Diddy’s star lawyer reveals intimate Cassie texts and nicknames from when they dated: Live trial updates

By GERMANIA RODRIGUEZ POLEO, CHIEF U.S. REPORTER and DANIEL BATES AT THE DANIEL PATRICK MOYNIHAN FEDERAL COURTHOUSE FOR DAILYMAIL.COM

Published: 14:00 BST, 15 May 2025 | Updated: 16:34 BST, 15 May 2025

Sean ‘Diddy’ Combs’ defense is cross-examining his ex-girlfriend and main accuser Cassie Ventura as he faces trial for sex-trafficking and racketeering in New York.

The music mogul’s attorney Anna Estevao’s line of questioning on Wednesday has emphasized the loving nature of his relationship with Cassie by showing the jury text messages where the singer refers to him as ‘pop pop’ – the same name she used for her grandfather.

The music mogul has kept a poker face this week as a pregnant Cassie described being physically and emotionally abused throughout their 10-year relationship.

In humiliating detail, she recounted a turbulent relationship with Combs that she said was consumed by violence and his obsession with a form of voyeurism where ‘he was controlling the whole situation.’ 

That included directing her encounters with male sex workers right down to the copious amounts of baby oil she applied to maintain the ‘glistening’ look he desired – as many as 10 large bottles a session.

Combs’ defense says he is guilty of domestic violence, but not of sex-trafficking or racketeering, and that the government is targeting him for his sexual preferences.

Jury sees ‘Freak Off’ text exchange between Diddy and Cassie

The defense is showing the jury a text coversation between Diddy and Cassie where the two discuss a Freak Off in August 2009.

All the explosive testimony from inside Diddy courtroom on Daily Mail’s podcast The Trial

To hear all the explosive testimony from singer Cassie Ventura and the other witnesses in Sean ‘Diddy’ Combs’ trial, tune in to Daily Mail’s hit podcast The Trial.

From sworn testimony to video evidence and the rapper’s every subtle move, our team of journalists take you inside the courtroom of the world’s biggest celebrity case.

Daily Mail has been following Diddy’s downfall from the very beginning. Join us as we hear from experts involved in the case, and members of the rapper’s inside circle.

Cassie reads 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.

‘I want it and I want to give you the same. I just think that I have to trust you beyond it and just being sexual. Do you know what I mean?’ Cassie wrote in one exchange.

‘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, this is THE ONLY man that will ever have this aggressive / sexual side of me.

‘The last time was mistake but since had made me feel a little dirty and grimey…that’s the only reason I go back and forth in my mind with wanting and not wanting to do….when we used to freak off when we were so in love.

‘There were no questions asked. It felt right. Like it literally made sense for the next step in our sex life. I get nervous that I’m just becoming the girlfriend you get your fantasies off with and that’s it. I don’t get the other part…anymore at least.’

Diddy’s lawyer calls Cassie ‘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.

Britney Spears dragged into Diddy trial

Cassie told the jury that Diddy brought popstar Britney Spears to her 21st birthday party in Las Vegas.

Diddy also allegedly brought singer songwriter Dallas Austin to Cassie’s party.

Cassie previously testified that Diddy kissed her during this party, leaving her confused as their relationship had been platonic until then.

She was already signed to his record label by that time.

Cassie shows signs of stress during cross-examination

The singer, who is weeks away from giving birth, has remained notably composed as she answers questions about alleged abuse and horrific sexual assault.

On Thursday, as she faced cross-examiantion, she held what appeared to be beads in her hands.

She also held what appeared to be a purple cube, perhaps a stress ball.

Cassie asked for more time with Diddy in texts shown to courts

One of the message Cassie read on Thursday 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.’

Rapper Boosie BadAzz voices support for Diddy

Rapper Boosie BadAzz took to X on Tuesday to react to Diddy’s trial and come out in his defense.

Defense shows jury loving texts between Cassie and Diddy

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

The first exhibits introduced by the defense 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.

‘Hundreds of freak offs’

As the prosecution ended its direct examination on Wednesday, they asked Cassie how many freak offs she participated in.

‘Impossible to know,’ she replied. ‘Hundreds.’

When asked if she’s been involved in any since ending her relationship with Combs in 2018, the witness said, ‘no.’

Cassie was also asked why she chose to take the stand against the music mogul.

I can’t carry this any more. I can’t carry the shame, the guilt, the way we… I was guided to treat people like they were disposable. What’s

Diddy’s mother and sons arrive for Cassie’s cross-examination

Diddy’s mother Janice Combs, 85, has been in attendance every day for his trial this week.

She is seen arriving to the federal courthouse on Thursday.

Some of Diddy’s sons were also seen entering the court for day four of the trial.

Diddy’s defense begins cross-examining Cassie

‘You and [Sean Combs] were in love for 11 years, right?’ was the first question from Diddy’s lawyer Anna Estevao, who will be cross-examining Cassie.

‘You believed he loved you?’

Estevao continued a line of questioning that emphasized that Cassie ‘knew the real Sean… a version he won’t let the rest of the world see.’

Diddy’s attorney Anna Estevao is pictured.

PICTURED: LA hotel room following Diddy’s assault on Cassie

The jury was shown images of a Los Angeles hotel room after Diddy allegedly threw a vase at Cassie during an assault caught on security cameras in 2016.

