Sean ‘Diddy’ Combs trial: Cassie’s graphic testimony of abuse

R&B artist Cassie Ventura’s movie premiere was days away in March 2016 when her then-boyfriend Sean “Diddy” Combs texted her asking what she was doing.

She already felt “trapped” in a cycle of physical and sexual abuse by him, she told a New York federal jury this week, outlining 11 years of alleged beatings, sexual blackmail and a rape.

She claimed Combs threatened to leak videos of her sexual encounters with numerous male sex workers while drug-intoxicated and glistening with baby oil as he watched and orchestrated the events, known as freak-offs.

“If I pleased him with a freak-off, then my premiere would run smoothly,” she said, according to reporting from inside the Manhattan courtroom from the Associated Press.

What happened next could end up being the beginning of the end of Combs’ public life.

Video footage from that March 2016 night shows Combs punching and kicking Ventura as she cowers and tries to protect herself in front of an L.A. hotel elevator bank. He then drags her down the hall by her hooded sweatshirt toward their hotel room. A second angle from another camera captures Combs throwing a vase toward her. She suffered bruising to her eye, a fat lip, and a bruise that prosecutors showed was still visible during the movie premiere two days later. She donned sunglasses and heavy makeup on the red carpet.

Ventura’s testimony is at the center of the federal trial accusing Combs of racketeering conspiracy, sex trafficking, and transportation for prostitution.

Sweeping allegations

The federal indictment alleges that Combs and his associates lured female victims, often under the pretense of a romantic relationship. Combs then allegedly used force, threats of force, coercion and controlled substances to get women to engage in sex acts with male prostitutes while he occasionally watched in gatherings that Combs referred to as “freak-offs.” Combs gave the women ketamine, ecstasy and GHB to “keep them obedient and compliant” during the performances.

The freak-offs, which prosecutors say sometimes lasted for days, were elaborately produced sex performances that Combs arranged, directed, masturbated during, and often recorded, according to the indictment. Prosecutors allege in a detention memo filed in court that the freak-offs occurred regularly from at least 2009 through 2023 and that the hotel rooms where they were staged often sustained significant damage.

Combs’ alleged “criminal enterprise” threatened and abused women and utilized members of his enterprise to engage in sex trafficking, forced labor, interstate transportation for purposes of prostitution, coercion and enticement to engage in prostitution, narcotics offenses, kidnapping, arson, bribery and obstruction of justice, prosecutors said. In bringing so-called RICO charges, prosecutors in opening statements said Combs was helped by cadre of company employees, security staff and aides. They allegedly helped organize the crime and “freak-offs” and then covered up the incidents. Thus far, Combs is the only one facing criminal charges related to the investigation.

Combs’ attorney this week said her client was far from perfect but that the charges were overblown.

“Sean Combs is a complicated man. But this is not a complicated case. This case is about love, jealousy, infidelity and money,” Combs’ lawyer Teny Geragos told jurors. “There has been a tremendous amount of noise around this case over the past year. It is time to cancel that noise.”

How Ventura and Combs met

Jurors heard that Ventura was 19 when she met the 37-year-old Combs in 2005, and she signed a 10-year contract with his Bad Boy Records label. About two years later, he had Britney Spears come to her 21st birthday party, where Ventura and Combs kissed and their relationship began, she said. She testified that the freak-offs became a way of life, and she even stepped away from her own birthday party for one.

Combs, she told jurors, required her to let a male sex worker urinate in her mouth. That man and others were paid thousands of dollars to have sex repeatedly for 36 to 48 hours, she told the jury.

On the stand, Ventura identified 13 male sex workers through photos presented by prosecutors that she said Combs’ had her recruit for the freak-offs. Hers and Combs’ relationship would end on a day in 2018 when she met him for dinner and he raped her on her living room floor, she testified.

Violence

During four days of testimony, Ventura, who is eight and a half months pregnant, described being raped, beaten at least six times, most severely in 2009.

In the 2009 attack, she testified that Combs was “stomping” on her face after he discovered she was dating rapper Kid Cudi. Kid Cudi, whose real name is Scott Mescudi, had his car torched a short time afterward. Prosecutors allege in court papers that Combs ordered it.

