Day 7 in Sean “Diddy” Combs’ federal sex trafficking and racketeering trial delivered another disturbing glimpse into the alleged underworld of one of hip-hop’s most powerful figures.
As prosecutors continue building their case around Combs’ alleged coercion and abuse, centered around drug-fueled, orchestrated sex parties dubbed “freak-offs”, Tuesday’s testimonies from former staff, a male escort, and Cassie Ventura’s own mother painted a chilling narrative of manipulation, control, and violence.
The Male Escort: Behind the Curtain of the “Freak-Offs”
One of the day’s most jaw-dropping testimonies came from Sharay Hayes, a longtime exotic dancer and escort who testified under oath that he participated in as many as a dozen sexual encounters with Cassie Ventura—at the direction of Sean Combs. Hayes testified that each encounter took place in dimly lit rooms adorned with candles, music, and covered furniture, where the goal was to “create a sexy scene,” but as he described it, these weren’t simple fantasies—they were heavily orchestrated performances executed under Combs’ watchful eye.
According to Hayes, Combs rarely engaged physically but directed Cassie throughout the acts, offering cues on lighting, body angles, and even specific instructions about climaxing. Hayes alleged he was compensated between $1,200 and $2,000 per session, many of which required him to use Cialis, Viagra, or “anything that could help me perform. It was a lot of pressure.”
At one point, he testified, Combs tossed condoms at him and demanded, “I’m ready to see you f— her.” That particular encounter, Hayes said, was his last. “A sexual scenario with a woman’s partner present giving directions was not the norm for me,” he told the court.
Defense attorneys attempted to portray the scenes as consensual. Hayes said Ventura never gave visible signs of discomfort during the sessions, but under redirect, he admitted he saw her “wince” and “sigh” at times—especially when Combs was giving her instructions. “There was a consistent awareness to Mr. Combs’ direction and his perception and desires during the moment,” he testified.
Cassie’s Mother Breaks Down Over Daughter’s 2011 Email
Adding emotional weight to the day was testimony from Regina Ventura, mother of Cassandra “Cassie” Ventura, who told the jury she became “physically sick” after receiving a 2011 email from her daughter detailing a violent incident involving Combs. The email, which prosecutors have not yet released publicly, reportedly contained graphic descriptions that prompted Mrs. Ventura to urge her daughter to leave the relationship immediately.
Her testimony added credibility and context to Cassie’s own harrowing four-day testimony from the previous week, where she described years of coercion, assault, and sexual abuse by Combs.
The Former Assistant Returns
David James, Combs’ former personal assistant, resumed testimony, confirming much of what other witnesses have echoed—that Combs controlled nearly every aspect of Cassie’s life. James testified that he was often tasked with preparing hotel rooms for the “freak-offs,” including procuring drugs and various items for the sex parties.
James also reiterated a troubling statement Cassie once made to him: “I can’t get out. He oversees so much of my life.” His testimony further reinforced the government’s narrative of a man who used power and fear to maintain control over women.
Guns, Platforms, and Lingerie: The Star Island Raid
Capping off the day was Homeland Security Special Agent Gerard Gannon, who led the high-profile March 2024 raid on Combs’ Miami mansion at 2 Star Island. The agent described how an 80-to-90-person federal task force had to breach the heavily guarded property. Inside Combs’ bedroom, agents recovered two AR-15 upper receivers, a 30-round magazine, and multiple gun parts with defaced serial numbers—illegally altered to prevent law enforcement tracking.
Notably, the weapons were found on the same shelving unit as lingerie and a pair of seven-inch platform heels. Gannon testified that the juxtaposition of weapons and sexually suggestive items hinted at the duality of Combs’ alleged lifestyle—opulence laced with control and danger.
The court was shown photographs of the raid, including a destroyed front gate and the estate’s waterfront view. Gannon will continue presenting evidence when court resumes on Wednesday.
Conspicuously Absent: The Combs Family
Observers noted the absence of Combs’ mother, Janice, and his sons Justin, Christian, and Quincy, all of whom were present throughout the first week of trial. While his sons had previously attended even the most graphic testimony, they did not return Tuesday.
Looking Ahead: Kid Cudi and Key Witnesses to Testify
Prosecutors indicated that Wednesday’s proceedings may include pivotal testimony from rapper Scott “Kid Cudi” Mescudi, whom Cassie dated briefly during her relationship with Combs. According to Cassie’s earlier testimony, Combs once threatened to blow up Cudi’s car—and days later, the vehicle mysteriously exploded.
Also scheduled to take the stand are Dawn Hughes, a psychologist specializing in trauma, and George Kaplan, another former Combs assistant. Their testimonies are expected to further corroborate patterns of abuse, control, and fear within Combs’ inner circle.
As the trial unfolds, each day continues to strip away the public-facing persona of one of hip-hop’s most iconic figures, revealing a darker narrative that, if proven true, could forever change the legacy of Sean “Diddy” Combs.
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Explosive Testimony Continues in Sean ‘Diddy’ Combs Federal Trial