June 10, 2025
Tuesday 6/10 Day 27. “A Very Terrible Day” — Jane’s Breaking Point and Diddy’s Threats
Day 27 delivers raw emotion as Jane returns to the stand, recounting the chaos, coercion, and psychological warfare of her final months with Diddy. From violent fights and “hotel nights” to chilling threats over sex tapes and housing, Jane’s texts and testimony expose the machinery of control at the heart of the prosecution’s case. As the jury hears about love-bombing, rent ultimatums, and the trauma of living as Diddy’s “on-call party girl,” Nate Oliver unpacks every explosive detail and previews what’s next as the trial enters its most pivotal week yet.
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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 diddycomb sex trafficking and racketeering trial. I'm Nate Oliver
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outside the Manhattan Federal Courthouse on Tuesday morning, June tenth.
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As we enter the sixth week of this historic trial. Today,
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I'm recapping Monday's testimony, one of the most emotionally charged
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and revealing days yet. Has Jane returned to the stand
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For her third day of testimony. Jane's account continued to
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lay bare the dark, coercive underbelly of her years with Ditty.
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She began by describing how, after returning to Los Angeles
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from Miami in twenty twenty two, she didn't see Ditty
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in person again until June eighteenth, twenty twenty four. That date,
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she told the jury, was a very terrible day. The
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two had planned a date night at her home, with
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Ditty's assistant arriving first to help set up decorations, candles,
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and stalk the fridge when Ditty arrived, Jane said they
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spent some time reconnecting in the backyard. Photos and a
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video recorded by Cassie Ventura were shown to the jury,
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with Ditty's voice heard in the background, but the night
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quickly turned. Jane testified that an argument erupted over Ditty's
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recent family trip to Utah. She accused him of seeing
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another woman, someone about twenty five years younger than him.
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In the heat of the confrontation, Jane admitted to pushing
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Ditty's head against a marble counter as he bent to
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tie his shoe. She said she also threw candles around
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the house, some of which splattered wax on Ditty's clothing.
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Jane described Ditty's reaction as furious, cursing at her as
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the argument escalated. She said she didn't see any injuries
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on him, but remembered the chaos and her own rage.
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I hated him in that moment, she told the court.
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The prosecution then shifted to a series of text messages
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and phone calls exchanged between Jane and Ditty in early
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twenty twenty four. Jane recounted how Ditty continued to arrange
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hotel nights, the term both used for the drug fueled
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multi partner sexual encounters that have become central to the
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prosecution's case. Jane read aloud her own texts, telling Ditty
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she was tired of the rent threats and hated living
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under the constant pressure to perform sexually or risk losing
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her home. She reminded Ditty that she was still struggling
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with debt after three years of being his on call
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party girl, and pleaded for more time to get on
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her feet. Ditty, in turn suggested they split peacefully and
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asked her to sign a document for closure. He told
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her that since she was now earning her own income,
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he hoped for a clean break, and mentioned that his
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accountant would insure her rent was paid on time. Jane's
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testimony grew even more raw as she described the psychological
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manipulation did he employed to keep her compliant. She recounted
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how he would love bomb her, showering her with affection
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and promises of quality time, only to lure her into
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another hotel night. She told the jury that Diddy would
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promise a romantic evening then spring male escorts on her
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at the last minute. In one message, Jane wrote, you
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talk to me and treat me like a piece of
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animal anyone can aft on. Diddy replied, you got it
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all wrong. In another Jane pleaded, I don't want to
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be locked in a room to perform and fulfill your fantasies.
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Coming to the realization of what this is. Diddy responded
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that her accusations were false and that she was tired
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of your false accusations. The jury also heard about the
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toll these encounters took on Jane's health and psyche. She
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described being forced into sex with multiple men, sometimes over
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marathon sessions lasting up to three and a half days.
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She spoke about chronic infections, exhaustion, and emotional numbness. I
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would pretend to enjoy it because I wanted to put
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on a good show, she said, but inside she was
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hating every minute. Jane testified that she would try to
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signal her discomfort, but Ditty would urge her to keep going,
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ignoring her pleas for rest or food. More. In a moment,
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the prosecution presented evidence of Jane's attempts to resist. She
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showed texts where she told Ditty she didn't want to
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play this role anymore and felt obligated to participate in
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these nights with you for fear of losing my housing.
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Legal analysts noted that this evidence is crucial for the
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sex trafficking charge as it demonstrates coercion and pressure linked
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to Ditty's financial support. Jane also described a chilling escalation
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after Cassie Ventura's twenty twenty three lawsuit against Ditty. She
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testified that reading Cassie's complaint was like reading my own story.
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The jury saw screenshots Jane took of three pages from
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the suit, which she said mirrored her own trauma. Jane
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texted Ditty about the lawsuit, describing her shock and sense
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of betrayal. The court then heard a recorded phone call
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from Ditty to Jane, made just days after Cassie's lawsuit
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was filed. Jane testified she didn't know the call was
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being recorded, but prosecutors argued it showed Ditty's efforts to
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control the narrative and keep Jane silent. In perhaps the
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most disturbing exchange, Jane testified that Ditty threatened to release
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sex tapes of their hotel nights and show them to
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her child's father if she didn't cooperate. She immediately reached
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out to Ditty's chief of staff, Christina Korum, texting, he
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just threatened me about my sex tapes that he has
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on two phones. These are sex tapes where I'm heavily
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drugged and doing things he asked me. Jane told the
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jury that these threats left her feeling trapped, humiliated, and
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terrified for her future. On cross examination, the defenses expected
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to focus on Jane's continued contact with Ditty after the
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alleged abuse, as well as sexually explicit messages she sent
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him between encounters. They maintained that while Ditty's relationships were
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unconventional and sometimes involved violence, all sexual acts were consensual,
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and that the women involved were adults who made their
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own choices. As the day ended, Jane broke down, reading
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her own texts aloud to the jury, describing three years
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of me trying to f strangers and how she felt
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like a side show and sex worker in my own relationship.
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The emotional weight in the courtroom was palpable, with several
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jurors visibly affected by her testimony. Looking ahead, the prosecution
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is expected to continue with more witnesses and evidence this week,
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including additional testimony about Ditty's alleged efforts to control and
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silence those around him. The defense, meanwhile, is preparing to
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challenge the credibility of Jane and other key witnesses, arguing
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that the government is criminalizing Ditty's lifestyle rather than proving
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a criminal enterprise. That's where we stand, after another day
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of bombshell revelations, emotional breakdowns, and legal brinkmanship. I'll be
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back tomorrow with every new twist, every legal battle, and
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every 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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Ditty Did He Do It? Was produced by Mark Francis
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and John McDermott for Kalaroga Shark Media. Some AI production
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assistants may have been used.
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