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Diddy trial: ‘In what universe?’ Judge lashes Diddy’s lawyers

The judge in Sean ‘Diddy’ Combs’ trial has lashed at the star’s lawyers for their treatment of his ex Cassie Ventura.

Sean ‘Diddy’ Combs trial: Sordid details of alleged sex parties revealed

WARNING: Graphic content

More harrowing details have come to light as Sean “Diddy” Combs’ trial continues in New York.

Star witness and Combs’ ex-girlfriend Cassie Ventura claimed on Thursday, US time, that the rap mogul overdosed on opioids at the Playboy Mansion.

But a series of texts from Ms Ventura to Combs could undermine her central claim that she eventually no longer wanted to participate in “freak off” sex parties.

Combs’ defence has suggested that she actually instigated some of them, while the judge has lashed out at the star’s lawyers for their treatment of Ms Ventura. “In what universe?” he fumed.

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Combs is charged with transportation to engage in prostitution, sex trafficking and racketeering. He could face life in jail for just the racketeering charge. Combs has plead not guilty.

Ms Ventura began her second day of cross examination by Combs’ lawyers on Thursday.

She claimed the alleged overdose occurred during a night of hard partying in Los Angeles that included a freak-off – a drug fuelled sex session between her, Combs and male sex workers – and a trip to a sex club.

The singer claimed an overdose took place when he continued the party at the Playboy Mansion without her.

Cassie Ventura claims that after a night of hard-partying in 2012, Sean ‘Diddy’ Combs overdosed on opioids. Picture: Kopaloff/FilmMagic
Cassie Ventura claims that after a night of hard-partying in 2012, Sean ‘Diddy’ Combs overdosed on opioids. Picture: Kopaloff/FilmMagic

“That evening, we had a freak off. We went to a sex club in San Bernardino. And then he had a party at the Playboy Mansion that night, and I went home,” she said.

“From what he told me, he took a very strong opiate that night, but we didn’t know what was happening, so we took him to the hospital,” she said.

Combs’ lawyer then asked, “During the entire duration of your relationship, you two were addicted to painkillers?”

“Very much so,” Ms Ventura replied.

Diddy is claimed to have overdosed after partying at the Playboy Mansion in Holmby Hills, Los Angeles, without her. Picture: AFP Photo / Frederic J. Brown
Diddy is claimed to have overdosed after partying at the Playboy Mansion in Holmby Hills, Los Angeles, without her. Picture: AFP Photo / Frederic J. Brown

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‘In what universe’: Judge offloads on Comb’s lawyers

At one point judge Arun Subramanian chided Combs’ defence team for taking too long to cross examine the heavily pregnant Ms Ventura after his lawyers said their questioning could stretch into next week. She has already been in the witness box for five days straight.

“In what universe did you not understand this was important,” pointing out Ms Ventura’s pregnancy and that he had said she should be off the stand by the end of this week.

Cassie Ventura and Sean Combs when the pair were together. Picture: Instagram Picture: Instagram
Cassie Ventura and Sean Combs when the pair were together. Picture: Instagram Picture: Instagram

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Ventura ‘always ready’ for freak offs

A central argument made by the US government’s lawyers is that Ms Ventura eventually felt coerced by Combs into taking part in freak offs.

But on Thursday, the defence revealed numerous texts and emails that, they claimed, showed she was a very willing participant.

In August 2009, two years after she and Combs started dating and around a year and a half after the freak offs began, Combs texted Ms Ventura asking “when do you want to freak off?”

“I’m always ready to freak off, LOL,” replied Ms Ventura

At one point, Combs messaged her saying: “One of my favourite times is when we freak off and we make love after.”

“I love when we make love after,” she replied.

Ms Ventura said her texts seeming to approve of freak offs were “just words at that point”.

Cassie Ventura takes an oath before testifying in Manhattan federal court. (Elizabeth Williams via AP)
Cassie Ventura takes an oath before testifying in Manhattan federal court. (Elizabeth Williams via AP)

16 texts that undermine Ventura’s claim

The court was also shown a string of at least 16 texts which the defence claimed showed that far from Combs demanding freak offs, it was Ms Ventura that sometimes instigated them.

