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Sean 'Diddy' Combs trial updates: Jury shown 'freak-off' videos before court adjourns for the day

AARON KATERSKY, MASON LEIB and EMILY SHAPIRO
8 min read

This story may contain accounts and descriptions of actual or alleged events that some readers may find disturbing.

This is week six of testimony in the trial of Sean "Diddy" Combs.


Latest Developments


Jun 16, 3:46 PM

Juror issues again discussed after court adjourns

When court ended for the day, the defense asked Judge Arun Subramanian to explain what, if anything, the jury was told about the dismissal of juror No.6 following questions about his candor.

Judge Subramanian said he would find out and inform the parties before court begins on Tuesday.

The judge did not address an issue with a second juror, which was the subject of a discussion when the courtroom was briefly closed to the public Friday.

The issue was not disclosed but involves alleged “communications with his former colleague” regarding his jury service, according to a letter from prosecutors.


Jun 16, 3:28 PM

Jury sees 'freak-off' videos before court adjourns for the day

The jury donned headphones and spectator screens went dark while the prosecution played excerpts of "freak-off" videos for the jury.

The videos were taken from a laptop turned over to prosecutors by Cassie Ventura, Sean Combs' former girlfriend.

The jury saw the footage after federal prosecutors sought to establish Ventura’s presence in hotels in New York City, to which they say travel was also arranged for male escorts for the purpose of participating in "freak-off" sex encounters.

One video lasted 39 minutes, 10 seconds, though the jury saw only a portion.

The jury also was shown a text exchange from 2013 between Combs and Ventura in which he texted, “Want to celebrate Christmas and have a 'freak-off?'”

The prosecution also presented subsequent text messages that summoned four escorts to the L’Ermitage Hotel in Beverly Hills, Calif.

Court has adjourned for the day.


Jun 16, 3:02 PM

Jury sees financial documents prosecutors say tie Bad Boy Entertainment to alleged 'freak-off' payments

Credit card statements presented by the prosecution showed that Sean Combs used his American Express card to pay for Cassie Ventura and a male escort, Jules Theodore, to fly separately to New York in December 2009.

The jury saw a bank statement that encompassed the entirety of the bill. The account holder is Bad Boy Entertainment Worldwide.

Federal prosecutors contend that Combs intermingled his business and his personal interests as part of an alleged criminal enterprise that he has denied.

The jury also saw a series of messages and invoices from October 2012. Bad Boy Entertainment was listed on the travel invoice for a ticket to New York for former Combs girlfriend Cassie Ventura. Prosecutors also presented a reservation at the Trump International Hotel in Columbus Circle which was made under the name Janet Clark, an alias for Ventura seen in text messages.

“Janet Clark 408,” Ventura messaged an escort known as The Punisher, asking him to arrive at 3:30 a.m.

Combs messaged Ventura, “You ready for tonight” and Ventura messaged back “I just gta get stuff.”

“You had all day,” Combs’ reply said. “It’s always something.”


Jun 16, 5:16 PM

Jury sees messages between Combs and male escort allegedly arranging travel

A summary witness for the prosecution, SDNY Special Agent DeLeassa Penland, is showing the jury a series of text messages, emails and documents pulled from one of Sean Combs’ electronic devices that they say relate to travel arrangements for a male escort named Jules, whom former Combs girlfriend Cassie Ventura has previously testified was hired to participate in so-called "freak-off" sexual encounters.

PHOTO: Sean 'Diddy' Combs listens as Assistant U.S. Attorney Emily Johnson questions Special Agent DeLeassa Penland during Combs' sex trafficking trial in New York City, June 16, 2025 in this courtroom sketch. (Jane Rosenberg/Reuters)
PHOTO: Sean 'Diddy' Combs listens as Assistant U.S. Attorney Emily Johnson questions Special Agent DeLeassa Penland during Combs' sex trafficking trial in New York City, June 16, 2025 in this courtroom sketch. (Jane Rosenberg/Reuters)

Text messages show Combs and Jules arranging a date and Combs sending him an itinerary for a Dec. 11 flight from Los Angeles to New York and instructions for “pickup inside baggage claim to London Hotel.”

An email from Combs shows him telling someone at his company to book the flight.

The court is now taking a lunch break.

Prosecutors have said they may rest their case as soon as Wednesday. Once they do, the defense has signaled it has as many as three witnesses lined up to testify beginning Friday, with additional witnesses possible.

Among the first defense witnesses expected to be called is Vashta Dunlap, who was a vice president at Combs' company, Bad Boy Entertainment.


Jun 16, 2:45 PM

Defense downplays employee involvement in alleged crimes in summary witness cross-examination

On cross-examination of the government’s first summary witness, paralegal Ananya Sankar, defense attorney Teny Geragos highlighted messages that the defense contends downplay the role of Sean Combs employees in allegedly procuring drugs for him.

