Diddy Trial Day 4 Recap: Cassie Faces Cross-Exam From Combs Lawyers Over Loving & Graphic Texts

Sean “Diddy” Combs‘ ex-girlfriend Cassie Ventura faced cross-examination Thursday (May 15) from defense attorneys, who showed jurors huge numbers of her emails and text messages in an effort to prove she was a willing participant in so-called “freak-off” sex shows.

Ventura, an R&B singer who dated Combs for 11 years, is at the very core of the case against him, in which prosecutors say Combs physically abused her and coerced her to partake in the freak-offs — drug-fueled sex with male escorts for his entertainment.

After two days of direct testimony in which Ventura told jurors that she felt she had no choice but to take part, she took the stand Thursday to face questions from Combs’ lawyer Anna Estevao, according to the Associated Press and the New York Times.

Much of the day was spent asking Ventura about emails and texts to and from Combs — some romantic, others sexually graphic. In one, she told Combs she was “always ready to freak off”; in another, she told him, “Wish we could have fo’d before you left.”

“Yes, at the time, I wanted to make him happy,” Ventura said at one point.

Combs was indicted in September, charged with running a sprawling criminal operation aimed at facilitating the freak-offs — elaborate events in which Combs and others allegedly coerced Ventura and other victims into having sex with escorts while he watched and masturbated. Prosecutors also say the star and his associates used violence, money and blackmail to keep victims silent and under his control.

It was Ventura’s civil lawsuit, filed in November 2023, that first raised allegations against Combs. Her case, which accused the star of rape and years of physical abuse, was quickly settled with a large payment from Combs, but it sparked a flood of additional suits from other alleged victims and set into motion the criminal probe that led to his indictment.

At opening statements on Monday (May 12), defense attorneys told jurors that Ventura and other women had consensually taken part in the sex parties. They admitted that Combs had committed domestic violence during their “toxic” relationship and had unusual sexual preferences, but that he had never coerced her into participating in his “swinger” lifestyle.

In questioning Cassie on Thursday, Estevao seemed intent on establishing that both she and Diddy had planned the elaborate events: “I’m too excited,” Ventura told Combs in one message from 2017, near the end of their long relationship.

When asked about those texts, Cassie seemed to push back on that suggestion, saying the things she said in the texts were “just words at that point.” That echoes her testimony from earlier in the week, in which she said the freak-offs left her feeling “humiliated” and “disgusting” but that she felt compelled to keep doing them.

The questions also focused on the complexity of Ventura’s relationship with Combs, including messages that seemed to show a loving relationship between the pair. In one, from 2010, she wrote: “Going to sleep now so it can be tomorrow faster and you can be home. Love you!!!”

Ventura confirmed as much in her answers: “I had fallen in love with him and cared about him very much.” She also admitted that she sometimes felt jealousy toward Combs over his numerous other romantic partners — another key message that the defense is seeking to relay to jurors about the couple’s relationship.

Ventura is expected to complete her testimony on Friday (May 16). After that, prosecutors will continue to call other witnesses, including a second alleged freak-off victim identified by the pseudonym “Jane” and an alleged employee victim identified by the pseudonym “Mia.” According to NBC News, prosecutor Maurene Comey said that Dawn Richard, formerly a member of the Combs-formed girl group Danity Kane who sued him for abuse in September, was expected to testify next. Defense attorneys will then have a chance to call their own witnesses. A verdict is expected by July 4.