Defence suggests it was Cassie who ended Combs’ career

Cassie Ventura, left, and Sean "Diddy" Combs, arrive at the Los Angeles premiere of "Can't Stop, Won't Stop: A Bad Boy Story" at the Writers Guild Theater, June 21, 2017, in Beverly Hills, Calif. (Photo by Chris Pizzello/Invision/AP File)

NEW YORK — The R&B singer Cassie has spent hours under cross-examination following two days of testimony recounting tumultuous details of life with her ex-boyfriend, Sean “Diddy” Combs.

Prosecutors allege Combs used his fame and fortune to orchestrate an empire of exploitation, coercing women into abusive sex parties. His lawyers argue that all the sexual acts were consensual, and although he could be violent, he never veered into sex trafficking and racketeering. Combs has pleaded not guilty to racketeering conspiracy; sex trafficking by force, fraud or coercion; and transportation to engage in prostitution.

Defence attorney Anna Estevao has led Thursday’s questioning, making Cassie read her sexually explicit texts out loud for the jury. Estevao suggested that it was Cassie who ended Combs’ career by making his sexual behavior public through a lawsuit — not the other way around.

Here’s the latest:

Testimony is over for the day

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 defence 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 defence is finished. Combs attorney Marc Agnifilo said he’ll let the court know in the morning whether the defence can finish so that Cassie doesn’t have to testify on Monday.

Estevao suggests Combs and Cassie had taken a ‘bad batch’ of MDMA the night he beat her

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.”

Combs’ attorney confronts Cassie about texts from night of 2016 hotel ‘freak-off’

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.

Defence points to instances when Cassie appeared eager to participate in `freak-offs’

In a July 2013 text message exchange, Comb’s defence 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.”

Estevao zeroes in on Cassie’s state of mind during her relationship with Combs

Using the text message exchanges at the heart of her cross-examination, the defence 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 responds to drug use questions

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 expresses occasional frustration during cross-examination

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 defence 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.

Jurors ponder the once-private communications of Cassie and Combs

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 acknowledges the audience

Combs, now 55 and with gray hair, has worn glasses as he alternates from computer screen to documents to conferring with the lawyers at his side. During a break, he stood at the defense table, 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.

Both Cassie and Combs have been 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.

Cassie is back on the stand for more defence questions

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 with 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.

Defence tells judge that Cassie may have to return 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 defence‘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.

The judge ultimately told the defence to finish its cross in the morning Friday to leave time for prosecutors to ask Cassie follow-up questions, while leaving open the possibility that she’ll have to return next week.

Defence tells judge that Cassie may have to return 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 defence‘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.

Addicted to what?

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.”

Was this all about a swingers lifestyle for Combs?

Defence lawyers made it clear before the trial that they intended to label a lot of Combs’ sexual behaviour 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.

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

Cassie testified that this happened maybe four times throughout the course of their decade-long relationship, and that Combs told her it was part of a “swingers lifestyle.”

Cassie powers through the explicit narration

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.

Cassie: `I definitely didn’t want anyone to know’

After going through a pile of Cassie’s years-old emails and text messages, defence 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.”

Defence suggests it was Cassie who ended Combs’ career

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.

A lighter moment

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.”

Cassie grew increasingly frustrated with Combs, messages show

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.

Defence has Cassie reading her sexually explicit messages for the jury

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 defence 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.

Now, about your tattoos ...

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.”

‘Beautiful and charming’

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.

And now, the questioning turns to the ‘freak-offs’

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.

Cassie reads 2010 email: ‘I don’t need your money’

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-fuelled 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.”

A loving, caring counterpoint

The defence 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.

‘I love you sooooo much it makes me cry’

Estevao is confronting Cassie with loving emails and text messages she and the hip-hop mogul exchanged early on, often using Blackberry devices in the era before iPhones.

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.”

Prosecutors are objecting frequently, and the judge is rejecting many of the objections, appearing to be giving the defence some breathing room in the early stages of its examination.

The cross-examination seems gentle, for now

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. This approach was the opposite as Estevao began 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.

The ground rules

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

He denied a request by defence 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, defence lawyers dumped 400 “enormous, duplicitous” documents as potential exhibits on prosecutors. A defence lawyer responded that many of the documents will never be offered as exhibits during the cross examination.

Will Diddy be in court each day?

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.

Cassie held up well under direct questioning by prosecutors. Now, the defence gets its turn

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.

Defence 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.

Who is who at the trial?

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 defence 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.

The cross examination of Cassie will soon be underway in Manhattan federal court

Defence 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.

Defence attorney Teny Geragos suggested yesterday during a discussion between lawyers and the judge that the gameplan for today was changing on the fly out of necessity.

She didn’t get into particulars but she told Judge Arun Subramanian that the questioning of Cassie by prosecutors over two days “has gone much differently than I expected.” She added: “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.

Defence attorney says infidelity will highlight cross-examination

After the jury was sent home for the day, lawyers squabbled over ground rules for the cross-examination of Cassie, which is set to begin at 9:30 a.m. EDT Thursday.

Agnifilo said infidelity would be the featured subject of the questioning that is expected to stretch until day’s end Friday.

“We have worn our defence on our sleeves since the first bail hearing,” Agnifilo said. “Everybody knows we are going to bring up infidelity and text messages of infidelity.”

What to know about Cassie

Cassie sued Combs in 2023 alleging years of rape and abuse. The suit was settled within hours, but was followed by dozens of similar legal claims and touched off a criminal investigation.

A singer, actor, dancer and model, Cassie’s professional ambitions began in adolescence, when she signed to the top-tier talent and modeling agency Wilhelmina. Her music career launched shortly thereafter, when she left her home state of Connecticut for New York, where she signed with manager Tony Mottola and first met Combs.

Cassie met Combs in 2005 when she was 19 and he was 37. He signed her to his Bad Boy Records label and, within a few years, they started dating.

The Associated Press