Ex-girlfriend testifies about alleged post-raid sex trafficking by Sean 'Diddy' Combs
The testimony of a woman who was Combs' girlfriend until his arrest last September highlights his activities after federal agents raided his mansions.
In the months after federal agents raided his mansions in Los Angeles and Miami, Sean “Diddy” Combs kept close contact with the prosecutors now trying to put him in prison.
His lawyers emailed the U.S. Attorney’s Office in Manhattan about his plan to fly from Miami to Los Angeles for his daughter’s high school graduation in May. They emailed again to say they’d “taken possession” of his mother’s and daughters’ passports, and they told prosecutors of Combs’ itinerary for a family “road trip” through Grand Canyon, Zion and Death Valley national parks last June.
All the while, prosecutors say Combs was victimizing a young woman through coerced sexual encounters with prostitutes identical to the so-called “freak offs” his former girlfriend Cassie Ventura detailed in the November 2023 lawsuit that prompted a federal criminal investigation.
The woman testified on Friday that Combs continues to pay the $10,000 monthly rent on her home from behind bars.
Prosecutors added her as a victim in Combs’ criminal case in a superseding indictment filed on Jan. 30, more than four months after he was arrested at the Park Hyatt hotel in New York City. The final indictment filed on April 3 identifies her as Victim-2 in one of two sex trafficking charges and one of two transportation to engage in prostitution charges. The other is Victim-1, who is Ventura. Ventura testified under her true name and never sought a pseudonym, but Combs’ lawyers in April agreed to allow the other woman to use one.
Her testimony has revealed how 55-year-old Combs continued his illegal encounters with prostitutes even after federal agents raided his mansions and he hired expensive lawyers to try to fend off the grand jury investigation that resulted in his indefinite incarceration.
Jurors last month heard about ketamine and Ecstasy found in Combs’ hotel suite, which is where his lawyers have said he was preparing to surrender to federal authorities. Combs also had baby oil and lubricant in the suite, despite agents seizing those same items from his homes in March 2024 as evidence of a possible sex trafficking conspiracy.
The rapper and business mogul’s girlfriend at the time of his arrest is testifying under the pseudonym Jane and will return to the witness stand Monday in U.S. District Judge Arun Subramanian’s courtroom in lower Manhattan.
A self-described “content creator, influencer,” Jane testified last week about a whirlwind romance with Combs that began in January 2021, broke in October 2023 then rekindled one month before agents Homeland Security Investigations raided his homes at gunpoint. She said she and Combs stopped using hotel rooms in 2024 and instead only hosted prostitutes at Combs’ mansions.
Jane said she last saw an escort named Paul in July 2024, which would have been after Combs returned from his national parks tour. She also said their last encounter with an escort named Don was in August 2024, which is one month before Combs’ lawyers say he planned to turn himself in but was instead arrested by armed federal agents.
“Now, in total, between May of 2021 and Sean’s arrest in 2024, do you know how many different men you were paired up with during these nights?” Assistant U.S. Attorney Maurene Comey asked, according to a court reporter’s transcript obtained by Legal Affairs and Trials.
“No. I don’t like to think about that,” Jane answered.
Jane’s testimony about Combs directing her encounters with male prostitutes mirrors Ventura’s testimony about Combs wanting to watch her have sex with male prostitutes in sometimes days-long sessions he called “freak offs” that involved baby oil and heavy drug use. Jane testified she and Combs referred to them as “debauchery or hotel nights” — jurors saw a text message from Combs in which he referred to a “freak off” — and she said they began as a seemingly one-time thing in May 2021 but soon became she and Combs’ only activity.
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Jurors on Friday saw 15 images from sexually explicit videos Combs took of Jane with Don and Paul and other prostitutes she identified in court as Antoine, Kabrale and Leo. They also heard an eight-minute audio recording from Combs’ phone of the woman discussing her desire to use a condom with a male prostitute from the company Cowboys 4 Angels when Combs entered the room. The images were shown only to jurors and Jane, but the recording was played in open court.
After the recording played, Jane testified that Combs can be heard telling her, “What are you guys doing? What do you want?’”
“I said, ‘Condoms, or I think Don said, ‘She’s looking for a condom,’” Jane testified.
