Diddy Trial's Most Disturbing Claims: Week Six Breakdown

Combs has been charged with sex trafficking, racketeering conspiracy, and transportation to engage in prostitution. He's maintained his innocence. If convicted on all charges, which also include arson and bribery, Combs could face a mandatory 15-year prison sentence, with the possibility of life behind bars.

The woman testifying under the name "Jane" had been involved with Combs for approximately three-and-a-half years, up to his arrest in September 2024. She detailed similar allegations to an earlier girlfriend, R&B singer Cassie Ventura, citing Ventura's November 2023 lawsuit as an eye-opening moment for her -- though it did not end their relationship.

Another girlfriend testified anonymously under the name "Mia," while the jury heard additional testimony from Ventura's mother and Scott "Kid Cudi" Mescudi, who was romantically involved with Ventura while she was still with Combs.

Multiple staff members who've worked for Combs' various business enterprises over the years have also testified, as have hotel staff where his "freak offs" occurred, and investigators involved in the raid on his Miami home and investigation into his affairs.

A centerpiece of the prosecution's case has been the viral video of Ventura's physical assault in the hallway of the InterContinental Hotel in Los Angeles in 2016, with jurors reliving that story from multiple individuals, including a security guard who alleged he was paid $100,000 by Combs directly to give him the only copies of that altercation.

As the prosecution argues coercion, the defense is countering with consent. But both sides agreed that in order to get to the bottom of the case, there would be a lot of witnesses and a lot of shocking details about Combs' sexual proclivities.

You can catch up on the first five weeks of testimony at the following links:

Text messages between Combs and Cassie were shown to the court on Friday morning.

"You hit me in my head two good times. That didn't make me feel good. I know I'm not crazy," she wrote in one exchange, before he said, "You have disrespected so much in last 12 months" and claimed she was talking to him like one of her "little f--kboys."

"You treat me like a hooker to be honest. You always want to call one and you have one," she later wrote. "This hooker has been here for 10 years ... I love our FOs when we both want it."

In another exchange, she said he "bashed my head in," before telling him, "just don't want to be beat down for being defiant or ever." She added, "All I wanted was to have a good time and you took all your anger out on me, per usual ... as soon as you get f--ked up, you drag me down the hall by my hair."

"That's not love, that's possession. I have bleeding cuts," she wrote, before he said "Any other woman in the world would’ve been so happy ... I and everyone knows you were acting like a bitch."

The jury has since been dismissed for the week.

Special agent for Homeland Security Investigations Joseph Cerciello also took the stand, claiming that during one of Comb's hotel stay -- at a room reserved under the name "Joseph Chavez" -- there was a $3,750 charge for damage.

There were "bodily fluids stained on the wood floor," per hotel records, as well as furniture.

The evidence chart Cerciello showed to the court also showed a text from Combs telling Jane to send escort service Cowboys 4 Angels $1,110 for flights and an "overnight rate."

There was also a $1,800 charge at another hotel for damaged furniture, smoking, and towels which appeared to be "soaked" with baby oil, which was "in the carpet as well."

The trial took a two-day break this week, as a juror was suffering from vertigo on Wednesday and the court took off Juneteenth on Thursday. One of Diddy's former assistants, Brandan Paul, took the stand Friday morning, after working for Combs from late 2022 up until his 2024 arrest. He has been granted immunity for his testimony and has been called a "drug mule" for Diddy.

Per Paul, he typically worked 80-100 hours a week, with a starting salary of $75,000. Eventually, that was bumped up to $100,000. As part of his job, he would set up Combs' hotel rooms and would sometimes go days without sleeping -- using Adderall and cocaine to stay awake. Per Paul, Combs told his staff he expected them to work like "SEAL Team Six."

Paul said he would obtain drugs for Combs, including marijuana and Xanax and claimed he saw Diddy use cocaine, ketamine, ecstasy, and pot. Text messages also showed him telling a dealer the drugs were for Combs.

