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Reading: Trial of the Decade: Tearful Casandra Ventura Testifies Diddy Beat and Humiliated Her
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Sarajevo Times > Blog > WORLD NEWS > Trial of the Decade: Tearful Casandra Ventura Testifies Diddy Beat and Humiliated Her
WORLD NEWS

Trial of the Decade: Tearful Casandra Ventura Testifies Diddy Beat and Humiliated Her

Published: May 15, 2025
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At the trial of Sean Diddy Combs, the notorious rapper and music mogul charged with organized crime, human trafficking and transportation for the purpose of prostitution, his ex-girlfriend Casandra Ventura said that Diddy controlled her entire life, beating her and forcing her into degrading sexual acts.

The prosecution’s main witness in a US federal court in New York spoke about the alleged physical and emotional abuse she suffered at the hands of the rapper during so-called “freak-off” encounters – sexual relations the couple had with male escorts.

Family and friends have been flocking to court these days to show their support for Sean Diddy Combs. He has pleaded not guilty to charges that include conspiracy to commit a criminal organization, sex trafficking and transportation for the purpose of prostitution.

Prosecutors questioned Ms. Cassandra Venetura – one of two key witnesses in the case – about her on-and-off relationship with Combs, which lasted 11 years.

Now 38, pregnant with her third child, Ventura met the famous American rapper when she was 19 and a rising singer, while he was 37.

His record company later signed her to a collaboration deal, and their romantic relationship began soon after.

At the time, she testified, she felt they were in a monogamous relationship, although she now knows he had other girlfriends.

She said she “fell in love” with this “charismatic entrepreneur and larger-than-life musician.” But, she says, it wasn’t long before she noticed another side of him.

Combs wanted to ‘control’ every part of her life

The singer said Combs paid her rent, her cars, her phone and “other technology” that he would sometimes take away from her to “punish” her.

“The control was about everything — from the way I looked … to what I worked on,” Ventura said.

In the end, as she confirmed before the court, that control became violent. Sean Diddy Combs would often “headbutt me, knock me down, drag me and kick me,” she tearfully testified.

She stated that she was left with swollen lips, bruises under her eyes and nodules on her forehead.

She said she felt “humiliated” because of “weird people”.

She also told the court how Mr. Combs engaged in depraved sexual acts during the first year of their relationship. They would hire a male escort or a stripper to have sex with a lady. Ventura as her partner Combs looks on.

Ventura told the court that at first she tried to endure those “encounters” so that Mr. Combs “made happy”. But she said she was regularly humiliated and that “those encounters” sometimes lasted three to four days.

“I felt pretty terrible and worthless,” she told the court, wiping away tears.

Mrs. Ventura told the court that she never wanted to have sex with anyone but Mr. Combs and that she used to take various drugs – marijuana, ecstasy and ketamine – all to help her behave to please Mr. Combs, but also to “distance himself”.

Drugs were “a way to not feel what it really was,” she said, “having sex with a stranger I didn’t really want to have sex with.”

Sean Diddy Combs brought male escorts to “freak-off” sessions

As prosecutors questioned Ms. Ventura about the “freak-off” sessions, she said Combs ordered her to find male escorts, strippers or dancers with whom she would have sex while he watched.

She said Diddy would pay the men between $1,500 and $6,000 in cash, depending on their “performance.”

The men were found through strip agencies and websites like Craigslist. Some of their photos were shown to the jury, including one of Daniel Phillip, who had finished his testimony the day before.

According to her testimony, Casandra Ventura and Sean Diddy Combs had these sessions in cities around the world, including Los Angeles, New York, Las Vegas and Ibiza, Spain.

Sometimes the men would be flown in during vacations, she said, and Mr. Combs would order her to tell staff to register them and arrange their travel under the pretense that they were new employees.

Among other charges, prosecutors are seeking to prove that rapper and producer Combs engaged in sex trafficking — that is, trafficking people for the purpose of sexual exploitation — and arranging their transportation for prostitution.

Combs “directed” everything, Ventura says

During questioning, one key claim Ms. Ventura made was that Combs had complete control over every aspect of the sexual encounters.

According to her, he would choose the clothes she would wear — including the extremely high heels she had to wear for hours — then dictate what sexual acts would be performed, as well as the lighting in the room.

“If Sean wanted something, it would happen,” she said. “I couldn’t say no.”

She added that sometimes she would take the initiative in choosing male escorts because Combs was “very busy,” but she did so solely at his behest.

She described the “freak-off” encounters as having a clearly defined “pattern” of sexual acts each time.

“He was in control of the whole situation,” she said. “He directed everything.”

At times, she tried to talk to Mr. Combs and tell him she felt “terrible,” but he would dismiss her concerns. In such cases, she said, she would give in, fearing he would get angry or question their relationship.

The trial is expected to continue with Ms. Ventura being cross-examined.

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