In a brutal cross-examination of the singer, Sean ‘Diddy’ Combs’ defence team have asked his ex-girlfriend Cassie Ventura why she “kept going back” to the rapper.
Sean ‘Diddy’ Combs’ defence team have asked his ex-girlfriend Cassie Ventura why she “kept going back” to the rapper.
The Bad Boy Records founder, 55, is on trial on federal charges including sex trafficking and racketeering, and his former lover, 38, was subjected to a sharp cross-examination on the stand on Thursday (15.05.25), in which the singer’s emotional testimony was challenged about raunchy texts she send Combs.
Cassie – who is eight months pregnant and expecting her third child with husband Alex Fine – has described her 11-year relationship with the 55-year-old rap mogul during her emotional testimony, which began in 2007 and ended in 2018, during several days of court proceedings in Manhattan federal court.
Anna Estevao, part of Combs’ defence counsel, pressed Ventura on why she “kept coming back” to the relationship, while reading aloud intimate and explicit text messages sent to Combs over the years.
“I’m a very lucky woman,” one message read, and when a second graphic message was read aloud, Ventura requested a break, visibly holding her pregnant belly.
Cassie has testified about the couple’s sex life and the “Freak-Offs” – sexual encounters involving Combs, her, and escorts or dancers – which she said began when she was 22.
She said the sessions, described by the defence as consistent with a swingers’ lifestyle, occurred weekly throughout much of the relationship.
Cassie insisted Combs introduced her to the practice, which he reportedly viewed as voyeurism.
The singer spoke of the “trust” she had for Combs, saying: “I just think that I have to trust you beyond it just being sexual. Do you know what I mean? In order for me to be more open with the things we do in bed, this aggressive/sexual side of me.”
Ms Estevao questioned Cassie about jealousy on Thursday, including tensions with Combs’ late partner Kim Porter, mother of three of his seven children.
Cassie said: “I had some jealousy of Ms Porter, yeah.”
She also acknowledged Combs’ jealousy of her fling with Kid Cudi, citing his stature in the industry.
And Cassie recounted incidents of alleged physical abuse, describing how Combs would hit her for “making the wrong face” or talking back.
“The best way to describe it is his eyes just go black,” she said.
Cassie added: “The version that I was in love with is no longer there.”
The prosecution presented a video and photos showing a 2016 assault in a hotel.
Cassie testified when she tried to leave, Combs blackmailed her with threats to release intimate photos and videos.
Following their 2018 breakup, Cassie accused Combs of rape, leading to a lawsuit filed in November 2023, which they settled within 24 hours.
Defence attorney Teny Geragos told the jury: “Sean Combs is a complicated man, but this is not a complicated case. This case is about love, jealousy, infidelity and money.”
Combs also faces charges including transportation to engage in prostitution and has pleaded not guilty.
He faces a maximum of life in prison if convicted.
Sean ‘Diddy’ Combs’ defence team ask his ex-girlfriend why she ‘kept going back’ to the rapper