Paul also claimed he sometimes had to set up and clean up after Combs' "wild king nights," which he understood included "partying, alcohol, sex, drugs." Of the setups, he said he packed the hotel rooms with everything, including baby oil, sheets, towels and alcohol. Of cleanup, he said he wore gloves "for sanitary reasons," as he stripped the bed and threw away empty baby oil bottles.

He said he only knew of Jane participating in them with Combs and said they stopped around the time Cassie filed her lawsuit.

Paul also said he was arrested for possession of cocaine while on a family vacation with Combs -- claiming it was actually Diddy's, but didn't tell that to cops out of "loyalty." He also said nobody told him to travel with the drugs, saying he put it in his bag and forgot it was there.

Under cross-examination, he said he was "absolutely not" Combs' "drug mule," and said he thought the "king nights" were consensual. Overall, he said his feelings about Diddy were "complicated."

Assistant US Attorney Emily Johnson broke down additional text messages between Combs and Ventura in the wake of the March 2016 InterContinental Hotel assault.

"Baby I cant say it enough Im so sorry!!!!!" Combs sent in one text.

Later that day, Ventura sent back, "I still have crazy bruising from Friday. I would be a dummy to subject myself to that possibly happening again."

"When you get f--ked up the wrong way, you always want to show me that you have the power and you knock me around. I’m not a rag doll, I’m someone’s child," she added.

In another text, Ventura wrote, "You treat me like Ike Turner," referring to Tina Turner's well-known abusive husband.

Defense attorney Teny Geragos cross-examined government witness DeLeassa Penland, a special agent with the U.S. Attorney’s Office testifying as a summary witness to bring more texts, voice and video communications to the jury.

Geragos' first question was about the lists of individuals associated with the various meetings, generally "freak-offs," in the prosecution's charts.

Penland testified, "If I did not have the evidence, their name is not in this chart," but the chart "does not have the name of every potential person that was at this gathering."

With this established, Geragos started reading off texts not included in the government's summary chart relating to Ventura, including on where she messaged Combs she was "always ready to freak-off," that were dated around the times of "meetings" on the chart.

She noted a meeting in late July 2012 that listed Ventura but not Combs, with Penland confirming there were no messages that she saw between Combs and Ventura related to that particular meeting. She did see messages between Ventura and "Islander LA," where the singer asked if he was available and told him to hurry as she had a flight.

Geragos pointed out multiple occasions where Ventura expressed consent, and even enthusiasm, about "freak-offs," in the defense's effort to counter her claims she was coerced or intimidated into participation, and noting these exchanges are absent from the prosecution's evidentiary presentation.

"I had a great time with you this weekend. Thank you," Combs wrote after one documented meeting. "Me too. I love you. I miss you," Ventura wrote back.

Penland reiterated that her only role was to confirm the underlying data was there to support what the government had put on the chart; it was not her job to add anything else to it.

A text from August 5, 2009 from Combs where he told her she could choose any date. Ventura responded she'd like a Friday night for the weekend to physically recover, but suggested if that weekend didn't work, she wouldn't be free again until August 28.

An August 7 text saw Ventura tell Combs she was looking forward to performing oral sex on him. The jury was then shown video that many news outlets believe to be likely explicit, and possibly repeated from Monday's afternoon testimony. These videos were blocked from the courtroom audience.

With Penland still on the stand, the prosecution looked at a flurry of text exchanges with Combs' staff after the March 5, 2016 InterContinental Hotel altercation.

At the same time Combs was texting with Ventura, there's a series of calls between him and former InterContinental security guard Eddy Garcia on March 7. Garcia had previously testified that Combs allegedly arranged to buy the "only copy" of the assault on Ventura captured by hotel security cameras, ultimately paying him $100,000.

A photo of Garcia's license plate was also captured that day, recovered from former chief of staff Kristina Khorram's phone, corroborating Garcia's testimony that he allegedly met Combs and Khorram for the exchange, where she took a photo of his plate.

Later that day, records show Ventura calling Combs, his former security guard Damion "D-Roc" Butler, and her apartment building before texting her former best friend Kerry Morgan, "I should have sued lol." Morgan replied, "Totally."

