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In the latest episode of his Ben After Dark podcast, political commentator Ben Shapiro delved into the testimony given by Cassandra "Cassie" Ventura in the ongoing trial of Sean “Diddy” Combs. In a clip shared on X on May 26, 2025, Shapiro discussed a detail from Cassie’s testimony pertaining to a nickname Diddy allegedly insisted she use throughout their relationship.
"Diddy went from 'Puff Daddy' to Puff Granddaddy," Shapiro wrote in the caption.
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According to NBC’s May 14, 2025, report, Cassie testified in court on May 13, on the second day of the rap mogul's high-profile trial, where she described her relationship with the rapper, marked by manipulation, violence, and blackmail that spanned over a decade.
As per E! News, during the May 13 testimony, Cassie revealed how she was compelled to use a deeply personal nickname for Sean Combs. The singer detailed that Diddy, who was 17 years her senior, wanted her to call him “Pop Pop,” a term she had originally used for her grandfather.
Referring to this revelation by Cassie, in the aforementioned clip, Shapiro critiqued what he described as a deeply inappropriate and perverse aspect of Diddy’s behavior. Drawing attention to the twisted nature of the chosen nickname, he remarked:
"Imagine being so perverse that you graduated from incest fantasies to multigenerational incest fantasies."
He further connected the nickname to Sean Combs’s long history of reinventing himself, referencing the artist’s evolution from “Puff Daddy” to other monikers over the years.
"At least now we know why he changed his name from Puff Daddy. He wanted to be Puff Granddaddy," Shapiro added.
Cassie discusses Diddy’s unsettling request in court testimony
On May 13, 2025, singer Cassie Ventura took the witness stand in a court case involving Sean “Diddy” Combs and offered disturbing details about the nature of their past relationship.
According to a Page Six report, Ventura shared an email exchange between herself and the Bad Boy Entertainment founder that revealed how Combs had insisted she give him a special nickname—one that she used to call her grandfather.
"He wanted me to have a nickname for him...He asked me what I called my grandfather, and I said I called him Pop Pop," she said.
Although she did comply with the request and referred to the rapper as "Pop Pop", looking back, she expressed that what had initially struck her as “weird at the time” now seemed deeply inappropriate and insensitive.
"But now I think it’s just disrespectful," she said.
In addition to demanding a deeply personal nickname, Cassie revealed that Combs also used pet names for Ventura, further highlighting the controlling tone of their relationship.
According to E! News, Ventura testified that he frequently called her “CC” and “Baby Girl,” suggesting a one-sided dynamic that infantilized her and asserted his dominance in the relationship.
What else did Cassie say about Diddy during her testimony on May 13?
As per the aforementioned Page Six report, on May 13, 2025, Cassie Ventura gave harrowing testimony in a federal courtroom, painting a disturbing portrait of the alleged abuse she endured at the hands of Sean "Diddy" Combs.
The singer detailed the extreme physical abuse she claimed to have suffered, adding that her ex-boyfriend would respond to minor provocations, or no provocation at all, with violence. Even something as subtle as an expression on her face could trigger an attack.
"He would bash me on my head, knock me over, drag me, kick me, stomp me on the head if I was down," she said.
Her testimony also revealed that the abuse was disconnected from her actions. It wasn’t always about something she said or did—sometimes it was merely the way she looked. She explained that she had to be constantly vigilant, knowing that a single expression could result in her "getting hit in the face".
Cassie also spoke emotionally about how Sean Combs's demeanor would transform, describing him as someone who seemed to become an entirely different person when enraged.
"His look would just change over, he would just become a different person...The best way to describe it is his eyes just go black. The version that I was in love with is no longer there," she said.
The R&B singer further detailed the alleged "Freak-Offs"- prearranged sexual encounters where she would be paired with escorts, and Diddy would direct the acts from a distance.
She revealed the orchestrated nature of the encounters, presented as acts of voyeurism where she would "perform" for Sean to "make him happy" because she was "in love" and wanted to meet his expectations.
According to the singer's testimony, one such "Freak-Off" incident reportedly lasted four days, leaving her physically drained due to drug use and dehydration.
At present, Sean "Diddy" Combs is embroiled in an ongoing trial for charges of sex trafficking, and racketeering. His trial started on May 12, 2025, and is expected to last 6-8 weeks.
Cassandra "Cassie" Ventura, who testified in this trial, is now taking time away from the spotlight as she expects her third child with her husband, Alex Fine.
