May 19, 2025

Monday 5/19 Day 11. Cassie’s Bombshells & The Danity Kane Reckoning

Show Notes
Transcript

Week three of the Diddy trial erupts as Cassie Ventura’s harrowing testimony rocks the courtroom and former Danity Kane star Dawn Richard takes the stand with shocking new abuse allegations. From explicit “freak off” revelations and blackmail threats to brutal beatings and celebrity drama, the prosecution’s case against Sean “Diddy” Combs grows darker and more tangled. As new witnesses and digital evidence loom, and the defense fights to paint Diddy as flawed but not criminal, Nate Oliver recaps every jaw-dropping moment from week two and previews the explosive showdowns ahead on Did He Do It?

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WEBVTT

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Warning. This episode contains references to sexual situations that may

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be disturbing to some listeners. Please proceed with caution. Callaroga

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Shark Media. Welcome back to Did He Do It? The

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Daily Podcast bringing you every raw, unfiltered detail from the

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Sean Diddycombs sex trafficking and racketeering trial. I'm Nate Oliver,

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reporting from outside the Manhattan Federal Courthouse on Monday, May nineteenth,

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as we kick off Week three of this blockbuster case.

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Let's rewind and break down everything that happened in Week two,

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a week that delivered some of the most explosive, disturbing,

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and headline grabbing testimony yet. Cassie Ventura, the prosecution star

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witness and Diddy's former partner, dominated the courtroom for four

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relentless days. Her testimony was nothing short of seismic. Cassie,

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eight months pregnant, described in graphic detail a decade of

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alleged abuse, humiliation, and control. She told the jury how

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Diddy orchestrated freak offs, drug fueled sex parties involving escorts

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and sometimes strangers, which he would direct and film. Cassie testified,

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I felt like property. I was told who I could

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see what I could wear, when I could leave the house.

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I was punished if I stepped out of line. She

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recounted being beaten, choked, and urinated on, sometimes forced into

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acts she called humiliating. In one chilling account, Cassie described

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Ditty urinating in her mouth, saying, Sean would urinate in

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my mouth, not super often, but often enough. I didn't

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want anyone to urinate on me. She said she was

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never asked for consent and was sometimes choked because, as

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she put it, there was too much urine in my mouth.

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The jury was own explicit video stills and heard about

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Ditty's alleged blackmail tactics, how he filmed sex acts and

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kept the recordings as insurance. Cassie testified that Ditty threatened

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to release these videos if she ever left or spoke out.

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He kept everything she said as insurance. Cassie also described

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a brutal twenty sixteen beating at the Inner Continental Hotel

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in Los Angeles. After a freak off, She said Ditty

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attacked her in a hallway, leaving her with a black

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eye and swollen lip. The jury saw security footage and

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photos of her injuries. Cassie revealed she is set to

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receive a multimillion dollar settlement from the hotel, telling the

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court I think it was ten million dollars. Her cross

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examination was equally intense. The defense, led by Anna Estevau

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and Mark Agnafilo, tried to paint Cassie as a willing participant,

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reading aloud affectionate texts and emails. In one, Cassie wrote,

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I love our f o's. She explained, loving f o's

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were just words. At that point, I said what I

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needed to say to get through it. The defense pressed

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her about her twenty million dollar civil settlement with Ditty,

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suggesting financial motives, but Cassie insisted I would give it

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all back if I could erase what happened to me.

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This isn't about money. This is about finally telling the truth.

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The defense also grilled Cassie about her relationships with other men,

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especially rapper Kid Cuddy. Cassie admitted to buying a burner

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phone to keep in touch with Cuddy, saying she feared

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Ditty's reaction if he found out. She described Ditty's rage

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and threats, including the notorious allegation that he orchestrated the

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bombing of his car. Sean wanted Scott's friends to be

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there to see the carget blown up in the driveway,

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she testified. Dawn Richard, former Danity Kaine Singer, was another

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Bombshell witness. She told the Cord about a two thousand

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and nine incident when Ditty allegedly Beats for taking too

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long to cook him dinner. He came down the stairs

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screaming belligerent, asking where his food was, and hit her

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over the head and hit and kicked her on the ground.

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Richard testified. She described Ditty grabbing a skillet and trying

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to hit Cassie, who fell to the ground and curled

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up in a fetal position as Ditty punched and kicked her.

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Richard said Ditty then dragged Cassie upstairs by her hair.

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The next day, Ditty called the women to the studio,

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told them what they saw was passion and handed them flowers,

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warning people go missing, and he was trying to take

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us to the top. Richard testified that this was not

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an isolated incident. She saw Ditty abuse Ventura often. Other

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witnesses added to the prosecution's portrait of a world ruled

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by fear and silence. Daniel Phillip, a former Mail dancer

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described being paid to have sex with Cassie while Ditty

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watched and filmed. Philip told the jury he was introduced

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to Ditty as someone who worked in importing and exporting,

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and that he was initially hired for a bachelorette party,

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only to find himself in the center of a freak off.

