May 21, 2025
Wednesday 5/21 Day 13. Sex Tapes, Guns & “The Punisher” — Diddy’s World Exposed
Day 13 blows the lid off Diddy’s empire as a former assistant reveals “freak off” secrets, Cassie’s mother testifies about blackmail and bruises, and a male escort known as “The Punisher” details wild, candlelit scenes with Diddy watching from the shadows. Homeland Security agents parade seized guns for the jury, and the courtroom reels from stories of threats, fear, and control. With celebrity names swirling and the gallery packed, Nate Oliver unpacks every jaw-dropping moment from the trial’s most shocking day yet on Did He Do It?
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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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Callaroga 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 Ditty Combs sex trafficking and racketeering trial. I'm
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Nate Oliver, reporting from outside the Manhattan Federal Courthouse on
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Wednesday May twenty, first day thirteen of this explosive case. Yesterday,
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the prosecution delivered a dramatic trio of witnesses, each peeling
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back more layers of Ditty's alleged world of control, intimidation,
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and sexual exploitation. First up was David James, Ditty's personal
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assistant from two thousand and seven to two thousand and nine,
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who painted a vivid picture of the bad boy empire,
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where as mister Combe's kingdom were all here to serve
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in it. James described a job that demanded total loyalty
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and secrecy, recalling how he was expected to stock hotel
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rooms with freak off supplies, baby oil, astroglide condoms, and
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a Louis Viton bag with ten thousand dollars in cash
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and up to thirty pill bottles, viagra, ecstasy, and even
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medication to increase sperm count. He testified that Ditty took
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ecstasy every day and that he often procured drugs under
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his own name. James described a culture of fear, with
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his security warning you know what rhymes with tired fired.
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He also recounted a chilling two thousand and eight incident
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he was ordered to drive Ditty in a bodyguard to
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confront sooge night at a diner, with Ditty sitting in
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the back seat armed with three handguns. I was real
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shook up by it, James said. This was the first time,
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being mister Combs's assistant, that I realized my life was
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in danger. James also described a bizarre scene at a
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Miami hotel. He walked in to find Cassie on a
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bed with a comforter up to her neck and a
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naked man with a very large endowment scurrying out of
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the room. He said Diddy later told him, I'm going
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to keep this footage in case I ever needed, referencing
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security camera footage of staff and guests on Cross. The
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defense pressed James about his own behavior and why he
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stayed so long James admitted the perks were good, but
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said I was exhausted, but you didn't say no to
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mister Combs. He also described being asked to file a
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false police report against Combs's chef, which he refused to do.
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Cassie's mother, Regina Ventura, took the stand for a brief
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but powerful appearance. She described how in December twenty eleven,
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Cassie sent her an email saying Diddy had threatened to
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release two explicit sex tapes and have someone physically harm
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her and wrapper kid Cuddy. I was physically sick. The
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sex tape threw me. Regina told the jury she and
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her husband took out a home equity loan to pay
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Ditty twenty thousand dollars after he demanded the money to
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recoup expenses when he discovered Cassie was seeing someone else.
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Regina said she wired the money to a bad Boy
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Records account and that it was returned days later for
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reasons never explained. She also testified about photographing bruises on
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Cassie's back, arm and leg. When Cassie came home for Christmas.
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She was bruised and I wanted to memorialize it, she said,
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The jury saw several of these photos, which were entered
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into evidence. Regina said she was scared for my daughter's
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safety and that Ditty's threats left her physically sick. The
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defense declined to cross examine her. The jury then heard
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from CHARAE. Hayes, a male escort and exotic dancer known
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as the Punisher, who testified about being hired eight to
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twelve times by Ditty and Cassie to create a sexy scene.
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Hayes described being greeted by Cassie in a batrob at
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Trump Tower, told to apply baby oil and perform in
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dimly lit rooms with candles and music, while Ditty watched
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from a distance, giving subtle directions about angles, lighting and positions.
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Hayes said Combs would sometimes throw condoms at him and
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instruct him to finish, meaning to have an orgasm on command,
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and that he was paid up to two thousand dollars
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per session.
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He told the.
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Court that the encounters were very sexually natured, different from
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my exotic dancing performances, and that he was specifically told
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not to acknowledge Ditty, who sometimes wore a veil over
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his face. Hayes described the pressure to perform and said
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he sometimes used viagra to meet Ditty's demands. On cross examination,
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Hayes said he never saw Cassie appear uncomfortable or coerced,
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but under redirect he admitted Cassie seemed hyper aware of
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Ditty's presence and would WinCE or sigh at some of
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his directions. There was a consistent wa awareness to mister
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Combs's direction and his perception and desires during the moment.
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Hayes said he also testified that he never developed feelings
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for Cassie, but felt special for being chosen. The jury
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was also shown photos of firearms, including AR fifteen rifle
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receivers and ammunition with defaced serial numbers, found in Ditty's
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Miami Beach home, stored alongside platform heels in Lingerie. Homeland
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security agent Gerard Gannon described the massive raid on Ditty's
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twenty thousand square foot property, which involved eighty to ninety agents,
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a vehicle to breach the gate, and a team on
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boats in case anyone tried to flee by water. Gannon
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held up the actual gun parts for the jury to
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inspect and explained how the upper and lower receivers could
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be connected to form a working assault rifle. The jury
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also saw images of the mangled gate and the waterfront dock,
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underscoring the scale and seriousness of the government's case. The
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courtroom was ten and packed, with the jury visibly affected
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by the explicit testimony and evidence. Ditty, dressed in a
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casual sweater and button up shirt, sat with his legal
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team stone faced as the most damning details were read
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into the record. The gallery was filled with reporters, legal observers,
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and a few industry insiders, all hanging on every word
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more in a moment. Court resumes today with Homeland Security
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agent Gannon continuing his testimony about the Miami raid and
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evidence collection. The jury is expected to see more items
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seized from Ditty's home, including additional firearms and digital evidence. Later,
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psychologist doctor Don Hughes, an expert in sex trauma and
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coercive control, will take the stand to provide context for
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the jury. Also expected this week George Kaplan, another former
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Ditty assistant, and kid Cuddy, who is set to testify
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about his relationship with Cassie and the threats Ditty allegedly
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made against him. Prosecutors are building a case that Ditty
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orchestrated a criminal enterprise of abuse, intimidation, and sexual exploitation,
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while the defense continues to argue that Ditty's world was
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unconventional but consensual, and that the government is criminalizing a
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swinger lifestyle. That's where we stand as the trial enters
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another dramatic day tomorrow. I'll bring you every new revelation,
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every legal twist, and every rumor from inside and outside
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the courthouse. I'm Nate Oliver, and this is Did He
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Do It?
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This episode of Diddy Did He Do It? Was produced
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by Mark Francis and John McDermott for Caalaroga Shark Media.
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Some AI production assistants may have been used.
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