Diddy trial: Cassie Ventura details rapper's alleged drug use in cross-exam

On Thursday, Sean Combs' former long-term girlfriend will be back on the stand for cross examination in his federal sex trafficking trial. For the past two days, Cassandra Ventura detailed what she described as years of physical, sexual, and emotional abuse at the hands of the 54-year-old music mogul. The prosecution alleges Combs ran a criminal enterprise to coerce victims into sex. Combs has pleaded not guilty to these charges.

NOTE: The following article contains disturbing details and video footage. Please read at your own discretion.

As the sex trafficking trial for Sean “Diddy” Combs enters its fourth day, Combs’ ex-girlfriend, Cassie Ventura, is on the stand to face cross-examination from Combs’ lawyers.

The R&B singer testified Wednesday that Combs raped her when she ended their decade-long relationship, and she described a life locked in physical abuse, which she says she couldn’t leave after he threatened to release degrading sexual videos of her.

She said the videos could ruin everything she’d worked for.  “I feared for my career. I feared for my family. It’s just embarrassing. It’s horrible and disgusting. No one should do that to anyone,” she said.

Ventura also spoke about an alleged incident in 2011 when Combs discovered that she had begun dating rapper Kid Cudi, whose real name is Scott Mescudi.

Combs, she said, went through Ventura’s phone and lunged at her with a “wine bottle opener” after he read text messages between the two.

Ventura testified that she ended things with Mescudi following Combs’ threats against them at the end of 2011. “Too much danger, too much uncertainty of what could happen if we continued to see each other,” she said.

Ventura said that Combs threatened to blow up Mescudi’s car and that he wanted Mescudi’s friends to be there when it happened.

Combs’ lawyers have acknowledged the rapper could be violent but maintain that the sexual acts were consensual. They say nothing he did amounted to sex trafficking or racketeering (the charges he faces), but insisted he just has unique sexual proclivities.

Day 4

Ventura, who is in the third trimester of pregnancy, returned to the witness stand in a black suit that looked almost like a tuxedo with a light-coloured blouse underneath.

Anna Estevao, a lawyer for Combs, opened her cross-examination by asking about her relationship with Combs. “You and Sean Combs were in love for 11 years. You loved him and believed that he loved you as well?” she asked.

“Yes,” Ventura replied.

Estevao continued to ask Ventura questions with “yes/no” responses about their relationship.

The first exhibits introduced by Estevao were text messages exchanged between Combs and Ventura in the early years of their relationship. In one, Combs wrote, “I’m truly a lucky man.” Ventura wrote back: “I’m a very lucky woman. … Love you so much.”

In one 2008 email, Ventura told Combs she was a lucky woman. “I love you sooo much,” she wrote after Combs thanked her for flying to Atlanta to be with him.

In August 2009, in a message sent by Combs, the rapper told her: “I love you sooooo much it makes me cry.”

Ventura replied: “U hungry pop pop?” (She testified Tuesday that Pop Pop was a nickname she used for Combs, while he sometimes called her Baby Girl.)

He said no, to which Ventura told him to let her know if he changed his mind.

When Combs’ lawyer asked Ventura why she wanted to spend so much time with him, she replied: “Because I fell in love with him.”

“He was charismatic — big personality, larger than life,” Ventura told the court. “The beginning of the relationship was really fast, fast-paced, scary. But the more time I spent with him, his real personality came out — sweet, attentive.”

The defence started to discuss the sexual encounters, known as freak-offs. “So, to make him happy you told him that you wanted to do freak-offs, right?” Estevao asked Ventura.

“No,” Ventura replied. “There’s a lot more to that.”

The jury was then shown a message from 2009 in which Combs and Ventura were discussing a freak-off with an escort named “Jules.”

“I’m always ready to freak off lolol,” Ventura wrote.

After viewing the text message, Ventura whispered to the Judge Arun Subramanian, who called a 10-minute break.

After the break, the defence showed more text messages that Ventura sent to Combs.

In a 2009 text message, Ventura wrote, “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 together. I get nervous that I’m just becoming the girlfriend that you get your fantasies off with and that’s it. I don’t get the other part… Anymore at least.”

Combs’ lawyer asked Ventura if her hesitation reflected in the text message came from concern that she wouldn’t be seen as the rapper’s “full girlfriend” because she was taking part in the freak-offs with male escorts.

“I think that’s a way to look at it I guess, yeah,” Ventura said.

Ventura laughed as Combs’ lawyer showed her an email she sent to him near the start of their relationship, almost 18 years ago.

“It’s making me giggle because it’s from 2007,” Ventura said, momentarily breaking the tension of a cross-examination that, so far, has required her to read and hear explicit messages she had exchanged candidly with Combs.

“I know,” Estevao responded. “We’re taking you back.”

In the email, Ventura wrote, “I’ve never felt so loved, safe and empowered since we’ve come together. On the other hand, your constantly weary of me.”

Estevao then asked Ventura 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,” Ventura responded.

Ventura was asked about Combs’ “swingers” lifestyle, and she testified that she sometimes watched him have sex with other women.

She said that this happened around four times throughout the course of their decade-long relationship.

Estevao asked Ventura if she thinks freak-offs were related to the swingers lifestyle.

“In a sexual way,” Ventura responded, before adding: “They’re very different.”

Combs’ lawyers said they don’t expect to be done questioning Ventura 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.

The defence’s revised timing “is the exact opposite of what I was told,” the judge said.

When asked whether she thought Combs was a drug addict, Ventura said, “I would say he was an addict.”

She accused Combs of using ecstasy and cocaine and told the court that he would become angry or volatile during drug withdrawals.

“I’m not a doctor, coming off of certain pills he would be pretty irritated,” she added.

Ventura said that Combs told drug dealers in Los Angeles to stop delivering drugs to her.

She also acknowledged that Combs had recommended that she get help for her drug issues.

On Wednesday, Ventura testified that she had an “off-and-on” addiction to opiates. She said she took them to come down off party drugs, including ecstasy, which she said she’d use during freak-offs. V told the court that she relied heavily on opiates because they numbed her emotions, allowing her to escape from the reality of the freak-offs.

Ventura said that Combs only wanted her to do drugs with him rather than with friends.

The defence lawyer highlighted instances of Ventura’s anger with Combs and her 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,” Ventura told Combs in a 2013 text message.

Ventura said Combs made it 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.

Ventura 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.

Ventura also told the court that there were never any drugs in the baby oil used during the freak-offs. Combs was accused in a lawsuit last year of spiking the baby oil with GHB.

What Combs is on trial for

U.S. prosecutors allege that for 20 years, behind the scenes, Combs was coercing and abusing women with help from a network of associates who helped silence victims through blackmail and violence.

Combs faces an indictment that includes descriptions of freak-offs, which are defined in the court doc as “elaborate and produced sex performances that Combs arranged, directed, masturbated during, and often electronically recorded.”

Numerous witnesses have come forward to accuse Combs of terrorizing people into silence by choking, hitting, kicking and dragging them, according to prosecutors. One indictment alleges that Combs dangled someone from a balcony.

Although dozens of men and women have alleged in lawsuits that Combs abused them, this trial will highlight the claims of four women.

Combs is charged with sex trafficking, racketeering conspiracy and transportation to engage in prostitution. He has denied all the charges against him and has rejected a plea deal, choosing to go to trial instead.

If found guilty in the New York court, he could face life in prison.

Day 3 testimony

Day 2 testimony

Global News will be covering the Diddy trial in its entirety. Please check back for updates. 

— With files from The Associated Press

© 2025 Global News, a division of Corus Entertainment Inc.

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