Diddy lawyers shock trial with Whitney Houston drug overdose bombshell after ripping Cassie to shreds

Diddy's defense attorney questioned Cassie about a time when the rapper overdosed in February, 2012, after taking painkillers.

'Was that around the time Whitney Houston died?' Cassie asked Diddy's attorney.

Yes... We had a Freak Off. We went to a sex club in San Bernardino. He had a party at the Playboy Mansion that night and I went home.

He took a very strong opioid that night, we didn't’ know what was happening so took him to the hospital.

Whitney Houston died on February 11, 2012, in an accidental drowning after taking cocaine.

It's unclear why the defense brought up her death.

Houston and Diddy are seen in 2010.

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.

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Judge Arun Subramanian said that the defense should finish Cassie Ventura's cross-examination by tomorrow. Diddy's lawyers said they couldn't promise that timeline.

Prosecutor Emily Johnson said she expects about an hour of more direct examination when the defense team finishes.

The jury has been dismissed for the day.

Cassie Ventura told the trial that Diddy did not want to get caught in the 'matrix' during their sexual escapades - meaning he didn't want to get 'too high.'

'It’s the high, and being too high where there wouldn't be anything sexual happening, we’d be too high,' she told the court.

When asked if the drug involved was ecstasy, she replied: 'Any drug.'

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.

Diddy has continued showing off a charismatic persona in the courtroom.

He stood at the defense table during a break Thursday, 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.

Last year, Diddy was accused of spiking the baby oil lubricant with GHB, known as the 'date rape drug.'

But Cassie confirmed to the court on Thursday that there were never any drugs in the baby oil used in the freak-offs.

Freak-offs would last for hours, and sometimes days, Ventura told the Manhattan courtroom.

Cassie 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.'

As Sean 'Diddy' Combs faces charges of sex-trafficking in Manhattan federal court, his relationship with the singer Cassie is at the center of the horrific allegations.

The music mogul's staggering downfall began when Cassie, real name Casandra Ventura, filed a bombshell lawsuit in 2023 detailing terrifying claims of sexual abuse and violence.

The lawsuit was settled for an undisclosed amount just a day after it was filed, but it was too late for Diddy's reputation, and the rapper was then hit with dozens of lawsuits including similar claims.

Gina Huynh, who says she dated the music executive for five years, described in a resurfaced interview from 2019 a time at which he allegedly became violent with her.

The model told the controversial blogger Tasha K that he allegedly 'stomped' on her stomach and repeatedly punched her in the head during one disturbing encounter.

Gina's relationship with Diddy reportedly began during a period in which he and Cassie (real name: Casandra Ventura) were on and off.

'He stomped on my stomach really hard — like, took the wind out of my breath,' Gina said in her interview, via Page Six.

'I couldn’t breathe. He kept hitting me. I was pleading to him, "Can you just stop? I can’t breathe,"' she added.

According to her, Diddy then began to pull at her hair and punch her repeatedly in the back of her head.

Cassie laughed on the stand Thursday as she recalled that she and Diddy used to call each other 'Get High partners.'

The singer said the Freak Offs lasted so many days - as much as four - because they did so many drugs during them.

'The drugs becam a thing over time. Became the main event for us,' she told the jury.

Kerry Morgan came up during Cassie's testimony on Tuesday as she described their former friendship.

Morgan, a model, was Cassie's best friend when she started dating Diddy, in 2007.

Cassie has claimed her friendship with Morgan became irreparably strained after Diddy assaulted her in 2018.

Cassie's lawsuit said: 'The incident resulted in a settlement between Mr. Combs and Ms. Morgan, and Ms. Ventura ended up paying Ms. Morgan additional funds in an attempt to resolve the dispute between her close friend and her abusive and controlling boyfriend. The relationship between Ms. Ventura and Ms. Morgan has been strained since this time.'

Just a year after she was last seen with Diddy, Cassie married Alex Fine, who was originally Diddy's personal trainer.

Cassie became pregnant soon after she started dating Fine.

The couple is currently expecting their third child.

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.

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.

O'Day who for years claimed she suffered abuse while working for Diddy, revealed she was in NYC during the music mogul's trial.

'Hey New York!!! Where y’all think I should head first?'

O’Day wrote on Wednesday.

The former Danity Kane star is supposed to testify in the trial sometime next week, according to Us Weekly.

Diddy suspected Cassie was having a revenge affair with the actor Michael B. Jordan, the court heard.

Cassie said she dumped the hip hop mogul in 2015 after seeing a video of him and a woman called Gina at an event while she was in South Africa filming 'Honey 3: Dare to Dance'.

She told a court in New York that Diddy suspected she got together with Jordan, who was in Cape Town at the same time while doing filming of his own.

