Sean ‘Diddy’ Combs Trial: Defense Lawyers Portray Cassie Ventura As Consenting To Freak-Offs Through Old Texts

Topline

In her third straight day on the witness stand, Sean “Diddy” Combs’ lawyers asked the music mogul’s ex-girlfriend Cassie Ventura about old texts they had shared as they aimed to portray the “freak off” sexual encounters as consensual, which she had previously described as “disgusting” and coerced in testimony earlier this week (Combs has pleaded not guilty to all five federal charges).

Sean “Diddy” Combs pleaded not guilty to five federal charges. (Photo by Shareif Ziyadat/Getty … More Images for Sean “Diddy” Combs)

Getty Images for Sean “Diddy” Combs

Key Facts

Ventura, whom Combs dated off-and-on between 2007 and 2018, took the stand again Thursday, the third day in what is expected to be a week-long testimony, possibly longer, as the prosecution’s key witness in Combs’ sex trafficking and racketeering trial.

Defense lawyers have asked Ventura to read aloud many text and email messages shared between her and Combs throughout her relationship, including one from 2009 in which she texted Combs: “I’m always ready for a freak-off lolol,” and in another message two days later, stating she wants “it to be uncontrollable,” NBC News reported.

Ventura pushed back on some of the texts as “just words at that point,” and she said she took part in the freak-offs, which involved Combs watching Ventura have sex with a male escort, because she ”wanted to make him happy,” adding, “it was a lot more than that.”

The defense also questioned Ventura about her love for Combs, as Ventura described him as “sweet” and “attentive” early in their relationship and a “big personality, larger than life,” pointing to a text from 2009 in which Ventura told Combs she loves him “so much it makes me cry,” the New York Times reported.

Ventura admitted she “had some jealousy” of Combs’ late ex-girlfriend Kim Porter, with whom he had three children, a claim the defense lawyers made in their opening statement, NBC News reported.

On Wednesday, Ventura testified Combs threatened to blackmail her with videos he recorded of Ventura performing during freak-offs if she upset him: “I would have to answer to my mother,” she said, according to the BBC, stating the videos “make me look like a slut.”

Combs’ legal issues began with a lawsuit filed by Ventura in November 2023, in which she alleged he raped her and subjected her to years of physical abuse; she testified Wednesday that she settled that suit for $20 million, the Associated Press reported.

Cassie Ventura Details Violence In Relationship With Combs

On the witness stand Tuesday, Ventura testified she and Combs would have “violent arguments” throughout their decade-long relationship, in which he would “too frequently” subject her to physical abuse: “He would smash me in my head, knock me over, drag me, kick me, stomp me in the head if I was down,” CNN reported. The court was once again shown footage of Combs attacking Ventura in a Los Angeles hotel in 2016, and Ventura testified she attended a movie premiere for “The Perfect Match,” a rom-com she starred in, with sunglasses to hide bruises Combs had given her. Ventura detailed another altercation in which Combs “knocked me around” in a car in 2007 or 2008, and Ventura said Combs had instructed her to stay in a hotel for a week so her wounds could heal, the New York Times reported. Ventura also detailed the physical and emotional toll of “freak-offs,” stating she would suffer urinary tract infections after performing in back-to-back freak-offs to the point that CIPRO, a common UTI antibiotic, no longer worked for her, NBC News reported. Combs subjected her to freak offs “weekly for a consistent amount of years,” the Washington Post reported. “I felt pretty horrible about myself. I felt disgusting. I felt humiliated,” Ventura said of the freak offs, adding she “couldn’t talk to anyone about it.” Combs also controlled Ventura’s singing career, she testified, stating he called “all of the shots” after he signed her to his Bad Boy Records when she was 19 years old, NBC News reported, and he controlled her image and physical appearance.

How Have Combs And Ventura Reacted In Court?

On Thursday, multiple outlets reported Ventura’s dynamic with Combs’ defense lawyer Anna Estevao was largely cordial and occasionally friendly, noting at one point Estevao called her “very beautiful and charming” to light laughter from the courtroom. Ventura is testifying while nearly nine months pregnant, and judge Arun Subramanian sparred with the defense Thursday afternoon over a slow cross-examination process. “In what universe did you not understand this is what was going to happen … you’re not telling me this wasn’t everyone’s understanding that this witness was going to be done this week?” NBC News reported. Subramanian asked the defense lawyers in a tense exchange after they claimed they may need the rest of the week for cross-examination, before Ventura returns for final questioning by prosecutors. Earlier Thursday, prosecutors said Ventura is “very pregnant,” adding: “We are afraid she could have the baby over the weekend. We want her off the stand before the weekend.” Subramanian also laid blame on prosecutors for Ventura’s tight questioning timeline, stating it “seems strategic” they called two witnesses to testify on Monday before Ventura took the stand. Ventura is pregnant with her third child with her husband Alex Fine, who is present in the courtroom Thursday. Combs appeared in the courtroom Thursday wearing a light-colored sweater and white collared shirt, as his family once again attended to support him.

