Sean ‘Diddy’ Combs sex trafficking trial: Key moments from May 15, 2025

If anyone had any doubt that Cassie is the trial’s star witness, Combs attorney Marc Agnifilo tried his best to erase it when he spoke several times Thursday out of the presence of the jury.

Once, he called her the “most important witness in a very important case.” At another point, he said she was “a critically important witness” and the “biggest witness in the case.”

Of course, the only witness who could rival Cassie’s testimony for relevance would be Combs himself. The decision to have Combs testify would be made after the government finishes presenting its case weeks from now. And ultimately, it will be up to Combs to decide.

In most criminal trials, defendants choose not to testify. With a celebrity, the decision whether to take the stand can be complicated and risky, especially if lawyers believe prosecutors failed to prove their case.

As Judge Arun Subramanian sent the jury home, he told them he plans to resume Cassie’s testimony promptly at 9:30 a.m. Friday. After the jury had left the room, the judge told defense lawyers they would have up to five hours to question Cassie on Friday.

Prosecutors said they expected to have no more than a half hour of questions for Cassie once the defense is finished. Combs attorney Marc Agnifilo said he’ll let the court know in the morning whether the defense can finish so that Cassie doesn’t have to testify on Monday.

Estevao closed her questioning for the day by suggesting to Cassie that she and Combs had taken a “bad batch” of the psychedelic stimulant MDMA during a “freak-off” that preceded his 2016 assault on her at a Los Angeles hotel.

“They were a bad batch, right?” the lawyer asked.

“I have no idea,” Cassie replied, concluding her testimony for the day.

Combs was seen in now-infamous security camera footage hitting and kicking Cassie as she tried to leave the Intercontinental Hotel following a “freak-off.”

Attorney Anna Estevao confronted Cassie with dozens of text messages that she exchanged with Combs before they agreed to engage in a “freak-off” at the Los Angeles hotel in March 2016 where Combs was caught on recordings kicking and dragging her by an elevator bank.

Estevao noted that in several of them, Cassie spoke using sexually explicit language, though the actual texts were not read to the jury. The lawyer was suggesting through the texts that Cassie encouraged the sexual meeting with an escort.

Cassie has testified that she could tell by the words Combs used in his texts that he wanted a “freak-off,” such as when he asked her about her plans so he could make his plans that night.

She said she wanted to get it over with to keep Combs happy so he wouldn’t spoil a movie premier she was attending three days later.

In a July 2013 text message exchange, Comb’s defense lawyer noted, it was Cassie who raised the idea of having a “freak-off,” writing to Combs: “Wish we could’ve FO’d before you left.”

Cassie has said she felt compelled to participate in such encounters to keep Combs happy and because she enjoyed spending one-on-one time with him afterward.

In a 2017 text message, Cassie told Combs: “I love our FOs when we both want it,” using the initials for “freak-off.”

On the stand Thursday, Cassie said: “I would say loving FOs were just words at that point.”

Using the text message exchanges at the heart of her cross-examination, the defense lawyer highlighted instances of Cassie’s anger with Combs and her admitted jealousy over attention he gave other women.

“You’re making me look like a side piece and that is not what I thought I was,” Cassie told Combs in a 2013 text message.

Cassie said Combs made clear from the early days of their relationship that he didn’t want her seeing anyone else. He’d get angry if he suspected her of cheating, she said.

But the same rules didn’t apply to him, she told jurors, and she confronted him after she saw social media posts connecting him to other women.

Cassie testified that after a few years with Combs she longed to be a bigger part of his life — but that he wouldn’t let her in.

She said she’d get angry that Combs was going on vacations with his children and his ex-partner, the late Kim Porter, and that he was spending holidays with them instead of her.

Cassie said Combs once communicated to drug dealers in Los Angeles to stop delivering drugs to her.

“At some point it happened,” Cassie said, though she said she didn’t know if it was 2016, when Combs’ attorney suggested it happened.