“When you later in the conversation said, ‘You promised,’ what were you referring to?” Comey asked.
“I’m referring to a conversation I had with him that I just preferred to wear condoms and if we can wear condoms,” Jane answered.
“And what had Sean told you in that conversation before this hotel night?” Comey asked.
“That it was fine,” Jane answered.
“That what was fine?” Comey asked.
“That we can wear condoms,” Jane answered.
“And then what happened when you actually got in the room?” Comey asked.
“I wasn’t able to wear condoms,” Jane answered.
Her testimony is the most graphic yet in a trial that opened May 12 and asks jurors to decide if Combs’ use of his businesses and employees to facilitate Ventura’s and Jane’s encounters with sex workers constitutes an organized crime conspiracy.
Prosecutors say the racketeering enterprise included bribery related to Combs paying $100,000 to a security company to obtain surveillance video of him beating Ventura at the Intercontinental Hotel in Los Angeles in 2016, and arson related to Combs’ ordering the torching of Scott “Kid Cudi” Mescudi’s Porsche convertible over his romance with Ventura. Jurors have heard testimony from former employees who said they helped set up hotel rooms for Combs, and they’ve seen business records that show he appeared to use company money for personal expenses indiscriminately.
In addition to Ventura and Combs’ most recent girlfriend, the prostitution charges also mention as victims “multiple individuals” including “commercial sex workers.” Some have testified, and Ventura and Jane have identified photographs of several.
Jane will be prosecutors’ lengthiest direct-exam: She began testifying last Thursday afternoon, and Combs’ attorneys may not begin cross-examination until Tuesday.
Miami meeting, then ‘Sesame Street’ nicknames
Jane testified she became friends with Combs in late 2020 after a “girls’ trip to Miami” that he financed because he was dating one of her friends. He exchanged numbers during a yacht party, “and that’s when we decided we should have a nickname.”
“And he said ‘Bert’ and I said ‘Ernie,’” Jane testified on Thursday, referring to the “Sesame Street” characters.
Jurors saw her first text exchange with Combs on Nov. 29, 2020. She began, “Bert.” He replied, “Ernie,” then wrote the next day, “Call me, Ernie. How are you?”
She said their first date lasted five days, then he took her on a birthday trip to Turks and Caicos and the Bahamas and gave her $10,000 to compensate for income she missed while vacationing instead of working. She took the drug Ecstasy for the third time in her life at Combs’ suggestion, and she testified that at the end of the trip she felt “even deeper in my feelings for Sean.”
“I want to say we even started using the L word. And I was really deep in it. I really fell head over heels for him,” Jane testified.
He told her was seeing other women, but, “In my heart, I just wanted to see Sean. So I was monogamous,” she said.
In case you missed it, my previous articles detailed the testimony of a former employee of Combs who testified under the pseudonym Mia and the testimony of Combs’ former employee Capricorn Clark.
Jane said Combs first discussed involving a prostitute in their sexual encounters in May 2021, and they ended up hosting one at a Miami hotel that night.
She said she thought it was a one-time thing: “We just did something so crazy, taboo, and fun, and sexy,” but “I didn’t think we would be doing that again like that.”
However, Jane testified, “That night just opened like a Pandora’s box in our relationship. It just completely set the tone for our relationship moving forward. … It was just a door that, like, I was unable to shut for the remainder of the relationship.”
Jane said she agreed to other sexual encounters “because I just really loved him at this point, and I just wanted to make him happy and I feared losing him.”
“I just wanted to be everything that he wanted and I wanted our time to be special every single time. And if that made him happy, I was willing to make him happy,” she testified.
Jane said Combs randomly gave her money (the most was $20,000) “just because,” and they eventually agreed to a two-year, monthly allowance of $10,000, through what she called a “love contract” and “verbal flirty thing.” Combs gave it to her by paying her monthly rent.
She told Combs “many times,” both verbally and in writing, that she didn’t want to have sex with other men, but “he just was dismissive or just wanted me to move on from the subject.”
Jane testified he also used her rental situation as leverage by telling her if they break up, “Do you need, like, what, three more months in the house? Because I’m not about to be paying for a woman’s rent that I’m not even seeing.”
She said she “felt frustrated” and “just obligated” to perform for Combs to keep him happy.
