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As Sean "Diddy" Combs' sex trafficking and racketeering conspiracy trial enters its sixth week, jurors were presented with text messages between the rapper and actress Cassie Ventura on June 17, 2025.
Disclaimer: This article contains mentions of alleged sexual abuse, drug use, and emotional abuse. Reader's discretion is advised.
For the unversed, Cassie Ventura is Diddy's ex-girlfriend and one of the government's key witnesses in the ongoing trial, who filed a civil lawsuit against him in November 2023 for alleged rape and years of abuse. The former couple dated for over a decade, starting in 2007.
During the trial on Tuesday, the jurors were shown text exchanges between Ventura and Diddy in which she suggested that they engage in a roleplay, where they would pretend to be strangers meeting at a Hermitage Hotel bar, according to NBC News. Ventura's texts reportedly read:
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"I am not Cassie" and "you're not Sean."
Ventura further wrote that their safe word would be pineapple, to ensure safety during the roleplay. In her earlier testimony, Ventura described this one-night stand as a desperate attempt to save her relationship with Combs, as per the outlet.
The Washington Post reported similar instances of roleplay being discussed on June 10, 2025, during the testimony of Combs' ex-girlfriend, identified by the pseudonym "Jane" in the trial.
During her testimony, Jane recalled several instances where the rapper allegedly coerced her into engaging with escorts in his infamous "freak offs." Jane added that these events typically involved s*xual role-playing scenarios orchestrated by Combs. She claimed that "a lot of cheating role play" would be involved, where Combs would ask her to pretend he was out of town and she was cheating on him with the "entertainer."
"I'm sneaking in this entertainer and it's just me and this entertainer and just fantasy talk about how Sean is on a plane," Jane testified.
Cassie Ventura testified that Diddy asked her to call him "Pop Pop"
During her testimony on May 13, Cassie Ventura alleged that Diddy asked her to call him "Pop Pop," the same name she used to call her grandfather, as per a report by People Magazine.
"I did it but now I think it was disrespectful," Ventura testified.
While on the witness stand for four days, Ventura recalled several instances of engaging in "freak offs," which would leave her emotionally and physically drained. She claimed that the drug-fueled events would sometimes go on for 72 hours, and she engaged in them to make Combs "happy," as per NBC News.
"I just felt pretty horrible about myself. I felt disgusting. I felt humiliated," she said.
Ventura labelled Combs as "a scary person." The outlet reported that Ventura claimed that Combs subjected her to psychological as well as physical abuse.
"When he got angry, his eyes went black. The version of him I was in love with was no longer there," she stated.
Ventura also added that Combs "controlled a lot of [her] life, even recording her in the midst of s*xual acts, calling them "blackmail material." She said that she feared he would leak those videos and put her "career in jeopardy" and "ruin everything [she] worked for."
Born on November 4, 1969, Sean "Diddy" Combs is currently held at the Metropolitan Detention Center in Brooklyn since his arrest on September 16, 2024.