She also acknowledged that Combs had recommended that she get help for her drug issues. Cassie said Combs only wanted her to do drugs with him rather than with friends.

Cassie has been exceedingly polite through her cross-examination, smiling at Combs’ lawyer.

But she has expressed occasional frustration, sometimes asking the attorney to rephrase or repeat her questions or to provide more context that could help her answer. At one point, Cassie complained that jurors weren’t hearing the full context of the text messages the defense was highlighting.

“This isn’t about what I feel is relevant right now, right?” Cassie said, glancing at the judge, Arun Subramanian. “Because there’s a lot we skipped over.”

Once Estevao is finished, prosecutors will have a chance to ask Cassie more questions and can give her an opportunity to provide any context she says is missing.

At points during the text-and-email-heavy testimony, jurors leaned forward in their seats to follow along as monitors displayed the often-lurid messages in front of the jury box.

One woman shook her head from side-to-side as a particularly explicit message was shown. A man stared intently at the screen, pressing his thumb to his chin. Other jurors appeared curious and quizzical, some looking at Cassie or jotting notes. One man fell into a routine, peering at each message on the screen and then looking up at Estevao as she asked Cassie about them.

Some jurors appeared bored only when the courtroom fell silent for minutes at a time while Cassie reviewed lengthy text exchanges before answering questions.

Combs stood at the defense table during a break, huddling with his lawyers while holding a pack of Post-It notes in one hand and a pen in the other.

At one point, he turned to the gallery and acknowledged a few reporters, a few rows back, who were studying his demeanor. “How you doing,” he asked.

Combs is wearing a beige sweater over a white button-down shirt and gray pants today. Cassie has a black suit-type coat over a baby blue top.

His daughters aren’t in the courtroom, on a day when explicit messages have been read and shown to the jury.

In the courtroom, both Cassie and Combs are being kept busy shuffling through documents or peering at them on computer screens as Estevao reads from dozens of exhibits.

This likely prevents some awkward moments that otherwise might arise through the nonstop airing of sexually charged conversations stretching from 2012 to 2017.

Combs, now 55 and with gray hair, is wearing his glasses as he alternates from computer screen to documents to conferring with the lawyers at his side.

Combs’ former girlfriend powered through the morning’s cross-examination, despite her advanced pregnancy.

The questioning took on such a friendly tone that occasionally it seemed like two girlfriends chatting — under the watchful eyes of the judge, 12 jurors, six alternates, a dozen lawyers, a packed courtroom audience and Combs — who has remained observant throughout.

Now she’s back, and seems more subdued, as Estevao shows her text messages in which she and Combs discussed picking up supplies for their sexual activities.

With her hair in a ponytail and a plastic bottle of water before her, Cassie is responding into a microphone, often answering yes in a soft voice as Estevao asks her to confirm what she wrote.

Testimony has resumed after a lively discussion between the judge and lawyers out of the jury’s presence about the need to get Cassie off the witness stand by the end of Friday.

Subramanian said there had been pre-trial discussions for months about the need to finish Cassie’s testimony this week, given her advanced pregnancy.

Agnifilo tried to blame prosecutors, saying it “seems strategic” that they called two other witnesses before Cassie, and suggesting they did so in an effort to limit the cross examination.

The judge told the defense to finish its cross in the morning Friday to leave time for prosecutors to ask Cassie followup questions. He left open the possibility that Cassie might have to return to the witness stand next week.

Combs’ lawyers said they don’t expect to be done questioning Cassie until the end of the day on Friday. If that happens, it’s possible she’ll need to come back to court on Monday so prosecutors can ask her more questions during a phase of testimony known as re-direct.

Subramanian noted that the sides had previously agreed that she would be done by week’s end, since she’s pregnant and due to give birth soon to her third child.

The defense’s revised timing “is the exact opposite of what I was told,” the judge said.