“My feeling of obligation really started to stem from the fact that my partner was paying my rent,” Jane testified.
Texts, notes capture complaints over ‘hotel nights’
Jurors saw texts and phone notes that Jane wrote chronicling her problems with Combs, including her jealousy of his romantic dates with other women following their prostitution-oriented “hotel nights.”
They also heard a voice message Combs left her in late November 2021 after she texted him, “Don’t say you fucking miss me and you’re bored over there. Just don’t say shit to me at all. You don’t deserve me.”
“Jane, how often did Sean speak to you using the tone and language we just heard in that voice note?” Comey asked.
“Often,” Jane answered.
“How many times did Sean call you ‘fucking crazy’ when you tried to raise concerns about having to do these hotel nights while other women he saw were treated differently?” Comey asked.
“He would call me crazy all the time,” Jane answered.
“How did it make you feel when he talked to you that way?” Comey asked.
“It would make me feel confused. Just down,” Jane answered.
Jurors also saw texts Jane wrote Combs in February 2022 in which she said, “I don’t ever want to do another hotel entertainment night with you. I didn’t even want to do those things with you on my birthday, but I wanted to make sure we had fun. I feel so cheap once again.”
“Over the next year, what sorts of activities or outings did Sean tell you that you would get to do with him?” Comey asked.
“He told me that we would go on more dates, that we would go on more trips, and we would travel and just do normal things together that I really craved to do,” Jane answered.
“How many of those things did you do?” Comey asked.
“Hardly none of them” Jane answered.
“Did you go on any trips?” Comey asked.
“No” Jane answered.
“What did you do most of the time you saw Sean over the next year?” Comey asked.
“Hotel nights” Jane answered.
Jurors saw a note that Jane wrote on her phone but never sent Combs.
“I don’t know why you’re calling me but I’m sorry I don’t want to do drugs for days and days and have you use me to fulfill your freaky wild desires in hotel rooms.”
Jane said it was meant for Combs but, “I didn’t have the courage to really say that to him.”
Another note on Dec. 12, 2022, said, “But for what. You want to call me for what. You going to ask me to come over to put you to bed because you were partying with another girl the night before. Ask for foot rubs and sleep till the next day to take another girl on a date or ask me to come over because you want escapism or debauchery. Keep me up for three days straight and then send thousands of roses, cars, jewelry, private island trips, date nights for someone else, and leave me to clean up my house and recover alone. I’m done being used by you. You are hurtful and damaging for me. I have to pull away from you because you have just crossed too many lines. Call you for what. So you can convince me to come over around you and what. Put you to bed and give you foot rubs because you were fucked up from partying with whoever the night before. Have me just sit there while you’re calling, texting, FaceTimeing, and sending voice notes to other girls. Or have me locked up in a hotel or trash my house for a three-day dirty escapism binge. Have me do all of that just to turn around to leave me to clean up and recover on my own while you buy thousands of roses, cars, jewelry, shopping, PJ flights, and set up the next flight and trip for someone else. I’m done being used by you. I don't feel good around you, and I need to stay away from you.”
“Jane, why did you write that?” Comey asked.
“I wrote that because these things were happening around this time where it was really hurtful to see that Sean was so capable of doing these really romantic, lovely gestures. But when it came to me, I was just always dealt and met with excuses,” Jane answered.
Jane also told Combs in a February 2023 text message she wanted to “do things outside of these rooms.”
“But that’s all you showed me over and over, what you wanted me for. I won’t miss it because I’m more than that,” she wrote.
Jane has not yet testified about why her relationship ended with Combs in October 2023 or why they got back together in February 2024. Her testimony is expected to last into Thursday, and I plan to write another article this week. I’ll also be in New York City the week of the 16th to watch the trial in person.
Judge threatens to remove Combs from courtroom
Judge Subramanian on Thursday threatened to have Combs removed from the courtroom if he makes facial expressions at jurors or otherwise tries to communicate with them.
The judge raised the issue after prosecutors emailed him Wednesday night about a New York Times article that reported Combs interacted with “someone who was on the jury relating to the temperature in the courtroom, not relating to a matter in the case.”
