Highlights from the ‘Diddy’ trial: Combs’ recent ex-girlfriend sobs while testifying

Jane will return to the witness stand on Monday when prosecutor Maurene Comey will resume her questioning.

Combs’ lawyers have not yet had a chance to question her.

In an August 2023 text message, he wrote: “Look at the roof over your head and that pretty smile,” referencing the rent arrangement and some dental work he paid for her.

Jane said Combs has been paying her rent since she moved into the home in April 2023, despite their breakup and his arrest last September.

After Combs went from celebrating her birthday to taking another woman on a trip to the Caribbean, Jane called him a “pathological liar” and said, “I can’t get this image of you lying to my face out of my mind.”

Jane told Combs that, by dating him, she had deprived herself of romance, love, travel and meaningful connections.

“This is about you finally treating me as a human being,” she wrote.
Jane said Combs told her he’d make it up to her by taking her to Turks and Caicos.

Jane desperately wanted alone time with Combs, she said, but before they left, he made her engage in yet another “hotel night.”

When they got to the archipelago, Jane said she was happy at first, but then Combs brought in a male sex worker for yet more encounters.

Jane’s lawyer Lindsay Lewis spoke up during a break in testimony while the jury was out of the courtroom. She said some media outlets and social media accounts have or are attempting to reveal Jane’s identity.

Judge Arun Subramanian didn’t immediately act on Lewis’ request. He asked her to send him any examples of concerning posts.

Subramanian noted that there’s little he can do about members of the public doing their own sleuthing to figure out Jane’s identity based on what she’s said on the witness stand.

The judge previously warned reporters and members of the public observing the trial not to describe Jane in detail. He’s also told sketch artists not to draw her.

Soon after co-opting her birthday into a “hotel night” in 2023, Combs jetted off to Turks and Caicos with another woman, Jane said.

She told jurors she saw Instagram posts of Combs and the woman in the Caribbean archipelago, where they spent some of their earliest times together.

“It broke my heart because I just finished my birthday with these guys having sex with me,” Jane testified. Combs was planning the trip during her birthday celebration, which involved her having sex with three men, she said.

In a text message, she told him: “It feels like you used me to get off and then go away for a week.”

Irritated with the imbalance of their relationship, Jane poured her thoughts into the Notes app on her phone in November 2021, drafting a message to Combs but never sending it.

“I don’t know what you’re calling me for, 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 wrote in the unsent missive.

Jane said she was tired of waiting for Combs to fulfill promises he’d made to her, such as date nights, togetherness, quality time and doing things she wanted to do — not the “hotel nights” that had come to dominate their relationship.

In November 2021, Jane confronted Combs about cheating on her after she saw Instagram posts from a woman who was at his Miami-area estate.

In an audio recording played in court, Combs explained that the woman had come to his house to work out. But Jane didn’t buy that and responded that the woman had been there for days.

Jane said she’d known that Combs was seeing other women, but the Instagram postings reinforced for her that he was giving another woman quality time she yearned for.

She said she felt used, telling jurors that at the time she thought: “It’s not me that he wants. It’s these nights.”

Afterward, Jane said, Combs called her on FaceTime and calmed her down, repeating a pattern she said happened each time she objected to continuing with “hotel nights.”

Jane wiped away tears as she recounted the many ill-effects of “hotel nights,” including constant back pain, frequent urinary tract infections and soreness in her genitals and pelvic areas.

Combs’ former longtime girlfriend, Cassie, testified she also suffered UTIs after enduring hours of sex during sex marathons involving Combs and male sex workers.

Both women testified they were made to have sexual encounters before they were fully recovered from UTIs.

The images were not shown to the courtroom audience or on monitors in overflow courtrooms, in keeping with the judge’s order barring evidence from being displayed to reporters and the public while Jane testifies.

Sometimes, it was a surprise to keep Combs happy, Jane said. Other times it was because he demanded it, she said.

“I knew it was to be expected,” she testified. “He expected me to coordinate a night where we had an entertainer join us.”

Combs would often ask for “hotel nights” in a roundabout way, Jane said, relying on a type of code they’d developed.

“He didn’t have to directly, specifically tell me to do things,” Jane said. “If he said, ‘I can’t want to see what you have for me,’ or something along those lines, I knew what task was being asked of me.”

Jane recalled another occasion where she told Combs she wasn’t interested in sexual encounters with other men. On a trip to New York in 2023, she said she told him, “I didn’t want to do it anymore, these nights with these men.”

