Editor’s Note: This story contains discussions of rape or sexual assault that may be disturbing. Reader discretion is advised. If you or someone you know has been sexually assaulted, you can find help and discreet resources on the National Sexual Assault Hotline website or by calling 1-800-656-4673.
(NewsNation) — Twelve jurors put on headphones and reportedly watched the most explicit evidence to date in the Sean “Diddy” Combs trial Monday: three video clips of the rapper’s “Freak-Off” sex parties.
According to The New York Times, the footage wasn’t shown to the full courtroom. Instead, jurors watched the explicit videos on screens that had privacy guards.
The Associated Press reported that at least one video was from October 2012, where prosecutors claim a “Freak-Off” took place at the Trump International Hotel and Tower in Manhattan. The videos played after receipts of flights and hotel bookings were presented as the prosecution attempted to connect the dots that point to Combs being engaged in sex trafficking.
They were all part of a larger argument that Combs is connected to his chief of staff, Kristina Khorram, and their organization of these parties.
Diddy would make guests rub each other with baby oil, sex worker claims
Sex worker Sharay Hayes, nicknamed “The Punisher,” told NewsNation’s Ashleigh Banfield that Combs would require guests to rub each other with baby oil on couches covered in sheets before engaging in more involved sexual acts.
True crime podcast host Lauren Conlin was in the courtroom while the jurors were presented the videos, and told Banfield that one woman tried to look away and occasionally cover her eyes while the videos played.
“She was horrified,” Conlin told Banfield. “It was very clear she was not enjoying what she was watching.”
Playing ‘Freak-Off’ videos for jurors was strategic: Court TV anchor
Ashley Willcott, an anchor on Court TV and a former judge, said the move to play the videos for the jurors as the prosecution approaches the end of their argument was strategic and is likely effective.
Sean “Diddy” Combs listens as Nicole Westmoreland cross examines Bryana Bongolan during Combs’ sex trafficking trial in New York City on June 5, 2025, in this courtroom sketch. (REUTERS/Jane Rosenberg) 
Sean “Diddy” Combs watches as Regina Ventura, the mother of alleged victim Casandra “Cassie” Ventura, testifies at his sex trafficking trial in New York City, New York, U.S., May 20, 2025 in this courtroom sketch. REUTERS/Jane Rosenberg 
FILE – Sean “Diddy” Combs appears at the premiere of “Can’t Stop, Won’t Stop: A Bad Boy Story” on June 21, 2017, in Beverly Hills, Calif. (Photo by Chris Pizzello/Invision/AP, File) 
Sean “Diddy” Combs looks on as defense attorney Nicole Westmoreland cross examines Dawn Richard during Combs’ sex trafficking and racketeering trial in Manhattan federal court, Monday, May 19, 2025, in New York. (Elizabeth Williams via AP) 
Ye, the rapper formerly known as Kanye West, leaves federal court during the trial of Sean “Diddy” Combs in New York, Friday, June 13, 2025. (AP Photo/Michael R. Sisak) 
Assistant US Attorney Madison Smyser, center, asks Special Agent Gerard Gannon, far right, to stand and show the jury the high heeled platform red shoes found along with fire arms during a search of Combs’ Star Island residence during Combs’ sex trafficking and racketeering trial in Manhattan federal court, Wednesday, May 21, 2025, in New York. (Elizabeth Williams via AP) 
Rapper Kid Cudi, center, arrives at Federal Court for the trial of Sean “Diddy” Combs, in New York, Thursday, May 22, 2025. (AP Photo/Richard Drew) 
Rapper Kid Cudi, center, arrives at Federal Court for the trial of Sean “Diddy” Combs in New York on May 22, 2025. (AP Photo/Richard Drew) 
FILE – Cassie Ventura, left, and Sean “Diddy” Combs appear at The Metropolitan Museum of Art’s Costume Institute benefit gala celebrating “China: Through the Looking Glass” in New York on May 4, 2015. (Photo by Charles Sykes/Invision/AP, File) 
Evidence photo submitted in the criminal case of Sean “Diddy” Combs shows injury to Casandra “Cassie” Ventura’s eyebrow 
CORRECTS NAME SPELLING: Witness Dawn Richard testifies in Manhattan federal court during the sex trafficking and racketeering trial of Sean “Diddy” Combs, Monday, May 19, 2025, in New York. (Elizabeth Williams via AP) 
Witness Kerry Morgan testifies in Manhattan federal court during the sex trafficking and racketeering trial of Sean “Diddy” Combs, Monday, May 19, 2025, in New York. (Elizabeth Williams via AP) 
Sean “Diddy” Combs (3rd from Left) and the “Making the Band 3” Girls – Dawn, Aundrea, Aubrey O’Day, Tiffany and Shannon (Photo by Michael Loccisano/FilmMagic) 
Cassie Ventura, right, walks out of the courtroom past Sean Diddy Combs after testifying in Manhattan federal court, Tuesday, May 13, 2025, in New York. (Elizabeth Williams via AP) 
Cassie Ventura takes an oath before testifying in Manhattan federal court on May 13 in New York. (Elizabeth Williams via AP)
“All it does is confirm everything they’ve heard from the witnesses, so that the jurors can say, ‘A-ha, not only do we see it, but everything these witnesses told us is true, they’re credible,’” Willcott told Banfield.
As the court entered the sixth week, Judge Arun Subramanian asked both sides how much time they would need. The prosecution said it will reportedly rest its case on Wednesday, after which Combs’ lawyers will begin to present their argument in defense of the 55-year-old rapper.
Diddy’s attorney says defense will take no more than 5 days
Marc Agnifilo, the lead attorney for Combs, said their presentation could be less than two days, but it wouldn’t take longer than five days. They had originally said their presentation would take around two to three weeks, so this might indicate that Combs won’t be testifying.
The court will not be in session Thursday for the Juneteenth holiday. Combs has pleaded not guilty to one count of racketeering conspiracy, two counts of transportation to engage in prostitution and two counts of sex trafficking.