Legal analysis

Legal experts say the testimony is designed to build the federal case against Combs, even if on the surface it does not appear directly related to the charges he’s facing.

“Why is the government talking about rape and assault when the charges are RICO and sex trafficking?” said former federal prosecutor Neama Rahmani. Well, he said, “what separates sex trafficking from consensual sex between adults — which the defense is arguing — is force, fraud or coercion.”

“Ventura’s testimony that she was given drugs to the point of throwing up … and forced to have sex when she was menstruating or had a UTI is evidence of coercion,” he said.

Rahmani said that Ventura’s portrayal of Combs as a gun-brandishing mogul who beat her on multiple occasions, tracked her movements and sent a security team to find her is evidence of force.

Then there were the alleged threats. She recounted that during a commercial flight in 2013, Combs pulled out his laptop and began playing a freak-off recording as they sat together. She said Combs told her that he was going to embarrass her and release them.

“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,” Ventura said.

Authorities raid Sean “Diddy” Combs’ Los Angeles home as part of an ongoing sex trafficking investigation

(Eric Thayer / Associated Press)

Rahmani said the racketeering charge against Combs requires prosecutors to prove the existence of a criminal enterprise.

“People typically think of the mob, street gangs, or drug cartels, but any loose association of two or more people is enough like Combs’ entourage,” the former federal prosecutor said. They must show two or more predicate acts over 10 years.

“That is why the evidence of bribery, kidnapping, obstruction, witness tampering and prostitution is important,” he said.

LAPD officer testimony

Israel Florez, a hotel security guard who confronted Combs in 2016, now a Los Angeles Police officer, testified Combs flashed a bundle of cash at him — something he believed was an attempted bribe. He rejected it, he said.

Combs’ defense is seeking to paint Ventura as participating in the behavior, recruiting and paying sex partners, acquiring narcotics and texting to push for freak-offs that were part of a swingers’ lifestyle. She is one of four alleged victims in the case, with jurors expected to hear from at least three of them.

On Thursday, defense attorney Anne Estevao had Ventura read a series of loving texts to Combs and got Ventura to testify she’d watched Combs have sex with another woman on multiple occasions. To support the swingers’ defense, the lawyer produced a 2009 text where the singer declared, “I’m always ready to freak off.”

Ventura sued Combs in the fall of 2023, accusing him of years of physical and sexual abuse, triggering a cascade of lawsuits and allegations by others who say they’re victims of Combs and eventually, a raid by Homeland Security on his L.A. and Miami homes and his arrest. Ventura acknowledged Wednesday that she got a $20-million settlement within days of filing her lawsuit.

Combs attorney pushes back

During opening statements in a Manhattan federal courtroom, Geragos, one of Combs’ defense attorneys, drew a distinction for jurors between the violence they would hear testimony about and the charges Combs was facing, saying “domestic violence is not sex trafficking.”

She said the video of Ventura’s assault in the hotel was indefensible, but that the singer “made a choice” to stay with Combs for 11 years.

After the attack, a friend called police to Ventura’s home, she testified. But when officers arrived, she did not identify Combs as the culprit.

The prosecutor asked her why she did not talk. “In that moment, I didn’t want to hurt him that way. I wasn’t ready,” she replied.

On Thursday, the defense cross-examining Ventura sought to change the narrative using dozens of text messages between Combs and Ventura. In a July 2013 text message exchange, Comb’s defense lawyer noted that Cassie raised the idea of having a “freak-off,” writing to Combs: “Wish we could’ve FO’d before you left.”

Using the text message exchanges, the defense lawyer highlighted Ventura’s admitted jealousy over the attention he gave other women.

“You’re making me look like a side piece and that is not what I thought I was,” Cassie told Combs in a 2013 text message.

Estevao tried to recast the hotel incident as the result of the two taking a “bad batch” of the psychedelic stimulant MDMA during a “freak-off” before the hotel beating.

During her testimony this week, Ventura testified that Combs allegedly overdosed on opioids while partying at the Playboy Mansion in 2012. While she wasn’t there, she said, he told her about it.

The Associated Press contributed court testimony for this analysis.