Combs didn’t listen, she said, and they proceeded with the encounter. Jane said she objected again in a subsequent conversation and Combs told her she didn’t have to engage in such sexual encounters anymore. But Jane said she felt obligated.

Just a few months earlier, she had moved into a home that was paid for by Combs.

Jane told jurors she was apprehensive about going to New York in the first place because she worried Combs was trying to set up a “hotel night.” Sure enough, on the flight, she said she received a text message from Combs asking: “Do you want entertainment tonight?”

Jane, who had been crying steadily when a lunch break was taken, returned composed to the witness stand after the hour-long break.

The jury was brought into the Manhattan courtroom shortly afterward. And the prosecutor, Maurene Comey, resumed her questioning, which began Thursday.

Immediately, Comey confronted her with a picture of one of the male sex workers.

Cassie, Combs’ girlfriend from 2007 to 2018, testified during the trial’s first week that her hundreds of marathon “freak-off” sessions with Combs and a male sex worker usually spanned multiple days in which she and Combs used drugs to stay awake.

Jane testified Friday that her longest “hotel night” with Combs and a male sex worker was three and a half days, while most went 24 to 30 hours.

Jane said she relied on ecstasy to dull her senses.

“I just feel like I had to take them. When I wouldn’t, it would feel too real, like the atmosphere,” Jane said. “And I didn’t want to feel like it was too real.”

Jane said Combs brought her to have sex with sex workers on her birthday in 2023, even though she was hoping for time alone with Combs.

Jane said she wasn’t interested in having her birthday subsumed by Combs’ fantasies. She said she turned into something of a robot, telling jurors, “I would just tune out and kind of get like in a zone.”

Jane said Combs’ mood soured when she asked for a condom for the sex worker to use.

Afterward, Jane said, Combs took her to another hotel suite, where he was loving and gave her cake and flowers.

But then, Jane said, another male sex worker came into the suite. When they were finished, Jane said, a third man entered the room.

It was “just hours and hours of that,” Jane said.

They will resume at 1:15 p.m. ET.

Combs was continuing to have so-called “freak-off” sex marathons as federal investigators were closing in on arresting him last year, Jane testified Friday.

Jane said she was involved in sexual encounters with male sex workers at Combs’ Miami-area estate as late as last August, just weeks before his arrest at a Manhattan hotel.

Jane estimated there were about five such encounters between February 2024 and his arrest last September. None of them were in hotels, a frequent venue for activities she dubbed “debauchery” and “hotel nights.”

Federal agents raided Combs’ home on ritzy Star Island, along with his home in Los Angeles, in March 2024.

Prosecutor Maurene Comey has been deftly mixing in questions for Jane that cut to the heart of the case, including charges of sex trafficking and forced labor.

As Jane was describing her many “hotel nights” with Combs and paid sex workers, Comey asked her, “who did the most work” during those encounters.

“It was all me, from just start to finish,” Jane testified.

When asking Jane about recruiting a sex worker, Comey underscored the geographic scope of the alleged crimes.

Jane testified that she’d booked flights to Los Angeles and New York for the Atlanta-based sex worker. One of Combs’ charges is interstate transportation for purposes of prostitution.

Later, Comey asked Jane about transporting drugs across state lines for Combs.

Jane described how she nervously smuggled pills in her checked luggage on commercial flights from Los Angeles to Miami.

Jane said both times Combs asked her to “pick up a package” at his Los Angeles mansion and bring it with her when she visited him at his Miami-area estate.

Jane testified that she wasn’t comfortable with the request, but Combs’ chief of staff Kristina “K.K.” Khorram told her: “It’s fine, I do it all the time.”

Jane said she delivered the drugs to Combs and ended up using some of the drugs with him.

Combs pledged to get clean from drugs in 2023, Jane said, but first wanted to have another of their “hotel nights,” dubbing it a “sobriety party.”

Jane testified that she typically took drugs to get through the encounters, but abstained that night in a Beverly Hills hotel room as Combs ingested ecstasy and cocaine.

After having back-to-back sex with two sex workers, she said, she felt sick and vomited in the bathroom. Jane said Combs came in and told her: “That’s good. You’ll feel better now that you’ve thrown up. So let’s go.”

Jane then went back to the party and had sex with a third man, she said, telling jurors she was “repulsed” and “deeply regretted” doing it.

