The Diddy Trial – The Explosive First Week
From Cassie Ventura’s harrowing account to Dawn Richard’s corroboration, the first week of testimony in the case against Diddy paints a chilling picture of manipulation and violence.
On Monday, May 12, opening arguments finally began in the federal trial against music mogul Sean "Diddy" Combs in New York. The case has ignited a media firestorm and is expected to stretch over two months. Here is a summary of the charges and what unfolded during the trial's explosive first week.
(Content warning: This article contains descriptions of violence against women and sexual assault. Reader discretion is advised.)
What is Diddy accused of?
The indictment consists of five criminal charges: two counts of sex trafficking, two counts of transporting individuals across state lines for the purpose of prostitution, and one count of racketeering—a sweeping charge often associated with organized crime.
Prosecutors argue that Combs led a decades-long criminal enterprise involving coercion, prostitution, and abuse. If convicted, he faces life imprisonment.
Notably, Diddy is not facing criminal charges for the violent assault of his then-girlfriend Cassie Ventura at The InterContinental Hotel in Los Angeles in 2016, a moment caught on hotel surveillance footage. The reason is California's statute of limitations.
However, it was that very assault that prompted Cassie to file a civil lawsuit against Combs in November 2023. Civil suits and legal actions between private individuals cannot result in prison sentences; they only result in financial damages.
Within 24 hours of the lawsuit becoming public, both parties reached a settlement. During this federal trial, we learned the amount: $20 million.
Because of that settlement, Diddy and his legal team have admitted to the assault, knowing that he cannot be charged again for the same incident.
But even though he cannot be criminally convicted for that particular act, prosecutors are using the 2016 video as evidence to demonstrate that violence was a key feature of their relationship and that the so-called freak-offs Cassie was forced to participate in occurred under duress or threat of violence.
How has Diddy responded?
Diddy's public stance has evolved as more information has emerged. In December 2023, shortly after settling with Cassie, he denied all wrongdoing. He claimed the allegations were fabricated attempts at a quick payday.
But when the hotel surveillance video leaked in May 2024, clearly showing him assaulting Cassie, Diddy appeared visibly shaken as he posted an apology video on Instagram. In it, he admitted to the assault, described it as a "dark period" in his life where he had "hit rock bottom". He claimed he had since sought help.
Despite that partial admission, he continues to deny all charges currently brought against him in this federal case.
Haven't over 100 people accused Diddy of abuse?
A total of 120 individuals have accused Combs of various forms of sexual misconduct. However, some of these claims have only been made to the media, while others remain under preliminary investigation. The vast majority are playing out in separate civil cases. Only a small handful of witnesses are part of this federal criminal indictment.
What were freak-offs?
"Freak-offs" is the name Diddy himself used to describe the drug-fueled sex parties he allegedly hosted since at least the early 2000s. They often followed his more mainstream celebrity events, acting as a secretive, debauched third act after official afterparties.
That context is important: not all celebrities seen at a Diddy-hosted event necessarily participated in a freak-off. For example, someone might attend Diddy's famous White Party in the Hamptons without having been present at what followed later that night. While speculation continues about which public figures may have participated, that remains unconfirmed.
As for the 2016 assault caught on camera, it allegedly took place at 11 a.m., when Cassie attempted to leave one of these freak-offs.
How did Cassie and Diddy meet?
The two met in 2006, the same year Cassie signed to Diddy's Bad Boy Records. She was a 19-year-old aspiring artist; he was already 36 or 37, a multimillionaire, and one of the most powerful figures in the music industry.
Diddy already had a reputation for aggression – rumors of violent behavior dated back to at least the late 1990s – and the power imbalance between them would shape their entire relationship.
In keeping with a familiar pattern, Diddy reportedly signed Cassie to a highly restrictive and exploitative record deal. She was contracted to deliver ten albums, a staggering figure for a newcomer. Given her age, inexperience, and the blinding influence of Diddy's celebrity status, she likely didn't fully grasp what she was signing away.
The contract gave him complete control over her creative and musical output. And sure enough: despite recording hundreds of songs, only one album was released: her debut, Cassie in the summer of 2006.
By 2007, the two began dating, though their relationship remained secret for years. They were on and off until they finally separated in 2018.
The Trial – Day 1
The prosecution delivered its opening statement on Monday, May 12, laying out the case against Diddy and previewing the graphic nature of what the jury would hear. One example: an incident in which Diddy allegedly forced a male sex worker to urinate in Cassie's mouth.
During these freak-off sessions, prosecutors say Diddy watched, directed, masturbated, referred to himself as "king," and often filmed the encounters.
