Ex-Assistant Reveals Behind-the-Scenes Cleanup After Sean ‘Diddy’ Combs’ Wild Sex Marathons

NEW YORK – Sean “Diddy” Combs’ former personal assistant testified Wednesday about the chaotic aftermath of the hip-hop mogul’s infamous sex marathons, describing how he was tasked with cleaning up hotel rooms—discarding empty booze bottles, baby oil, and drugs—making sure everything looked spotless like nothing had happened.

George Kaplan, who worked for Combs from 2013 to 2015, told jurors at Combs’ federal sex trafficking trial that a key part of his job was protecting Combs’ public image. “That was very important to him, and that’s what I focused on,” Kaplan said.

Kaplan described how Combs would sometimes call him to deliver a “medicine kit” — a bag filled with prescription pills and painkillers — and even sent him out to buy illegal drugs like MDMA (ecstasy). He said Combs often threatened his job, once even scolding him over the wrong size bottled water.

Kaplan was granted immunity to testify after initially wanting to plead the Fifth Amendment. Prosecutors allege Combs used his music and fashion empire to facilitate and hide his misconduct, threatening employees to keep them silent.

Adding to the drama, Combs’ longtime girlfriend, R&B singer Cassie, testified that Kaplan quit after witnessing Combs physically abuse her.

Kaplan’s testimony will continue Thursday, followed by rapper and actor Kid Cudi, who is expected to speak about his brief relationship with Cassie in 2011. Prosecutors claim Combs was so enraged by the relationship that he arranged to have Cudi’s convertible firebombed.

Police Raid Finds Guns, Drugs, and Baby Oil Linked to ‘Freak-Offs’

On Wednesday, a federal agent showed jurors two handguns seized in a March 2024 raid on Combs’ Miami-area home, along with photos of ammunition and a wooden box labeled “Puffy” (one of Combs’ nicknames) containing psilocybin, MDMA, and other drugs.

The raid, which involved 80 to 90 agents, an armored vehicle, handcuffed employees, and boat patrols, also uncovered evidence of “freak-offs”—wild sex parties—including dozens of bottles of baby oil and lubricant.

Combs’ lawyer called the search an overreach, noting similar raids were conducted at his Los Angeles mansion.

The investigation began soon after Cassie filed a lawsuit in November 2023 alleging years of abuse and forced participation in hundreds of freak-offs. Cassie later settled the suit for $20 million.

The Case Against Combs and Victim Testimonies

Combs denies all charges, insisting that the case is about domestic violence, not racketeering or sex trafficking.

A psychologist testified about the complicated dynamics of abusive relationships, explaining how victims often develop a “low sense of self” and stay with abusers out of hope for love and compassion experienced during early “honeymoon phases.” The expert also explained how memories of abuse can become confused or jumbled over time.

Cassie shared her story, testifying that although she and Combs broke up, they still took part in freak-offs. During one encounter, Combs discovered she was seeing Kid Cudi by checking her phone.

Cassie’s mother, Regina Ventura, recounted receiving a fearful email from her daughter in December 2011, in which Cassie said Combs was so angry about her relationship with Cudi that he threatened to release explicit videos and have harm come to both of them. Scared for Cassie’s safety, Regina sent Combs $20,000 — which he returned days later.

Cassie said she ended her relationship with Cudi before the year was out, overwhelmed by the danger and uncertainty.

After reuniting with Combs, Cassie testified, Combs warned her that he planned to blow up Cudi’s car in front of his friends.

“It was just too much,” she said. “Too much danger, too much uncertainty about what could happen if we kept seeing each other.”

This high-profile case continues to unfold as more witnesses are set to testify, shedding light on the dark side of fame and power in the entertainment industry.