“I hated it so much,” she said.

One of the prosecution’s central arguments is that Combs coerced women to submit to his sexual fantasies by using his fortune to make them reliant on him.

To bolster that claim, Prosecutor Maurene Comey had Jane read aloud texts in which she complained to Combs that it seemed that “hotel nights” were “the only reason you have me around and pay for the house.” She said in the messages that she was “doing things that make me disgusted with myself.”

Still, she expressed her love for Combs, saying in the messages that “my heart is really in this and it’s breaking.”

By September 2023, Combs had been paying Jane’s rent for about five months. Comey asked Jane what she feared would happen if she stopped doing hotel nights.

“That he would take it away, that Sean would take the house away,” Jane responded.

It was then that Comey asked her how Combs responded to her messages. “He said: ‘Girl stop,’” Jane answered.

As Jane broke into sobs talking about how she “just really wanted my partner to get sober” when she tried to do a “hotel night” without drugs in October 2023, Combs tapped his fingers against one of his legs, occasionally glancing toward the jury or his lawyers and away from Jane.

Jane tried to put an end to so-called “hotel nights,” texting Combs in 2023 that she longed to return to the early days of their relationship, before the drug-fueled encounters started to dominate their time together.

Jane told Combs that she felt obligated to perform for him and that she regretted ever getting involved in the encounters, writing: “ever since I opened Pandora’s box, I haven’t been able to close it.”

“I don’t want to keep feeling like that,” she wrote, telling Combs that she wanted them to “talk like adults and figure out where we’re going from here.”

Combs responded: “Girl, stop.”

Jane acknowledged sending sexually explicit text messages to Combs between their hotel encounters, telling jurors she wanted to convey her love and interest in having sex with him — not strangers.

At times, she said, she did lean into his fantasies, sending graphic messages describing what she said she wanted to do with sex workers while Combs watched. On the witness stand Friday, she said she sent those messages because she wanted to make him happy.

In reality, she said, she wanted the encounters to stop.

“I didn’t like them,” she said. “I was realizing this was becoming the dynamic of what we were.”

Jane testified that Combs intervened to stop a man she identified as Don from using a condom, even after she requested it. The moment was captured in audio played for the jury.

She said it happened during their first “hotel night,” which Combs had arranged, and that he blocked condom use again in a later encounter.

Jane testified that Combs “guilt tripped me out of it. It wasn’t something he wanted to see.”

Prosecutors played an audio tape in which Jane asked a man to wear a condom who was about to have sex with her.

It was the first time jurors in the trial, now in its fourth week, heard any recording from what Jane has called “hotel nights” and what Cassie called “freak-offs.”

During hotel nights, a male sex worker would have sex with Jane while Combs watched, according to testimony.

Later in the testimony Friday morning, Jane broke into sobs as she described crying on two occasions during “hotel nights” with Combs.

Jane wept as she told jurors how Combs ignored her “subtle cues” that she wanted to stop engaging in sex acts during their drug-fueled “hotel nights.”

She said she’d tell him she was tired or hungry or make gestures and facial expressions indicating that she didn’t want to continue. Combs, she said, would tell her to keep going and “finish strong.”

Asked by a prosecutor why she didn’t tell him directly that she wanted to stop, Jane said, “I just, I don’t know,” as she cried loudly.

Comey, the prosecutor, questioned Jane about sexual subjects right from the start on Friday, beginning with a trip Jane said she took with Combs to Las Vegas in 2023 when they had a “hotel night” with an “entertainer.”

The prosecutor asked Jane if Combs ever used the word “freak” with her. Jane said he would say “he wants his freak.” She said she understood that to mean “he wanted me to be wild and sexual.”

Jane’s description of “hotel nights” has closely paralleled Cassie’s earlier testimony about “freak-offs” she had with male sex workers, under Combs’ direction.

Jane is back to resume her direct examination by Assistant U.S. Attorney Maurene Comey.

The jury has entered the room. Combs, wearing a dark sweater on Friday, is conversing with his lawyers and writing notes.

The judge gave prosecutors a small victory prior to the resumption of testimony when he ruled that statements Jane made that cast a disparaging light on the sexual performances she endured during her three years of dating Combs can be used during her examination.

Defense lawyers had argued they should be inadmissible. But the judge said the opening statement by the defense opened the way for admission of the exhibits because the defense asserted that Jane was a willing participant and that sexual activities were all consensual.