In court, Diddy appeared with gray hair, a detail that didn't go unnoticed. Media outlets like The New York Times and BBC reported that Diddy lacks access to hair dye in detention.
But the timing also sparked speculation: similar visual transformations have been seen before in the courtroom strategies of Harvey Weinstein and Bill Cosby, appearing older, weaker, and, perhaps, more sympathetic.
After opening arguments, the prosecution called its first two witnesses:
Witness 1: Israel Florez
A hotel security guard, Florez, described responding to reports of a disturbance on one of the floors. Exiting the elevator, he saw a distressed Diddy wearing only a towel. Cassie, visibly injured, curled up on the floor.
Florez: "As soon as I walked out, the best way I can describe it is a devilish stare. He was just looking at me … looking at me with no movement."
He said he tried to separate the two and calm Diddy down. At one point, Diddy allegedly offered him money, something Florez interpreted as a bribe. He declined, instead telling Diddy that the hotel had no intention of escalating the situation and asked him to ensure no further disturbances before checkout.
Witness 2: Daniel Phillip
The second witness, Daniel Phillip, is a male sex worker. He testified that he was paid up to $6,000 to have sex with Cassie while Diddy watched and directed. Sessions sometimes lasted up to ten hours, and Diddy would occasionally withhold payment if dissatisfied.
The last two encounters allegedly ended with Diddy physically assaulting Cassie in front of Phillip.
Philip: "I asked her why she's staying with this guy if he's hitting her and beating her like this. I tried to explain to her that she's in real danger if she stays with him. She basically tried to convince me that, 'It's OK, I'm OK.'"
Phillip testified that he didn't report the incidents out of fear. He also claimed Diddy photographed his license plate, which he interpreted as an intimidation tactic.
Extreme misogyny in comment sections
I've observed a familiar pattern in the media cycle. Reputable outlets initially publish careful accounts of courtroom developments. Click-driven platforms like No Jumper, Complex, and DJ Akademiks follow up with sensationalized summaries and provocative and misleading headlines, stirring the pot and feeding the comment sections.
What's there is harrowing: a flood of misogyny, mostly, but not exclusively, from men, mocking or minimizing the allegations. Posts about the trial routinely generate hundreds of comments ridiculing Cassie or questioning her motives.
It is difficult to say how representative these comments are of men's real-life views. But if they are representative, the situation is dire.
The cruelty is hard to overstate. One recurring sentiment stands out: men expressing sympathy not for Cassie, but for her husband, writing things like "man, her husband must really be going through it."
It's depressing to see that a particular kind of men are so incapable of seeing women as human beings that they can read about all the horrors a woman has been subjected to and still conclude that the real victim is her husband.
Another common refrain reveals staggering ignorance: why is Cassie testifying after settling for $20 million? They fail, or refuse, to understand that this is a federal criminal case. If the U.S. government calls her as a witness, she is legally obligated to testify.
Other Witnesses
Several more women are expected to testify, many of them anonymously.
One, identified only as "Jane", says she began dating Diddy in 2020 and was forced to have unprotected sex with sex workers, against her will.
Another, referred to as "Mia", worked as his personal assistant and will testify about multiple instances of rape.
Other witnesses will include former employees, additional sex workers, and members of Diddy's inner circle. According to prosecutors, their testimonies will establish a pattern of manipulation, exploitation, and abuse spanning two decades.
Day 2 & 3: Cassie Ventura's Testimony
Tuesday and Wednesday were dominated entirely by the prosecution's star witness: Cassie Ventura. Now eight months pregnant, she took the stand to testify. An experience that, by any measure, is difficult to imagine.
Instead of doing what a heavily pregnant woman might want to do during that period – resting, turning inward, and preparing for the birth of the child – Cassie was forced to relive and articulate the darkest chapter of her life. During parts of her testimony, she had to examine explicit images from the so-called "freak-offs" to identify herself and others involved, doing so in full view of the judge and jury.
The court has not released a full transcript of the proceedings, but journalists in the room have compiled summaries of key moments. Here are the most significant revelations from her time on the stand:
Cassie testified that Diddy controlled every aspect of her life. He could show up any time, banging on her door, furious over real or imagined infractions.
In the early days of their relationship, she said, they didn't have nicknames for each other until Diddy asked her what she used to call her grandfather. When she said "Pop Pop," he allegedly responded that he also wanted that to be her nickname for him.
She testified that Diddy arranged for male sex workers to be flown in from Los Angeles and Miami, which is central to the case: transporting people across state lines for the purpose of purchasing or facilitating sex is a federal offense. While Cassie said she was often expected to handle the bookings, Diddy footed the bill.