Subsequent phone records showed Combs calling Ventura, with photos of them found on her phone from that night. He also made calls to Garcia that night twice, then again on March 8, with one call going to voicemail, and the two of them finally connecting March 9. Their next communication was on March 25, when Combs called Garcia and they spoke for a minute.

Garcia had testified that Combs had called him a few weeks after the alleged exchange, asking if anyone had asked about either the hotel incident or the video. Garcia told him he'd heard nothing, according to his testimony.

Penland continued her testimony on Tuesday morning, claiming Combs paid for flights and hotels for male escorts on his American Express card.

Text messages between Combs and Ventura between the two following the March 5, 2016 altercation at the InterContinental were also shown. First, he called her three times, which went unanswered, before they briefly spoke in two one-minute calls.

"I went and checked everything and spoke to security. Jules left so you’re good and as long as you don't disturb the other guests they'll leave you be," she then wrote him.

He, however, demanded she "call me now," claiming "the cops are here."

They briefly spoke for just 18 seconds, before further calls went unanswered by Ventura. "You gonna abandon me all alone," he then allegedly texted, begging her to call him.

"I have a premiere Monday. 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," she fired off in response. "You are sick for thinking it's okay to do what you've done. Please stay far away from me."

"I'm about to be arrested ... If you don't pick up you'll never here [sic] my voice again," he added, as more of his calls went unanswered. NBC News notes that this was possibly untrue as no one called police to the InterContinental Hotel on that date.

Ventura also texted Combs' former chief of staff Kristina Khorram, "This is crazy he won't stop. Please tell him the neighbors are about to call the police." She also told Khorram to "please takeaway whatever keys he thinks he has," before Khorram pleaded with Ventura to speak with him "for 5 minutes." The two did talk later that day.

On March 7, she also texted Combs, "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." Photos on her phone from that night showed the two together.

The next witness called to the stand was another summary witness. This time, U.S. Attorney’s Office special agent Deleassa Penland was brought on to discuss flight records, beginning with a man named Jules Theodore, a frequent escort hire for Combs and Ventura "freak offs."

The Washington Post notes the chart has 71 entries, with Penland telling the court they only included individuals for whom they have video footage confirming they were at a "freak off."

This is a key component of the government's efforts to build a case of sex trafficking, as Theodore traveled from Los Angeles to "party" for one weekend in December 2009 at the London Hotel in New York.

Penland testified that a flight itinerary and hotel arrangements were made for a visit to the London Hotel between December 11 and 14. The travel charges are being presented in court as support for the charges of transportation to engage in prostitution charges.

She read aloud in court some messages between Combs and the man coordinating travel for this trip. Combs followed with an email to the personal finance director for his executive office saying he needed to book a flight under the man's name, per CNN.

The finance director sent Combs back a flight itinerary, with Penland testifying that Theodore's flight itinerary was found in Combs Global's records. Flight records for Theodore and Ventura placed both of them in New York at that time. Records also showed that flights and hotels were paid with Combs' American Express card.

A travel invoice for Ventura's October 10, 2012 flight from LA to NYC was sent to Bad Boy Entertainment. This was followed on October 13 with a message from Combs asking if she was "ready for tonight."

Messages from Ventura with two separate men were then show giving them information for a room in New York reserved under the name "Janet Clark." One of the men texted he was in another room, reserved under the alias "Frank Black."

Both rooms were paid for with cash and an American Express card, totaling $795.63 at the Trump International Hotel & Tower, including a movie, breakfast, and refreshments. There were videos from these "freak offs," recorded October 14, recovered from Ventura's device.

On another occasion, in 2013, texts between Combs and Ventura were shown surrounding setting up a "freak off" with four different men to "celebrate Christmas." Texts then show Ventura coordinating with one service and the other men individually to set up staggered arrival times.

Paralegal specialist Ananya Sankar with the U.S. Attorney's Office for the Southern District of New York continued her summary cross-examination as the defense dug into some texts and exchanges from "Jane," the recent ex-girlfriend of Combs whose testimony dominated much of the last week in court.

In one message from Valentine's Day 2022 shared with the jury, Jane expressed she was "excited to surprise him" in a message to Combs then-chief of staff Kristina Khorram, sharing photos of a hotel room adorned with rose petals and heart balloons.

