May 23, 2025
Friday 5/23 Day 15. Kid Cudi's Bombshell & Diddy’s “Freak Off” Fallout
Day 15 delivers pure courtroom fireworks as rapper kid Cuddy takes the stand, recounting a firebombed Porsche, break-ins, and Diddy’s chilling threats over Cassie. Diddy’s ex-assistant spills secrets of “freak off” setups and private jet violence, while Cassie’s makeup artist reveals black eyes and busted lips hidden from the world. Hotel managers and FBI agents expose the wild, oil-soaked aftermath of Diddy’s parties and a digital trail of control. As the jury reels and Memorial Day break looms, Nate Oliver unpacks every jaw-dropping twist from the most explosive day yet on Did He Do It?
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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.
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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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Friday May twenty, third day fifteen of this explosive case.
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Thursday's testimony was some of the most dramatic yet, with
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the highly anticipated appearance of Grammy winning rapper Kid Cuddy,
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plus damning details from Ditty's former assistant, a Beverly Hills
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hotel manager and Cassie's longtime makeup artist. Kid Cuddy, dressed
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in a black leather jacket and jeans, took the stand
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and immediately commanded the courtroom's attention. He told jurors about
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his brief romance with Cassie Ventura in twenty eleven and
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how everything changed when Diddy found out. Cutty described getting
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a call from Cassie, who was nervous and scared after
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Ditty discovered their relationship. That same day, Cutty learned Ditty
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had broken into his Hollywood Hills home. Cutty described arriving
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to find Christmas presents for his family unwrapped, his dog
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locked in the bathroom, and his security cameras repositioned. I
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called the police. I was worried for my safety and Cassie's.
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Cutty testified. He said Cassie was visibly shaken and described
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her as very stressed, nervous, scared, didn't know what Shawn
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Combs would do. Just a few weeks later, Cutty's Porsche
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nine to eleven was destroyed in a fire bombing. Cutty testified,
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my dog's babysitter called and said my car was on fire.
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The jury saw photos of the charred Porsche, a hole
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cut in the convertible roof and a Molotov cocktail found inside.
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It looked like the top of my Porsche was cut
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open and that's where the Molotov cocktail was put in.
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Cutty said. He told the court he believed Didty was
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behind the arson, though Diddy denied it. When they met
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an intense confrontation at a Los Angeles hotel, Cutty described
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Ditty as standing by the window like a Marvel supervillain,
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calm and cold, When Cutty asked what would happen about
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the car did he replied, I don't know what you're
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talking about. Cutty said he left convinced Diddy was lying.
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Years later, at SOHO House, did he unexpectedly apologized. Man,
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I just want to apologize for all that bullshit, Cutty
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told the jury. After the apology, I found peace with it.
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Cutty also testified that Cassie confided in him about Ditty's abuse,
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saying he would hit her sometimes kick her. He broke
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up with Cassie because the drama was getting out of
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hand and he worried for both their safety. On cross examination,
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Ditty's lawyer tried to paint cass he is living a
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double life, seeing both men at once. Cutty admitted Cassie
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told him she and Ditty were broken up, but she
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was still seeing Ditty for freakoff sex marathons. He said
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he didn't know the full extent of Cassie's relationship with
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Ditty at the time. Next, the jury heard from George Kaplan,
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Ditty's former assistant, who described a complicated relationship with the mogul.
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Caplan testified he worked eighty to one hundred hour weeks
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setting up hotel rooms under aliases like Frank Black, cleaning
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up after freak offs, and even picking up drugs for Ditty.
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He described being paid one hundred and twenty five thousand
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dollars a year, but living in constant fear of being fired,
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sometimes over something as small as the wrong water bottle.
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He pushed me to depths I didn't know I had,
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Caplan said. Despite his respect for Ditty, Caplan said the
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violence he witnessed shook me tremendously. He recounted seeing Ditty
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physically violent with Cassie on a private jet to Life,
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Vegas in twenty fifteen, hearing glass break, Cassie's screaming and
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no one intervening. Cassie screamed, isn't anybody seeing this? Caplin testified.
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He said he didn't respond because he was twenty three
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in his dream job and didn't want to jeopardize his career.
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He also described Ditty throwing apples at another girlfriend, Gina,
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in a rage, and said he eventually quit because he
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wasn't comfortable fixing certain situations for Ditty, especially after seeing
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Cassie with a black eye and being asked to pick
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up medicine for her. Caplan's testimony was peppered with moments
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that showed the strange mix of admiration and fear that
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working for Ditty inspired. He called Ditty a god among men,
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saying he didn't just push me to my deepest depths,
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he introduced me to depths I didn't know I had.
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Caplan said he still thinks fondly of many aspects of
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their work together and even wishes Ditty well on his birthday,
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but made it clear that witnessing the violence changed everything
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for him. In my heart of hearts, I knew what
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was happening, and I felt an element of guilt that
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I didn't do anything to stop it, he told the jury.
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The jury also heard from Mila Morales, Cassie's longtime makeup artist.
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Morales testified that she saw Cassie with injuries only once,
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during Grammy's weekend in twenty ten. She described waking up
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in a hotel room to yelling and screaming, then seeing
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Cassie emerge with a swollen eye, busted lip, and knots
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on her head. Morales said she packed up Cassie and
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took her to her own home for a few days,
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where a doctor friend checked Cassie for a concussion. Morales
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said she was afraid of Sean. I feared for my
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life and never called the police out of fear. She
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also described how Diddy demanded final approval on Cassie's looks,
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requiring photos to be sent to him for approval before events.
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Sean always made sure the look was perfect. Morales testified
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on cross Morales submitted she had spoken about the incident
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in interviews but was never paid for them, and that
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she never spoke to police about what she saw. Frederick Zimmar,
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general manager of the Lrmitage Beverly Hills, also took the stand.
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He testified that Ditty made hotel reservations under aliases like
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Frank White, Frank Black, and Jackie Starr, and that his
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guest profiles included notes like always spills candlewax on everything
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and uses excessive amounts of oil. Housekeeping logs showed repeated
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complaints about candle wax and oil stains, and Ditty was
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charged extra for damages. Zimmer said Ditty's rooms were often
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put out of order after his stays for deep cleaning.
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The jury saw records of reservations dating back to two
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thousand and eight with profiles merged and names changed multiple times,
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a pattern prosecutor say was meant to hide Ditty's activities
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more in a moment. The day ended with FBI agent
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Josh Croft testifying about extracting data from Cassie's laptops. Croft
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described how one MacBook Pro had been reset to factory default,
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but he was able to recover data linked to the
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user Frank Black. Another laptop was damaged but yielded partial information.
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Prosecutors are building a digital trail to support Cassie's claims
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and show the extent of Ditty's efforts to control and
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monitor her. Judge Aaron Supermanian ended the week early, sending
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jurors home from Memorial Day weekend and reminding them to
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avoid news coverage and maybe watch the Knicks avenge their
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game one loss. Court resumes Tuesday, with testimony expected from
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Capricorn Clark, Ditty's longtime executive assistant, as well as witnesses
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from the Los Angeles Police and fire departments. As the
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trial barrels forward, the prosecution is tying together a narrative
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of violence, intimidation, and control, While the defense insists Diddy's
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world was wild but consensual. The stakes couldn't be higher.
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If convicted, Diddy faces life in prison. That's where we
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stand as the week wraps up. I'll be back Tuesday
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with every new revelation, every legal twist, and every rumor
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from inside and outside the courthouse. I'm Nate Oliver and
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this is Did He 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 Calaroga Shark Media.
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Some AI production assistants may have been used.
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