She described how he repeatedly demanded freak-offs, pressuring her until she gave in. The longest sessions could last up to four days, after which she often needed IV fluids and massages just to recover physically.
During the freak-offs, she said she regularly used drugs, mainly ketamine. Not for recreation, but to dissociate, to numb her awareness of what was happening to her.
Cassie made it clear: she hated every moment of it. She said she felt humiliated and that the only personal time she got with Diddy was between these orchestrated, degrading encounters.
The freak-offs, she testified, followed a consistent script. Diddy would direct every act. At times, he'd prevent the escorts from ejaculating until he gave the go-ahead. Afterward, she said, he would sometimes take her into another room and ask her to rub his chest with the semen of the escorts.
Baby oil and lubricant, she added, were constant features. Diddy allegedly demanded they be reapplied every five minutes. His instructions were specific: "You need to put on more oil. You need to be glistening. You need to be shining."
Throughout her testimony, jurors were shown photos of physical injuries she says he caused. In one instance, he allegedly hit her, knocking her over so her eyebrow struck the headboard, splitting the skin. Diddy then reportedly instructed his security to take her to a plastic surgeon. She still bears the scar.
She said she frequently wore heavy makeup and sunglasses to cover the marks on her face.
Cassie recounted one incident that took place during the Cannes Film Festival, where Diddy allegedly became enraged and kicked her off a boat without shoes or a passport. On the flight home, she tried to avoid him by booking a separate seat, but he managed to switch seats so that he was next to her. During the flight, he allegedly pulled out his laptop and showed her a freak-off video as a threat.
She also described how Diddy's staff – bodyguards, drivers, assistants – routinely witnessed the violence. At least once, she said, a staff member physically prevented her from escaping. On another occasion, she was allegedly taken to a hotel and kept there for a week, isolated, so she could recover from her injuries.
During one of their breakups, she began seeing rapper Kid Cudi. When Diddy found out, she said, he lost control, threatening violence and again warning he would release the videos.
Near the end of her testimony, Cassie spoke about the long-term psychological toll. In 2023, plagued by flashbacks, she said she became suicidal. She planned to walk into traffic on a highway, but her husband stopped her. Afterward, she began trauma therapy.
Finally, she recounted the end of her relationship with Combs. In August 2018, after catching him with another woman, she decided to leave him for good. They had one last dinner together, which seemed relatively calm. But when he drove her home, he allegedly forced his way into her house and raped her on the living room floor.
Day 4: The Defense Strikes Back
On Thursday, May 15, Diddy's defense team began its cross-examination of Cassie Ventura. It focused heavily on the nature of their relationship. Many of their text messages were read aloud.
Given that they were together for eleven years, it can be assumed that there must have been periods of normality or even times where they expressed love for each other. It was these moments of intimacy, affection, and mutual desire that the defense sought to highlight. Their strategy: show that their relationship, while tumultuous, was not the product of coercion or trafficking, but of mutual toxicity.
Here are some of the key parts:
They read multiple text messages that painted Cassie as a willing participant in freak-offs, or someone who expressed a desire for Diddy. In one message, she allegedly wrote: "Baby I want to F.O. so bad,"…followed by plans to keep the session short so she'd have time to recover before attending an event.
Cassie countered that these texts were being presented without context and that she often used language like that to appease Diddy or to avoid triggering his anger.
The defense also emphasized their shared drug use, chronicling a pattern of substance abuse that they suggested blurred the lines of consent. They also pointed to episodes of jealousy and infidelity, seeking to portray the relationship as volatile, but not criminal. In doing so, the defense appeared to be constructing an argument that their relationship, while clearly damaged and dysfunctional, did not meet the legal threshold for trafficking or organized abuse.
Day 5: Final Day of Testimony from Cassie Ventura
On Friday, May 16, Cassie Ventura returned to the witness stand for her fourth consecutive day of testimony. The defense continued its cross-examination, aiming to undermine her credibility and reshape the narrative around her relationship with Diddy.
Here are the most significant developments:
The defense also zeroed in on the timeline of the alleged rape in 2018, which Cassie said occurred after a dinner at the end of their relationship. There appeared to be confusion about whether it happened in August or September.
Using old text messages, the defense established that Cassie had consensual sex with Diddy at least once after the alleged rape. She confirmed this, explaining that her emotional bond hadn't simply vanished, despite the breakup and the abuse she endured. That sexual encounter reportedly happened while she was in the early stages of dating her now-husband, Alex Fine.
