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Prosecutors from the Southern District of New York began winding down their sprawling case against Sean Combs in the sixth week of the hip-hop mogul’s sex trafficking and racketeering trial, showing the jury several charts that tied elements of their case together.
Charging Combs with the sex trafficking of his ex-girlfriend Casandra “Cassie” Ventura and “Jane,” as well as two counts of transportation to engage in prostitution, prosecutors used copious records to show how Combs used his businesses to fund flights for Ventura, Jane, and various male escorts to participate in days-long sexual encounters known as “freak-offs.”
Linking back to a range of documents — including photos, text messages, bank statements, hotel records, and travel itineraries — prosecutors were able to identify more than a dozen instances where Combs paid for the flights of a male escort to fly cross-country between 2009 and 2024.
Among the records were hotel invoices for thousands of dollars worth of damages in the aftermath of alleged corresponding freak-offs. Housekeeping photos attached to the expensive bills showed messy suites, baby oil-soaked duvets, soiled sheets, and blood-stained linens.
This week also brought Combs’ recent former employee to the stand, Brendan Paul, who has been referred to as Combs’ alleged drug “mule” in various civil lawsuits. The 26-year-old was arrested for cocaine possession when federal officials pulled up on Combs during the March 2024 raids on his homes. When asked by Combs’ defense attorney Brian Steel if he agreed with the “mule” descriptor, Paul laughed. “Absolutely not,” he said.
Paul said it was his own mistake the drugs were found in his personal luggage, saying he had earlier swept Combs’ room and accidentally stashed the substance in his bags. He didn’t tell police the drugs weren’t his out of “loyalty.”
Still, Paul admitted to purchasing and delivering drugs to Combs between five and 10 times throughout his 18-month tenure as Combs’ personal assistant, adding he considered the amount equated to “personal use.” Paul said he paid between $300 and $500 for “hard drugs,” such as ecstasy, cocaine, ketamine and tusi. Separately, he said he helped restock Combs’ supply of marijuana every other month, paying $4,200 for two strains of weed at eight ounces each.
Although brief, Paul’s testimony was used to bolster prosecutors’ charge of a racketeering conspiracy against Combs. The 55-year-old, who pleaded not guilty to five felony charges, is accused of using his billion-dollar empire as a criminal enterprise. In the background of his business dealings, Combs allegedly kept a stash of illicit substances that he sometimes distributed to others and allegedly instructed a team of loyal staffers to carry out acts of bribery, arson, and kidnapping.
Here are the key moments from the trial’s sixth week:
Jury Issues
After last week’s heated debate over whether one of the jurors could continue serving in light of the 41-year-old Department of Corrections employee’s conflicting answers over his residence, U.S. District Judge Arun Subramanian dismissed the man on Monday.
“Even if this juror had an excuse or explanation for the inconsistencies in the record, that would be yet another set of shifting answers on basic questions about the juror’s residence,” Subramanian said while issuing his ruling. “This would only heighten the specter that the juror’s trying to shade answers in an effort to remain on the jury. In other words, there’s nothing the juror could say at this point that would put the genie back in the bottle and repair the damage to his credibility.”
Apart from the juror, there was a separate issue related to another juror last Friday. The courtroom was sealed as the parties discussed the matter, which had been considered resolved early in the week. However, details of the sealed meeting were leaked to a media outlet, prompting a stern warning from the judge Tuesday morning. “Somebody is lying,” Subramanian said after questioning both sides if the leak came from their camps. He added everyone “is on notice” that any further violation of his orders could result in civil or criminal sanctions.
Wednesday brought yet another juror hiccup, this time due to a juror experiencing a bout of vertigo, leading to court being canceled for the day.
Combs’ Crass Texts To Ventura After Alleged Beating
Prosecutors introduced a new set of text messages between Combs and Ventura Friday, as their relationship began to disintegrate. The messages were included as part of a summary chart compiling the dozens of times Combs and Ventura organized a freak-off as prosecutors allege Ventura was a sex trafficking victim through physical force and coercion.
