June 17, 2025

Tuesday 6/17 Day 32. “The Heart of the Enterprise” — Triple-X Evidence, Drug Trails, and Witness Pressure

Show Notes
Transcript

Day 32 delivers the most explicit evidence yet as the jury watches graphic “freak-off” videos pulled from Diddy’s own devices—bringing weeks of testimony to life in the courtroom. Prosecutors connect the dots with texts, emails, and financial records showing a web of payments, drug deals, and meticulous logistics behind the scenes. Former assistant Jonathan Perez details cash drops, the infamous Gucci pouch, and the pressure to keep secrets, while new evidence reveals efforts to bribe and intimidate witnesses. As the defense insists it’s all a consensual “swinger lifestyle,” Nate Oliver breaks down every jaw-dropping moment from a day that could define the entire case.

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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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Callarogashark 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 Diddy Combs sex trafficking and racketeering trial. I'm Nate

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Oliver outside the Manhattan Federal Courthouse on Tuesday morning, June seventeenth,

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after a Monday in court that delivered the most explicit

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and pivotal evidence yet. Monday's session was dominated by what

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prosecutors called the heart of the enterprise, the infamous freak

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Off videos. For the first time, jurors were shown graphic

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footage of the drug fueled, multi partner sex parties that

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have been described in testimony for weeks. These videos, pulled

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from Ditty's own electronic devices, were played in a closed

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courtroom with only the jury, judge, attorneys, and Ditty himself present.

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Reporters in the public were excluded due to the explicit

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nature of the content. According to prosecutors, the video showed

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Ditty orchestrating and participating in prolonged sexual encounters with multiple

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women and male escorts, sometimes filmed in luxury hotels, sometimes

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in his own home. The jury saw clips that match

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the testimony of Jane, Cassie Ventura and others, depicting scenarios

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involving drugs, cash payments, and what prosecutors argue was clear

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evidence of coercion and trafficking. The atmosphere in the courtroom

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was tense and silent, with jurors taking notes and some

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appearing visibly disturbed by what they saw. Alongside the videos,

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prosecutors introduced a trove of financial documents and digital communications.

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Special Agent DELIASA. Penland, a summary witness for the prosecution,

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walked the jury through text messages, emails, and payment records

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tying Bad Boy Entertainment directly to the freakoff payments. Credit

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card statements showed Ditty using his American Express card to

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pay for flights for Cassie Ventura and mail escort Jewels Theodore,

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with Bad Boy Entertainment as the account holder. The jury

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saw bank statement covering the full bill and travel invoices

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listing Cassie under the alias Janet Clark, matching text messages

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arranging for a male escort known as the Punisher to

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arrive at three thirty am at the Trump International Hotel

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in Columbus Circle. The jury also saw messages between Ditty

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and mail Escort Jewels arranging a December eleventh flight from

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Los Angeles to New York, with Ditty sending the itinerary

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and pickup instructions for the London hotel. Emails from Ditty

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to staff showed him instructing assistance to book travel and

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accommodations for these events, while additional texts revealed how Ditty's

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team coordinated logistics, payments, and secrecy. Prosecutors argued that this

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digital paper trail demonstrates not just participation, but leadership and organization,

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hallmarks of a racketeering enterprise. Jonathan Perez, Ditty's former personal assistant,

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returned to the stand to provide more context about the

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logistics and drug use behind the scenes. Perez testified under

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immunity describing how he procured drugs for Ditty, xanax, cocaine,

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and molly from contacts known as Guido and Baby Girl.

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He explained that payments for these drugs came from Ditty's

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security team, a Gucci pouch or a top drawer. The

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jury was shown a photo of the pouch, which Perez

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said was always filled with narcotics and cash, and was

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a staple during King Knights. Perez described being instructed by

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another assistant to look for the pouch in the restroom

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and always return anything found outside of it. In texts,

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Perez confirmed that cocaine was sometimes found in a separate bag,

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but it was emphasized that it should never leave the

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Gucci pouch. Perez also described the cash flow behind these events,

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testifying that he would sometimes deliver as much as three thousand,

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five hundred dollars in cash to Jane at Ditty's request

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to pay for guests or other expenses related to the

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freak Off parties. In one message, Perez wrote, seven hundred

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dollars went to Guido, confirming the payments for drugs. He

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explained that he was compelled to testify under an immunity

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order after invoking the Fifth Amendment, making him the fourth

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witness to receive immunity in this trial. The jury also

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heard about efforts to silence witnesses. Prosecutors presented call and

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text logs showing Ditty's bodyguard, Damien's d Rock Butler repeatedly

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reaching out to Miya, a former assistant who previously testified

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under a pseudonym. In the days and weeks after Cassie's

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lawsuit became public, d Rock called and texted Miya, urging

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her to talk to Ditty and offering to send my

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sister a gift. Mia testified that these overtures terrified her,

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and prosecutors alleged that Ditty's team orchestrated a campaign of

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intimidation and attempted bribery to keep witnesses quiet. On cross examination,

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the defense worked to downplay the role of Ditty's employees

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in procuring drugs or arranging sex, highlighting techts where staff

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distanced themselves from drug dealers and insisted Ditty handled those

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matters personally. Defense attorney Tenny Garrigos pressed the prosecution's summary witnesses,

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arguing that Ditty's world was wild, consensual, and part of

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a swinger lifestyle, not a criminal enterprise. The defense also

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pointed out that many of the messages and payments could

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be interpreted as gifts or private arrangements between adults. Munday

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also brought a reminder of the trial's high stakes and scrutiny.

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Judge Aaron Subramanian reaffirmed his decision to dismiss Juror number six,

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who had provided conflicting information about his residency. The defense objected,

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arguing that the removal of a jur of color in

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favor of a white alternate could disadvantage Ditty, but the

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judge stood by his ruling, emphasizing the need for honesty

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and impartiality. The judge also repeated warnings to Ditty about

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courtroom conduct after prosecutors again raised concerns about Ditty's visible

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reactions to testimony and attempts to engage the jury more

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in a moment. With the prosecution signaling it may rest

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as soon as Wednesday, the trial is poised to enter

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a new phase. The defense is preparing to call its

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first witnesses, including Vashta Dunlap, a former vice president at

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Bad Boy Entertainment, and possibly others who will testify to

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Ditty's character in business practices. Legal analysts say the defense

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will likely focus on undermining the credibility of key witnesses,

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challenging the interpretation of the videos and messages, and arguing

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that the government has criminalized consensual adult behavior. As Monday's

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explicit evidence verberates through the courthouse, the stakes for Ditty

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could not be higher. If convicted, he faces the possibility

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of life in prison. The prosecution's case has now laid

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out a detailed, graphic, and deeply disturbing portrait of an

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alleged criminal enterprise built on sex, drugs, money and silence.

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That's where we stand after a day of bombshell videos,

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digital paper trails and legal brinkmanship. I'll be back tomorrow

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with every new twist, every legal battle, 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 Caalaroga Shark Media.

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Some AI production assistants may have been used.