Sean ‘Diddy’ Combs Hamptons 'Freak Off' Details Aired at Trial

Hamptons references galore emerged in testimony at Sean ‘Diddy’ Combs sex trafficking trial at Manhattan federal court, where he faced allegations of forcing women to have drug-fueled orgies he called “freak offs.”

Among those who took the stand were Cassandra Ventura, Combs’ ex-girlfriend and singer, who alleged that she was forced to participate in these freak offs, including in the Hamptons with Combs and an escort named Dave. She testified that she blacked out during the freak off due to being intoxicated with the nervous system depressant drug gamma-hydroxybutyrate, or GHB, and woke up naked in the shower — then continued.

“I felt pretty horrible about myself. I felt disgusting. I felt humiliated,” Ventura testified. “I didn’t have the words to show how horrible I felt. I couldn’t talk to anyone about it.”

This incident isn’t the only connection Combs has to Long Island. He was the owner of 40 Hedges Banks Drive, a just under one-acre property in East Hampton for approximately two decades. He would regularly use the house to host ultra-exclusive parties, often with Hollywood’s elite in attendance.

Plaintiffs from other lawsuits against Combs contend that these gatherings weren’t what the public perceived them to be, alleging that their abuse happened at these elite parties.

In a lawsuit filed on Oct. 14, 2024, a man claimed he was 16 when he attended one of the rapper’s parties in the Hamptons in 1998. After meeting Combs, they moved to a more private area where he was ordered by Combs to remove his pants so he could examine him, according to the lawsuit.

Combs allegedly told the boy it was “a rite of passage” and “the route to becoming a star.” The lawsuit additionally claims Combs told the boy it was a way for him to prove himself, asking the teen: “Don’t you want to break into the business?”

In another October 2024 lawsuit, a man who worked for a security firm at one of Combs’ white parties alleges that he sexually assaulted him. While at the event, he became ill after consuming two alcoholic drinks provided to him by Combs. The man alleges Combs pushed him into a van and pinned him down, assaulting him.

Another woman, who was a 17-year-old at the time, claims to have drunk a drugged alcoholic drink at Combs’ 2004 Fourth of July Party in the Hamptons, causing her to lose consciousness. She woke up to “throbbing pains in her vaginal and anal areas,” and was only able to leave the party after “agreeing not to contact the police in exchange for the return of her purse and phone,” according to the lawsuit.

Additionally, Leslie Cockrell, a music scout, alleges in a February 2025 legal complaint that she was drugged and assaulted by Combs at a Hamptons party in 1999. The security guard who drove Cockrell home after the assault told her to be grateful Combs had chosen her and to accept what had happened, according to the complaint.

The jury reached a verdict on July 2 to conclude the seven-week-long trial, finding Combs not guilty of sex trafficking and racketeering conspiracy, but guilty of lesser charges of transportation to engage in prostitution.

If you or someone you know has experienced sexual assault, the Rape, Abuse, Incest & National Network’s sexual assault hotline offers confidential, free support to survivors and their loved ones at 800-656-HOPE (4673).