The first week of Sean Combs’ federal trial concluded with a flurry of powerful testimony, emotional revelations, and a witness list stacked with familiar names. 

At the center of it all stood Cassie Ventura, Diddy’s ex-girlfriend and the prosecution’s star witness, who delivered nearly 20 hours of testimony that spanned four days. She painted a disturbing portrait of life behind the velvet rope, recounting years of alleged abuse, manipulation, and degradation. And when she finally stepped down from the stand, she left the courtroom with more than a few dropped jaws.

Let’s get into it.

Cassie’s Testimony: Abuse, Control, and “Freak Offs”

Cassie, now heavily pregnant, testified in agonizing detail about her decade-long relationship with Sean “Diddy” Combs, which she said began when she was just 19 and signed to his label, Bad Boy Records. What started as a glamorous industry relationship quickly turned dark, she claimed, detailing how Combs allegedly beat her, controlled her image, dictated her music career, and forced her to participate in weekly “freak-offs”—drug-fueled sex parties that became the basis for many of the federal charges now facing the music mogul.

“He would smash me in my head, knock me over, drag me, kick me, stomp me in the head if I was down,” she said on the stand. She even alleged that after one brutal attack in 2008, he made her stay in a hotel to recover in isolation. In another chilling moment, she described how she wore sunglasses to a red carpet premiere to hide the bruises he left on her face.

Her physical and emotional suffering, she testified, was compounded by recurring urinary tract infections from back-to-back “freak-offs” that grew so frequent, the antibiotics stopped working. Through tears, Cassie said she’d “give back every dollar of that $20 million settlement to have never experienced a freak-off.”

Cross-Examination: A Tense Legal Chess Match

Sean Combs’ defense attempted to dismantle Cassie’s credibility during cross-examination. They zeroed in on inconsistencies in the timeline of her alleged 2018 rape—August or September?—and pointed to texts that painted a different picture. One message read: “I do love you. I would just prefer not being one of your girlfriends anymore.” Another showed her texting Diddy after their alleged final sexual encounter, saying she’d had “a great time.”

Defense attorney Anna Estevao, who led the questioning, kept things relatively cordial despite the intensity of the moment, even calling Cassie “very beautiful and charming,” drawing nervous laughter from the courtroom. But behind the pleasantries was a clear strategy: to present Cassie as a willing participant in her relationship with Combs and the “freak-offs.”

Cassie didn’t deny that she had once texted, “I’m always ready for a freak-off lolol,” but she dismissed it as a survival tactic. “They were just words at that point,” she said.

With Cassie’s due date rapidly approaching, the court raced against the clock to complete her testimony. Prosecutors feared she might go into labor mid-trial, which could have led to a mistrial. Judge Arun Subramanian expressed visible frustration with the defense’s attempts to extend questioning into the second week of the trial. “In what universe did you not understand this witness was supposed to be done this week?” he snapped.

Dawn Richard Testifies: Witness to Violence

As if the week hadn’t been emotional enough, Friday also brought testimony from singer Dawn Richard, a former member of the girl group Danity Kane, which Diddy assembled on the reality show, Making the Band, as well as the group Diddy-Dirty Money, founded in 2009. Richard testified she witnessed Combs attack Cassie in that year, corroborating Ventura’s narrative of abuse.

Richard’s testimony adds weight to the prosecution’s depiction of Sean Combs as not just volatile, but dangerous. According to prosecutors, Combs didn’t just operate like a controlling boyfriend—he ran what they called a “criminal enterprise.”

The Alleged Enterprise: Drugs, Escorts, and Violence

Prosecutors opened the trial by describing Sean Combs as the architect of an organized network that facilitated abuse behind the scenes of fame. Government attorney Emily A. Johnson painted a disturbing picture: Combs allegedly drugged women, used his staff to coordinate “freak-off” nights, paid male escorts to perform while he watched, and frequently resorted to violence when his ego was bruised.

One chilling account from a male escort, Daniel Phillip, described how he was paid to have sex with Cassie while Diddy watched from the corner of a hotel room. This scenario, he said, happened multiple times.

Security guard Israel Florez also took the stand, recounting the aftermath of the 2016 hotel assault—captured on security footage and already seen by some jurors. Florez recalled seeing Combs sitting in a towel, staring with a “devilish” glare and offering him a stack of cash not to speak about what happened. He refused the bribe.

The Defense: “Bad Boy for Life,” But Not a Criminal?

Teny Geragos didn’t mince words in her defense of Combs, admitting her client’s behavior was “indefensible,” “dehumanizing,” and “every bad word you can think of.” But, she argued, bad behavior does not equate to federal crimes. “He is physical. He is a drug user. You may know of his love of baby oil,” Geragos quipped to the jury. “Is that a federal crime? No.”

Geragos insisted Cassie was a “willing participant” and not a victim of trafficking, suggesting she only left when she realized she’d never be Combs’ wife.

Geragos even took aim at Cassie’s motivations, accusing her of jealousy toward Kim Porter, Sean Combs’ longtime partner and mother of three of his children.

Jury Makeup and Sean Comb’s Courtroom Demeanor

The jury—eight men and four women with diverse professional backgrounds from deli clerk to scientist—appeared engaged throughout the week. Six alternates sit ready in case another juror cannot continue.

Meanwhile, Diddy, who has appeared in court gray-haired, dressed in khakis and a sweater, has kept busy in the courtroom. He’s been spotted flipping through a blue notebook, whispering to his attorneys, and even blowing kisses to family members seated behind him. This, despite being held in Brooklyn’s notoriously rough Metropolitan Detention Center since his arrest in September 2024.

What’s Next?

As the second week begins, all eyes are on the prosecution to see who they call next and whether the testimony continues to support their claims of racketeering, sex trafficking, and forced prostitution. If convicted on all five counts, Sean Combs could face life in prison.

One thing is clear: the first week of this trial has already shaken the foundation of the industry that helped build Sean Combs, and as more voices come forward, it’s evident this case is about far more than one man’s downfall. It’s about reckoning with power, silence, and the high cost of fame behind closed doors.

Stay tuned. 

SEE ALSO:

There Is No Defending Diddy

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