“That is why there is a sword that I must fall on,” Combs’ lawyer Marc Agnifilo responded. He suggested that prosecutors muddled the timing by calling two witnesses before bringing Cassie to the stand.

Participants were told the trial will resume at 1 p.m.

As the lunch hour approached, Estevao questioned Cassie about addictions as it related to Combs.

“Would you say he was an addict?” the lawyer asked. “I would say he was an addict,” Cassie responded.

“What was he addicted to?” Estevao asked. “Success,” Cassie initially said.

When the lawyer asked if Combs was addicted to opiates, Cassie said: “At a point, yes.”

Estevao asked her how she knows. Cassie answered: “Because he told me.”

Defense lawyers made it clear before the trial that they intended to label a lot of Combs’ sexual behavior as reflective of a swingers lifestyle.

Now Estevao is asked Cassie directly if she thinks “freak-offs” were related to this lifestyle.

“In a sexual way,” Cassie responded, before adding: “They’re very different.”

A day earlier, Cassie told prosecutors they went to swingers clubs together several times in Los Angeles and Las Vegas.

At one point, acknowledging Cassie’s potential discomfort, Estevao told Cassie: “If you ever don’t want to read the message, I can read it for you.”

She thanked the lawyer for the offer but kept going.

Three times, the courtroom fell quiet as Cassie spent several minutes silently reading through paper copies of long text message exchanges between her and Combs. One was 14 pages. Another was 25 pages. A third exchange was 8 pages.

Cassie wanted to familiarize herself with these threads before being asked questions about them.

While prosecutors have focused on Combs’ desire to see Cassie having sex with other men in marathons of sexual activity, she says she sometimes watched Combs have sex with other women.

Under questioning by Combs’ lawyer, Cassie testified that this happened maybe four times throughout the course of their decade-long relationship. She said Combs explained it as part of a “swingers lifestyle.”

As Estevao and Cassie read aloud steamy text messages that the hip hop mogul and R&B star wrote each other in July 2012, Combs appears relaxed at the defense table, sitting back in his chair with his hands folded before him and his legs crossed.

After going through a pile of Cassie’s years-old emails and text messages, defense questioning pivoted to the highly orchestrated encounters in which Cassie says Combs watched as she engaged in sex acts with male sex workers.

Early on, Cassie testified, she disguised herself with wigs and masquerade masks because while Combs was a recognizable star, she was an up-and-coming R&B singer and neither of them wanted people finding out.

“The encounter itself was pretty crazy,” Cassie told jurors. “I really followed his lead on that because I had never done it before.”

Nearly two hours into cross examination, the questioning of Cassie seems to have taken a turn from what had been mostly friendly questioning.

Estevao asked Cassie if it’s “fair to say” that Combs’ career was ruined after she sued him in November 2023, making public for the first time the concept of “freak-offs.”

“I could understand that,” Cassie responded.

Cassie testified earlier this week that when she tied to end their relationship, Combs threatened to end her career by releasing degrading sexual videos of her.

Cassie laughed as Combs’ lawyer showed her an email she sent to Combs near the start of their relationship, almost 18 years ago.

“It’s making me giggle because it’s from 2007,” Cassie said, momentarily breaking the tension of a cross-examination that, so far, has required her to read and hear explicit messages she had exchanged candidly with Combs.

“I know,” Combs’ lawyer Anna Estevao responded. “We’re taking you back.”

Yet more messages read in court show that Cassie was growing frustrated with the state of her relationship with Combs. They weren’t yet public with their courtship, and in a December 2009 email, Cassie told the hip-hop star she needed something more from him than a sexual partnership.

Responding to a sexually explicit email from Combs, Cassie wrote: “I like that. I want it and I want to give you the same. I just think that I have to trust you beyond it just being sexual.”

“Do you know what I mean?” the message continued. “In order for me to be more open with the things we do in bed, I need to feel safe, like home, like this is my husband, and this is THE ONLY man that will ever have this aggressive/sexual side of me.”