As he has throughout the trial, Judge Arun Subramanian is meeting with prosecutors and defense lawyers in the courtroom on Friday before the jury is brought in so disputes about evidence can be settled.

The judge also discussed efforts to improve the ability of Combs to communicate with his lawyers from the Metropolitan Detention Center in Brooklyn, where he has been held since his September arrest.

A former personal assistant who accuses Combs of rape testified Monday that she continued sending the hip-hop mogul loving messages for years after her job ended in 2017 because she was “brainwashed.”

The woman, testifying under the pseudonym “Mia,” pushed back at defense lawyer Brian Steel’s suggestions that she fabricated her claims to cash in on “the #MeToo money grab against Sean Combs.”

Steel had Mia read aloud numerous text messages she sent Combs. In one from 2019, she told Combs that he’d rescued her in a nightmare in which she was trapped in an elevator with R. Kelly, the singer who has since been convicted of sex trafficking.

“And the person who sexually assaulted you came to your rescue?” Steel asked incredulously. He rephrased, asking if she really dreamed of being saved by a man “who terrorized you and caused you PTSD?” Prosecutors objected and the judge sustained it.

Bryana “Bana” Bongolan, a friend of Cassie and a graphic designer who is suing Combs, testified Wednesday that in 2016, Combs held her over the edge of a balcony at a Los Angeles high-rise for 10 to 15 seconds, an episode she said traumatized her and left her with lasting night terrors.

On Thursday, defense attorney Nicole Westmoreland challenged Bongolan’s credibility, suggesting she lied or exaggerated. The lawyer noted Combs was on tour for much of September 2016, including East Coast shows around the time cellphone metadata shows Bongolan photographed her injuries.

“You agree that one person can’t be in two places at the same time,” Westmoreland asked.

“In like theory, yeah. It’s hard to answer that one,” Bongolan replied.

She also acknowledged smoking marijuana with Combs not long after, and attending one of his concerts and a private party roughly a week later.

“You weren’t too fearful enough to not go to Mr. Combs’ event, were you?” Westmoreland asked.

“I always had a feeling inside, but yes, I went,” Bongolan said.

Before Jane testified Thursday, while jurors were at lunch, Judge Arun Subramanian said he saw Combs energetically nodding at the jury twice while his lawyers cross-examined a prior witness. The judge warned that any further attempts to engage with jurors could get Combs ejected from the courtroom.

“There should be no efforts whatsoever to have an interaction with this jury,” Subramanian told Combs’ lawyers.

Combs seemed relaxed and smiled broadly afterward, possibly reacting to his attorney’s withering cross-examination. He has been active in his defense throughout the trial, regularly writing notes and consulting with his legal team.

A single mother, Jane said she got to know Combs during a “girls’ trip” to Miami in 2020 with a friend who was dating him. Jane said she dated him from 2021 to 2024, in what began as a loving and passionate relationship.

However, she grew emotional — lowering her head and wiping tears — as she explained how the relationship changed in May 2021, when Combs began sharing his sexual fantasies involving her with other men and role-playing. She agreed to go along, thinking it was a one-time event sometime in the future that would make him happy.

Within hours, she said, she was in a Miami hotel room watching Combs’ assistants set up for a group sex encounter.

Jane’s description of “hotel nights” closely paralleled Cassie’s earlier testimony. Both described trying to rush through the encounters just to get them over with. Jane said the encounters sometimes lasted over 24 hours.

The judge has taken steps to protect Jane’s anonymity, including warning observers not to describe or sketch her in a way that would reveal her identity.

Combs’ recent ex-girlfriend described enduring drug-fueled sex marathons until the hip-hop titan’s arrest in September as the key witness began testimony Thursday.

The woman, using the pseudonym “Jane,” is among several witnesses at Combs sex trafficking trial who accuse him of violence, including his former girlfriend, R&B singer Casandra “Cassie” Ventura.

Cassie testified in the trial’s first week that Combs assaulted her repeatedly and forced her into “hundreds” of encounters with male sex workers called “freak-offs” while Combs watched, directed and sometimes filmed.

Jane said she repeatedly told Combs, in person and in writing, that she didn’t want to have sex with other men. But Combs, who paid her rent and controlled other parts of her life, kept pressuring her and she felt “obligated,” she said.

Jane spoke barely above a whisper to an attentive jury. Several jurors leaned forward as she testified, while Combs mostly stared at her, but she never appeared to look back.

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