Week 2: “The Punisher” and Cassie’s Mother Testify in Diddy Trial

From the sexually exploitative to the emotionally devastating, the testimony in Sean “Diddy” Combs’ trial continues to uncover disturbing new layers. This week, the prosecution introduced two voices from very different walks of life. Both of which, they argue, point to the same pattern of sex, control, and coercion.

“The Punisher” and the Freak-Offs

Perhaps the most salacious testimony of Week 2 came from Sharay Hayes, an exotic dancer who went by the nickname “The Punisher.” Hayes recounted in matter-of-fact detail how he was drawn into Combs’ “freak-off” world as a paid participant in Cassie’s coerced threesomes.

The dancer described a bizarre first encounter in late 2012 when Cassie (using a fake name) contacted him, claiming it was her birthday and that her “husband” wanted to hire a male stripper for her.

Hayes arrived at a Manhattan hotel expecting a typical bachelorette-style performance for a group of women. Instead, he claims he found Cassie alone and clad in lingerie, accompanied by a mysterious naked man hiding his face with a burqa-like cloth sitting in the corner.

Hayes described being paid in cash, first $800, then an extra $1,200 after performing in what he soon realized was a staged sexual encounter. It wasn’t a one-time thing. Hayes testified that he discovered the masked man was Sean Combs during a subsequent booking at Manhattan’s Essex House Hotel.

Hayes’ lurid account provides testimonial evidence of the sex trafficking pattern Cassie alleged, essentially a paid sex show orchestrated by Combs using Cassie’s body.

It also mirrors the testimony of an earlier escort witness who described similar encounters. On the opening day of the trial, another male entertainer testified that in 2013, he was paid to have sex with Cassie while Combs watched after being lured under the guise of a “bachelorette party” performance.

Prosecutors argue these weren’t consensual kinks but calculated crimes involving drugs, deception, and coercion for Combs’ gratification. Combs’ lawyers, for their part, have emphasized that these male participants never saw Combs threaten Cassie or physically force her during the sessions, implying that Cassie was an eager participant. Indeed, Hayes acknowledged under oath that he did not witness violence or drug use during the “freak-offs” he attended despite the deeply unsettling power dynamic at play.

Cassie’s Mother Speaks

One of the most emotionally charged moments of Week 2 came when Cassie’s mother, Regina Ventura, took the stand. Though her testimony was brief (under 30 minutes), it delivered a damning glimpse into the lengths Combs allegedly went to terrorize Cassie and those close to her.

Ventura testified that in late 2011, while Cassie and Combs were briefly broken up, an enraged Combs demanded $20,000 from her and threatened to release two explicit sex videos of Cassie because he’d discovered Cassie was dating someone else

In a panicked email, Cassie confided to her mother that Combs had not only vowed to leak the tapes but also to send someone to hurt both Cassie and the new boyfriend, rapper Kid Cudi.

“The sex tapes threw me… I felt physically sick,” Regina Ventura said.

Fearing for her daughter’s safety, Cassie’s mother said she took out a home equity loan and paid Combs the $20,000 he demanded. Surprisingly, she claims the money was returned days later, and Cassie abruptly reconciled with Combs. The alleged extortion had achieved its purpose: Cassie was back under Combs’ control.

Regina Ventura’s testimony was so potentially explosive that defense attorney Marc Agnifilo unsuccessfully fought to exclude it, arguing it was “purely prejudicial.” However, a federal judge allowed the jury to hear it as evidence of “potential extortion.”

The defense chose not to cross-examine Cassie’s mother, letting her account stand unchallenged in court. Jurors also saw photographs of bruises on Cassie’s body from late 2011, which her mother testified Cassie had when she came home for Christmas that year, around the same time as the sex tape incident.

Homeland Security: The “Freak-Off Kit”

Meanwhile, law enforcement testimony in Week 2 reinforced the notion of Combs’ double life. U.S. Homeland Security agent Gerard Gannon testified about the March 2024 raid on Combs’ Miami mansion that turned up a trove of incriminating items.

Agents using an armored vehicle and boats breached the property’s gates and seized parts of two AR-15 rifles, along with what can only be described as Combs’ personal “freak-off kit”: 7-inch stiletto heels, lingerie, sex toys, bottles of lubricant, and baby oil, plus other paraphernalia allegedly used in his marathon orgies.

The Trial Continues with More High-Profile Witnesses

After two weeks of testimony, the case against Sean “Diddy” Combs expanded and sharpened in focus. What began with Cassie Ventura’s courageous, graphic account of alleged abuse has now been echoed by multiple voices: a pop star protege, a longtime friend, a former assistant, a distraught mother, and an adult entertainer from an entirely different walk of life. Each has added pieces to a puzzle depicting a powerful celebrity who allegedly lived a secret life of predation and violence behind the façade of music industry success.

Combs has vehemently denied all charges, and his defense team continues to portray the accusers as exaggerating consensual experiences or seeking financial gain.

The trial, expected to last around two months, will press on with yet more high-profile witnesses in the coming days. Notably, rapper Kid Cudi is set to testify by next week, potentially recounting the alleged retaliation he faced for dating Cassie.

As the prosecution’s case gains momentum, Combs faces the very real possibility of losing his freedom. If convicted on the most serious counts, the 55-year-old music mogul could be sentenced to anywhere from 15 years to life in prison.

Week 2’s revelations have left court observers stunned and riveted, and there is a sense that this landmark trial is only just beginning to reveal its deepest secrets. For all of Sean “Diddy” Combs’ Bad Boy bravado, the testimony so far has painted a starkly different legacy. One that a jury will soon have to judge.

If you or someone you know needs help, support is available. For sexual assault assistance, contact the National Sexual Assault Hotline at 1-800-656-HOPE (4673). If you’re experiencing domestic violence, the National Domestic Violence Hotline offers confidential support at 1-800-799-7233. Victims of human trafficking can reach out to the National Human Trafficking Hotline at 1-888-373-7888. These resources are available 24/7 to provide help, guidance, and support—you are not alone.