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Homeland Security agent Yassin Binda detailed how investigators pieced together

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ENCRYPTID messages, videos, and financial records, finding hidden hard drives

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and burner phones, some stashed in designer boots at Ditty's

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Miami mansion. Binda testified that many witnesses were initially too

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frightened to cooperate, some bound by non disclosure agreements, others

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simply terrified of retaliation. The defense tried to counter the

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avalanche of accusations by framing Ditty as a flawed but

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not criminal figure, a man with a history of violence

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and substance abuse, but whose partners were consenting adults. They

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argued that the government was criminalizing unconventional relationships and consensual acts,

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not uncovering a criminal syndicate. Throughout the week, the courtroom

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was a crucible of emotion. Cassie broke down in tears,

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describing the psychological toll, telling the jury, I can't carry

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this anymore. I can't carry the shape the guilt. What's

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right is right, what's wrong is wrong? Did He? Dressed

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in muted tones, sat stone faced between his lawyers, occasionally

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glancing at the jury or conferring quietly with his team.

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His family, including his mother and sons, remained a steady

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presence in the gallery, their faces tense as the most

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graphic details spilled out. Outside the courthouse was a circus.

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The Daily Mail, New York Post and other tabloids splashed

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every salacious detail across their front pages. Tiktoker's live streamed

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from the sidewalk. Vendors hawked did he do it? T

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shirts and coffee mugs, Protesters and supporters traded chance, and

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the media camped out under umbrellas, waiting for the next bombshell.

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Even as the weather turned dreary, the crowds didn't let up,

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some camping out overnight for a seat inside. Week two

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saw a parade of music industry faces and reality TV

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personalities outside the courthouse. Dawn Richard's appearance drew a crowd

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of Danity Caine fans, while rumors swirled about surprise witnesses

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from Ditty's bad boy records days. Security was tight, with

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high profile vehicles spotted in the underground garage and extra

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officers stationed at every entrance. There was even a brief

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commotion when a well known rapper's entourage tried to cut

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the line We'll be back in a moment. Week three

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kicks off with the prosecution preparing to call even more

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witnesses from Ditty's inner circle. Don Richard is expected to

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continue her testimony, and prosecutors say her account is crucial,

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not only because she herself has accused Ditty of sexual assault, deprivation,

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and underpayment, but because she witnessed Ditty's violence toward Cassie often. Richard,

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wearing a yellow and white checkered suit, looked Ditty in

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the eye as she took the stand. She described Ditty

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as belligerent, demanding to know where his food was, and

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recounted how he hit her over the head and hit

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and kicked her on the ground. Richard said Diddy then

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dragged Cassie upstairs by her hair and the next day

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warned the women people go missing. Defense attorney Mark Agnifilo

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objected to Richard's testimony, but prosecutors argued it was directly

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relevant to the pattern of abuse. They noted Richard has

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flown across the country to be here today. Fellow former

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Danity Caine member Aubrey O'Day is also expected to take

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the stand soon, adding to the star power and tension

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in the courtroom. Prosecutors alleged that Combs used his fame

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and fortune to orchestrate an empire of exploitation, coercing women

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into abusive sex parties. His lawyers continued to argue that

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all sexual acts were consensual and although he could be violent,

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he never crossed the line into sex trafficking or racketeering.

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The week ahead could see even more bombshells on the

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witness list. Jane, who will testify about being coerced into

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unprotected sex with escorts and suffering a brutal beating from Combs. Mia,

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a former personal assistant who will describe being compelled to

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perform sex acts and being raped by Combs. Additional mail,

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sex workers, and former employees from Ditty's businesses all expected

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to shed light on the alleged machinery of control and abuse.

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More digital evidence text messages, emails, and possibly audio recordings

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may be introduced to further corroborate the prosecution's case. Judge

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arn Supermanian has made it clear he wants the trial

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to move efficiently, especially given Cassie's advanced pregnancy and the

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emotional toll on all involved. He's warned both sides to

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resolve evidentiary disputes outside the jury's presence and to avoid

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trial by ambush, a phrase he used earlier in the week.

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As we kick off week three, the stakes couldn't be higher.

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Shawn Combs faces five criminal charges, including racketeering, conspiracy, sex

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trafficking by force, and transportation for prostitution. If convicted, he

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could spend the rest of his life behind bars. The

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coming days promised more fireworks, more revelations, and more of

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the high stakes drama that's kept the world watching. That's

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where we stand as the new week begins tomorrow, I'll

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bring you every new revelation, every legal twist, and every

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rumor from inside and outside the courthouse. I'm Nate Oliver

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and this is Did He Do It? This episode of

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Did He Did He Do It? Was produced by Mark

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Francis and John McDermott for Caalaroga Shark Media. Some AI

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production assistants may have been used