The defense then suggested that Cassie had financial difficulties in 2023, when she filed her civil lawsuit and ultimately settled with Diddy for $20 million. They claimed that after receiving the settlement, she canceled plans for a tour. They also argued that, before receiving the money, Cassie, her husband, and their children moved in with her parents in Connecticut to cut costs.
Cassie pushed back, stating that neither the canceled tour nor the move had anything to do with money. Instead, she said, the family was simply relocating to the East Coast and temporarily stayed with her parents during the transition.
The defense played an audio clip of Cassie threatening another man's life. According to their framing, she believed he had stolen or discovered a video from the freak-offs.
They also presented a 2012 text exchange between Cassie and Diddy. In it, Diddy asked whether she wanted to have a freak-off "one last time." She allegedly responded, "no," adding that she wanted a freak-off for "the first time for the rest of our lives" – a phrase the defense used to suggest a kind of ongoing desire or consent.
The prosecution then re-questioned Cassie, offering important context to that same exchange. They read additional texts from Cassie: "I want to see you, but I'm emotional right now. I don't want to do one last time. I'd rather not do it at all." This nuance, they argued, clearly contradicted the defense's interpretation.
Homeland Security Agent Yasin Binda Testifies
Next, the prosecution called Homeland Security agent Yasin Binda, who participated in the raid on Diddy's properties in September 2024. Binda testified that during the search, authorities seized:
Large quantities of baby oil and lubricants
Prescription medications
Cash
Illegal drugs
The prosecution offered this inventory to reinforce the accounts of witnesses who had described freak-offs involving all of the above.
Singer Dawn Richard Takes the Stand
Before the day ended, prosecutors called a powerful final witness for the week: Dawn Richard, a former member of Diddy's groups Danity Kane and Diddy Dirty Money, who worked closely with him between 2004 and 2011.
Richard recounted a 2009 incident at Diddy's Los Angeles mansion. She and Cassie were in the kitchen when Diddy stormed down the stairs, yelling about why his food wasn't ready.
Richard: "He came downstairs screaming, belligerent, asking where his food was, and proceeded to hit her over the head, kicked her, and beat her to the ground in front of us."
Richard said he grabbed the frying pan Cassie had been using to make eggs and struck her with it. Though the pan may not have hit her hard, Cassie collapsed into a fetal position, seemingly to shield herself. Diddy then allegedly continued hitting and kicking her, eventually dragging her upstairs, where the assault continued.
Richard admitted that she did not intervene, was paralyzed by fear, and did not call the police.
She said Diddy called her in for a private meeting the next day. There, he reportedly justified the attack, claiming it resulted from "a passionate relationship" and assuring her that Cassie was fine. He allegedly warned her not to speak about what she saw, saying, "People disappear." Richard said she understood that as a threat.
She is scheduled to continue her testimony on Monday, May 19.
What Is This Trial Really About?
I'm far from a legal expert, but based on the cross-examination of Cassie, the legal battle hinges on consent.
Diddy's defense has argued that Cassie was a willing participant in their sexual relationship, including the freak-offs. During cross-examination, they read text messages that showed Cassie agreeing to meet with him despite knowing what might await.
But the prosecution disputes that version completely. They argue that Cassie's apparent participation wasn't consent but survival. They cite the 2016 hotel video as proof of what she was up against. And beyond physical violence, prosecutors point to the threat of reputational ruin. Diddy had filmed the freak-offs, they say, and used that footage to manipulate and silence her.
At the heart of the case is this question: When someone says "yes" while under the threat of violence, under emotional coercion, under fear of blackmail – is that truly a yes?
Under U.S. federal sex trafficking laws, the answer is no. Consent given under duress, threats, manipulation, or fear of retaliation is not legally considered consent.
The defense has to walk a tightrope. On the one hand, they cannot appear to attack or dehumanize Cassie too openly – that risks alienating the jury.
On the other hand, their entire case depends on casting doubt on her narrative by using her own words, like old text messages, to portray a complicated, non-traditional, and dysfunctional relationship, but not one that meets the criteria for trafficking or organized crime.
The Road Ahead
As noted, the trial is expected to run for at least eight weeks, and there are likely many twists. While I do not intend to write weekly updates, this piece offers a snapshot of the trial's opening chapter – what the case is about, and what emerged during the first week.
Rest assured: I'll likely write some follow-ups.
Statement from Cassie and Her Husband
Following the conclusion of her testimony on Friday, Cassie's attorney delivered brief public statements from both Cassie and her husband, Alex Fine. The couple is expecting their third child very soon.
In his statement, Fine addressed the disturbing trend of people portraying him as either the victim or the "hero" in Cassie's story, particularly after the traumatic details of her abuse were made public.
