May 14, 2025

Wednesday 5/14 Day 8. Cassie Breaks Her Silence

Show Notes
Transcript

Cassie Ventura takes the stand in a dramatic day of testimony that leaves the courtroom-and the internet-reeling. She details years of alleged abuse, control, and the infamous “freak off” parties at the heart of the prosecution’s case against Diddy. The jury watches shocking hotel surveillance footage, while a former stripper testifies about secret encounters and threats. Emotions run high as Diddy’s family reacts and social media explodes with debate. Legal experts weigh in, the defense pushes back, and rumors swirl about surprise witnesses ahead. Nate Oliver breaks down every twist in this can’t-miss episode of Diddy Do It?

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WEBVTT

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

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The daily podcast following Every Twist in the sex trafficking

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and racketeering trial of Sean Diddy Comb's I'm Nate Oliver.

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Outside the Manhattan Federal Courthouse on Wednesday, May thirteenth, yesterday,

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the courtroom was electrified as the prosecution called its two

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most anticipated witnesses so far. The day began with Cassandra

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Cassie Ventura herself taking the stand, now thirty eight and

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visibly pregnant. Cassie described a decade long relationship with Combs

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that began when she was just nineteen and signed to

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his label. She told the jury that Combs controlled nearly

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every aspect of her life and career, from what she

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wore to who she spoke with, and recounted how she

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recorded hundreds of songs under his direction that were never released.

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Cassie's testimony painted a harrowing picture of abuse. She described

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how so called freak Off's prolonged drug fueled sex parties

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with sex workers became her full time job, leaving her

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with little time for anything but recovering and trying to

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feel normal again. She told the jury that Combs would

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knock her down, drag her, kick her, and stomp on

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her head if she resisted his demands. Cassie also said

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he would have staff or friends track her down if

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she didn't answer his calls, and that he would sometimes

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send someone to physically find her. The jury was shown

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the infamous twenty sixteen hotel surveillance footage previously aired by CNN,

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depicting Comb's kicking and dragging Cassie in a hallway, then

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hurling a vas in her direction. Israel Floores, the security

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director at the Beverly Hills hotel, testified that he found

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Cassie with a black eye and that she declined his

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offer to call the police. Floores told the jury that

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Comb's tried to pay him off to keep quiet, but

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he refused, telling Combs, I don't want your money, just

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go back into your room. The second witness, Daniel Phillip,

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a former mail stripper, described being recruited by Cassie for

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freak off parties orchestrated by Ditty. Philip testified that he

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was paid thousands of dollars on multiple occasions between twenty

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twelve and twenty fourteen to have sex with Cassie while

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Combs watched, sometimes giving instructions and recording the encounters on

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his phone or camcorder. Philip said some of these sessions

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lasted up to ten hours, though he spent much of

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the time waiting alone. Philip recounted two incidents of physical

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abuse he witnessed. In one, Combs called for Cassie, and

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when she didn't respond immediately, he threw a liquor bottle

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at the wall, grabbed her by the hair, and dragged

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her into the bedroom. Philip remembered Cassie crying out I'm sorry,

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while Combs yelled when I tell you to come, you

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come now, not later. In another incident at a Manhattan hotel,

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Philip heard Cassie shouting I'm sorry as if she were

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being struck. She ran into the living room, jumped into

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his lap, and was visibly trembling. Philip said he never

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reported the violence because Combs had threatened him after taking

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a photo of his driver's license. The defense, led by

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Tenny Garragos, acknowledged that Combs had a temper and committed

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acts of domestic violence, but insisted the case was about love, jealousy, infidelity,

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and money, not sex, trafficking or racketeering. Jiragos argued that

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the encounters were consensual between adults and suggested that Cassie

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and other accusers were motivated by financial gain, highlighting Cassie's

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previous thirty million dollar lawsuit and quick settlement. The day

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was not without emotional moments. During the most graphic testimony,

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Combe's daughters left the courtroom and his son was seen

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comforting his grandmother. The jury, a diverse mix of New

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Yorker's watched intently and took notes as the prosecution and

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defense painted ste darkly different pictures of the relationship at

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the heart of the case. We'll be back in a moment.

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On social media, Cassie's testimonies set off a firestorm. The

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hashtag Diddy trial was trending, with users split between support

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for Cassie and skepticism about the prosecution's case. One viral

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post compared the day's testimony to a scene straight out

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of a Netflix thriller. Others debated whether the jury can

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truly remain impartial with so much public attention and graphic

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evidence circulating online. Legal experts weighed in across cable news

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and legal blogs. Several commentators argued that the hotel video

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could prove pivotal, especially since it was corroborated by both

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Cassie and the hotel security director. Some analysts pointed out

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that the defense's strategy of admitting to violence but denying

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trafficking is a high stakes gamble that could backf with

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a jury looking for clarity. Inside the courtroom, the emotional

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temperature was high. Ditty's daughters left during the most graphic testimony,

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and the jury appeared visibly moved. A few jurors were

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seen taking extra notes, and one alternate was seen shaking

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her head as the video played looking ahead. The judge

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has announced that today's session will feature further cross examination

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of Daniel Phillip, with the defense expected to challenge his

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credibility and motives. There's growing speculation that a surprise witness

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from Ditty's management team could take the stand later this week,

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potentially offering new insight into the inner workings of Combe's empire.

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The prosecution is also expected to introduce additional evidence, possibly

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including more surveillance footage and audio recording said to capture

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Comb's giving instructions to his staff. All eyes remain on

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the schedule for more testimony from Cassie, and other members

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of Ditty's inner circle. As the trial promises more revelations

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in the days to come. That's where we stand as

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the trial enters an other day tomorrow. We'll bring you

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the latest from inside and outside the courthouse with every twist,

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rumor and headline. I'm Nate Oliver and this is Diddy

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do It.