Subramanian began the day by telling the courtroom he wanted “to remind everyone to make sure that you are minding your facial expressions and there should be no attempts from anyone here to interact with, communicate with, or influence the jury.”
“And I’ve reminded and asked the security here that’s in the courtroom as well as the court staff to monitor this conduct and report on any violations. If there are violations, the court will take swift action” the judge said.
Comey raised the issue again during Combs’ lawyer Nicole Westmoreland’s cross-examination of Bryana Bongolan, who testified that Combs dangled her over a balcony in 2016.
Comey said Combs “is testifying from counsel table by nodding his head vigorously yes in response to Ms. Westmoreland’s questions.”
“The jury is seeing it, and then we see them writing down. So our concern is the defendant is testifying by nodding affirmatively in response to Ms. Westmoreland’s questions,” Comey told the judge after the jury left for a break.
Subramanian said he didn’t see anything, “but I take it the government observed this during the questioning.”
Westmoreland said she’d speak with Combs, “but I’m looking straight ahead at the witness.”
“I’m not suggesting that Ms. Westmoreland is intentionally trying to do this. I’m suggesting that the defendant is himself trying to take advantage of the leading questions without Ms. Westmoreland’s knowledge to testify by nodding vigorously yes in response to her questions,” the judge said.
Combs’ lawyer Alexandra Shapiro said she doesn’t believe “that’s fair” but “will go over to him before the questioning resumes and re-warn him of your Honor's admonition.”
Later in Bongolan’s testimony, Subramanian said he himself saw Combs and told his lawyers after the jury left the courtroom, “There was a line of questioning where your client was nodding vigorously and looking at the jury. And there was a subsequent moment, we had a sidebar, and I looked and I saw your client looking at the jury and nodding vigorously during that line of questioning. That is absolutely unacceptable.”
Combs’ lawyer Marc Agnifilo said, “It’s not going to happen again, Judge,” and Subramanian replied, “It cannot happen again.”
“If it happens again — if it happens even once — I will hear an application from the government to give a curative instruction to the jury, which you do not want. Or I will consider taking further measures, which could result in the exclusion of your client from the courtroom. Do you understand that?” said Subramanian, a 2023 Joe Biden appointee.
“I understand, Judge,” Agnifilo said.
Subramanian told Agnifilo “to have a conversation with your client to make sure that he understands, and everyone should understand, that I really meant it. That there should be no efforts whatsoever to have any interaction with this jury.”
“Understood, Judge,” Agnifilo said.
The next morning, Agnifilo told Subramanian that Combs “assured me he didn’t mean anything by it.”
“He was reacting to the witness on the stand. That being said, we’ve addressed it. But I also want the court to know how seriously we take these things,” Agnifilo said.
That’s when Subramanian said prosecutors first raised the issue based “based on New York Times reporting,” so “in open court before the jury came in, and without pointing any fingers at any particular person, I was very clear that all of the parties, and in fact members of the public in the back, should not … make any attempts to interact with the jury.”
“I couldn’t have been clearer. And it was maybe a half hour or 45 minutes later when the incident happened that we were talking about,” Subramanian said.
Shapiro said she whispered at Combs to stop before testimony resumed and was “really taken back personally” when the judge publicly admonished him.
“I felt personally kind of, quite frankly, a bit upset about it because I tried to follow your Honor’s instruction,” Shapiro said. “And then Mr. Agnifilo did follow up during a longer break when there was actually an opportunity to speak to the client. So I just want your Honor to understand that.”
Subramanian said he understands, “but to be perfectly frank” he saw the interaction and it “was inappropriate.”
“No one would have misunderstood my instruction that I had given about 30 minutes earlier. So I regarded that as being outright defiance of the court’s order in that moment as to that one incident. And it required a firm instruction in open court so that there was absolutely no misunderstanding about how we would proceed moving forward because these are serious matters and people have to act with the proper decorum in the Court,” the judge said.
Subramanian said he has “no doubt that moving forward, we are all going to be following the rules."
“And I have no doubt that defense counsel has properly instructed their client and I take nothing of it,” Subramanian said.
“I mean it when I say everyone has been doing a great job and working cooperatively and doing their best to follow the rules of the court. So I take nothing from that. But the instruction was necessary to make sure that we don’t have any issues moving forward,” the judge said.
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