That included the sex party that occurred before the infamous CCTV footage emerged of Combs beating Ms Ventura in a Los Angeles hotel corridor in March 2016.

The pair had been messaging ahead of Ms Ventura doing some promotional work for her singing career in the days ahead.

Combs asked Ms Ventura what her plans were for the night and she said she might go out with friends but she had to remain fresh for her work commitments.

Seemingly fine to not see her that night, he told her to “get some rest” and then in multiple texts after that said she should “have fun” and that he loved her. Ms Ventura, however, sent him explicit sexual messages in return and wrote that she wanted to have sex. Combs said he needed to know either way so he could “plan the rest of my night”. Eventually she said she would come around later that night for a freak off.

Ms Ventura disagreed she had instigated that sex party. Rather, she said, she knew Combs well enough that his texts were pushing her into agreeing to a freak off.

Sean 'Diddy' Combs, right, stands and looks at jurors as they file into the jury box. (Elizabeth Williams via AP)
Sean 'Diddy' Combs, right, stands and looks at jurors as they file into the jury box. (Elizabeth Williams via AP)

Graphic messages force Cassie to ask for a break

Further messages from around the same time were more sexually-focused.

“I wanna be nasty for you,” wrote Mr Combs in December 2009.

The jury were also shown texts from 2012 of Combs’ asking Ms Ventura if she was “horny” and her replying “you like it when I moan”.

The court was shown even more graphic texts about sexual positions and Ms Ventura describing male genitalia.

“I can’t wait to watch you,” wrote Combs, about his girlfriend having intercourse with another man.

“I want you to get real hot.”

Ms Ventura replied: “Me too. I want to be uncontrollable”.

Janice Combs (R), mother of Sean
Janice Combs (R), mother of Sean "Diddy" Combs leaves the federal court during a break in the Sean "Diddy" Combs' sex trafficking trial in New York City on May 15, 2025. (Photo by ANGELA WEISS / AFP)

Another explicit text the singer wrote — in which she graphically described what she couldn’t “wait” for her then-boyfriend to do to her — led Ms Ventura to ask the judge for a break. The singer — who is eight months pregnant — was seen grabbing her belly with both her hands at the time.

Her husband, Alex Fine — who is the father of her two, soon to be three, children — was present inside the courtroom.

A Sean ‘Diddy’ Combs' fan holds a sign outside federal court. Picture: Angela Weiss / AFP
A Sean ‘Diddy’ Combs' fan holds a sign outside federal court. Picture: Angela Weiss / AFP

‘Dirty, grimy’

Nonetheless, not all of Ms Ventura’s communications with Combs about freak offs were positive.

In 2009, after Combs said he wanted to “get nasty” Ms Ventura said she needed to feel she “trusted” the star “beyond it being just sexual”.

“The last time was a mistake,” she said, referring to a sex party.

“It made me feel dirty and grimy, not sexual and sensuous.

“That’s the reason I go back and forth in my mind with wanting and not wanting to do freak offs when we’re so in love.”

Ms Ventura wrote that initially freaks offs “felt right” but later “I get nervous I’ve just become the girlfriend that you get your fantasies off with and that’s it”.

Media are seen outside the Manhattan Federal Court on May 15, 2025 in New York City. Picture: John Lamparski / Getty Images North America / Getty Images via AFP
Media are seen outside the Manhattan Federal Court on May 15, 2025 in New York City. Picture: John Lamparski / Getty Images North America / Getty Images via AFP

Earlier in the week, Ms Ventura had given testimony where she claimed she was “sexually inexperienced” when she met Combs. She said Combs “introduced me to the idea of oral sex” at the Trump International Hotel in New York.

“It was not something I did or understood.”

But defence lawyer Anna Estevao raised the fact that Ms Ventura had already been in a relationship with music producer Ryan Leslie.

“It wasn’t the first time you’d been dating an older man, right?” she asked.

Ms Ventura conceded she had been in a romantic relationship immediately before Combs.

Originally published as Diddy trial: ‘In what universe?’ Judge lashes Diddy’s lawyers

Original URL: https://www.weeklytimesnow.com.au/news/world/diddy-trial-cassie-ventura-faces-grilling-after-brutal-rape-claim/news-story/6e24db1e20f42da911cde3f4c298b68a