Combs’ lawyers are seeking to portray Cassie as a willing participant in Combs’ “freak off” lifestyle.

These communications between Cassie and Combs are graphic — describing for example what she wanted to do during the ‘freak-offs’ — and Estevao is making Cassie read them out loud, word by lurid word, while the lawyer reads Combs’ parts.

The judge is allowing these emails, which don’t discuss what happened, but rather what she was anticipating or wanting to have happen at the time.

After an extensive discussion on what evidence the defense could present, the judge disallowed messages reflecting attempts by Combs to learn whether Cassie was having sex with other men she was dating. So far, these other messages have been within the boundaries set by the judge.

Estevao asked Cassie how many tattoos she had, triggering an objection from prosecutors that was overruled by the judge.

Cassie then revealed that she had three tattoos when she met Combs, including one on the inside of forearm that said: “No Regrets.”

The gentle questioning of Cassie by Estevao may have reached a crescendo when the Combs lawyer was asking her about her early music career and a successful first album.

At one point, Estevao said: “And you’re very beautiful and charming.” Light laughter could be heard in the courtroom, prompting the lawyer to say: “Well, it’s true.”

Cassie responded by thanking her.

The judge has agreed, allowing her to leave the witness stand after more explicit messages were put on display. The jury also has been given a break.

The sexual events Combs staged dominated much of the testimony from Tuesday and Wednesday. Now Estevao is asking about the subject and displaying text messages to the jury in an apparent effort to show Cassie’s enthusiasm for them. Estevao is reading Combs’ parts of the email and text exchanges and having Cassie recite what she wrote to him at the time.

— “When do you want to freak off? Lol” Combs asked in August 2009.
— “I’m always ready to freak off,” she replied.

Two days later, Cassie sent an explicit message to Combs.

— “I can’t wait to watch you. I want you to get real hott,” he replied.
— “Me Too, I just want it to be uncontrollable,” she said.

But another message Cassie read points to fractures in their relationship, which according to her earlier testimony devolved into violence and Combs’ increasing obsession with seeing her have sex with strangers during drug-fueled sex parties he called “freak-offs.”

In an April 2010 email, she expressed disappointment that Combs would rush her off the phone and wasn’t spending time with her.

Cassie read the email in court: “That’s not being in a relationship with someone that you love and are in love with ... I am really hurt by the way you deal with me, I don’t need your money, I need some attention.”

The defense has Cassie reading out loud from the warm emails and messages she exchanged with the hip-hop star early on. Portraying them to jurors as a loving, caring couple is a counterpoint to two days of testimony about forced sex and violence.

Combs was charismatic, with a larger-than-life personality, she testified. “I had fallen in love with him and cared about him very much,” she acknowledged.

In a flashback to another era, testimony about the early relationship between Combs and Cassie has contained frequent references to the BlackBerry devices that they used to communicate with one another.

Before Apple founder Steve Jobs introduced the iPhone in 2007, the BlackBerry was so popular and addictive that it was nicknamed the “CrackBerry.” The Canadian company that marketed it was valued at $85 billion at around the time Combs and Cassie began dating.

Correction: A previous version of this post mistakenly said the market value was $85 million. It was $85 billion.

He’s sitting back in his chair, with his legs crossed, conferring with Agnifilo, who’s seated next to him.

Estevao is confronting Cassie with loving emails and text messages she and the hip-hop mogul exchanged early on.

In one 2008 email, Cassie told Combs she was a lucky woman. “I love you sooo much,” she wrote after Combs thanked her for flying to Atlanta to be with him.

In August 2009, in a message sent when Combs went by the moniker “Puffy,” the rap star told her: “I love you sooooo much it makes me cry.”

Cassie replied: “U hungry pop pop?” She testified that Pop Pop was a nickname she used for Combs, while he sometimes called her Baby Girl. He said no, to which Cassie told him to let her know if he changed his mind.

