A federal courtroom in Manhattan bore witness to a series of bombshell allegations Monday morning as the civil trial against hip-hop mogul Sean “Diddy” Combs officially began.
A male sex worker testified Monday that he was paid thousands of dollars to have sex with singer Cassie Ventura while Sean “Diddy” Combs watched, gave instructions, and sometimes filmed the encounters.
Daniel Phillip, a dancer turned escort, told the court he was initially hired to strip at a bachelorette party at Manhattan’s Gramercy Park Hotel. When he arrived, Ventura allegedly asked him to give her a massage with baby oil while Combs — clad in a white robe, baseball cap, and a bandana over his face — watched from the corner of the room.
Phillip said Combs introduced himself as being in the “importing and exporting” business, but he recognized the voice as the famous music mogul. “He was sitting there while I had sex with Cassie. He was watching and pleasuring himself,” Phillip testified.
He described a repeated arrangement in which Cassie allegedly paid him up to $6,000 per encounter, often with Combs present. “Sometimes he gave us instructions. Sometimes he filmed,” Phillip added.
One of the most disturbing moments in court came when Phillip claimed Ventura requested that he urinate on her. “Cassie was actually the one that asked me to urinate on her,” he said. “Apparently I was doing it wrong, because they both told me.”
The paid sex arrangement came to an abrupt end, Phillip said, after he witnessed Combs become physically violent with Ventura. “I heard slapping. She was screaming, ‘I’m sorry,’” Phillip told jurors. He said Ventura then ran to him naked and jumped in his lap.
“My thoughts were that this was someone with unlimited power,” Phillip testified. “And chances are that, even if I did go to the police, I might still lose my life.”
His testimony supports the broader claims by federal prosecutors, who allege that Combs orchestrated a years-long enterprise involving sex trafficking, racketeering, drug distribution, and prostitution. Combs has pleaded not guilty to all charges.
In opening remarks, Assistant U.S. Attorney Johnson laid out a detailed and disturbing case against the music entrepreneur, alleging a decades-long pattern of abuse, coercion, and sex crimes that spanned over 20 years and involved multiple women, including singer Cassie Ventura and another woman identified only as “Jane.”
Presided over by Judge Arun Subramanian, the trial began with the swearing in of jurors and firm instructions from the bench, eight of whom a men and four women. “Questions are not evidence,” the judge reminded the panel. “Only answers and documents are evidence.” He further warned that a witness using a pseudonym should not be considered less credible for that reason.
The prosecution did not mince words as it began its narrative. “To the public, he was a cultural icon, a businessman, larger than life,” said AUSA Johnson. “But there was another side to him.”
Combs, one of the most successful people in the music industry was painted as a man who orchestrated a shadow operation of violence, drugs, and sexual exploitation, allegedly supported by his staff and inner circle.
At the core of the government’s case is the testimony of Cassie, a former Bad Boy Records artist who once enjoyed national acclaim under the tutelage of Combs. Prosecutors allege that Cassie’s career was tightly controlled by Combs, who reportedly blocked her opportunities, controlled her music output, and isolated her from the industry.
According to AUSA Johnson, Combs, 55, used his power and influence to control every aspect of her life—both personally and professionally. “He beat her, blackmailed her with sex tapes, and coerced her into weekly ‘freak offs’—drug-fueled sexual encounters with male escorts that he arranged, watched, and recorded,” said Johnson.
Graphic details of Cassie’s abuse were presented to the jury, including claims that Combs kicked her, dragged her by the hair, stomped on her face, and forced her into degrading sexual acts.
The Pattern: Introducing “Jane”
The government also introduced another key witness known as “Jane,” a single mother who became involved with Combs in 2020. Prosecutors allege Jane, like Cassie, was drawn into a similar cycle of control, violence, and sexual exploitation. “He discouraged her from working, pressured her into drug use, and manipulated her emotions with promises of love,” said Johnson.
In one shocking account, Jane is said to have locked herself in various rooms of her home during a violent encounter, only to have Combs break through each door until he could physically overpower her. Even after she fought back, he allegedly demanded she “call up an escort and perform.”
Organized Chaos: The Alleged Inner Circle
Combs didn’t act alone, as prosecutors claim his bodyguards, personal staff, and chiefs of operations helped him maintain a lifestyle rooted in secrecy and manipulation. From organizing flights, drugs, and cash for escorts, to allegedly kidnapping employees and setting cars on fire, the inner circle reportedly enabled and concealed the alleged crimes.
“This was not about a celebrity’s private preferences,” said Johnson. “This was criminal. It was coercive. It was violent.”