Cassie said she 'wasn't there' to see how Combs reacted when he found out about her relationship with Jordan.

Cassie and Diddy eventually patched things up and stayed together until 2018.

The singer did not say she had an affair with the actor while on the stand, but she did reveal the roman in her 2023 civil lawsuit against the mogul.

Cassie said that she began a ‘flirtatious relationship’ with Jordan while she was in South Africa - and that they did have an affair.

‘She spent New Year’s Eve with this actor but Mr Combs soon found out’, the lawsuit stated.

‘Mr. Combs called the actor and threatened him; the actor proceeded to call Ms. Ventura and tell her: ‘You really need to call ‘Mr Combs’.

Cassie admitted on the stand that she was jealous of Diddy's ex Kim Porter because the mogul was still publicly linked with the mother of his children.

She said she would be upset when Diddy spent special occasions with Porter and his children instead of with her.

Diddy and Porter were in an on-off relationship from 1994-2007.

Porter had been photographed with Combs and their kids in the months before her death in 2018.

Cassie wrote in a text to Diddy in March, 2017: 'Please don’t play victim.

'That’s all you wanted and that’s why I was upset.

'I love our FOs when we both want it.'

Diddy's attorney has been trying to prove that, despite her claims, Cassie was not coerced into participating in the grueling sex sessions.

When asked about what she wrote, Cassie replied: 'I would say that loving FOs were just words at that point.'

Judge 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.

The mogul's family, including his mother Janice and six of his seven kids, has supported him since his arrest last year and have been present in the courtroom every day this week.

His three daughters - 18-year-old daughter Chance and 17-year-old twins D’Lila and Jessie - were in court on Monday and Tuesday and heard horrific testimony from the first three witness including Cassie.

However, Diddy's daughters were not seen going inside the federal courthouse on Wednesday as Cassie is to resume her testimony.

Only Diddy's mother Janice Combs and sons Quincy, 33, Justin, 30, and Christian, 26, were seen entering court on Wednesday and Thursday.

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.'

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.'

Judge Subramanian has imposed a strict 5pm deadline on Friday May 16 for the defense to finish cross examining the witness.

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.

Combs appears relaxed at the defense table, sitting back in his chair with his hands folded before him and his legs crossed.

He has been allowed to wear his own clothes for the trial.

However, he has to rotate between five looks throughout the trial, which is expected to last about eight weeks.

He can only have up to five pairs of pants, shirts and socks and only two pairs of shoes - with no laces.

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.'

Estevao questioned Cassie about addictions as it related to Combs.

'Would you say he was an addict?' the defense 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.'

Cassie said Combs would become more violent when he was gouing through Opioid withdrawals.

Cassie is being questioned about her relatiopnship with music producer Ryan Leslie, who she dated before she met Diddy.

Diddy's lawyer has made a point of noting that Leslie is 10 years older than Cassie, so Diddy was not her first experience with an older men.

Cassie began dating Leslie when she was 19 years old, and has a tattoo of his initials on her body.

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.

Estevao repeated Cassie's claim that she was afraid Diddy would release tapes of the freak offs. Cassie said in direct examination that this was part of why she felt she could not say no to the star.

The attorney then had Cassie confirm that the public did not learn of the freak offs until she filed her lawsuit in 2023 against Diddy.

Unlike other high-profile cases, the rapper's trial will not be televised as it is in federal court.

Electronic media, including cameras, are banned in the Manhattan court room.

A sketch artist's work will be the only visuals coming out of the courtroom.

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.'

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.

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.

Britney, Diddy and Cassie are pictured in Las Vegas in 2007. They were accompanied by Cassie's then-boyfriend Ryan Leslie.

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.

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.'

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

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

Diddy's lawyer Anna 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.

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 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.

On Thursday, Diddy mentioned to his lawyer Anna Estevao that he was 'proud' of her for the work she was doing on his case. The message was caught on a hot mic in the courtroom.

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

'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.'

In one particularly damning exhange, Cassie wrote in a text to Diddy in March, 2017: 'Please don’t play victim.

'That’s all you wanted and that’s why I was upset.

'I love our FOs when we both want it.'

Diddy's attorney Anna Estevao is pictured.

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.

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.

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.

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.'

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.'

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.

Sean 'Diddy' Combs blew a kiss to his mom and made a heart with his hands as she led his family into the courtroom to support him in his racketeering and sex trafficking trial.

The disgraced music mogul's criminal trial kicked off in Manhattan's federal court on Monday, eight months after he was first arrested and hit with a host of charges.

His family, led by his mom Janice, have been steadfast in their support of the 55-year-old.

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.

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.

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 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.

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.'