May 15, 2025

Thursday 5/15 Day 9. Secrets, Scandals, and Showdowns

Show Notes
Transcript

Day 9 of the Diddy trial erupts with fierce cross-examination as Daniel Phillip faces the defense’s relentless grilling over his “freak off” party testimony. A former personal assistant reveals the secretive, high-pressure world inside Diddy’s camp, including hush money deliveries and Cassie’s visible bruises. Emotions run high in the courtroom, with Diddy’s family shaken and the jury riveted by every detail. Outside, rumors swirl about surprise celebrity witnesses and new evidence. As legal experts debate game-changing testimony and social media explodes, Nate Oliver breaks down all the drama and what’s coming next on Diddy Do It?

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Calaruga Shark Media Welcome back to Didy Do It, the

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daily podcast following every raw, unfiltered twist in the sex,

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trafficking and racketeering trial of Sean Ditty. Comb's I'm Nate Oliver,

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reporting from just outside the Manhattan Federal Courthouse on Thursday,

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May fourteenth, Yesterday, the courthouse was a pressure cooker of scandal, fear,

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and spectacle as Cassie Ventura returned to the stand, visibly

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pregnant and clutching a tissue. Cassie's voice wavered, but never

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broke as she peeled back the curtain on her decade

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with Ditty, a story that's less romance more cautionary tale.

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She described meeting Combs at nineteen, signing a ten album deal,

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and being swept into a world that looked glamorous from

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the outside, but was, in her words, a gilded cage.

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Cassie testified that Ditty micro managed her every move, what

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she wore, who she spoke to, even what she ate.

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She said she was isolated from friends and family, her

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phone monitored, and her schedule dictated by Ditty's moods and whims.

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The heart of her testimony was the freak offs what

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she called her full time job. Cassie described marathon, drug

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fueled sex parties where she was expected to perform for

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Ditty and his friends, sometimes with strangers or hired sex workers.

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She said she was often given ecstasy or cocaine, not

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always by choice, and that Ditty would sometimes film the

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encounters or direct them like a movie. The jury sat

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stonefaced as Cassie described being passed around like a party

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favor her words raw and unvarnished. I lost track of

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my own body, she said. I was there for his pleasure,

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not mine. Cassie didn't shy away from the violence. She

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described being knocked down, dragged by her hair, kicked and

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stomped on, and when she resisted Ditty's demands. She said

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he'd call her dozens of times a day, and if

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she didn't answer, he'd dispatch staff to find her, sometimes

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threatening her with consequences if she tried to leave. She

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recounted one night when she locked herself in a bathroom,

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only for Ditty to break down the door and drag

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her out, screaming. He told me nobody would believe me

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if I ever talked, Cassie told the jury. He said

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he'd ruin me. The prosecution played the now infamous hotel

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surveillance footage showing Ditty kicking and dragging Cassie in a hallway,

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then throwing a vas at her. Security chief Israel Flores,

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now an LAPD officer, testified that he found Cassie with

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a swollen purple eye, and that Ditty tried to pay

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him off to keep quiet. I don't want your money.

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Just go back into your room, Flores recalled, saying Cassie,

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Flores said, refused to call the police, her fear written

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all over her face. But the day's darkness didn't end there.

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Daniel Phillip, a former mail stripper, took the stand and

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described being paid by Cassie between twenty twelve and twenty

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fourteen for sex acts while Ditty watched, sometimes filming, sometimes

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barking orders. Philip said these freak offs could last up

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to ten hours. He described waiting alone in hotel rooms

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for Ditty's signal, then being summoned for encounters that he

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said felt transactional and degrading. Philip told a jury he

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saw Ditty assault Cassie more than once, but never intervened,

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admitting I was afraid I'd seen what happened to people

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who crossed him. The defense, led by Tenny Garagos, tried

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to paint all of this as consensual. Ditty as a jerk,

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maybe even a monster, but not a criminal. They admitted

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to domestic violence, substance abuse, and a bad temper, but

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insisted the relationships were about sex, money, and fame, not trafficking.

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Jergos grilled Philip about selling his story to tabloids, d

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jesting he was in it for the payday. She also

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pointed to Cassie's thirty million dollar lawsuit and quick settlement,

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calling her testimony revenge not truth. But the prosecution hammered

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the power dynamic and the fear. Assistant US attorney Elizabeth

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Johnson called Ditty the king of his own criminal empire,

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using money, staff, and intimidation to keep women compliant and silent.

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Johnson introduced evidence of non disclosure agreements, cash payments, and

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threats to ruin anyone who spoke out. The jury heard

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about Jane, another alleged victim, who was kept financially dependent

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on Ditty and forced into freak offs herself. There was

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testimony from a former assistant who described delivering cash stuffed

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envelopes to women threatening to go public and being told

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don't ask questions, just do it. The emotional toll was

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visible during the most graphic testimony. Ditty's daughters left the

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courtroom in tears, and his son was seen comforting their grandmother.

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Cassie's friends in the gallery wept quietly. Even some jurors

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looked shaken. One alternate scene wiping her eyes as the

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hotel video played again. Outside the courthouse was a circus.

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Media tents lined the block, TV crews broadcasting every lurid detail.

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People were selling their spots in line for hundreds of dollars.

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The air was thick with rumors, whispers of more celebrity witnesses,

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of surprise, evidence of audio recordings that could blow the

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case wide open. Security was tight, with police searching bags

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and checking credentials at every entrance. On social media, the

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hashtag Diddy trial exploded. Some users called Cassie a hero,

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others accused her of chasing money and fame. Viral posts

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compared the trial to a Netflix true crime doc in

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real time, and debated whether the jury could possibly stay

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impartial with so much graphic evidence and tabloid frenzy. Legal

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analysts on cable news and legal blogs argued over the

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day's bombshells. Some said the assistants testimony about hush money

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and non disclosure agreements could be a turning point, giving

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jurors a glimpse into how Ditty's inner circle operated. Others

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warned that the defense's aggressive cross examination of Philip risked

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looking like bullying, especially with the jury visibly affected by

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the testimony more in a moment. Looking ahead, today's session

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is expected to bring even more fireworks. Cassie's closest friend

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is set to testify, reportedly ready to back up Cassie's

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story with text messages and emails. Prosecutors are pushing to

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introduce audio recordings said to capture Ditty instructing staff to

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get rid of people who talk. The judge is expected

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to rule on the admissibility of this evidence, which could

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add a whole new layer to the case. There's talk

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of another high profile witness waiting in the wings, someone

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from Ditty's management team who may have firsthand knowledge of

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payouts and threats. The defense is expected to keep attacking credibility,

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painting every witness as an opportunist, but the prosecution seems

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determined to show that This was a criminal enterprise built

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on fear, control and silence. That's where we stand as

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the trial gets darker, messier, and more explosive by the day.

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Tomorrow will bring you every new revelation, every rumor, and

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every raw moment from inside and outside the courthouse. I'm

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Nate Oliver, and this is Diddy do It.