June 8, 2025

Sunday 6/8. Bonus: Inside the “Freak Off” Machine — Power, Secrecy, and Survival in Diddy’s World

Show Notes
Transcript

With the courtroom dark for the weekend, Nate Oliver pulls back the curtain on the infamous “freak off” parties at the heart of the Diddy trial. Through chilling testimony from Cassie, assistants, hotel staff, and male escorts, discover how these nights were meticulously planned, enforced with NDAs and cash, and fueled by drugs, fear, and control. From luxury suites trashed with oil and candle wax to the psychological toll on everyone involved, this episode exposes the machinery of silence, blackmail, and trauma behind the headlines. Did He Do It? delivers the most in-depth look yet at the secret rituals that prosecutors say powered Diddy’s empire.

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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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podcast bringing you every raw, unfiltered detail from the Sean

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Diddycomb's sex trafficking and racketeering trial. I'm Nate Oliver, and

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with the courtroom doors closed for the weekend, we're using

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this break to take you deeper than ever before into

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the heart of one of the most disturbing and pivotal

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aspects of the entire case, the so called freak Off parties.

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For weeks, the phrase freak off has echoed through the courtroom,

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growing from a salacious rumor into a chilling symbol of

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the prosecution's case. Prosecutors alleged these weren't just wild nights.

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They were the engine of Ditty's power control, and they

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argue his criminal enterprise. Today, we're piecing together how these

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parties worked, who was involved, and why they're at the

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very center of the government's argument. Let's start with the planning.

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According to testimony from Cassie Ventura, former assistants like George

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Caplan and even mail escorts, freak offs were never spontaneous.

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They were meticulously orchestrated, with a level of detail that

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rivals any Hollywood production. Assistants would receive explicit instructions book

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a suite, usually at a luxury hotel, under an alias

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like Frank Black or Jackie Starr. The room had to

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be stripped of identifying details, with connecting suites reserved for

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privacy and security. Sometimes entire floors were blocked off and

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staff were instructed to avoid the area or if necessary,

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to look the other way. George Kaplan, Ditty's former assistant,

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described how he'd arrive hours before Ditty and his guests,

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setting the stage. Candles were lit and strategically placed. Bottles

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of high end alcohol, gatorade, and water were arranged on

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every surface. The mini bar was stocked, and party favors

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a euphemism for drugs were laid out, sometimes in ornate

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bowls or gold plated boxes. Caplan said he'd also lay

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out baby oil, sexual lubricant, lingerie, and on occasion, costumes

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are props. It was like prepping a movie set, Caplin

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told the jury. Everything had to be just right, or

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you'd hear about it. Afterward. Caplan would return to clean up.

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He described finding broken glass, empty pill bottles, used condoms,

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and brown crystallized powder he didn't recognize. Housekeeping Logs from

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hotels like Lrmitage, Beverly Hills and the Inner Continental in

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Los Angeles documented repeated complaints about candlewax, oil stains, and

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rooms left in disarray. One hotel manager testified that Ditty's

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rooms were often put out of order for deep cleaning,

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with charges for oil damage and biohazard remediation, sometimes running

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into the thousands. But the logistics were just the surface.

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The real machinery of a freak off was psychological. Cassie

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Ventura's testimony was especially wrenching. She described being forced to

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participate in these parties, threatened with violence or blackmail if

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she refused. Cassie said Ditty would make her have sex

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with strangers or male escorts while he watched, filmed, or

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directed the action. Sometimes, she said she was given drugs MDMA,

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ketamine or cocaine, either handed to her directly or slipped

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into her drink. Eventually it became a job for me,

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Cassie told the jury, these events consumed my life and

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left me exhausted, dehydrated, and emotionally numb. She described how

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after a freak off off, she'd sometimes lock herself in

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the bathroom and cry or call her mother in the

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middle of the night, desperate for comfort. Other witnesses echoed

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Cassie's account. Mia, another former assistant, described being forced to

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work through the night, sometimes for days on end, making

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sure everything was perfect for Ditty's guests. She said she

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was pressured to take stimulants to stay awake, and was

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threatened with being fired or blacklisted if she ever spoke out.

