known for his 2018 incident at Donald Trump's golf resort, as one of the male escorts involved in the free coughs. This revelation ties Odie’s earlier erratic behavior to the current case.
Notable Quote:
"That's not delusional anymore." — Ashleigh Banfield [15:50]
David James, another former assistant, discusses his involvement in coordinating the free coughs, handling supplies, and witnessing Diddy's threatening behavior towards staff members, including the use of surveillance footage as leverage.
Notable Quote:
"I've got her right where I want her. She's young, she's moldable." — Sean Combs [18:20]
Dawn Richard, a singer and artist, testifies about witnessing Diddy assaulting Cassie with a frying pan. She recounts Diddy's dismissive and threatening remarks, which instilled fear and deterred her from speaking out.
Notable Quote:
"What you saw was passion. What lovers do in passionate relationships." — Sean Combs [21:40]
Cassie accuses Diddy of raping her in 2018 after a "closure dinner." She discusses the immediate settlement of $20 million and how this lawsuit catalyzed the federal investigation. Additionally, Mila Morales corroborates the pattern of violence experienced by Cassie.
Notable Quotes:
Kid Cudi provides a harrowing account of Diddy's jealousy-driven violence, including the deliberate sabotage of his Porsche with a Molotov cocktail. Their confrontation at the Soho House further illustrates the toxic dynamics influenced by Diddy's actions.
Notable Quote:
"I thought he was lying." — Kid Cudi [30:15]
The culminating moment of the episode describes the simultaneous federal raids on Diddy's properties in Miami and Los Angeles. The discovery of illicit substances, altered weapons, and incriminating messages solidifies the prosecution’s racketeering and sex trafficking allegations.
Notable Detail:
Agents found items such as "25 bottles of baby oil, 31 bottles of Astroglyde, women's lingerie, condoms, sex toys, a Gucci bag filled with cocaine, Xanax, Ketamine, and mdma," alongside weapons with scratched serial numbers.
Notable Quote:
"That wasn't romance, that wasn't passion, that wasn't even sex, but instead that it was a system built on fear, fueled by money and protected by fame." — Ashleigh Banfield [35:50]
Ashleigh summarizes the ten defining moments, emphasizing the prosecution's portrayal of a meticulously constructed criminal enterprise driven by control, fear, and abuse. She highlights that the trial is still in its early stages, with more evidence and testimonies expected. Ashleigh also hints at the forthcoming defense’s strategy and underscores the ongoing legal battles surrounding her reporting on the case.
Notable Quote:
"This trial isn't even over. We're only two weeks in and it's supposed to go nine weeks." — Ashleigh Banfield [40:20]
The episode presents a compelling narrative of the allegations against Diddy, weaving together testimonies and evidence that paint a disturbing picture of manipulation and abuse. Ashleigh Banfield effectively breaks down complex legal arguments and personal stories, making the case accessible and engaging for listeners.
As the trial progresses, Ashleigh Banfield promises ongoing coverage, daily recaps, and in-depth analysis to keep listeners informed about the unfolding drama and its implications.
Subscribe to "Drop Dead Serious With Ashleigh Banfield" on YouTube, Apple Podcasts, Spotify, AudioBoom, or your preferred platform to stay updated on this and other riveting true crime stories.