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.
Diddy Trial Text Messages with Cassie – May 15, 2025
Diddy Trial Text Messages with Cassie – May 15, 2025
Diddy Trial Text Messages with Cassie – May 15, 2025
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.
All the explosive testimony from inside Diddy courtroom
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.
08:16
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 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.
08:03
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.
07:53
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.’
07:15
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.
07:00
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.
06:57
‘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
06:54
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.
Janice Combs, mother of Sean “Diddy” Combs arrives at federal court for Sean “Diddy” Combs’ sex trafficking trial in New York City on May 15, 2025. Sean “Diddy” Combs used violence and threats of reputational ruin to control women he abused for years, New York jurors heard May 12 during opening statements of the federal sex trafficking trial that was followed by the case’s initial graphic testimonies. The panel of 12 jurors and six alternates responsible for determining Combs’s fate heard of the famed artist’s explosive outbursts and an attempt to preserve his own reputation and power of celebrity through bribery. (Photo by ANGELA WEISS / AFP) (Photo by ANGELA WEISS/AFP via Getty Images)
(L-R) King Combs, son of Sean “Diddy” Combs and Quincy Brown, stepson of Sean “Diddy” Combs, arrive at federal court for Sean “Diddy” Combs’ sex trafficking trial in New York City on May 15, 2025. Sean “Diddy” Combs used violence and threats of reputational ruin to control women he abused for years, New York jurors heard May 12 during opening statements of the federal sex trafficking trial that was followed by the case’s initial graphic testimonies. The panel of 12 jurors and six alternates responsible for determining Combs’s fate heard of the famed artist’s explosive outbursts and an attempt to preserve his own reputation and power of celebrity through bribery. (Photo by ANGELA WEISS / AFP) (Photo by ANGELA WEISS/AFP via Getty Images)
06:47
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.
‘Yeah,’ Cassie replied.
‘You loved him?’
‘I did.’
‘You believed he loved you?’
‘Yes.’
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.
Anna Estevao – Lawyer in Diddy Trial – https://www.linkedin.com/in/anna-estevao-b23a45318/
06:38
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.
Diddy Hotel Photos
Diddy Hotel Photos
06:26
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.
Diddy jury recoil in shock as they are shown photos from ‘Freak Offs’
Jurors in the trial of Sean ‘Diddy’ Combs were yesterday shown images from the sex parties that the hip-hop mogul masterminded.
06:20
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.
Sean Combs, right, and Cassie Ventura, attend The Metropolitan Museum of Art’s Costume Institute benefit gala celebrating the opening of the Heavenly Bodies: Fashion and the Catholic Imagination exhibition, May 7, 2018, in New York. (Photo by Charles Sykes/Invision/AP)
06:15
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.’
06:13
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.’
06:10
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.