Just a few days later, Khorram reached out twice to Jane to tell her Combs was pushing her to figure out plans. Jane replied, "My answer to him is no and it is still no." Khorram said she'd relay the message, but to let her know if anything changed.

Highlighting another exchange about where funding might be coming from for Combs' extracurricular activities, defense attorney Teny Geragos noted a message from former head of security Damion "D-Roc" Butler where he asked for approval for a disbursement from an account identified as 'PD personal.'

This is essential for the defense to try and show that funds from Combs' business enterprises were not used for any of these activities, as it weakens the government's racketeering claims.

Text messages also gave some insight into Combs' relationship with Khorram, with an exchange from November 2023 -- shortly after Cassie's lawsuit -- showing she was willing to call him out. "If you cannot be honest with me, this doesn’t work," she wrote. "We all know what your Kryptonite is and where you don’t make the best choices."

In the messages shared with the jury, Khorram told Combs that him keeping things to himself is what put them in this "situation we are all in right now." She told him she felt they were about to relive it over again, per NBC News.

She told the hip-hop mogul she thought he was being dishonest with her, to which Combs responded, "Come take my phone." Khorram said it wasn't about that and if he was starting to lie to her, it would "break" her.

Combs' staff was keeping tabs on him in the wake of Ventura's November 2023 lawsuit that exposed "freak offs" to the world. The jury saw texts from former head of security Damion "D-Roc" Butler, who checked up on Combs, telling him, "If you need a real friend, I'm here."

They also revisited some message between Butler and "Mia," an alias used in court by a former assistant who chose to testify anonymously, where Butler had given Combs Mia's number and then was working as the middleman attempting to get Mia to either take Combs' calls or call him herself.

"Your boy said to call him. He doesn’t want or need you to do anything. He just called me," Butler texted her on December 5, 2023. Two months later, he sent her, "Good morning. How are you doing? Did you ever speak to P. He called me a couple days ago."

Even as Butler was trying to communicate with Mia, he was sending Combs copies of the responses he was getting in February 2024.

"Let me know when you reach her," Combs replied after Butler sent him a message from Mia on February 4saying that her debt was her problem and she'd figure it out one day.

Combs also tried to reach her multiple times himself over the next few days.

On February 7, he sent her, "Hey. I don’t wanna be blowing up your phone. Just needed to talk to you for 10 minutes. Just need my memory jogged on some things. You were my right hand for years, so I just to speak to you to remember who was even around me. And it would be good to hear your voice. But if you don’t want to, all good. Just let me know. Love. Hope you’re well."

He then sent a copy of that message to Butler, adding, "I’ve been trying to reach her, she ain’t picking up the phone." Butler then tried to call Mia twice; she did not answer.

On cross-examination, defense attorney Teny Geragos confirmed that Butler told Combs Mia's number was ringing as if she was out of the country at the time, and that there are no records of Combs attempting to call Mia again after that.

On Monday morning, the jury reviewed multiple emails between Combs' former chief of staff Kristina Khorram and various personal assistants about planning and setting up "freak offs" at hotels for him and Ventura in 2016. These texts were read with paralegal specialist Ananya Sankar on the stand as a summary witness.

The jury was then shown similar messages from November 2021, still involving Khorram, relating to coordinating a "hotel night," which is what his most recently girlfriend, who testified anonymous as "Jane," called "freak offs." These were events allegedly involving a woman involved with Combs romantically having sex with a hired man while Combs watched and directed from the side (and sometimes got involved).

In a text from Combs on November 14, 2021, the mogul told Khorram he didn't want the hotel to know that it was him booking the room so he wouldn't have to deal with "unneeded charges." Various hotel staffers have testified that "freak offs" often led to additional cleaning charges.

Another exchange shared with the jury, this one dated February 2022, talked about how Combs' "damage charges on the one hotel are always high." This would correspond to Combs' time with "Jane," who called the events "hotel nights."

A message sent to her from Khorram told her to ask the hotel "if they can bring up like 15 bath towels." Jane responded that Combs always brought cash and requested his security bring around $5-10k -- with Khorram relaying this request to Combs.