In one such text message, Kristina Khorram, Combs' former chief of staff, said that she doesn't talk to Guido, whom the prosecution said is a drug dealer, but that Combs talks to Guido himself.

PHOTO: Assistant U.S. Attorney Meredith Foster questions Ananya Sankar during Sean 'Diddy' Combs' sex trafficking trial in New York City, June 16, 2025 in this courtroom sketch. (Jane Rosenberg/Reuters)
PHOTO: Assistant U.S. Attorney Meredith Foster questions Ananya Sankar during Sean 'Diddy' Combs' sex trafficking trial in New York City, June 16, 2025 in this courtroom sketch. (Jane Rosenberg/Reuters)

Sankar is now off the witness stand.

The next witness is Special Agent DeLeassa Penland of the United States Attorney’s Office for the Southern District of New York, who reviewed charts and data. She is a second summary witness for the prosecution.


Jun 16, 11:56 AM

Jury sees more messages between 'Mia' and Combs bodyguard

The jury is seeing more text messages that the prosecution is presenting with the intent to show how Sean Combs and his team reacted to former Combs girlfriend Cassie Ventura's lawsuit against him.

Combs' former assistant, who previously testified under the pseudonym “Mia,” told the jury that Combs’ bodyguard Damian Butler, known as D-Roc, repeatedly called and texted her in the days and weeks after news of the lawsuit became public, urging her to talk to Combs.

D-Roc is not testifying but a summary witness read for the court some of the call and text logs from his phone that appear to show him in close communication with Combs while he is chatting with "Mia."

"Mia" testified that the outreach from D-Roc and Combs “terrified” her. The messages appear to show that "Mia" brushed off D-Roc’s repeated offers to “send my sister a gift.”

Federal prosecutors allege that Combs orchestrated a criminal enterprise with the assistance of his bodyguards to pressure witnesses like "Mia" through attempted bribery “to stay silent and not report what they experienced or knew.”


Jun 16, 10:47 AM

Jury sees collection of messages from Combs employees about 'freak-offs,' alleged drug deal

The jury is seeing and hearing a disjointed smattering of text and audio messages meant to try and reinforce testimony from other witnesses about hotel rooms, drugs and travel.

Prosecutors presented one group of messages between Sean Combs’ chief of staff Kristina Khorram and Combs’ travel arranger Jessica Ruiz discussing a flight for "Jane," a prior witness and ex-girlfriend of Combs who testified under a pseudonym, and a male escort named Paul.

Another group of messages involved discussions of paying a drug dealer, and Combs’ request for 15 molly pills.

Prosecutors also presented a text from one of Combs’ assistants that read, “got to reup on baby oil and s---” after receiving instructions to set up a hotel room for a "freak-off" sex session with former Combs girlfriend Cassie Ventura.

The prosecution told the court that the messages were taken from electronic devices seized from Khorram, who has not testified during the trial. Khorram has denied any wrongdoing.

In a 2018 exchange presented to the jury, after Ventura texted Khorram “I can’t do the violence,” Khorram messaged back, “stay focused, not worth derailing.”


Jun 16, 9:33 AM

Summary witnesses to take the stand as prosecution expects to rest case this week

The racketeering and sex trafficking trial of Sean Combs begins a sixth week of testimony today with a pair of summary witnesses meant to help the jury organize the hundreds of exhibits they have seen so far.

We've been told it is possible that Ye, the rapper formerly known as Kanye West, will make another appearance early this week, as he did last Friday.

The last substantive witness for the prosecution is expected to be a former assistant to Combs, Brendan Paul.

Prosecutors have said they expect to rest their case as soon as Wednesday and no later than Friday. There will be no court proceedings Thursday, which is the Juneteenth federal holiday.


Jun 16, 9:18 AM

Judge upholds decision to dismiss juror ahead of week 6 of testimony

Judge Arun Subramanian declined on Monday to change his mind about juror No.6, upholding his decision to remove the juror and replace him with an alternate.

“The record raised serious concerns as to the juror’s candor and whether he shaded answers to get on and stay on the jury,” Subramanian said. “There’s nothing the juror could say at this point to put the genie back in the bottle.”

The first alternate juror is a 57-year-old architect from Westchester.

The judge said he took seriously the defense concern about race -- juror No.6 is Black -- but he said, “this jury does not raise those concerns.” He also said it is “inappropriate to consider race” in deciding whether the juror’s responses to questions about where he lived were appropriate.

At the conclusion of court on Friday, Judge Subramanian dismissed juror No.6 over what he said were "inconsistencies" in statements the juror made about where he lived, saying that the alleged inconsistencies raised questions about the juror's candor and ability to follow instructions.


Jun 16, 8:08 AM

Testimony to resume today; prosecution could rest their case this week

Testimony in the trial of Sean “Diddy” Combs will resume on Monday for its sixth week.

Federal prosecutors have said that they expect to rest their case no later than Friday and possibly as soon as Wednesday.

Click here to read the rest of the blog.

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