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Mia recalled seeing Cassie hide from Ditty at parties, whispering

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He's going to kill me, and said that after some

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freak offs, Cassie would be left with visible injuries bruises, cuts,

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and once a black eye that had to be covered

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with makeup before a public appearance. Male escorts, including one

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who went by the nickname the Punisher, testified about being

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paid thousands of dollars to participate in these events. They

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described being given instructions by Ditty or his staff, sometimes

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being filmed, and always being told to keep One escort

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said he was paid in cash and signed a non

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disclosure agreement before ever setting foot in a hotel room.

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Another described Ditty as calm, almost clinical, directing the action

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from the sidelines and sometimes joining in. It was like

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a performance, but there was always this edge, like if

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you did something wrong, there'd be consequences. One escort testified

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the aftermath of a freak off was often as chaotic

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as the event itself. Hotel staff described rooms trashed with candlewax,

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broken furniture, and stains that required deep cleaning. Security supervisors

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like Eddie Garcia testified about being called to handle complaints

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or to erase evidence, sometimes being offered cash or gifts

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in exchange for their silence. In one instance, Garcia described

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being paid one hundred thousand dollars to hand over the

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only copy of a surveillance video showing Ditty assaulting Cassie.

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After a particularly violent freak off, garcias that he signed

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a non disclosure agreement with a million dollar penalty and

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was told by Ditty, don't make any big purchases. Prosecutors

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have argued that these parties were not just about sex,

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they were about power. By orchestrating freak offs, Didty allegedly

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maintained control over his partners and employees using the threat

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of exposure, violence, or financial ruin to keep everyone in line.

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Witnesses described a culture of silence enforced by non disclosure agreements,

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cash payments, and the ever present fear that crossing Ditty

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would mean losing everything. Cassie's mother testified about wiring twenty

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thousand dollars to Ditty after he threatened to release explicit

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videos of her daughter, calling it the price of keeping

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Cassie safe. Former staff described being required to sign NDA's

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so strict that even mentioning Ditty's name in public could

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trigger a lawsuit more in a moment, the psychological toll

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was immense. Mia described how after years of working for Ditty,

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she developed PTSD, panic attacks and insomnia. She said she

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still jumps when she hears certain songs or smells baby oil.

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Cassie testified that she lost her sense of self, describing

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how she became a shell of the person she once was.

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You start to believe you deserve it, She told the

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jury that you're not worth saving. The defense, for its part,

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insists that the freak offs were consensual, that everyone involved

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was an adult, and that Ditty's world was wild but

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not criminal. They've pointed to social media posts and interviews

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in which some witnesses described Ditty as generous or the

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life of the party, But as more testimony piles up,

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the prosecution's portrait of the freakof machine has become harder

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to ignore. A world where pleasure, pain, and power were

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inextricably linked, and where the price of admission was often secrecy, silence,

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and survival. Legal experts say the freak Off parties are

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central to the prosecution's racketeering case. They're not just salacious details,

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their evidence of a pattern, a system, and prosecutors argue

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a criminal enterprise built on fear and control. The government

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has introduced hotel bills, wire transfers, and digital evidence text messages, emails,

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and even encrypted chats showing how assistance coordinated logistics, paid escorts,

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and managed the aftermath. One Homeland security agent testified that

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the proximity of weapons, drugs, and sex supplies in Ditty's

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Miami mansion was consistent with a high level operation, not

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just a celebrity's eccentric lifestyle. As the trial moves forward,

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the freak Off parties remain at the center of the

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government's case. They're not just about what happened behind closed doors.

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They're about how power is wielded, how PSI is bought,

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and how sometimes the truth finally comes to light. That's

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our deep dive for today. When court resumes, will be

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right back with every new revelation, every legal twist, 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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Did He Did He Do It? Was produced by Mark

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Francis and John McDermott for Calaroga Shark Media. Some AI

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production assistants may have been used.