Cassie Becomes Emotional on Stand While Describing Confusing Sexual Experience with Diddy at Trump Hotel

Casandra “Cassie” Ventura took the stand at Sean “Diddy” Combs’ trial and described meeting with the music mogul at the Trump International Hotel and Tower in Manhattan.

Ventura, a key witness for the prosecution at Combs’ sex trafficking trial, was in a relationship with the Bad Boy Records founder for several years.

The Trump Tower rendezvous occurred after an encounter at Ventura’s 21st birthday in Las Vegas.

“I wanted to be around Sean for the same reasons as everyone else at the time — this exciting, entertaining, fun guy who also happened to have my career in his hands,” Ventura testified on Tuesday, becoming emotional on the stand.

Ventura testified that Combs allegedly introduced her to oral sex, noting that there was a 17-year age gap between the two.

“Sean taught me how. He gave me oral sex, I did not reciprocate — I just went home,” Ventura testified. “I heard about it from him. He made me feel crazy for not reciprocating but I didn’t understand and I was in a relationship with someone else.”

“I was so young and I didn’t have the vocabulary and was just trying to understand it,” Ventura continued. “I was sexually inexperienced. Leaving him was always confusing. I felt special and not a lot of people got that time.”

Combs was arrested in September 2024 based on an indictment filed by the U.S. Attorney’s Office for the Southern District of New York. He is facing charges of racketeering, sex trafficking and transportation to engage in prostitution.

Ventura accused the music mogul of sexual assault, rape and physical violence in a lawsuit in November 2023. The lawsuit was settled the following day before a wave of dozens of civil suits were filed, similarly accusing Combs of sexual violence.

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The 2024 indictment accused him of using his music empire to manipulate and lure women with promises of romance and then force them, using threats and coercion, to participate in highly orchestrated sex-acts at so-called “Freak Off” parties, which sometimes lasted several days.  

During the “Freak Off” parties, the indictment alleges that Combs used a variety of controlled substances to keep his victims obedient and compliant, sometimes unknown to the victims. The indictment named Combs the ringleader of the violent enterprise which is tied to several accusations of suspected kidnapping, arson, drug crimes and widespread sexual abuse. 

Combs, who previously operated a global music empire, has been in custody at the Special Housing Unit in Brooklyn’s Metropolitan Detention Center with greying hair. Opening statements began in his trial on Monday, May 12. He could face up to life in prison if convicted.

If you or someone you know has been sexually assaulted, please contact the National Sexual Assault Hotline at 1-800-656-HOPE (4673) or go to rainn.org.