June 9, 2025
Monday 6/9 Day 26. The Weight of Truth — Jane’s Harrowing Testimony and the Trial’s Turning Point
As the trial resumes after the weekend, Nate Oliver revisits the explosive testimony from last week, focusing on Jane’s graphic account of relentless sexual coercion, drug-fueled "freak offs," and psychological control. With mounting physical and digital evidence, the prosecution’s case grows stronger, while the defense prepares to challenge the credibility of key witnesses. Nate unpacks the emotional toll, the legal battles, and what’s expected in the coming days as the trial moves toward a dramatic conclusion.
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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 Ditty Comb's sex trafficking and racketeering trial. I'm Nate
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Oliver outside the Manhattan Federal Courthouse on Monday, June ninth.
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As another pivotal week in this historic case is about
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to begin with the courtroom doors about to open, Let's
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take a deep breath and look back at the extraordinary,
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often harrowing testimony from last week, a week that saw
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the prosecution's case reach new heights of intensity and detail
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and left the public, the press, and the jury reeling.
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The week was dominated by the testimony of Jane, the
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pseudonymous ex girlfriend, whose account has become one of the
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most graphic and emotionally charged in the trial so far. Jane,
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who was in a relationship with Ditty from twenty twenty
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one until his arrest in twenty twenty four, described a
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world of relentless sexual coercion, drug fueled freak offs, and
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psychological manipulation that left her broken, exhausted, and desperate to escape.
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Jane's story began with what she described as a whirlwind romance,
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long walks on the beach, lavish vacations, and affectionate nicknames,
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but by twenty twenty one, things turned dark. Ditty began
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orchestrating hotel nights what other witnesses like Cassie Ventura, called
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freak offs. Jane told a jury that about ninety percent
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of her sexual encounters with Ditty involved another man, usually
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a male escort or performer, and that these nights were
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almost always filmed by Ditty on his cell phone. At first,
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Jane said she went along with the encounters out of
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love and fear of losing Ditty, but as the months
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wore on, she began to resist, telling Ditty, both in
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person and in writing, that she didn't want to have
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sex with other men. He would dismiss her concerns, sometimes
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calling her irrational or promising to stop, only for the
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hotel nights to continue. The prosecution presented the jury with
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fifteen images Jane said were taken during these encounters. Jane
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testified that Ditty was present for every hotel night, instructing
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her on how to behave what to say, and even
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what positions to hold for extended periods, all for his
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own viewing pleasure. She described suffering from chronic urinary tract infections,
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yeast infections, and physical pain as a result of these
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prolonged drug fueled sessions. She said she would pretend to
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enjoy it because she wanted to put on a good show,
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but inside she was hating every minute. Jane also described
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the logistics. Diddy would hand cash to mail escorts after
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the sessions, and if he ran low, would call his
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security team or chief of staff to bring more money.
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She recounted a particularly traumatic birthday, expecting a romantic evening
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only to find male escorts waiting in her hotel suite.
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She recalled how she was made to go back and
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forth between the men all night. When one man left
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in the morning, Ditty told her Don is coming and
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she had sex with him too. The prosecution played audio
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from a video where Jane asked a male performer to
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use a condom. Ditty's voice can be heard interrupting and
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expressing his disapproval. Jane testified that Ditty twice rebuffed her
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requests that male performers wear condoms, making her feel guilty
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for even asking. When asked why she didn't insist, Jane
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replied that she didn't want to let her lover down.
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She said she felt she had no real choice, especially
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after Ditty threatened to stop paying her rent if she
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refused to participate. Jane's testimony was often interrupted by tears,
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and at one point the judge called a break when
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she was unable to answer why she pretended to be
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okay with the freak offs if she hated them so much.
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She described the sense of dread that would set in
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every time Ditty texted her about entertainment or hotel nights.
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She described how Ditty's assistance would prepare the rooms in advance,
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sometimes illuminating them with red lights, and how she would
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arrive to find everything set up for another night of coercion.