In April 2010, Cassie told Combs: “Going to sleep now so it can be tomorrow faster and you can be home. Love you!!!” Combs replied: “Love my baby.”

The first exhibits introduced by Estevao are messages exchanged between Combs and Cassie in the early years of their relationship. In one, Combs writes “I’m truly a lucky man.” Cassie writes back: “I’m a very lucky woman. ... Love you so much.”

Prosecutors are objecting frequently to exhibits introduced by Estevao. The judge is rejecting many of the objections, appearing to be giving the defense some breathing room in the early stages of its examination.

Estevao has begun by questioning Cassie in a gentle tone of voice. It’s notable because so many cross-examinations can begin with efforts to unsettle and agitate a witness.

Estevao’s approach is the opposite.

Estevao began Cassie’s cross-examination by asking about their relationship. Cassie responded yes to a series of questions.
— “You and Sean Combs were in love for 11 years. You loved him and believed that he loved you as well.”
— “Yes.”
— Your love of Combs explained explained “why it hurt so badly when he lied.”
— “Yes.”
— “When he cheated on you,” Estevao continued.
— “Yes, Cassie said.

Cassie is returning to the witness stand. Cassie came to court Thursday in a black suit that looked almost like a tuxedo top. She had a light colored blouse underneath.

Family members, including Combs’ mother and children, have been arriving together in a black van

There usually aren’t many last minute ground rules to go over for questioning a witness, but lawyers can argue for an hour and stay up until 3 a.m. filing letters over minor facets of law that court observers untrained in legal precedents wouldn’t know or care about.

During a nearly one hour long discussion Thursday morning about evidence that can be introduced on cross examination, the judge noted that with one of his rulings, “99.9 percent of evidence is not being impaired.”

Judge Arun Subramanian began Thursday by talking to lawyers about evidence as final ground rules are set before the cross examination by defense attorney Anna Estevao begins.

He denied a request by defense lawyers to introduce text communications between Combs and Cassie that would include references to specific sexual acts.

Letters were filed with the judge overnight from both sides. The judge said he wanted to eliminate “unfair prejudice or victimization” of witnesses.

Prosecutors also complained that overnight Wednesday, defense lawyers dumped 400 “enormous, duplicitous” documents as potential exhibits on prosecutors. A defense lawyer responded that many of the documents will never be offered as exhibits during the cross examination.

Yes. Combs, 55, has been held at a federal jail in Brooklyn since his September arrest. His formerly jet-black hair is now almost completely gray because dye isn’t allowed at the detention center.

Combs, who had his own fashion line, wore yellow jail uniforms in pretrial hearings. But for the trial, the judge said he can have up to five button-down shirts, five pairs of pants, five sweaters, five pairs of socks and two pairs of shoes without laces.

He interacted with his lawyers but remained largely stoic as Cassie testified on Tuesday. During a break, he made a heart shape with his hands and mouthed “thank you” to one of his twin daughters. He also blew a kiss to his mother.

Under federal court rules, no photos or video of the trial will be allowed. Courtroom sketches are permitted.

She cried several times but for the most part remained composed and matter-of-fact as she talked about some of the most sensitive subjects anyone could imagine expressing, in a courtroom packed with family and friends of Combs, journalists and one row of spectator seats occupied by Cassie’s supporters.

Cassie is in the third trimester of pregnancy with her third child with personal trainer Alex Fine. They married in 2019 and she sued Combs in 2023.

Defense lawyers have indicated that the cross examination of Cassie that will begin this morning will likely be finished by the end of Friday’s court session.

▶ Read more about the life and career of Cassie

The trial is in the courtroom of U.S. District Judge Arun Subramanian. He’s a Columbia Law School graduate who once clerked for Supreme Court Justice Ruth Bader Ginsburg and was appointed a federal judge by President Joe Biden in 2022.

