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Home » All Listicles » Two Down, More To Go! 6 MAJOR Moments From Sean ‘Diddy’ Combs’ Second Week On Trial For Sex Trafficking (RECAP)

Two Down, More To Go! 6 MAJOR Moments From Sean ‘Diddy’ Combs’ Second Week On Trial For Sex Trafficking (RECAP)

By Cassandra - 2025/05/27
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Two Down, More To Go! 6 MAJOR Moments From Sean 'Diddy' Combs' Second Week On Trial For Sex Trafficking (RECAP)
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Jurors heard from a dozen witnesses during the second week of testimony in the Sean “Diddy” Combs trial as prosecutors sought to prove instances of sex trafficking and racketeering. Kid Cudi took the witness stand, and so did singer Dawn Richard, formerly of the group Danity Kane. There was more testimony from witnesses who said they saw Combs beating his former girlfriend, Cassie. Jurors also heard testimony about guns, extortion, and a car being set on fire. The trial resumed on Tuesday (May 27) after the Memorial Day holiday.

RELATED: One Down, More To Go! 5 MAJOR Moments From Sean “Diddy” Combs’ First Week On Trial For Sex Trafficking (RECAP)

1. Brick By Brick! Prosecutors Focus On Racketeering Charge

Much of the case presented by prosecutors so far has revolved around accusations that Combs physically and sexually abused Cassie for years. Additionally, there’s been testimony that he coerced her into sexual encounters called “freak-offs” with men who were paid thousands of dollars to have sex with her.

RELATED: “Hundreds” Of “Freak Offs” Later, Who Are The Male Escorts Testifying & Named In Diddy’s Trial? (PHOTOS)

Yet Sean Combs isn’t only charged with sex crimes. He’s charged with racketeering. Prosecutors say they will prove that Combs used his businesses and employees “to carry out, facilitate, and cover up his acts of violence, abuse, and commercial sex.” Some of those employees testified in Week 2.

Take George Kaplan, for example. He worked as a personal assistant for Combs from 2013 to 2015. Kaplan told jurors he’d toss out liquor bottles and drugs and clean up baby oil from Combs’ hotel rooms after the music producer finished freak-offs. He said he never reported abuse to authorities, even after Combs allegedly beat up Cassie on a private jet.

Meanwhile, another personal assistant, David James, testified that Diddy had him stock hotel rooms with Viagra, condoms, baby oil, and lubricant, among other supplies. He also recalled Sean Combs holding three handguns on his lap as they drove to a Los Angeles diner looking for his record industry rival, Suge Knight — a Death Row Records co-founder.

2. Cassie’s Mom Tells Jury Diddy Demanded $20,000 For Sex Tape

LIVE UPDATES: Cross-Examination Concludes For Diddy's Ex-Assistant, Cassie's Mom, Regina Ventura, Takes The Stand (Day Seven)
John Lamparski/Getty Images/Jon Kopaloff/FilmMagic

Cassie briefly dated Kid Cudi during a period of time when it looked like she might split with Combs.
Cassie’s mother, Regina Ventura, testified that she felt “physically sick” after her daughter sent her an email saying Combs had learned about the relationship with Cudi and planned to retaliate by releasing sex tapes of the singer. On the trial stand, Regina also said Diddy contacted her and angrily demanded $20,000. The music producer allegedly said he was owed the money for his investments in Cassie’s career.  Regina said she tapped home equity to wire the funds to Combs’ business. Several days later, the money was returned.

RELATED: Lie-Detector Tests, Mention Of Suge Knight & A $20,000 Demand: Diddy’s Ex-Assistant & Cassie’s Mom Take The Stand (Day Seven)

#1

3. Kid Cudi Testifies About A Break-In And A Firebombed Car

Kid Cudi testified Thursday (May 22) that Cassie sounded “very stressed, nervous, just scared” when she called him in December 2011 to say that Combs had learned they were dating. Cudi said he was confused because he thought Combs and Cassie had broken up. Then, he said, one of Combs’ assistants called. She said Combs and an aide were in Cudi’s home, waiting to speak with him. She also said she had been forced into a car to join them.

