Introduction:
The Diddy Trial in NYC is shaking the entertainment world to its core. On May 5, proceedings began in New York City against music mogul Sean “Diddy” Combs, who is facing explosive charges involving sex trafficking, racketeering, and prostitution. What started with jury selection has snowballed into a daily court spectacle featuring disturbing testimony, high-profile names, and deeply unsettling allegations. Here’s your inside look at how it’s all unfolding—day by day.
May 5: Diddy Trial NYC Opens With Intense Jury Selection
The courtroom buzzed as jury selection kicked off. Diddy, 55, entered the room wearing a white-collared shirt under a sweater, ditching the prison garb per the judge’s prior approval. Even though he was offered a plea deal that might’ve shortened his sentence, Diddy turned it down, standing firm on his not-guilty claim.”
Opening the process with a quip about Diddy’s many aliases and comparing the jury list to “Lord of the Rings,” Judge Arun Subramanian tried to ease tensions. But things quickly got serious as multiple potential jurors admitted they had seen the 2016 video, released by CNN, of Diddy allegedly assaulting ex-girlfriend Cassie. One woman called the footage “damning” and was promptly dismissed.
May 6: Star Power and Delicate Jurors Stir Trial Challenges
As the Diddy Trial NYC progressed, the judge refined questions about celebrity associations. Jurors were now asked if they knew stars like Kanye West, Michael B. Jordan, and Michelle Williams, rather than just being familiar with them.
Frustration mounted as jurors were dismissed for Crohn’s disease, hearing issues, and even emotional sensitivity—one woman claimed she fainted during a classroom discussion on oral sex.
May 7: Social Media Spiral, Abuse Allegations, and Cassie’s Controversial Claims
The trial took a surreal turn as one juror explained the concept of “doomscrolling” to the judge, who admitted he doesn’t use social media. Diddy’s attorney, Benjamin Brafman, revealed plans to argue that Cassie also abused Diddy, framing their relationship as toxic and two-sided.
The judge postponed a decision on whether domestic violence claims would be allowed into evidence.
May 12: Opening Statements Paint Starkly Opposing Pictures
With the jury finalized, opening statements began. Prosecutor Emily Johnson described Diddy as someone who ran a “criminal enterprise,” allegedly organizing wild, abusive sex parties known as “freak offs.” The prosecution accused him of beating Cassie, threatening her with explicit videos, and using staff to cover up assaults. They emphasized this wasn’t about his “private sexual preferences”—this was criminal behavior.
Diddy’s lawyer, Teny Geragos, admitted Diddy had a history of violence but argued that this wasn’t sex trafficking. “Yes, he loved baby oil. That’s not a federal crime,” she said. Geragos insisted that all alleged participants in the events had acted with full consent.
May 13: Graphic Testimonies Detail Alleged ‘Freak Offs’
The court heard from Israel Florez, a former hotel security guard, who recalled finding Diddy in a “demonic state” and Cassie visibly terrified in the now-infamous 2016 incident.
Then came Daniel Phillip, who testified he was paid thousands to have sex with Cassie while Diddy watched and sometimes recorded. “It’s just for insurance,” Diddy allegedly told him while snapping a photo of Phillip’s ID—an act Phillip viewed as a threat.
May 13 (Continued): Cassie Takes the Stand with Chilling Allegations
Cassie’s emotional testimony laid bare a disturbing relationship filled with control, violence, and humiliation. She said Diddy recorded her during sex, used blackmail, and pushed her into using drugs to endure the “freak offs.” She described being choked while urinated on by escorts allegedly found via Craigslist, sometimes even during her periods.
Cassie also described feeling creatively restricted, claiming Diddy’s influence hindered her musical growth.
May 14: Cassie vs. Diddy—Round Two
Cassie continued her testimony, addressing rumors that she, too, was abusive. She admitted to minor physical altercations but claimed Diddy’s attacks left visible marks, unlike hers. She also revisited the 2016 video incident and accused Diddy of raping her near the end of their relationship.
May 15: Defense Cross-Examines Cassie Over Diddy Abuse Trial Allegations
On Day 3 of Cassie’s testimony in the high-profile Diddy abuse trial, the defense team came out swinging. Cassie faced intense questioning from attorney Ana Estevao, who delved into her past with Diddy and probed their rumored drug use. The defense, on the other hand, tried to reframe Diddy’s unsettling actions as simply part of an open, ‘swinger-style’ relationship. Estevao pointed to messages Cassie had sent Diddy—professing love and expressing enjoyment of “Freak Off” sessions. When asked about a message where she said she loved parties, Cassie clarified, “At that time, saying I loved Freak Off was just a phrase.”
Cassie also spoke about her 2015 break from Diddy when she briefly dated actor Michael B. Jordan. Despite being with someone else, she continued participating in Diddy’s notorious “Freak Offs,” admitting, “It became a job.”