The prosecution team consists of eight assistant U.S. attorneys, seven of them women. They include Maurene Ryan Comey, daughter of former FBI Director James Comey. She was among the prosecutors in the trial of Ghislaine Maxwell, who was convicted of luring teenage girls to be sexually abused by Jeffrey Epstein.

Combs’ team of seven attorneys is led by New York lawyer Marc Agnifilo, who along with his wife Karen Friedman Agnifilo, is also defending Luigi Mangione, the man accused of killing UnitedHealthcare CEO Brian Thompson.

Also on the defense team is Atlanta attorney Brian Steel, who represented Young Thug in a trial that went on for nearly two years before the rapper pleaded guilty to gang, drug and gun charges.

Defense lawyers say they’ll be scrutinizing how infidelity fueled the combustible nearly 11-year relationship between the R&B singer and the music mogul who controlled her career.

Defense attorney Teny Geragos suggested to the judge Wednesday that they had to change today’s gameplan on the fly.

She told Judge Arun Subramanian that the questioning of Cassie by prosecutors over two days “has gone much differently than I expected. ... So we are kind of changing our strategy.”

Agnifilo later told the judge that questioning Cassie about infidelities is important. “Everybody knows that we are going to bring up infidelities, that we’re going to want to bring up text messages of infidelities, and these text messages are often in colorful language,” he said.

For more than two decades, Combs was one of hip-hop’s most opportunistic entrepreneurs, spinning his hitmaking talents into a broad business empire that included a record label, a fashion brand, a TV network, deals with liquor companies and a key role in a reality TV show.

But U.S. prosecutors say behind the scenes, Combs was coercing and abusing women with assistance from a network of associates who helped silence victims through blackmail and violence.

▶ Read more about the timeline of major events in his rise and fall.

Cassie testified that her life reached a climatic moment in early 2023 when she had “horrible flashbacks” as she was shooting a music video. She said she went home after the video shoot and her two kids were asleep but her husband was there. Cassie said she remembered “telling him you can do this without me. You don’t need me here anymore.”

With that, Cassie said she couldn’t take the pain anymore and “tried to walk out the front door into traffic and my husband would not let me.” Weeks later, she was undergoing rehab and trauma therapy.

Asked why she’s testifying at Combs’ criminal trial, she said: “I can’t carry this anymore. I can’t carry the shame, the guilt.”

Cassie testified about several other violent episodes. Early in their relationship in 2007, she said he repeatedly hit her and knocked her to the floor of a vehicle with a blow to her head. In 2011, when he learned she started dating rapper Kid Cudi, she said Combs lunged at her with a corkscrew and kicked her in the back.

After the 2011 attack, she said she lied to her mother at Christmas that it was the first time Combs hit her.

Cassie also testified that she saw Combs pull one of her friends back over the railing of a balcony in Los Angeles. She said she saw him hit a different friend of hers in the head with a hammer.

Cassie said she was experiencing post-traumatic stress disorder before ending her relationship with Combs in 2018, and was blacking out and sleepwalking.

Cassie’s testimony is exposing the dark underside of a relationship that, for years, played out publicly in pictures of the couple smiling on red carpets and celebrity events. She said she met Combs in 2005, when she was 19 and he was 37. Combs signed her to a 10-year contract with his Bad Boy Records label. Within a few years, they started dating, Cassie said.

They were photographed in 2016 attending the premiere of the film “The Perfect Match,” only two days after Combs beat and kicked Cassie at a Los Angeles hotel — an attack captured on security camera footage. After the footage was leaked last year, Combs apologized. Jurors were shown that footage as well as photos of the couple at the premier.

Cassie, now 38, calm and poised after an emotional first day of testimony, said she used makeup to cover bruises and wore sunglasses to hide a black eye for the premiere. She said she sneaked into a popcorn closet at the movie theater to switch dresses for an after-party so bruises on her legs wouldn’t be visible.

Addressing the Manhattan courtroom for a second day, Cassie said Combs forced his way into her Los Angeles apartment and raped her on the living room floor after she said she was breaking up with him.