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Home / Lifestyle

Two words from Cassie Ventura became the legal turning point of Sean Combs verdict

By Benedict Brook
news.com.au·
3 Jul, 2025 04:51 AM6 mins to read

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Cassie Ventura with Sean "Diddy" Combs in 2018. Photo / Jeff Kravitz/FilmMagic

Cassie Ventura with Sean "Diddy" Combs in 2018. Photo / Jeff Kravitz/FilmMagic

For weeks, 12 jurors sitting in a sky-rise Manhattan courtroom heard just how degrading Sean Combs could be. But in the end, it came down to two words in a text.

For seven weeks, witness after witness described how the music mogul and singer, better known as Diddy, threatened and assaulted the people around him.

One assistant described how furious Combs was when he bought the star the wrong-sized water bottle.

CCTV footage was shown to the court of Combs beating his ex-girlfriend, Cassie Ventura, outside a hotel lift.

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A friend of Ventura described in shockingly vivid detail several alleged encounters with Combs, including one in which she said she was dangled over a balcony 17 storeys up.

But, as startling as these claims were, none of them mattered in the end.

Even Combs’ lawyers admitted he had committed domestic violence and that jurors would likely find him a “jerk”.

But Combs wasn’t charged with assault, violence or threats.

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Rather, he was facing two counts of transportation to engage in prostitution, two counts of sex trafficking, and one count of racketeering.

Early today (NZ time), the jury found him not guilty on the most serious charges of racketeering and sex trafficking, both of which could have led to life imprisonment.

However, he was found guilty of transportation to engage in prostitution in connection with Ventura and a second woman, who gave evidence under the name of “Jane”.

Combs, 55, could yet face 20 years in jail for those convictions, with bail denied by a judge as he awaits sentencing in October.

The prosecution’s failure to convict Combs on other charges could, essentially, have come down to two words sent in a text by Ventura to Combs: “always ready”.

At the outset of the trial, in mid-May, Combs’ lawyers did not try to sugar-coat their client’s actions.

The evidence might prove domestic violence, they told the jury, but it did not prove any of the federal charges.

“Sean Combs is a complicated man, but this is not a complicated case,” said defence lawyer Teny Garagos at the time.

There would be multiple times when the jurors might think Combs was “mean” or a “jerk”.

But, she added, “This case is about voluntary adult choices in consensual relationships.

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“Being a willing participant is not sex trafficking.”

Disturbing freak-off parties

At the centre of the allegations was Combs’ so-called “freak-offs”. These involved one of Combs’ partners having sex with a paid male sex worker, while the star watched, directing the scene and often masturbating.

The jury heard about the vast amounts of baby oil and lubricant in which Combs demanded that those taking part should slather themselves; about the copious drugs consumed; about Ventura being urinated on; and the filthy state in which hotel rooms were left.

Photos taken by law enforcement officers after they raided Sean "Diddy" Combs' room at the Park Hyatt Hotel in Manhattan showed bottles of baby oil, lubricant and bags of pink drugs. Photo / US Department of Justice
Photos taken by law enforcement officers after they raided Sean "Diddy" Combs' room at the Park Hyatt Hotel in Manhattan showed bottles of baby oil, lubricant and bags of pink drugs. Photo / US Department of Justice
Further items found in Combs' room at the Park Hyatt Hotel on September 16, 2024. Photo / US Department of Justice
Further items found in Combs' room at the Park Hyatt Hotel on September 16, 2024. Photo / US Department of Justice

“The evidence will show the sexual conduct was coercive and criminal,” prosecution lawyer Emily Johnson said.

“He made women have sex when they didn’t want to be there”.

Ventura and others insisted that, over time, they were less and less willing to take part in the freak-offs. They only did so because they were, in one way or another, forced to.

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The problem for the prosecution was the digital paper trail that often suggested otherwise.

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

“I’m always ready to freak off, LOL,” she replied.

Ventura said those texts were “just words at that point”.

But it wasn’t a single text exchange.

The court was shown a string of at least 16 texts from March 2016, which the defence claimed showed that, far from Combs demanding freak-offs, it was Ventura who sometimes instigated them.

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In one instance, Combs asked Ventura what her plans were for the night. She replied that she had to remain fresh for her upcoming work commitments.

He told her to “get some rest” and that he loved her.

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.

Ventura disagreed that 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.

Combs and Ventura before their relationship ended. Picture / Instagram
Combs and Ventura before their relationship ended. Picture / Instagram

The prosecution argued that Combs and his “inner circle” helped to facilitate crimes including kidnapping, arson and sex crimes “again and again”.

Multiple former staff members testified, luridly describing how they would set up the freak-offs, and the lube and baby oil – and sometimes drugs – they would painstakingly procure. Some described how they would clean up the rooms afterwards so the hotels would be less inclined to complain or – potentially – sell pictures of the rooms trashed by a star.

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But the jury wasn’t convinced that Combs’ staff were assisting in any of the crimes with which he was charged. It wasn’t even clear whether they knew exactly what occurred at the freak-offs, aside from a lot of sex involving a lot of lube.

Being convicted on two of five charges is not the ideal outcome for Combs. But being found not guilty of the others is a victory of sorts.

Moments after the verdict, Ventura’s lawyer, Doug Wigdor, said his client had shown “unquestionable strength” in court.

“Although the jury did not find Combs guilty of sex trafficking Cassie beyond a reasonable doubt, she paved the way for a jury to find him guilty of transportation to engage in prostitution.

“She displayed unquestionable strength and brought attention to the realities of powerful men in our orbit and the misconduct that has persisted for decades without repercussion.”

‘Case was weak from the start’

Nicole Brenecki, a New York trial attorney, claimed the prosecution’s case fell apart because it was “built more on sensationalism than a solid legal basis”.

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“RICO [racketeering] charges require proof of an ongoing criminal enterprise with co-ordinated activity by multiple actors, not just deviant parties and disgruntled ex-girlfriends,” she told the New York Post.

“Add to that the lack of paper trails, co-operating witnesses inside the alleged ‘enterprise’, or any clear hierarchy of criminal role, and you’re left with smoke, but no fire – and a not guilty verdict follows.”

The evidence indicated that Combs’ ex-girlfriends appeared to have “willingly taken part in [the] freak-offs”, she said.

“Voluntary participation, no matter how controversial, doesn’t equal organised crime.”

David Seltzer, a managing partner at a criminal law firm in New York not involved in the case, agreed.

“The Government’s case was weak from the start.

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“They tried to put a square peg in a round hole, using mobster-like charges, when all they had were glorified state court charges.”

Lawyer John W. Day said the trial was a “huge win” for Combs’ defence team.

“It means the jury did not buy the stories of Cassie and Jane, and most likely believed they were enjoying life with Diddy voluntarily, and all the trappings of that world.”

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