The couple were in New York City when Combs texted Ventura on March 13, 2017 inquiring about a potential freak-off.
Nine hours later, after Ventura and Combs had a brief discussion about male escorts and exchanged information about a hotel room, Ventura texted Combs about an apparent physical altercation that had occured. “WTF. Really,” she writes. “I think it will always be black and white. You threw out all my shit. I can dig it … You [beat] my head in.”
The couple briefly argued over text, with Combs accusing Ventura of being “crazy” and “flipping” on him. “So we’re clear this time. We’re taking a break,” Combs asks. “This is really how you wanna leave this? You sure.”
“No, I just don’t want to be beat down for being defiant or ever,” Ventura responds. “You treat me and make me feel like I don’t matter.”
Combs then responds crassly, accusing Ventura of starting the fight for resisting him during a freak-off. “You really think you can have me jerk my dick for ten hours and not come,” Combs writes. “Your [sic] nuts. One minute you down asking about shit. Then the next minute you acting like you doing something you don’t want to. Make up your minds. I’m trying to figure out how I get this nut out my dick.”
Days later, Ventura and Combs seemed to be in the process of making up. “I knew if I said no to it in New York, it would have been a problem,” Ventura writes. “Those were my last nights with you. You only see me one way. You treat me like a hooker, to be honest. You always want to call one so bad, and you have one. This hooker has been here for 10 years.”
Ventura later adds, “Please don’t play victim. If you can, go to our last messages. That’s all you wanted, and that’s why I was upset. I love our FO’s when we both want it.”
Incessant Calls and $100,000 Alleged Payoff
From the start of the trial, both prosecutors and Combs’ defense team have highlighted the events of March 5, 2016, at the InterContinental Hotel in Los Angeles as a key piece of evidence. Beyond the disturbing hotel surveillance footage of a towel-clad Combs kicking, stomping, and dragging his cowering girlfriend back towards their hotel suite during the middle of a freak-off, prosecutors allege the events that followed offer a clear view into how Combs’ alleged criminal enterprise operated in real-time.
Through summary witness and US Attorney’s Office Special Agent DeLeassa Penland, prosecutors showed jurors a detailed timeline of events, beginning from the evening of March 4, 2016. Text messages and phone records between Combs and Ventura show the two discussing having a freak-off that night, with Combs instructing Ventura to call “Garren,” the owner of the escort service Cowboys 4 Angels.
By 7:30 p.m., the timeline shows the plan is in motion. “Hey you,” a number listed under the name Skyler texts Ventura with a smiley face at 7:49 p.m. “G told me to say hello and let you know I can be there around 1030 to 11.” Ventura and the man exchange a few messages, trying to land on a time, but by 6:00 a.m., the two don’t appear to have met. “I know you’re doing a damn good job. I wanted to say to keep it up,” Skyler texted Ventura at 6:23 a.m. on March 5. “I’m going to lay my head down soon, so just call me if we’re getting together.” (Ventura previously testified she was in the room with Combs and “Jules,” a male escort. A hotel security guard also said he observed an unknown man in the room.)
The timeline shows no further activity that morning until Combs calls Ventura’s phone eight times in rapid succession around 11:30 a.m. (The hotel surveillance video is not part of the timeline.) Ventura doesn’t answer Combs’ calls. Instead, from the back of a car, she snaps three photos of herself with a fat, busted lip with dark sunglasses covering her eyes, according to metadata extracted from her phone.
Over the next hour, Combs frantically tries to contact Ventura more than 30 times. He tries a range of approaches: demanding for her to call him back, pleading that he’s about to be arrested by police officers, accusing Ventura of abandoning him, and threatening he’ll never speak to her again. Ventura responds sparingly, the timeline shows. “I have a premiere Monday,” she texts Combs at 12:10 p.m. “For the biggest thing I’ve ever done in my life. I have a black eye and a fat lip. It was time for me to go. You are sick for thinking it’s okay to do what you’ve done.” She adds, “Please stay far away from me.”
