SEAN COMBS TRIAL MAY 21 – 22, 2025
WENDY WILLIAMS WAS ON THE WITNESS LIST BUT MAY BE TOO ILL TO TESTIFY. SHE'S BEEN TESTIFYING ABOUT THE FREAK OFF PARTIES FOR TWENTY YEARS
BY SNN.BZ STAFF
Sean “Diddy” Combs Trial: Key Testimonies from May 21 and May 22, 2025.
The federal sex trafficking and racketeering trial of Sean “Diddy” Combs continued to unfold with gripping testimonies on May 21 and May 22, 2025, shedding light on allegations of abuse, coercion, and criminal enterprise. Witnesses, ranging from personal associates to law enforcement and experts, provided detailed accounts that painted a complex picture of Combs’ relationships and operations. Below is a summary of the testimonies delivered over these two days in court.

May 21, 2025 Testimonies:
Regina Ventura: On May 21, 2025, Regina Ventura, the mother of Combs’ ex-girlfriend Cassie Ventura, took the stand, delivering an emotional testimony about her daughter’s alleged abuse. She recounted discovering bruises on Cassie in 2011 and photographing them as evidence, later learning Combs demanded $20,000 to return explicit videos of her daughter. Ventura described taking out a home equity loan to meet the demand, which was later repaid, and expressed feeling “physically sick” at the situation, highlighting the coercive control prosecutors allege Combs exerted over Cassie.

Sharay Hayes: Sharay Hayes, a male escort who performed under the name “The Punisher,” testified on May 21, 2025, about his involvement in 8-12 of Combs’ alleged “freak offs” starting in 2012. He described a specific encounter at Trump International Hotel where he was paid $800-$1,200 to create a “sexy scene” with Cassie Ventura, orchestrated by Combs. Hayes noted Ventura appeared professional but occasionally showed subtle signs of discomfort, such as sighs or winces, providing insight into the dynamics of the events central to the prosecution’s racketeering charges.

David James: David James, Combs’ former personal assistant, began his testimony on May 21, 2025, detailing his role from 2006 to 2008, which included stocking hotel rooms with supplies and undergoing lie detector tests to ensure loyalty. He recounted witnessing Combs’ drug use and abusive behavior toward Cassie Ventura, including an incident where Combs, armed with handguns, considered confronting rival Suge Knight. James’ testimony, which continued briefly the next day, underscored the volatile environment prosecutors claim was part of Combs’ criminal enterprise.

Gerard Gannon: Homeland Security Investigations Special Agent Gerard Gannon testified on May 21, 2025, about the March 2024 raids on Combs’ Miami and Los Angeles properties. He detailed finding AR-15 parts with defaced serial numbers, drugs including MDMA and pink powder, and sex-related items like baby oil and lingerie. Gannon’s testimony, which extended into the following day, emphasized the physical evidence supporting allegations of drug-fueled “freak offs” and illegal activities tied to Combs’ enterprise.
Dawn Hughes: On May 21, 2025, forensic psychologist Dawn Hughes provided expert testimony on the dynamics of domestic violence, explaining how victims like Cassie Ventura might remain in abusive relationships due to physical, psychological, and financial control. She highlighted how abusers manipulate victims through fear and dependency, offering context for Ventura’s prolonged relationship with Combs. Hughes’ insights bolstered the prosecution’s narrative of coercion and control central to the sex trafficking charges.
May 22, 2025 Testimonies:
Scott “Kid Cudi” Mescudi: On May 22, 2025, rapper Scott Mescudi, known as Kid Cudi, testified about his brief 2011 relationship with Cassie Ventura, during which she confided in him about physical abuse by Combs, including hitting and kicking. Mescudi recounted Combs’ alleged threat to blow up his car, which later exploded under mysterious circumstances, though he clarified Ventura never mentioned sexual abuse. His testimony provided a personal perspective on the alleged violence Ventura endured.
Mylah Morales: Mylah Morales, a makeup artist, testified on May 22, 2025, about a disturbing incident during Grammy weekend in 2010 at the Beverly Hills Hotel. She described hearing yelling and screaming after Combs entered a bedroom with Cassie Ventura, later seeing Ventura with a swollen eye, busted lip, and knots on her head. Morales sheltered Ventura at her home afterward, and her testimony offered a firsthand account of the physical abuse alleged in the prosecution’s case.
George Kaplan: George Kaplan, another former assistant to Combs, continued his testimony on May 22, 2025, after starting the previous day. Granted immunity, he described his 15-month tenure as Combs’ “bag man,” handling logistics like drug purchases, including MDMA, and cleaning up after “freak offs.” Kaplan’s account of the demanding role and its connection to Combs’ alleged illicit activities provided prosecutors with evidence of a structured criminal operation.
Gerard Gannon: On May 22, 2025, Special Agent Gerard Gannon concluded his testimony, focusing on digital evidence extracted from three laptops belonging to Cassie Ventura. One laptop had a user profile under Combs’ alias, Frank Black, suggesting his control over her digital environment. Gannon’s testimony reinforced the physical evidence from the Miami raid, tying it to the broader allegations of coercion and racketeering in Combs’ enterprise.
These testimonies, spanning personal accounts, expert insights, and law enforcement findings, continue to build the prosecution’s case against Combs, with the trial ongoing and further developments expected.