Cudi said he raced to his house, but Combs was gone. He testified that he found open Christmas gifts, and his dog was locked in the bathroom. After the break-in, his dog was “very jittery and kind of on edge all the time,” he said. The following month, someone set fire to Cudi’s car, destroying it.

Cudi said he met with Diddy at a Los Angeles hotel the day after the car incident to squash their beef. When he walked in, he said that Combs was staring out the window, standing with hands behind his back “like a Marvel supervillain.” At that meeting, Sean Combs denied having anything to do with the burned car, but Cudi said he didn’t believe him.

RELATED: Kid Cudi Says Diddy Looked Like “Marvel Supervillain” During Meet-Up After His Car Was Set On Fire (TESTIMONY RECAP)

#2

4. Dawn Richard Tells Of Death Threats

The first witness of week two, Dawn Richard, got her big break in the music business as a cast member on Combs’ reality TV show, ‘Making the Band.’ She performed with two Combs-backed groups, Danity Kane and Diddy — Dirty Money. But Richard said Combs threatened her life after she saw him beat Cassie and try to hit her with a skillet in 2009. She said Combs told her and another woman that they “could go missing” if they didn’t stay quiet. She said she saw Combs beat Cassie frequently. “He would punch her, choke her, drag her, slap her in the mouth,” Dawn Richard testified. 

#3

5. Cassie's Former Bestie Explains End Of Friendship

Kerry Morgan said she had a falling out with Cassie, her friend of 17 years, after Combs attacked her in a rage in 2018. At the time, he allegedly demanded to know who Cassie was cheating on him with. Morgan said he slung a hanger at her head and tried to choke her. The incident reportedly left her feeling dizzy, vomiting, and concussed, with finger imprints on her neck.

A month later, Morgan met Cassie at a pizza parlor while contemplating a lawsuit. At the meeting, Cassie had her sign a nondisclosure agreement for $30,000. But then, she said, Cassie “told me she thought I was milking it, that I was overexaggerating.” They haven’t spoken since.

#4

6. Hotel Manager Says Diddy Always Left An Expensive Mess

One of the last witnesses of the week was Frédéric Zemmour, the general manager of L’Ermitage Beverly Hills in California. He revealed that Diddy’s guest profile noted that he “ALWAYS spills candle wax on everything and uses excessive amounts of oil.” The profile instructed staff to “place the room out of order upon departure for deep cleaning.”

“Please authorize an extra $1000 when guest stays with us to cover any room damages,” Combs’ guest profile said.

Witnesses have testified that Combs liked to use candles and baby oil during freak-offs.

#5

Honorable Mention: Comic Relief Seeps Into Trial About Violence

Despite the trial’s serious subject matter, there have been a few light moments. On Thursday, Combs’ former personal assistant, George Kaplan, shared that his ex-boss “loves applesauce.” Combs nodded and smiled as Kaplan recounted that he “eats it on the side or on top of a lot of things.”

“Cheeseburgers?” defense attorney Marc Agnifilo asked. “Cheeseburgers being one of them,” Kaplan said as laughter broke out across the courtroom.

RELATED: Diddy Trial Week 2: Dawn Richard, Cassie’s Ex-Bestie, Combs’ Former Employees, Kid Cudi & MORE Testify (RECAP)

Associated Press Staff Michael R. Sisak and Larry Neumeister contributed to this report via AP Newsroom.

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Cassandra Santiago

Cassandra Santiago

Cassandra Santiago is a multimedia journalist, editor, and editorial strategist with over a decade of experience shaping conversations across arts, entertainment, culture, and global news. A graduate of the University of Iowa, she has built a cross-platform career spanning newspapers, magazines, radio, and digital media. She joined The Shade Room five years ago and currently serves as a Senior Editor, where she leads editorial direction, oversees exclusive coverage, and trains and edits a team of writers. Cassandra has played a key role in developing high-impact content and editorial strategies for an audience of more than 30 million, contributing to platform growth, engagement, and monetization across multiple channels. In addition to her leadership role, she remains a daily contributor, with her articles generating more than 41 million views since 2023. Beyond The Shade Room, Cassandra offers freelance social media strategy services, speaks on the influence and impact of Black media at public panels, and owns Did It For You, an event design company in the DC, Maryland, and Virginia area. She is Poynter Institute–certified and was named to the DMV’s 35 Under 35 list in 2024.

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