Sean ‘Diddy’ Combs Trial Day 8 Recap: Former Assistant Testifies On Drug Pickups, Hotel Setups, And “Protecting” The Boss

Wednesday, May 21, marked another dramatic turn in the federal sex trafficking and racketeering conspiracy trial of Sean “Diddy” Combs, with testimony from a Homeland Security agent, a forensic psychologist, and perhaps most damningly, a former assistant who painted a picture of unrelenting loyalty, whispered threats, and clandestine cleanup jobs—all allegedly in service of shielding one of the most powerful men in hip-hop from scrutiny.

From “Freak Off” Supplies to Firearms

Homeland Security Special Agent Gerard Gannon resumed testimony from earlier in the week, methodically walking the jury through a collection of items seized from Sean Combs’ Miami mansion during a 2024 raid. The visual display included AR-15 components with defaced serial numbers, a loaded .45-caliber handgun found in a red suitcase, and no less than 31 bottles of baby oil—items prosecutors have dubbed Combs’s “freak off supplies.” They were shown alongside photos of lingerie, platform heels, lubricant, and a Gucci bag stuffed with designer drugs: MDMA pills (including orange ones stamped with Tesla logos), cocaine, and ketamine.

Defense attorney Teny Geragos, aiming to undercut the drama, questioned the raid’s militarized approach and pointed out that no weapons were found on staff during the search. Still, the visual evidence—firearms and sex paraphernalia stored together—seemed to bolster the prosecution’s claim that Combs used coercion, drugs, and violence to organize his notorious “freak off” sex parties.

Forensic Psychologist Breaks Down the Trauma

Next on the stand was Dr. Dawn Hughes, a forensic psychologist and seasoned expert witness. Though she never examined Sean Combs or alleged victim Cassie Ventura, Hughes testified broadly about the psychological bonds and coping mechanisms common among victims of prolonged abuse.

According to Hughes, victims often remain in abusive relationships out of fear, shame, or financial dependency. “There’s almost always love,” she told the jury, explaining that emotional highs and lows can create a powerful psychological tether between victim and abuser. She described Ventura’s trauma patterns—drug use to dissociate, fragmented memories, returning to Combs after abuse—as consistent with abuse survivor behavior.

Defense attorney Jonathan Bach took aim at Hughes’ credibility, painting her as a prosecution regular and challenging the relevance of her “general” testimony. Bach pointedly asked if she had ever testified for a man accused of a sex crime. “No, I don’t evaluate offenders,” Hughes responded. But on redirect, prosecutor Mitzi Steiner revealed that Hughes had, in fact, previously been retained by one of Combs’s own defense attorneys—Brian Steel—undermining the idea that Hughes’s expertise is biased by allegiance.

George Kaplan: Loyalty or Liability?

The day’s most explosive testimony came from George Kaplan, Sean Combs’s former assistant, who was granted immunity just before taking the stand.

Kaplan testified that during his 15-month stint working for Combs, he was responsible for a wide array of personal tasks, including curating what became known as the “hotel bag.” This kit—delivered on short notice to hotel rooms under the alias “Frank Black”—was stocked with clothes, candles, liquor, baby oil, and Astroglide lubricant, all reportedly for Combs and his female “guests.”

When the parties ended, Kaplan was expected to clean the rooms himself. Why not leave that to hotel staff? “I would see often that hotels would sell videos and images and try and embarrass celebrities and other figures,” Kaplan said. “And that was something I wanted to avoid.” The prosecution used this statement to frame Kaplan as an unwitting accomplice in a wider cover-up operation.

But perhaps most damning was Kaplan’s testimony that Combs directed him—on at least two occasions—to pick up drugs. In one instance, Combs allegedly handed Kaplan cash and a phone number in Miami. Kaplan met the dealer, secured the MDMA, and handed it over. A similar transaction allegedly took place in Hollywood, with Kaplan picking up an unknown substance and delivering it to Combs without asking questions.

Trial Continues with More Witnesses Ahead

Prosecutors had initially hoped to call rapper Kid Cudi (Scott Mescudi) to the stand Wednesday. According to Cassie Ventura’s prior testimony and a settled lawsuit, Sean Combs allegedly threatened to blow up Cudi’s car after discovering the two were romantically linked. That threat reportedly came true when Mescudi’s car exploded outside his home—an incident prosecutors may seek to connect to Combs’s alleged pattern of violence and control. Cudi is now expected to testify on Thursday, pending scheduling.

Despite the weight of the testimony, the government stated they are ahead of schedule and may wrap up the week’s proceedings early.

Wednesday’s proceedings gave the jury a clearer glimpse into the machinery that prosecutors allege propped up Diddy’s double life—one of luxury and celebrity on the outside, and one fueled by fear, manipulation, and abuse behind closed doors. With more witnesses—including potential victims and high-profile figures—expected in the coming days, the trial is rapidly becoming a watershed moment in the legal accountability of one of the entertainment industry’s power players.

SEE ALSO:

There Is No Defending Diddy

Sean Combs’ Legal Team Claims ‘Mutual Abuse’ In Relationship With Cassie Ventura

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