On top of text exchanges about setting up and managing hotel rooms, the jury saw exchanges involving Combs, Khorram and other staff members about buying drugs from a dealer dubbed "Guido."

In one thread, Faheem Muhammad, Combs' head of security, gets approval to pay thousands of dollars to Guido for drugs, including marijuana, on a thread including Combs, Khorram, Guido, and Combs' accountant.

Another thread showed Combs confirming an order of "Molly, 15 pills," which he said he needed Muhammad to pick up before a flight to Miami. He then instructed Khorram not to text about it, per NBC News.

There were also text messages related to some of the alleged violence Ventura had previously testified she endured during her decade-long relationship with Combs. In May 2017, she texted Khorram "wtf" and told her she "should talk to him."

"No one deserves being dragged by their hair," Ventura texted Khorram. "I locked the door for my safety." She also said she had no belongings or money with her. Khorram replied she would try to talk to Combs and help Ventura get her things.

Sankar also shepherded the jury through revisiting voice messages after Ventura's lawsuit between Combs and Jane, that she did not know he was recorded. There were also photos from around that time, dated December 28, 2023,  recovered from Khorram's device that were from another phone.

"I don’t believe the lovey dovey stuff. You don’t need to go there for me. I was confused and couldn’t concentrate for three years and feel extremely exploited, heartbroken and manipulated by you," read one message written from Jane to Combs.

Another stated, "You’re the only opportunist here. You exploited the fuck out of me. You win. 3 years of being used and you had three years of fun with my body." Jane had testified sending both of these letters.

A few hours after the photos of these messages were taken, Jane texted Khorram, "he just threatened me about my sex tapes that he has of me on two phones. He said that he would expose me and send them to my child’s father."

The first witness called by the prosecution was a summary witness. These are individuals called by the government to submit summary charts into evidence to help the jury gain more clarity around the testimony of other witnesses.

This is done by entering things like text messages and other relevant information into evidence without specifically having them brought up as discussion points in testimony.

Ananya Sankar is employed by the government at the U.S. Attorney's Office for the Southern District of New York. She testified that she had reviewed and could verify the accuracy of these charts summarizing prosecution exhibits.

On the stand, Sankar said she had reviewed hundreds of pages of documents related to this case, including text messages, phone call logs, audio files, videos, and images.

She read aloud a text exchange about "freak offs"/"hotel nights" between oft-mentioned then-chief of staff Kristina Khorram and one of Combs' assistants, Ryan Lopez. A hotel manager in Week 2 cited Lopez's name on the account used to book Combs' hotel rooms.

"Lol think I saw one of the cowboys today. You can spot them in a lobby like a escort. I forgot to tell you about it," Lopez texted Khorram on December 29, 2019, as read aloud by Sankar in court.

Khoramm sent back four laughing face emojis and the question, "Btw how long is he gonna stay awake?" Lopez replied, "Lol I’m guessing until tomorrow night." That corroborates stories from both Ventura and "Jane," who stated that one service used to find escorts was called Cowboys 4 Angels. They also both stated these sessions could go multiple days.

After five full weeks, Judge Arun Subramanian followed through on last week's intention to dismiss juror number 6 over inconsistencies in his answers about where he lives. The defense argued that this dismissal of a Black juror for a white alternate would impact the diversity of the jury.

Subramian argued that "it would be improper to let the race of the juror and the alternate juror factor into the proper course here all."

As for the juror, he also declined the defense's wish to allow him to be questioned further, as he worried it would give him another chance to "shade" his answers.

Subramian said that when questioned last week, the juror seemed to be making an effort to stay on the jury. He also said there's some evidence he may be acting with a personal agenda.

Juror number 6 was replaced with the first alternate, a 57-year-old white man who works as a manufacturing architect with a master's degree in mechanical engineering. He told the court he's heard some media coverage of the allegations against Combs on the radio.

The judge also stated there is an issue with a different juror -- that is completely unrelated to the juror number 6 situation. He said he intends to further question that juror after the jury is dismissed today.