Security Guard Israel Florez Said Combs Had ‘devilish Stare’ After Altercation

Israel Florez, then a security guard at the Los Angeles hotel where Combs attacked ex-girlfriend Cassie Ventura in 2016 in an incident captured on surveillance cameras, testified first at the trial. He said Venture appeared “scared” after the altercation, NBC News reported, and testified that Combs was sitting in a towel with a “devilish stare.” Florez said Combs approached him with a stack of money, telling him: “Don’t tell nobody,” but Florez rejected the apparent bribe, AP reported. Also on day one, Daniel Phillip, a male escort, was the second to take the stand, testifying he was paid by Ventura to have sex with her at a hotel in 2012 while Combs watched in the corner and masturbated, the New York Times reported, and then repeated the service multiple times with the couple at various hotels.

Diddy’s Defense Attorneys Say He Is Violent But Not A Sex Trafficker

Geragos denied Combs’ violent behavior constitutes acts of sex trafficking or other federal crimes. “He is physical, he is a drug user, you may know of his love of baby oil. Is that a federal crime? No,” Geragos told the jury, NBC News reported. Geragos addressed the hotel surveillance footage of Combs attacking Ventura, calling his actions “indefensible,” “dehumanizing” and “virtually every bad word you can think of,” but said it is “not evidence of sex trafficking,” CNN reported. Geragos argued Ventura was a “willing participant in their sex life” while with Combs and claimed Ventura left Combs on her own terms when she realized she would “never be his wife, never be his love of his life,” CNN reported. Geragos said Ventura was “jealous” of the relationship between Combs and his late ex-girlfriend, Kim Porter, with whom Combs had three children. Geragos also portrayed Combs’ other sexual partners as consenting adults and denied they were victims of trafficking.

Prosecutors Allege Diddy Ran ‘criminal Enterprise’ With Freak-Off Parties And Violence

Attorney Emily A. Johnson delivered the opening statement for the prosecution, accusing Combs of running “a criminal enterprise.” Johnson described one night in which Combs allegedly learned Ventura was seeing another man while they were together, so he enlisted an employee to break into the man’s house, the New York Times reported, though the employee did not find the man. Instead, Combs allegedly beat Ventura “brutally.” Johnson described Combs’ “freak-off” parties, which she says were also referred to as “wild king nights” or “hotel nights,” alleging Combs’ company would pay for parties and hotel rooms in which Combs would allegedly force women to take drugs and have sex with male escorts in encounters Combs sometimes recorded, the AP reported. Johnson described multiple alleged incidents of Combs committing acts of violence, including an incident in 2009 in which he allegedly stomped on Ventura’s face, and another in which Combs grabbed an unnamed woman in a chokehold and kicked her to the ground before drugging her and coercing her into participating in a freak-off, the Times reported.

What Do We Know About The Jury?

The 12 jurors are composed of eight men and four women, the New York Times reported, with six alternates composed of four men and two women. Defense attorneys representing Combs protested some of the struck jurors to the judge, alleging the prosecutors struck seven prospective Black jurors, amounting to a pattern, the AP reported. Subramanian rejected the defense’s claim, stating the prosecution gave “race neutral reasons” for why each juror was struck and that the defense did not give evidence of discrimination. The jurors range in age from their 30s to their 70s, span jobs including a scientist, massage therapist, deli clerk and investment analyst, and they hail from Manhattan, the Bronx and Westchester County, the Times reported. Some of the jurors said they have seen a video of Combs attacking ex-girlfriend Ventura in a Los Angeles hotel, which is expected to be shown at trial. The defense previously struck a juror who said the video made Combs look like an “angry, hostile person,” the Times reported.

How Is Combs Reacting In Court?

Combs arrived at the courthouse sporting gray hair, which is no longer black as he does not have access to hair dye in jail. He is wearing a light gray sweater and a white collared shirt with khaki pants, the Washington Post reported, and he blew kisses to his family, who are seated in the second row behind him, while walking into the courthouse. Throughout the jury selection process, Combs has donned black-framed glasses and has been actively flipping through a blue notebook and whispering with his defense attorneys, the Post reported.

What Is Sean “diddy” Combs Charged With?

Combs faces five federal charges: two counts of sex trafficking, two counts of transportation to engage in prostitution and one count of racketeering conspiracy. The fourth and fifth charges, one additional count each of sex trafficking and transportation to engage in prostitution, were added by prosecutors in April in a superseding indictment concerning an alleged unnamed victim, referred to as “Victim-2.” Combs has pleaded not guilty to all charges and rejected a plea deal earlier this month. Federal agents raided Combs’ homes in March 2024, and he was arrested by authorities in September 2024 after being indicted by a grand jury. While awaiting trial, Combs has been held at the Metropolitan Detention Center in Brooklyn, a jail known for poor conditions that has also housed disgraced crypto executive Sam Bankman-Fried and currently houses Luigi Mangione, accused of the killing of UnitedHealth CEO Brian Thompson.