Sean “Diddy” Combs’ ongoing sex crimes trial took a disturbing turn on Monday, May 12, as harrowing testimonies and explicit details of the music mogul’s alleged actions left even his own family shaken.
The hip-hop icon’s three daughters — Chance Combs, and 18-year-old twins D’Lila and Jessie — left the courtroom twice during the day’s proceedings as graphic accounts of sexual abuse and violence were laid bare before the jury.
The trial, now underway in a Manhattan courtroom, centers on charges of sex trafficking, racketeering, and transporting individuals for prostitution.
Combs, 55, has pleaded not guilty to all counts, with his attorneys framing his lifestyle as “unconventional” but consensual.
One of the day’s most unsettling moments came when Daniel Phillip, a former male escort and stripper manager, testified about being hired by Combs’ ex-girlfriend, Casandra “Cassie” Ventura, to engage in sexual acts with her while Combs allegedly watched and pleasured himself in the corner.
“I was shocked,” Phillip said. “It came out of nowhere. I was terrified.”
He claimed the encounters often stretched for hours, sometimes under the influence of drugs, and described witnessing Combs physically assault Ventura, including dragging her by her hair as she screamed apologies.
Phillip said he never reported the incidents out of fear for his life, describing Combs as “someone with unlimited power.”
As Phillip delivered his graphic testimony, Combs’ daughters quietly left the courtroom, visibly distressed, only to return later and exit again when the details became too much to bear.
Adding to the prosecution’s case, jurors were shown a 2016 hotel surveillance video — now widely circulated online — capturing Combs violently assaulting Ventura at the InterContinental Hotel in Los Angeles.
In the clip, he is seen shoving her to the ground and kicking her as she lay motionless. Both his daughters and his mother, Janice Combs, remained in the courtroom during the video’s showing, staring ahead as the footage played.
The prosecution, led by Assistant U.S. Attorney Emily Johnson, painted a grim picture of Combs as a man who used his fame and loyal inner circle to operate what she called a “criminal enterprise” spanning over two decades.
“There’s another side to Sean Combs,” Johnson told jurors. “A side that ran a criminal enterprise,” involving sex trafficking, violence, drugs, and coercion.
Johnson particularly focused on two alleged central victims: Cassie Ventura and another unnamed ex-girlfriend.
She accused Combs of manipulating Ventura’s music career and threatening her into non-consensual, degrading sexual acts with male escorts during infamous “Freak Off” parties — multi-day sex parties allegedly filmed by Combs.
The prosecution’s first witness, former hotel security guard Israel Florez, recalled the morning of March 5, 2016, when he responded to a distress call about a woman on the sixth floor.
He testified finding Ventura visibly shaken with a bruised eye, while Combs lounged nearby in a towel with a “devilish” look on his face. Florez alleged that Combs tried to silence him afterward by offering him a wad of cash, which he refused.
Combs’ defense, led by attorney Teny Geragos, sought to downplay the allegations, arguing that while Combs’ personal life may be unconventional, it didn’t amount to a criminal conspiracy.
“Domestic violence is not sex trafficking,” Geragos told the jury, suggesting the women involved had the freedom to leave but chose to stay.
Still, with gut-wrenching testimony, video evidence, and harrowing accounts of abuse, the courtroom remained tense throughout the day.
Diddy’s family members were seen supporting one another, with his children holding hands and his mother photographed leaving the courthouse alongside his publicist.
The trial resumes Tuesday, with Cassie Ventura expected to take the stand — a highly anticipated testimony that could prove pivotal in this explosive, high-profile case.
