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Sean 'Diddy' Combs defense turns to tough cross-examination of Cassie Ventura at NYC sex trafficking trial

Molly Crane-Newman, New York Daily News on

Published in News & Features

NEW YORK — A lawyer for Sean “Diddy” Combs began grilling his longtime former partner, Casandra Ventura, on Thursday after the jury heard two days of devastating testimony from the R&B singer known as “Cassie” about being subjected to years of horrific and dehumanizing abuse.

Attorney Anna Estevao was tasked with carefully threading the needle on Ventura’s cross-examination, with the defense acknowledging in its opening statement that she was beaten savagely by Combs.

The rap mogul’s lawyers say he may have been violent but is innocent of charges alleging he ran a criminal enterprise and trafficked victims for sex; they maintain the case is about infidelity, love and financial greed and that “freak offs” — dayslong, drug-fueled sexual performances with male commercial sex workers — were consensually entered into by the alleged victims.

Estevao launched into cross-examination by pulling up sexually explicit and affectionate texts Ventura sent Combs around 2009, and introduced correspondence showing Ventura was sometimes enthusiastic about freak offs, with other portions indicating she was uncomfortable with them early on.

“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, and this is the only man that will ever have this aggressive/sexual side of me,” read one email from Ventura to Combs dated in 2009 that was shown in court.

“The last time was a mistake but since has made me feel a little dirty and grimy as opposed to sexual and spontaneous. That’s the only reason why I go back and forth in my mind with wanting and not wanting to do it.”

Ventura took the stand as the trial’s star witness on Tuesday and, over two days of questioning by the prosecution, shared countless devastating accounts of being brutally battered by Combs throughout their nearly 11-year relationship and coerced into hundreds of demeaning sexual performances he orchestrated.

Photos of Ventura’s injuries accompanied many of her accounts, and jurors have watched explosive surveillance footage of Combs pummeling Ventura in an L.A. hotel after she sought to escape a March 2016 freak off.

She said she first met Combs, 17 years her senior, when she was 19 and signed to Bad Boy Records, and said they began dating within a couple of years. Ventura said she was sexually inexperienced when they started sleeping together and that it was her first adult relationship.

The “Me & U” singer said Combs taught her about “voyeurism” and a “swingers lifestyle,” directing her to find escorts on websites like Craigslist — usually Black men whose appearance he would vet — and arrange their travel to hotels and properties nationwide. She said he usually masturbated while directing her and the strangers to perform lurid acts during the freak offs, including making men urinate on her in sessions that lasted for days, at least once a week over a period of years.

Asked why she engaged in the encounters she said she never wanted to participate in, Ventura said she lived in constant fear of Combs’ violent wrath and his power over her career and that he had threatened to release footage of the dehumanizing performances.

 

“Whatever was going to make him not be angry at me and threatening me, I was willing to do. Yeah, I just didn’t want to feel scared anymore and one thing he made me feel like I was good at,” Ventura said Wednesday.

“The leverage of having an incriminating or a derogatory, humiliating video of somebody, telling them they’re going to release it if you don’t behave the way they want you to or whatever the case may be. It was just always like that,” she said.

Ventura described Combs’ psychological and physical abuse as ultimately demolishing her sense of self, stifling her career, and leading her to contemplate suicide. She revealed Wednesday that he settled a lawsuit she brought in November 2023, just 24 hours after she filed it for $20 million. The criminal probe soon followed.

Asked by Estevao on Thursday whether she knew her suit ruined Combs’ reputation, she said, “I could understand that.”

Combs, 55, has pleaded not guilty to racketeering conspiracy, two counts of sex trafficking by force, fraud or coercion, and two counts of transportation to engage in prostitution. He could face life in prison if convicted.

Enabled by a network of well-paid employees, virtually unlimited resources, and immense influence, the feds say the multimillionaire Bad Boy Records co-founder abused, threatened, and coerced women and others into realizing his sick sexual desires, shield his reputation, and hide his criminality from 2004 to 2024.

Ventura on Wednesday testified about him threatening to have his henchmen incinerate Kid Cudi’s car after learning she was dating him in 2011, not long before it exploded in the rapper’s driveway.

The sex trafficking counts allege Combs enticed and transported Ventura and Jane, which is a pseudonym, to engage in sex acts with commercial sex workers by force and fraud and after coercing them into depraved freak offs under the guise of a romantic relationship. The jury is also expected to hear from a former personal assistant of Combs who will allege he sexually assaulted her.

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©2025 New York Daily News. Visit at nydailynews.com. Distributed by Tribune Content Agency, LLC.

 

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