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The emotional toll was immense. Jane described how Ditty would
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keep her high on ecstasy or other drugs during these sessions,
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sometimes for hours or even over eighteen hour stretches. She
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described blacking out vomiting after being forced to have sex
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with multiple men in a row, and being told by
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Ditty that she'd feel better after throwing up, so they
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should continue. She said that after these episodes, Ditty would
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push her to finish strong, ignoring her pleas for rest, food,
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or comfort. He was disgusted at her crying, Jane told
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the jury, and would say not to do that right now,
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that he couldn't deal with it. He was too high.
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Jane's account closely mirrored Cassie Ventura's earlier testimony, with both
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women describing a pattern of being forced into encounters with
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male sex workers dubbed freak offs or hotel nights, and
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being subjected to violence, surveillance, and blackmail. Jane said she
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would send Ditty subtle cues saying she was tired or hungry,
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making faces and gestures, but he ignored them, insisting she
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finished strong, or calling her irrational for objecting. When she
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tried to talk about ending the encounters, Diddy would shut
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her down or change the subject. The prosecution also introduced
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text messages between Jane and Ditty, including one where Jane
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wrote that she no longer wanted to play this role
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in his life, that it was dark, sleazy, and made
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her feel repulsed. She said she didn't want to feel
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obligated to engage in these nights out of fear of
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losing her home. Ditty's reply girl stop. Jane testified that
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by September twenty twenty three, Ditty had been paying her
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rent for about five months, and she feared that if
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she refused to participate in hotel nights he would take
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her house away. The jury saw a copy of her
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lease for a ten thousand dollars per month home, an
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amount Jane said she could never afford in her own
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more in a moment. Throughout the week, the prosecution reinforced
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Jane's account with corroborating testimony and forensic evidence. Jurors saw photos,
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financial records, and heard from hotel staff about the elaborate
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and secretive logistics surrounding these events. Other witnesses described similar
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patterns of coercion, secrecy, and the use of NDAs and
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cash payments to keep staff and participants silent. The judge, meanwhile,
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kept a tight rein on the courtroom. After observing Ditty
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nodding vigorously at the jury during testimony, Judge Aaron Subramanian
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issued a stern warning any further attempts to influence the
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jury through facial expressions, gestures, or eye contact could result
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in Ditty being removed from the courtroom for the remainder
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of the trial. The judge's warning was clear that the
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integrity of the trial would not be compromised as we
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look ahead to today. In the coming week, the prosecution
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is expected to continue with more witnesses and evidence. Jane
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is likely to face cross examination from the defense, which
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has signaled it will focus on her continued contact with
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Ditty after the alleged abuse, as well as sexually explicit
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messages she sent him between encounters. The defense maintains that
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while Ditty's relationships were unconventional and sometimes involved violence, all
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sexual acts were consensual, and that the women involved were
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adults who made their own choices. Legal analysts say the
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prosecution's narrative of a world where Ditty used his wealth, celebrity,
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and psychological manipulation to coerce women into sex has grown
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more compelling with each new witness. The emotional weight of
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Jane's testimony, combined with the mounting physical and digital evidence,
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has cast a long shadow over the defense's case. The
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trial is expected to continue building toward a dramatic conclusion,
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with the prosecution aiming to tie together the stories of
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Cassie Mia, Capricorn, Clark and Jane into a pattern of
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racketeering and sex trafficking. The defense, meanwhile, we'll try to
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poke holes in the witness's credibility and argue that the
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government is criminalizing Ditty's lifestyle, not proving a criminal enterprise.
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That's where we stand as the doors open on another
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week in this historic trial. I'll be back tomorrow with
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every new revelation, every legal twist, and every rumor from
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inside and outside the courthouse. I'm Nate Oliver, and this
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is Did He Do It? This episode of Ditty Did
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He Do It? Was produced by Mark Francis and John
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McDermott for Calaroga Shark Media. Some AI production assistants may
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have been used.
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135
00:08:32.120 --> 00:08:34.240
136
00:08:34.279 --> 00:08:37.679
137
00:08:37.759 --> 00:08:41.519
138
00:08:41.600 --> 00:08:45.200
139
00:08:45.279 --> 00:08:49.840
140
00:08:49.879 --> 00:08:52.279
141
00:08:52.360 --> 00:08:56.480
142
00:08:56.519 --> 00:08:57.120