Sean Combs’s former girlfriend, who has said he pressured her into a pattern of degrading sex marathons with male escorts, was confronted by the defense on Wednesday with a stream of text messages surrounding those encounters.
The woman, who is testifying under the pseudonym Jane, finished her second day of cross-examination as Mr. Combs’s lawyers seek to portray her as a willing participant in the sex nights. Mr. Combs is facing sex-trafficking charges related to Jane and another former girlfriend, as well as racketeering conspiracy. He has pleaded not guilty to all charges.
Here are some takeaways from the 21st day of the Combs trial.
Jane is questioned on a trove of her text messages.
In one exchange in late 2021, a pornographic actor who regularly participated in what the couple referred to as “debauchery” or “hotel nights” texted Jane to marvel that a recent encounter had been the “roughest sex we ever had.”
Jane responded that it was “def one for the books,” alongside a series of emojis, including what Jane described as a “mind-blown” emoji.
Prosecutors say Mr. Combs coerced Jane into these nights. She has testified they left her feeling disgusted, used and sometimes physically sick, saying that Mr. Combs tended to be dismissive when she voiced her aversion to them. The nights often involved copious amounts of drugs, with Mr. Combs watching, masturbating and sometimes filming while Jane had sex with men they called “entertainers.”
While questioning Jane, Teny Geragos, one of Mr. Combs’s lawyers, focused on messages from Mr. Combs in which he appeared to be solicitous about what she wanted to do sexually.
In a 2022 exchange with Mr. Combs, Jane said she wanted to “make love” to him alone, writing, “I haven’t selfishly had you to myself for five months.” She has testified that she only endured the sex with other men in order to get alone time with him.
“I’m fine with the other stuff but I really just need you right now,” she wrote to him.
Mr. Combs responded, “Whatever you want.”
The text messages presented by the defense are in sharp contrast to the tone of many highlighted by the prosecution from later in their relationship. In those Jane told Mr. Combs she felt violated and traumatized by those nights, once declaring she was not a “sex robot.” She has testified that she had complex feelings about the encounters, saying that she felt pressure to please her boyfriend despite her own aversion.
At one point, Jane appeared overcome by emotion, grabbing a tissue from the box beside her, while reading a loving message she wrote to Mr. Combs, whom she dated from 2021 up until his arrest in 2024.
The defense underscored times when Jane took an active role in setting up hotel nights.
Jane testified that she bought supplies such as lubricant and male erection pills, which she said she hoped would speed up the unwanted encounters. Once, Jane planned a hotel night for Valentine’s Day, suggesting that the couple could have two male “entertainers” there at the same time.
“If I see him, there’s a request for a hotel night, so I’m just adapting to my circumstances, I’m adapting to my environment,” Jane testified.
Under questioning from the prosecution, Jane said that she personally reached out to two pornographic actors who eventually became involved in hotel nights. She said she did so to assert some measure of control over who she had sex with.
During her direct testimony, the prosecution sought to highlight a lack of agency. Jane said she felt “obligated” to continue participating because Mr. Combs started paying her $10,000-a-month rent in Los Angeles in 2023. She testified that he started to use the house as “leverage” for her to continue participating in the sex nights.
She also described a violent brawl with Mr. Combs in 2024, when he was under criminal investigation. She testified that afterward, when she had welts and a black eye from his blows, he demanded she perform oral sex on an escort despite her protests. She said she took the Ecstasy pill he gave her and complied.
Jane was pressed on her account of an unwanted birthday surprise in 2023.
Jane has testified that she often read “undertones” of expectation in her boyfriend’s messages or in his interactions and that led her to be agreeable or try to cater to the kind of voyeuristic sex he often requested.
Ms. Geragos pressed Jane on one of the times that she “went along”: a night of sex on her birthday in 2023 at a Nobu hotel in the Miami area.
Expecting a night alone with her boyfriend, Jane was surprised, she said, when Mr. Combs said, “I’m so excited to see what entertainment is tonight.”
“You just accepted it, right?” Ms. Geragos asked, citing Jane’s words under questioning from the prosecution.
“I just complied with it,” she replied.
That night, Jane said, when she asked for a condom to have sex with the hired escort, Mr. Combs gave her “dirty looks” and said, “you better not ask for a condom,” using an expletive. He eventually gave the escort a condom, she testified. For her birthday that year, Jane said, she received flowers, cake and jewelry, and had sex with three escorts that night.
After her birthday, Ms. Geragos highlighted a text that Jane sent Mr. Combs in which she said she “loved and appreciated every detail you put into my bday.”
Seeking to explain the message, Jane testified that “despite enduring one of these nights, I can block them out and just focus on the love I had for Sean.”
The defense hammered home that Jane at times ‘agreed’ to sex with escorts.
In response to Ms. Geragos’s questions about why she repeatedly agreed to hotel nights, the calm and matter-of-fact tone that Jane had maintained for most of her five days on the stand was at times shaken by apparent irritation.
“You had agreed to it, right?” Ms. Geragos asked her, referring to a night at L’Ermitage, a luxury hotel in Beverly Hills, Calif., where Jane said she ended up vomiting in between sex with escorts.
“Unfortunately, yes,” Jane replied.
Ms. Geragos kept pressing her.
“You regret now that you agreed to it, is that fair?” Ms. Geragos asked her.
Jane kept elaborating: “I resent him for knowing how much I loved him and knowing I couldn’t say no to him.”
Olivia Bensimon contributed reporting.
Julia Jacobs is an arts and culture reporter who often covers legal issues for The Times.
Ben Sisario, a reporter covering music and the music industry, has been writing for The Times for more than 20 years.
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