June 12, 2025

Thursday 6/12 Day 29. “Captivated and Consumed” — Jane’s Final Cross, Yacht Lies, and the High Price of Survival

Show Notes
Transcript

Day 29 finds Jane still under fierce cross-examination as Diddy’s defense zeroes in on money, jealousy, and her role in the “hotel nights.” Jane pushes back, revealing the emotional chaos, manipulation, and fear that kept her trapped. She recounts broken promises, a birthday ruined by coercion, and the heartbreak of discovering Diddy’s betrayals on social media. With new testimony from a forensic psychologist explaining trauma and control, and prosecutors previewing a financial paper trail, Nate Oliver unpacks every contradiction, confession, and courtroom clash from a day that lays bare the high cost of surviving Diddy’s world.

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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.

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

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The Daily Podcast bringing you every raw, unfiltered detail from

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the Sean Dittycombs sex trafficking and racketeering trial. I'm Nate

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Oliver outside the Manhattan Federal Courthouse on Thursday morning, June twelfth,

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after another marathon day of testimony that further exposed the

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inner workings and emotional cost of Ditty's world. Wednesday's session

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was all about Jane, who returned for her sixth day

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on the stand still under relentless cross examination from Ditty's

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defense team. The courtroom was tense as Attorney Tenny Garagos

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pressed Jane on every aspect of her relationship with Ditty,

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her finances, her choices, her words, and her pain, trying

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to unravel the prosecution's narrative of coercion and control. The

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defense zeroed in on the financial support Jane received from Ditty,

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highlighting the ten thousand dollars a month rent, the forty

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thousand dollars security deposit, and the steady flow of gifts

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and travel Garagos read aloud affectionate texts, including ones where

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Jane called Ditty her crack pipe and protector, and pointed

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to messages where Jane sometimes initiated hotel nights or helped

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arrange the logistics with male escorts. Jane, emotional but resolute,

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explained that her participation was never truly voluntary. She told

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the jury, I did what I had to do to

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keep the peace. I felt compelled to engage in activities

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that my partner wanted. She described a cycle of lavish

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affection followed by sudden demands, threats to cut off support,

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and the constant fear of losing her home, her stability,

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and her child's security. The defense also tried to paint

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Jane as a willing participant, suggesting she enjoyed the perks

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of Ditty's lifestyle and was motivated by jealousy or revenge.

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They pointed to texts where Jane expressed anger about Ditty's

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other girlfriends and questioned whether he'd bought them luxury gifts.

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Jane acknowledged her jealousy and her longing for a normal,

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exclusive relationship, but said those feelings were twisted by the

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emotional chaos Ditty created, I was already so captivated from

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the start, she said, I fell for someone without fully

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grasping the terms and conditions of our relationship. One of

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the most dramatic moments came as Jane described a four

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day trip to Miami in twenty twenty three. She told

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the jury Diddy promised her a romantic yacht getaway after

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a hotel night with escorts. Instead, after the encounter, Jane

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discovered on social media that Ditty had taken another woman

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on the same yacht trip he'd promised her. She described

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feeling defeated and used, and later saw Ditty boast about

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having sex for forty eight hours with the other woman.

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In a podcast interview, the jury saw a text Jane

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sent Ditty, I don't want to be used and locked

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in a room to perform and fulfill your fantasies. Coming

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to the realization of what this is, Didy replied that

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it was just podcast talk, then dismissed her concerns as

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false accusations. Jane testified that by then Ditty had been

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paying her rent for six months, and she felt obligated

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to fulfill his sexual desires. Jane's testimony grew even more

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emotional as she described her birthday in twenty twenty three.

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She recounted how after a sushi dinner did he surprised

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her with a male entertainer for a hotel night, despite

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her repeated please that she didn't want it. It was

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my birthday and I didn't want to engage in this,

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she told the jury, her voice breaking. I just sat

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on the couch, positioned myself for intercourse, wanting to get

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it over with. I asked Sean for a condom. He

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looked at me disapprovingly, shaking his head and said you

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better ask for an e fing condom. Jane said. Ditty

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was dismissive and disappointed, walking away as the encounter unfolded.

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She described these nights as lasting twenty four to thirty hours,

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often without sleep, and sometimes involving multiple partners. Sometimes it

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would happen repeatedly with one person and then again with another.

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Jane testified, I often suppressed what I truly wanted to express.

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The defense continued to press Jane about her continued contact

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with Ditty after alleged assaults, as well as her decision

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not to immediately go to the police or file a lawsuit.

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Jane explained that she was a single mother, entirely dependent

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on Ditty for her rent and childcare, and terrified of

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losing everything. When I was with Sean, I was entirely

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consumed by him, she said. She described how she stopped

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working and traveling to ensure she was always available for

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Ditty's demands, and how she felt bitness after being exposed

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to a lifestyle built on emotional manipulation and pressure. The

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defense also sought to highlight inconsistencies in Jane's timeline, questioning

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her about specific dates and events to suggest memory lapses

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or exaggerations. They pressed her on her interactions with Ditty's

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security team, probing whether she ever reported any incidents to

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them or sought help. Jane explained that fear and loyalty

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complicated her decisions and that she often felt isolated despite

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being surrounded by staff. More in a moment, prosecutors introduced

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more text messages showing Jane's attempts to negotiate boundaries with Ditty,

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including pleas for breaks from the relentless hotel nights and

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requests for emotional support. These messages painted a picture of

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a woman caught between love and fear, trying to maintain

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some control in a situation that was spiraling out of

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her hands. The courtroom also heard from a forensic psychologist

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who testified about the effects of prolonged trauma and coercive control,

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explaining how victims often develop coping mechanisms that can appear contradictory,

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such as maintaining contact with abusers or expressing affection despite

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ongoing abuse. This expert testimony aimed to bolster Jane's credibility

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and help jurors understand the complex dynamics at play. Additionally,

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the prosecution previewed upcoming evidence related to Ditty's financial transactions,

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including payments to third parties that may have been used

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to facilitate the freak off parties or to silence witnesses.

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This financial trail is expected to be a key component

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in demonstrating the organized nature of the alleged criminal enterprise.

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The day ended with a tense exchange between the judge

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and defense council over courtroom decorum, as the judge reiterated

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the importance of maintaining professionalism and warned against any attempts

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to intimidate witnesses or influence the jury through nonverbal cues.

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These additional layers of testimony and evidence further deepened the

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narrative of control, manipulation, and abuse that the prosecution is building,

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setting the stage for what promises to be a dramatic

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continuation of the trial. That's where we stand after another

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day of bombshell testimony, legal brinkmanship, and emotional revelations. I'll

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be back tomorrow with every new twist, every legal battle,

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and every rumor from inside and outside the courthouse. I'm

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Nate Oliver, and this is Did He Do It? This

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episode of Did He Did He Do It?

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Was produced by Mark Francis and John McDermott for Caalaroga

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Shark Media. Some AI production assistants may have been used.