On red carpets from Los Angeles to the French Riviera, Sean “Diddy” Combs and the R&B singer Cassie intertwined arms, radiating an attractive and carefree façade for the cameras.
But behind closed doors, she said, she “felt trapped.”
In the first week of testimony in Combs’ federal sex trafficking trial in New York, Cassie, whose real name is Casandra Ventura, described over four days on the witness stand a tumultuous relationship with the music impresario that began in her early 20s and lasted on and off for over a decade. As the government’s star witness, her responses gave a window into a world centered around paid sexual encounters lasting days and sometimes occurring weekly — known as “freak offs” — that she said she was forced to endure under the threat of physical and psychological abuse.
Sign up for the “Diddy on Trial” newsletter for key developments and analysis
The “freak offs” were so regular, she said, they “became a job.”
Much of what Ventura, 38, testified to was graphic, from the sex acts with male escorts to the violence, including the fights with Combs that left her covered in bruises, she said, if she attempted to rebuff a “freak off.” A visibly pregnant Ventura also recounted how, she said, Combs raped her on her living room floor in 2018, which he has denied.
But as explicit as the line of questioning was from the prosecution, it was necessary, some legal experts say, because it helped to lay a foundation for the federal government’s case in the weeks to come. Ultimately, 12 jurors must decide whether Combs, 55, violated federal laws against racketeering conspiracy, sex trafficking and transportation to engage in prostitution. He has vehemently denied all five counts against him, but if found guilty of even one, he could face a lengthy prison sentence.
Rachel Maimin, a former federal prosecutor for the Southern District of New York, said a crucial piece of evidence — security video from a 2016 assault in a Los Angeles hotel hallway in which Combs, wearing only a white towel, could be seen beating and dragging Ventura — is going to stick in jurors’ minds. On the stand, Ventura explained the incident was the result of her trying to leave a “freak off,” which sometimes occurred in hotel suites around the world.
Ventura “really was able to tell a story from start to finish,” Maimin said. “She was able to get into some of the more upsetting and disturbing pieces of the case, including the video of when Combs is beating her. It sets the stage for the rest of the case, where the prosecution is going to have to back up her testimony with all of their evidence.”
Ventura said it was under the direction of Combs that she would use drugs and have sex with male escorts, some found on Craigslist and paid upward of $6,000. Meanwhile, she said, Combs’ security was around constantly to provide supplies, including the drugs, condoms and baby oil.
Hanging over their relationship, she said, was the fear that Combs might blackmail her with recorded videos of the sex acts.
She panicked, she said, when she was hosting an event in Atlantic City, New Jersey, in 2014 and “someone I was working with said they saw a sexually explicit video of me.” She quickly texted Combs, and told jurors that any leaked footage “would put my career in jeopardy” and “could ruin everything I worked for.”
A year earlier, Ventura said, she was mortified when she saw Combs watching sexually explicit videos of her while they flew home on a commercial flight after having attended the Cannes Film Festival in France.
“He pulled up ‘freak off’ videos on his laptop that I thought were deleted,” Ventura testified. “He was showing them with other people around. I said, ‘You are embarrassing me.’ I was scared. I felt trapped. How do you get out of this situation?”
But to stave off his rage, she said, she then arranged a “freak off” within hours of them landing, otherwise, “he said the videos would be released.”
Mitchell Epner, a former federal prosecutor for the District of New Jersey who now practices criminal defense in New York, said Ventura’s testimony has been key, because if jurors find her to be credible, she helps the prosecution’s case that alleges sex trafficking did occur by means of “force, fraud or coercion.”
“If she was coerced by violence or threats of violence or blackmail materials into participating in the ‘freak offs’ over her objections, then the trial is over,” Epner said. “Everything else, which will go on for weeks, will not matter if the jury accepts that she was a credible witness, and they believe beyond a reasonable doubt that she was telling the truth when she said I didn’t want to do these things, he knew I didn’t want to do these things, and the only reason I did them was that I was afraid that he would beat me or that he would release the videos.”
He added that the way Combs’ defense team painted him in their opening statements as a “very flawed individual,” prone to violence and jealousy in his relationships, was striking.
“It’s one of the strangest trials that we’ve seen because the prosecution and defense agree about so many of the facts,” Epner said.
During cross-examination, defense lawyer Anna Estevao got Ventura to speak about her love for Combs. Text messages were shown that suggest she knew she had the agency to walk away from him after they fought.
Other messages also showed her appearing to be a willing participant in the sexual encounters: “I’m always ready to freak off,” she wrote in 2009.
“For the defense in the case, the key to the castle is persuading the jury that everything done here was consensual,” said Mark Zauderer, a veteran trial and appellate lawyer in New York.
Ventura also told Estevao that she settled her 2023 lawsuit in which she accused Combs of rape and abuse for $20 million, and initially her lawyer asked for $30 million as she had planned to write a book about her relationship with Combs. (Combs did not admit to wrongdoing in settling the suit.)
Zauderer said jurors may see that sum as either Ventura having “vindicated herself” after what she endured or “the defense is trying to cast it as that she was just looking for money.”
Maimin, the former federal prosecutor, said she still wants to see how prosecutors will further Ventura’s testimony to show how Combs allegedly wielded his power and business pursuits — built around Bad Boy Records, which he founded in 1993 — as a “criminal enterprise.”
In their indictment, prosecutors say Combs “relied on the employees, resources and influence of the multi-faceted business empire that he led and controlled — creating a criminal enterprise whose members and associates engaged in, and attempted to engage in, among other crimes, sex trafficking, forced labor, kidnapping, arson, bribery, and obstruction of justice.”
“I don’t know that she got them all the way there,” Maimin said of Ventura’s testimony.
“As a matter of law, it is enough just to have the testimony of one witness,” Maimin said, “but given the complexity of the charges against him, including the racketeering conspiracy part, it would be very difficult to say you’ve proven your case beyond a reasonable doubt without corroborating evidence.”
Neither the prosecution nor the defense has released full witness lists for the trial, which is expected to last at least eight weeks.
Dawn Richard, a former member of the girl group Danity Kane, founded by Combs, took the stand briefly late Friday as the prosecution’s next witness and is expected to continue testifying Monday. Richard filed a lawsuit last year against Combs, alleging he groped, assaulted and imprisoned her, and that she also saw him beating Ventura.
A lawyer for Combs called the allegations “manufactured” and said Richard was seeking “a pay day.”
Other witnesses for the prosecution in the coming days may include Ventura’s mother and a personal assistant of Combs.
If you or someone you know is facing domestic violence, call the National Domestic Violence hotline for help at (800) 799-SAFE (7233), or go to www.thehotline.org for more. States often have domestic violence hotlines as well.
