Cassie Ventura is being grilled by the defense lawyers of her ex-boyfriend Sean "Diddy" Combs in his federal sex-trafficking trial in Manhattan on Thursday. The defense team is expected to spend hours, possibly days, catch the pregnant R&B singer in lies, do her character assassination, and find inconsistencies in her testimony.
This comes after Ventura spent two very emotional days on the witness stand describing in detail how Diddy allegedly raped her, violently assaulted her, forced her into drug-fueled sexual orgies with strangers during "hundreds" of "freak-offs," and manipulated her by threatening to release "humiliating" sex tapes. Needless to say, Ventura is going to have a tough time on Thursday.
Ventura's Grilling Session Begins
Combs, 55, has pleaded not guilty to charges including one count of racketeering conspiracy, two counts of sex trafficking by force, fraud or coercion, and two counts of transportation for prostitution.
However, Thursday could be different. On Wednesday, the music mogul's lawyer, Anna Estevao's, questioning centered on the affectionate side of Diddy's relationship with Ventura as she showed the jury text messages where Cassie calls him "pop pop"—the same nickname she used for her grandfather.
The music mogul has maintained a calm expression this week while the pregnant Ventura described the physical and emotional abuse she endured during their decade-long relationship.
On Thursday, Ventura admitted that she didn't know of anyone knowing about Diddy's "freak-offs" until they were exposed to the public through her 2023 lawsuit. "Fair to say [Combs'] career was ruined," Combs lawyer Anna Estevao said.
"When your lawsuit was published in November 2023, you understand his career was ruined, right?"
"I could understand that, yeah," Cassie replied.
Diddy's Defense Shows Ventura's Love Letter to Diddy
Ventura smiled when Sean "Diddy" Combs' attorneys read out an email she had written to him just a few weeks after celebrating her 21st birthday. "It's making me giggle because it's from 2007," Ventura told the court.
In the email, Ventura wrote how "grateful" she was to be part of the much older music producer's life, but also expressed that she sensed he was "constantly wary" of her.
She also mentioned that she believed her friend Kerry Morgan "would have been the better one to go after since I've witnessed (more than once) you realizing that she is way better fitting for you than I am."
"It's hard for me to handle that," she wrote. "I'm hurt that you think that I'm a malicious person."
Ventura earlier said that during the early stages of taking part in the "freak-offs," she wore masks and wigs to hide her identity because she was afraid that if the videos Combs recorded of the sexual encounters were made public, it would ruin her music career.
In graphic detail, Ventura detailed a turbulent relationship with Combs, claiming it was marked by violence and his fixation on a type of voyeurism where he maintained full control over every aspect.
She said this control extended to directing her encounters with male sex workers, including instructing her to use large amounts of baby oil—up to 10 full bottles per session—to get the "glistening" appearance he desired.
Combs' legal team has admitted his history of domestic violence but denies the charges of sex trafficking and racketeering. They argue that the prosecution is unfairly targeting him because of his sexual lifestyle preferences.