Estevao even brought up an online rumor about baby oil used in these encounters being laced with date-rape drugs—something Cassie flat-out denied. Still, the judge reprimanded the defense for prolonging their line of questioning while Cassie, visibly pregnant, remained on the stand.
May 16: Homeland Security Testifies, Don Richard Describes Violent Incident
After Cassie wrapped up her testimony in the ongoing Diddy abuse trial, federal agents and other witnesses took the stand. Special Agent Yasin Binda recounted raiding Diddy’s Manhattan hotel room in September 2024, where authorities found five bottles of baby oil, lube in the tub and nightstand, and a Louis Vuitton bag containing ketamine, MDMA, and a bottle labeled for “Frank Black.”
Former Danity Kane member Dawn Richard stunned the courtroom by detailing a 2009 incident where she allegedly saw Diddy attack Cassie with a skillet in his LA home. She recalled, “He was raging, came into the kitchen, and tried to hit her in the head with a pan.”
Although the defense tried to dismiss Richard’s claims, prosecutors argued that this pattern of violence fostered an environment where Diddy felt untouchable.
May 19: New Witnesses Strengthen Case in Diddy Abuse Trial
Richard returned to the stand, asserting that she’d witnessed Diddy physically abuse Cassie “often”—including in 2010 while celebrities watched and stayed silent.
Cassie’s former friend Keri Morgan also testified. She recounted an incident where Diddy allegedly lashed out with a wooden hanger after discovering Cassie had been seeing another man. He allegedly struck her so hard she vomited and suffered injuries. Later, Diddy and Cassie reportedly tried to silence Morgan with a $30,000 NDA, which she accepted—cutting off all contact with Cassie from that point on.
Next came David James, Diddy’s ex-personal assistant, who worked for him from 2007 to 2009. James testified to grueling work conditions, claiming he worked 6–7 days a week from 8 a.m. to 4 p.m., often without breaks, earning $70,000 a year.
James described a “drug bag” Diddy traveled with—packed with $10,000 cash, over 30 pill bottles, and even ecstasy pills shaped like Obama’s head. He alleged that Diddy sometimes used his name to obtain prescriptions and claimed supplying baby oil and drugs was part of his job—paid in cash by Diddy’s security.
May 20: Claims of Threats, Drugs & Dangerous Orders Emerge in Diddy Abuse Trial
James testified further about a New Year’s Eve party where he was caught drunk on camera. Later on, Diddy supposedly warned him that he’d ‘keep the footage safe,’ just in case it ever came in handy as leverage. James recalled once working 21 straight days, and said a colleague was hospitalized for dehydration after 24 hours on duty. One saying among Diddy’s crew stuck with him: “Do you know what tired means? Fired.”
James also revealed an unsettling incident involving Suge Knight. According to him, Diddy once armed himself with three handguns and ordered James and others to confront Knight.
He also claimed Diddy pressured him to file a false police report against former chef Jordan Atkinson—an order James resisted by pretending to comply.
Cassie’s mother, Regina Ventura, also testified, claiming she once took out a $20,000 home equity loan to pay Diddy when he allegedly threatened to release sexually explicit videos of Cassie. She said he returned the money days later.
May 21: More Shocking Discoveries in Diddy Abuse Trial Raid & Psychological Analysis
The trial resumed with DHS Agent Gerard Gannon presenting items seized during a raid on Diddy’s Star Island mansion in Miami. Among the findings were dozens of baby oil and lubricant bottles, cocaine traces on a Gucci bag, and MDMA tablets—some branded with the Tesla logo. A .45-caliber handgun and multiple rounds were also discovered.
Forensic psychologist Dawn Hughes took the stand next, explaining why victims often stay in abusive relationships. Referring to Cassie’s past testimony about using drugs to “disconnect” from reality while with Diddy, Hughes said it’s not uncommon. She emphasized how an abuser’s “wealth, access, and power” can silence victims. “Fear,” she said, “is incredibly paralyzing.”
Final Witness: Diddy’s Former Assistant Alleges Toxic Work Culture
The final testimony came from George Kaplan, Diddy’s executive assistant from 2013 to 2015. Kaplan described a toxic work environment where he was frequently threatened with termination—even for minor mistakes like bringing the wrong size water bottle. He claimed he bought MDMA for Diddy and was constantly on edge.
The Diddy Abuse Trial So Far: A Culture of Control, Intimidation, and Fear
From Cassie’s harrowing accounts to ex-employees detailing years of alleged misconduct, the Diddy abuse trial has peeled back the veil on a disturbing world of drugs, violence, and psychological domination. As more witnesses are set to testify, the full scope of Diddy’s alleged behavior continues to shock the nation.
Conclusion:
The Diddy Trial NYC is rapidly becoming one of the most gripping and disturbing celebrity cases in recent history. With damning testimony, explicit claims, and emotionally raw moments piling up day by day, this courtroom saga is far from over. And as Cassie, anonymous witnesses, and even security guards take the stand, the world watches a legacy unravel—one statement at a time.
