May 16, 2025
Friday 5/16 Day 10. Cassie Under Fire
Day 10 of the Diddy trial brings relentless courtroom drama as Cassie Ventura, eight months pregnant, endures a marathon cross-examination. The defense bombards her with explicit texts, questions about her past, and accusations of financial motives, while Cassie stands firm on claims of coercion, violence, and control. Tensions explode over evidence, legal teams clash, and the judge struggles to keep order. Outside, tabloids and social media dissect every salacious detail as the world waits for the next bombshell. Nate Oliver breaks down the rawest moments yet in this gripping episode of Diddy: Did He 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 that digs into every gritty, unfiltered detail
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of the Seawan Ditty Comb's sex trafficking and racketeering trial.
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I'm Nate Oliver, reporting from outside the Manhattan Federal Courthouse
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on Friday, May sixteenth. Yesterday's session was a marathon of
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cross examination, as Cassie Ventura, eight months pregnant, and the
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prosecution star witness, faced the full force of Ditty's defense team.
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The courtroom was tense from the outset. Cassie, composed but
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visibly weary, took the stand for a third straight day,
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her testimony now stretching over twelve hours in total. The defense,
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led by Anna Estevao, wasted no time, launching into a
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barrage of pointed questions designed to chip away at Cassie's
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credibility and the prosecution's narrative of coercion and abuse. Estevou
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started by pressing Cassie on the origins of her relationship
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with Combs, highlighting that she was dating another music industry figure,
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Ryan Leslie, when she met Ditty. The defense then pivoted
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to the heart of the case, the so called freak offs.
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Jurors listened as este Vau read out a series of
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explicit text messages and emails between Cassie and Ditty, some
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dating back more than a decade. In one exchange, Cassie texted,
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I love rfos, a reference to the parties at the
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center of the case. When asked about this, Cassie replied
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loving foss were just words at that point, insisting that
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her participation was coerced, not voluntary. The defense didn't stop there.
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They introduced additional messages in which Cassie appeared to joke
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about sex and express affection for Ditty, including one where
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she replied, lol me two, I want to have fun
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with you after Ditty suggested a freak off. Estevou argued
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that these exchanges showed a relationship built on mutual desire,
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not fear. Cassie, sticking to her story, testified that her
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words massed a much darker reality, one where she felt trapped, manipulated,
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and unable to escape Ditty's control. The cross examination grew
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more heated as the defense zeroed in on Cassie's twenty
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million dollars civil settlement with Ditty, suggesting that financial motives
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played a role In her testimony, Cassie, giving short direct answers,
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denied any ulterior motive, describing the settlement as a way
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to finally break free from years of trauma. The defense
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also grilled her about her relationships with other men, including
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rumors about Michael B. Jordan and rapper Kid Coody. Cassie
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admitted to buying a burner phone to keep in touch
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with Kid Cooty, fearing Ditty's reaction if he found out.
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The defense tried to paint a picture of mutual jealousy
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and infidelity, suggesting that both parties contributed to the toxicity
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of the relationship. Tensions in the courtroom flared for when
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the defense sought to introduce even more text messages and
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emails as evidence. The prosecution objected, leading to a heated
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exchange before Judge Arun Subramanian. The judge ultimately allowed some messages,
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but warned both sides to avoid trial by ambush. He
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also reminded everyone that Cassie must finish her testimony by
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the end of the week given her advanced pregnancy. The defense, however,
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signaled they may need more time, raising the possibility that
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Cassie could be called back for redirect questioning on Monday.
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Cassie's testimony also delved into Ditty's alleged substance abuse. She
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described how he would binge on ecstasy and cocaine, then
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crash for days, only to become irritable and demanding during withdrawal.
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Cassie testified that Ditty's need for control was relentless. He
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would call her repeatedly, demand constant updates on her whereabouts,
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and send staff to track her down if she didn't answer.
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She described being isolated from friends and family, her phone,
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mind monitored, and her movements dictated by Ditty's suspicions and anger.
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The defense, for their part, acknowledged Ditty's history of violence
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and substance abuse, but argued that these issues did not
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amount to racketeering or sex trafficking. They characterized the relationship
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as unconventional, fueled by jealousy and passion, and insisted that
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Cassie and other women were motivated by money and revenge.
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At one point, the defense highlighted that Cassie had not
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only forgiven Ditty in the past, but had continued to
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live with him and travel together even after some of
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the most serious alleged incidents. The prosecution countered by emphasizing
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the psychological manipulation at play. Cassie described how Ditty would
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both uplift and undermine her, calling her a queen in
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one breath and threatening her in the next. She testified
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that Ditty used his power and influence to control her career,
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block opportunities, and keep her financially and emotionally dependent. The
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jury was shown images of Cassie these bruises allegedly inflicted
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by Ditty, and watched the infamous twenty sixteen hotel surveillance
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video showing him assaulting her in a hallway. Beyond the
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personal drama, the courtroom was also a battleground for legal maneuvering.
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The defense and prosecution sparred over the admissibility of evidence,
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especially regarding text messages that touched on Cassie's sexual conduct
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with other men. The judge invoked the rape shield law,
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weighing the relevance of these messages against the risk of
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unfairly prejudicing the jury. Throughout it all, did he sat
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at the defense table, dressed in a honeycolored sweater and
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white collared shirt, conferring quietly with his legal team, His family,
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including his mother and sons remained a steady presence in
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the gallery, their faces tense as the most graphic details
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spilled out. An open court outside the courthouse buzzed with activity.
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The line to get in was shorter than earlier in
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the week thanks to dreary weather and heavy fog, but
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the media, TikTokers and diehard Ditty supporters kept the energy high.
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The Daily Mail and other tabloids splashed Cassie's cross examination
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across their front pages, zeroing in on every salacious detail,
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from explicit texts to rumors of additional celebrity witnesses waiting
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in the wings. Legal analysts and social media pundits were
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quick to weigh in. Some argued that the defense's strategy,
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admitting Diddy's history of violence but framing the relationship as
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consensual and fueled by mutual jealousy, was risky but might
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resonate with jurors exhausted by the endless parade of explicit details.
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Others pointed out that the prosecution's evidence, including the hotel
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video and Cassie's medical records, painted a picture of a
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relationship defined by coercion, fear, and psychological control. More in
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a moment looking ahead, today's session is expected to bring
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the final chapter of Cassie Ventura's testimony. The defense will
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likely continue hammering away at her credibility, focusing on inconsistencies,
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financial settlements, and her own admissions of infidelity. Prosecutors are
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preparing to redirect, hoping to reinforce Cassie's account of violence, blackmail,
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and the machinery of control that allegedly kept her and
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others trapped in Ditty's orbit. There's also speculation that the
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prosecution may introduce new digital evidence, including more text messages
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and possibly audio recordings, to further corroborate Cassie's claims. As
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the trial barrels into its second week, the stakes couldn't
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be higher did He faces five criminal charges, including racketeering, conspiracy,
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sex trafficking by force, and transportation for a prostitution. If convicted,
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he could spend the rest of his life behind bars.
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The outcome may hinge on whether the jury believes Cassie
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Ventura's harrowing account or the defense's portrait of a toxic
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but ultimately consensual relationship. That's where we stand as the
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trial and enters another day tomorrow. I'll bring you every
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new revelation, every legal twist, and every rumor from inside
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and outside the courthouse. I'm Nate Oliver and this is
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Diddy do It.
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