After two days of testimony about how her relationship with Sean “Diddy” Combs grew violent and coercive, Cassie Ventura faced six hours of grueling cross-examination on Thursday, as defense attorneys attempted to cast doubt on her credibility and portray her as a willing participant in their sexual activities.
Defense attorneys turned to a decade of archived text messages to question Ventura about the consistency of her earlier testimony, highlighting her apparent eagerness to engage in Combs’ lifestyle of swinging at drug-fueled orgies. They insist that she was not a victim of sex trafficking or racketeering and that Combs is innocent of the federal charges he’s facing.
During other portions of the cross-examination, Combs’ attorney Anna Estevao appeared to use seemingly mundane messages – like planning dates or expressing their romantic feelings to one another – as an opportunity to humanize Combs, who occasionally nodded his head as his lawyers questioned Ventura.
Combs’ lawyers have argued that, while he has made mistakes, engaged in domestic violence and abused drugs, he never sexually assaulted or trafficked anyone. Seated next to his lawyers, Combs appeared engaged in the cross-examination and at one point signaled a heart with his hands toward the wife of his main defense attorney, a former prosecutor whose clients now include alleged UnitedHealthcare CEO murder suspect Luigi Mangione, who has entered a not guilty plea.
Ventura’s testimony as the star witness for the prosecution is expected to conclude tomorrow, given concerns that the singer, now eight months pregnant, could go into labor as early as this weekend.
Lawyer Anna Estevao cross-examines Casandra “Cassie” Ventura during Sean “Diddy” Combs’ sex trafficking trial in New York City, May 15, 2025, in this courtroom sketch.
Jane Rosenberg/Reuters
Defense lawyers use text messages to show mutual affection between Combs and Ventura
Ventura openly acknowledged in both her direct and cross-examinations that she loved Combs for more than a decade and hoped to build a life with him. She told jurors she fell in love with Combs shortly after they met, and jurors saw messages from the start of their relationship.
“We’ve only really had one week of each other just together and I can say that it’s been the best and worst,” Ventura wrote in 2007. “I’m sad, mad, frustrated and hurt that you just don’t feel like I’m the right one.”
Jurors also saw messages from August 2009, when the couple first went public with their relationship, and other messages from more than two years into their relationship.
“I love you so much it consumes my life,” she wrote in April 2010.
Ventura testified that while the messages appeared positive, she began to see a different side of Combs as they spent more time together – one that she said was prone to violence, jealousy and rage.
“The more time I spent with him and got to know him, his real personality — or at least what I thought was his real personality — came out,” Ventura testified.
Defense lawyers press Ventura about apparent willingness to engage in freak-offs
During her direct examination, Ventura acknowledged she first agreed to participate in a freak-off to make Combs happy by indulging in his sexual fantasy. She said she quickly realized she did not enjoy the drug-fueled orgies that could go on for days and included her having sexual encounters with prostitutes and strangers.
To counter Ventura’s assertion she was coerced to plan and participate in freak-offs, defense attorneys presented a series of messages apparently showing a different attitude. “I’m always ready to freak off,” she wrote in August 2009.
Jurors also saw text messages that suggested Combs expressed interest in Ventura’s desires, though she had previously testified those did not matter to Combs. The messages also seem to show she attempted to please Combs by preparing for the freak-offs, including by visiting a sex shop in advance of an orgy.
“Trying to find something to impress you,” she wrote in one message. At least one of the jurors raised his eyebrows as an explicit message was shown in court.
Defense attorneys pressed Ventura about her reasons for being reluctant to engage in freak-offs, suggesting she was frustrated not by the violence or coercion but rather because she wanted more from the relationship.
“When we used to freak off when were so in love. There were no questions asked, it felt right, like it literally made sense for the next step in our sex life together. I get nervous that I’m just becoming the girlfriend that you get your fantasies off with and that’s it. I don’t get the other part,” Ventura wrote in a message to Combs from December 2009.
During her first two days of testimony, Ventura testified at length about a 2016 episode when she said she tried to leave a freak-off but was attacked by Combs – an assault that was captured on surveillance video and shown to jurors. On cross-examination, Ventura was shown text messages that suggested she was eager to participate in the freak-off, and Combs’ violence might have been influenced by his drug use.
“The drugs that you and Mr. Combs took that day were a bad batch of MDMA, right?” Estevao said.
“I have no idea,” Ventura asked.
Defense attorneys suggest relationship was defined by mutual jealousy
Defense attorneys pressed Ventura about the flaws in her relationship with Combs, arguing the jealousy and infidelity went both ways for the couple.
Ventura admitted she “had some jealousy” of Kim Porter, the late mother of four of Combs’ children, and was upset when Combs continued a relationship with another woman.
“It was disappointing and hurtful to find out you weren’t the main girlfriend?” Estevao asked.
“Yes,” Ventura replied. “It didn’t pertain to every situation, but I was definitely jealous of certain situations he was in.”
Jurors were shown text messages showing Combs and Ventura expressing anger about each other’s infidelity, with Combs seeing another woman while Ventura was in a relationship with actor Michael B. Jordan. Ventura was asked about her relationship with Kid Cudi – whose real name is Scott Ramon Seguro Mescudi, and who she previously testified she stopped seeing because of tension with Combs – and how she said Combs “lunged” at her when he discovered their relationship during a freak-off.
“Did you feel justified in cheating on him with Mr. Mescudi because of Mr. Combs’ infidelity?” Estevao asked.
“I could have, I don’t know,” she answered.