Around the same time, Combs’ personal team launches into action. His longtime security member Damion “D-Roc” Butler, chief of staff Kristina Khorram, and personal assistant all try to locate their boss and calm him down. “Tell him he needs to get out of there before they call the police,” Butler texted Khorram at 2:31 p.m. — around the time Ventura’s best friend Kerry Morgan claimed Combs turned up to Ventura’s apartment, banging on the door with a hammer. “He not picking up.”
The staffers also try to convince Ventura to get in touch with Combs. “Talked to him,” Khorram messaged Ventura at 3:27 p.m. “He promised me he won’t go back over if you will just talk to him on the phone for 5 minutes.”
Later that night, at Combs’ alleged bidding, Khorram and Combs’ assistant attempt to contact InterContinental Hotel security guard Eddy Garcia and pump him for information about the altercation. “Say they had a fun drunk night to try and get more info,” Khorram instructs the assistant. “Did you get security #? PD is asking … What is Eddys last name?”
The following morning, March 6, photos indicate that Ventura is with Butler, who is messaging Combs on the side. “Her face don’t look bad,” Butler texts Combs at 9:37 a.m. “She good. Call her. She smiling and laughing.” Combs then proceeds to call Ventura, speaking with her for 13 minutes.
About two hours later, Combs calls Garcia. Throughout the day, Combs and Khorram make contact with Garcia seven more times. Meanwhile, photos show Ventura is back at Combs’ home for a dress fitting for her upcoming movie premiere, still wearing dark sunglasses.
On the morning of March 7, Combs calls Ventura twice. They speak briefly before Ventura texts him. “I’m serious, but I’m not,” she writes at 9:46 a.m. “This was supposed to be a really exciting day for me and I wish I could just crawl in bed and stay there until I look better.”
Roughly two hours later, Combs reaches out to Garcia again. After a total of 15 phone contacts between the pair throughout the afternoon, Khorram snaps a picture of Garcia’s driver’s license. (During his testimony, Garcia said he brokered a deal with Combs for the hotel videotape, receiving a cash payment of $100,000 that he split among himself and two other hotel security members.)
By 6:30 p.m. that night, photos show Combs and Ventura together at his house, getting ready for the red carpet for the premiere of her movie.
Destroyed Hotel Rooms
Prosecutors entered into evidence photos of the thousands of dollars worth of hotel damages that Combs racked up in the aftermath of alleged freak-offs. Housekeepers at the London in West Hollywood routinely flagged extensive damage to the rooms, submitting photos of the suites in complete disarray.
Bottles of Combs’ DeLeón tequila, empty champagne, and half-drunk wine bottles are seen littered around the room, with couches, chairs, and flooring soaked with lubricant and baby oil. The images also show heaps of dirty towels and linens thrown into a pile, sometimes spotted with blood or a purple residue.
During a stay in mid-June 2023, a hotel record from The London noted that a housekeeper noted “the room’s “new mattress was soaked in oil,” and she couldn’t “place new sheets on the bed due to the mattress being soaked by the oil.”
What’s Next
After six weeks and more than 30 witnesses, prosecutors are expected to rest their case by Monday afternoon. The trial’s wind-down will progress rapidly, as jurors could start deliberating as early as Friday.
Although Combs’ lead attorney, Marc Agnifilo, said last week that the defense’s case could take between two and four days, he amended his position on Friday and said they could rest as soon as Tuesday. Agnifilo hasn’t confirmed who Combs would be calling to the stand but previously indicated a former Bad Boy HR executive and a psychiatrist could be among their key witnesses.
The shortened timeline is likely due to this week’s abbreviated schedule. The court was closed on Thursday, June 19, for Juneteenth and a half-day was already scheduled for Friday. However, a juror calling out sick on Wednesday due to a bout of vertigo resulted in only two full trial days.
Judge Subramanian has repeatedly told the jury, with assurances from both the defense and government, that he expects the trial to be wrapped by the July 4th holiday. Combs’ defense team likely wants the jury to have ample time to reach a verdict to avoid antsy jurors rushing into a decision because of their looming holiday plans.
