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Home » All Listicles » One Down, More To Go! 5 MAJOR Moments From Sean ‘Diddy’ Combs’ First Week On Trial For Sex Trafficking (RECAP)

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

By Cassandra - 2025/05/19
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Diddy Trial Trafficking Racketeering Recap Major Moments Week One Sean Combs 
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Testimony in the sex trafficking, racketeering, and prostitution engagement trial of Sean ‘Diddy’ Combs began last Monday (May 12). Week one opened a window into what prosecutors claim was a sleazy world of group sex, drugs, and violence behind the hip-hop mogul’s glittering, larger-than-life persona.

RELATED: Diddy Trial Everything: Opening Statements, Cassie Testimony & Dawn Richard Takes The Stand (LIVE UPDATES)

Much of the testimony was cringey. Combs’ ex-girlfriend, Cassie, recalled him allegedly beating and pressuring her into degrading sexual performances known as “freak offs.” A former security guard, male escort, Homeland Department agent, and former Dainty Kane member, Dawn Richard, also took the stand.

Despite only being week one, bombshell after bombshell dropped in that New York City courtroom. We’re heading into week two of testimony on Monday (May 19), but here are five MAJOR moments from the trial so far.

1. Defense Agrees Diddy Is Violent, But Slams His Trial Charges

Diddy’s lawyer, Teny Geragos, took an unconventional approach to defending Combs in her trial opening statement. She agreed that the hip-hop impresario has a “bad temper.” Geragos even said Sean Combs is prone to violent outbursts that are often fueled by alcohol, jealousy, and drugs. However, she insisted his actions align with domestic violence charges and that there isn’t proof he engaged in sex trafficking and racketeering.

“Sean Combs is a complicated man. But this is not a complicated case,” she said in court. “This case is about love, jealousy, infidelity, and money.”

Additionally, Geragos argued that Combs’ sexual habits were part of a swinger lifestyle involving consenting adults. She opened week one by reminding jurors that “kinky” sexual desires don’t equate to sex trafficking.

RELATED: Say WHAT?! Here Are The Top 8 BOMBSHELL Statements Shared Since Diddy’s Federal Trial Has Kicked Off

2. Jurors See Videos & Photos Of Combs Attacking Cassie In Hotel

The packed courtroom went silent while jurors watched security camera video of Sean Combs assaulting Cassie in a Los Angeles hotel in 2016. For context, the video shows the R&B singer walking down a hallway toward the hotel’s elevators. Moments later, Combs comes around the corner, strikes her and throws her to the ground before kicking her and then dragging her back toward their hotel room.

Jurors also saw photos of damage in the hotel hallway, including flowers on the floor and soil spattered against a wall. Later, as Cassie testified about the attack, jurors saw photos of her swollen lip.

The trial’s first witness was a former hotel security guard, Israel Florez. He testified that Combs attempted to bribe him with a stack of money, including a $100 bill on top. Florez claimed that Diddy said, “Don’t tell nobody.” Florez said he responded, “I don’t want your money. Just go back into your room.”

3. Cassie Spares NO Details While Describing “Freak Offs”

The ‘Me & U’ singer also testified that Diddy was into voyeurism, the act of watching other people engage in sensual or sexual acts. Additionally, she said he dictated every aspect of sex events he dubbed “freak-offs,” “Wild King Nights,” and “Hotel Nights.”

RELATED: Big Baby Oil Bottles & Urine Acts: Cassie Reveals SHOCKING Details About Diddy’s Alleged “Freak Offs”

The “highly orchestrated” affairs involved male sex workers, heavy drug use, and plenty of lubrication. “It was his fantasy,” Cassie testified. The musician claimed each “freak-off” involved about 10 large bottles of heated-up baby oil.

“It was such a mess,” Cassie said on the stand while heavily pregnant with her third child. “It was like, ‘What are we doing?'”

She also said Combs asked her to perform degrading and painful sex acts with male sex workers. Cassie said eventually she was doing “freak-offs” weekly for a decade, with the final one in 2017 or 2018. “The freak-offs became a job,” Cassie recalled.

She said she felt she couldn’t refuse because she feared the videos would be made public. Jurors also heard from Daniel Phillip, who said he was a professional stripper paid to have sex with Cassie while Combs gave instructions. He testified that he once saw Combs drag Cassie by her hair as she screamed.

RELATED: From Freak-Offs To Stompings, Cassie Testifies In Trial About Alleged Violent Relationship With Diddy (Day Two)

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4. Messages Between Diddy & Cassie Show A Complicated Relationship

During their cross-examination of Cassie, defense lawyers aimed to show she was an enthusiastic participant in his sex marathons.

“I’m always ready to freak off,” she wrote in one 2009 message read in court.

Later that year, however, Cassie expressed frustration with the state of their relationship and told Combs she needed something more from him than sex.

In a 2017 text message, Cassie told Combs: “I love our FOs when we both want it,” using the initials of freak-off. On the stand, Cassie explained: “I would say loving FOs were just words at that point.”

RELATED: Freak-Off Texts, Emails & Mention Of Ryan Leslie: Diddy’s Defense Unleashes Cross-Examination On Cassie (Day Four)

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5. Singer Dawn Richard Says She Witnessed Diddy Beating Cassie

The former cast member on Diddy’s MTV reality show ‘Making the Band’ testified that she saw him physically attack Cassie on multiple occasions. During a 2009 incident in his home, Dawn Richard said Combs tried to strike Cassie in the head with a black skillet before he put his arm around her neck and dragged her up the stairs.

“I was scared for her and scared to do anything,” she said. “I had never seen anything like that before.”

Richard, who was later a member of the Combs’ band Diddy — Dirty Money, sued the producer last year. Her lawsuit accuses him of physical abuse, groping, and psychological abuse during the years they worked together. His representative denied the claims at the time.

RELATED: From Mention Of Kim Porter To Gina Huynh To Chris Brown: Cassie’s Cross-Exam Concludes, Dawn Richard Testifies In Diddy’s Trial (Day Five)

Associated Press Staff contributed to this report. 

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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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