A version of the footage was aired by CNN last year.

Jury recoils in shock as they are shown photos from ‘Freak Off’ sex parties

Jurors in the trial of Sean ‘Diddy’ Combs were yesterday shown images from the sex parties that the hip-hop mogul masterminded.

The New York courtroom fell silent as the jury members viewed five still pictures of so-called ‘Freak Offs’ on their screens, which were blocked from public view.

One male juror’s eyebrows went up as he saw the images, while a female juror swallowed hard and appeared to move her head side to side.

Cross examination of Cassie will soon be underway

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.

Sean Combs and Cassie Ventura attend The Metropolitan Museum of Art’s Costume Institute benefit gala in 2018, the year they broke up.

Jury hears claims of terrifying violence

A defense complaint that testimony about violence was not specific enough prompted a prosecutor to elicit a history of notable events of violence Cassie said she suffered at the hands of Combs.

The first, she testified, came early in their relationship in 2007. Cassie said she was at a dinner with ‘Sean and friends’ when she spotted Combs flirting with somebody.

She said she shrugged her shoulders when somebody else who saw it looked at her. But then, she said, Combs attacked her in a car after they left the venue.

‘He knocked me around and was just hitting me,’ she said.

Cassie testified that she fell to the floor of the car after Combs hit her on the side of the head. ‘I was just shocked,’ she said. ‘I didn’t necessarily understand what happened and why he was so angry.’

She said she went home and ‘hid out after that.’

REVEALED: Diddy’s texts ‘threatening Cassie after their break up’

In 2019, Diddy texted Cassie: ‘If I was you, I would get me my money.’

He apparently wanted to be reimbursed after Cassie married Alex Fine, a personal trainer Diddy initally hired for her.

‘YOU WILL NOT BE THREATENING ME,’ Diddy texted, adding that Cassie had ‘too many iPads full of skeletons.’

Cassie replied: ‘Do you want me to tell the truth? It’s way deeper than iPads.’

Diddy’s family document their every move as disgusting details of his freak-offs unfold in court

The emotional cost that Sean ‘Diddy’ Combs’s trial is having on his family is all being caught on camera, DailyMail.com can reveal exclusively.

One of the rap mogul’s trusted inner circle of film makers is shadowing his six children and his 85-year-old mother Janice to federal court in their large black minivan each day.

And Roodmy Poulard is nailing their every move and emotion when they are not actually inside the building, where cameras are not allowed.

Diddy’s courtroom gesture to mom Janice as she leads family supporting him at trial

Diddy became violent over Cassie’s romance with Kid Cudi, jury hears

Cassie said Diddy found out that she had been dating Kid Cudi after going through her phone following a Freak Off in Los Angeles in 2011.

‘It was a time when we were not in the greatest place,’ Cassie said of her relationship with Diddy.

‘I remember him pulling a wine bottle opener between his fingers and lunging at me. Eyes blacked out, super angry and I got out of there.’

He told me about videos he had he was going to release and he was going to hurt Scott (Cudi) and I.

Cassie said after the assault she used a burner phone to call Cudi, who then picked her up.

The singer’s settled lawsuit with Diddy claimed he blew up Kid Cudi’s car after learning of their romance.

Cassie wears a power suit as she heads to be grilled by Diddy’s lawyers

Diddy’s lawyers are expected to begin cross-examining Cassie on Thursday, when they will get the chance to challenge her credibility or poke holes in her account of what happened.

Cassie told the jury Diddy raped her in 2018

The R&B singer testified Wednesday that the mogul raped her when she ended their decade-long relationship, after he locked her in a life of physical abuse by threatening to release degrading sexual videos of her.

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.

Prosecutors accuse Combs of exloiting his status as a powerful music executive to violently force Cassie and other women to take part in sexual encounters. He is charged with crimes including racketeering and sex trafficking by force, fraud or coercion. Several other accusers are set to testify.

50 Cent continues trolling Diddy

50 Cent has continued using his social media to troll Diddy as he stands on trial.

He shared a post on Instagram mocking Diddy after a lawsuit claimed he had a ‘tootsie roll-sized penis.’

The rapper also shared an AI-generated image showing shirtless Diddy sitting in a blue inflatable children’s paddling pool in a back yard while riding on a large inflatable yellow duck.

The images appear to have been inspired by Cassie’s claim under oath that Diddy had ordered her to get into an inflatable pool filled with baby oil while clothed in an outfit purchased from a sex shop.

New Diddy accuser claims he raped her with ‘tootsie roll-sized penis’

A woman going by Jane Doe filed a lawsuit against Diddy saying he raped her – but that she was relieved when she saw the size of his penis ‘because she knew it wouldn’t hurt that much,’ according to TMZ.

Jane Doe says she met the mogul in 2001 and the two hung out a few times before he raped her at his Manhattan apartment.

She claims Diddy pushed her down on his bed, put his hand on her throat and said: ‘I’m going to suck the life out of you.’

The suit claims Diddy held her down before ‘pulling out his erect bare-skinned penis which appeared to be the length and girth of a large Tootsie Roll.’

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Diddy’s star lawyer reveals intimate Cassie texts and nicknames from when they dated: Live trial updates

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