By Deandrea Hamilton | Editor
Turks and Caicos, May 15, 2025 – When he booked his infamous “freak offs” in the Turks and Caicos, Sean “Diddy” Combs used an alias and dragged an unwilling girlfriend to be part of the sexual exploits reportedly staged in hotel rooms in the Caribbean hot spot; that’s what came out in testimony from Cassie Ventura, the prosecution’s first witness in the scandalous sex trafficking trial.
Ventura, who dated Combs for 11 years, described a dark underworld of weekly “freak offs” allegedly arranged by the hip-hop mogul, beginning when she was just 22. Speaking in harrowing detail, she told the jury the encounters—held in locations including New York, Los Angeles, Miami, Ibiza, and Turks and Caicos—often lasted days, fueled by drugs Combs allegedly supplied: cocaine, ecstasy, and molly.
In one Turks and Caicos incident, Ventura said she was ordered into a blow-up pool filled with baby oil, testifying, “At that point, I couldn’t say no… If Sean wanted it to happen, that’s what was going to happen.” Prosecutors revealed Combs used aliases like “Frank White” and “Frank Black” when booking hotel rooms for these encounters in the territory.
Ventura described being physically and sexually abused, forced to find escorts—sometimes via Craigslist—and comply with rigid demands, including specific lighting, clothing, and even nail polish. She said Combs often recorded the events and threatened to release the footage if she disobeyed him. “I felt disgusting and humiliated,” she said, recalling one instance where escorts urinated on her at Combs’ direction.
The most disturbing moment came when jurors were shown still images from the freak offs. Many appeared visibly stunned.
A now-infamous 2016 video showing Combs assaulting Ventura in a hotel hallway was tied to one such incident. She claimed she tried to flee a “freak off” before her movie premiere but was beaten and left with a black eye. When asked how often he threw her to the ground, she replied, “Too many to count.”
Cassie and Combs ended their relationship in 2018. She is now married and appeared at trial visibly pregnant, supported by her husband in court.
The trial continues today with Ventura’s cross-examination. Prosecutors must prove racketeering and sex trafficking charges. Combs, who has denied all allegations, faces life in prison if convicted.
It remains unclear if any witnesses from Turks and Caicos will be called to testify.