On a rainy Tuesday in New York City, Cassie Ventura — pregnant and poised — was seen leaving her home on her way to court.
But this wasn’t just another hearing.
The singer was preparing to testify against her ex-boyfriend, Sean “Diddy” Combs, in a federal trial that’s grabbing national headlines.
Diddy, once a music industry titan, is now facing a slew of disturbing charges.
Prosecutors accuse him of running a sex-trafficking ring and criminal enterprise for two decades — using his fame, money, and power to manipulate, threaten, and abuse women.
At the heart of it all is Cassie, a former protégé turned key witness.
Diddy’s Legal Team Tries to Block Cassie’s Husband from the Courtroom
Before Cassie could even take the stand, Diddy’s lawyers tried to have her husband, Alex Fine, removed from the courtroom.
Their argument? They might call him as a witness later in the trial.
They claim Fine had knowledge of a 2018 incident where Cassie was allegedly raped by Diddy, even referencing a text Fine once sent to Diddy, saying he wanted to “beat the f— out of him.”
Interestingly, the defense was fine with Cassie’s brother staying in the courtroom.
Prosecutors pushed back, arguing that Fine is part of Cassie’s emotional support — especially since she’s heavily pregnant.
The judge split the difference: Fine could stay for most of her testimony, but not all of it.
Cassie Testifies: How It All Began
Taking the stand, Cassie painted a haunting picture of how her relationship with Diddy turned dark.
She recalled that they started off platonic, but things shifted on her 21st birthday in Las Vegas.
Diddy kissed her in a hotel bathroom — something she said left her confused and unprepared.
“I didn’t even understand what was happening,” she told the jury.
“He introduced me to sexual things I wasn’t ready for. I was still in a relationship with someone else.
I was young, naive, and had no vocabulary for what was happening.”
“Freak Offs” and Coercion: Cassie Describes Disturbing Requests
Cassie testified that at just 22 years old, Diddy asked her to participate in what he called “Freak Offs” — group sex encounters often fueled by drugs.
“I was scared.
Nervous.
But I also loved him,” she said.
“My stomach dropped when he first brought it up.
I didn’t feel like I could say no.”
She explained that Diddy controlled every aspect of her life — from her career to her wardrobe — and that fear of violence or blackmail kept her from resisting.
Physical Abuse Allegations: “Too Frequent to Count”
Cassie’s voice dropped as she recounted instances of physical abuse.
She said Diddy would bash her head, drag her by the hair, stomp on her, and leave her bruised and bleeding.
“I had busted lips, red eyes, knots on my forehead… It was just too frequent,” she said quietly.
A Star Witness Begins Her Testimony
As Cassie stepped into the witness box, courtroom observers held their breath. It was a pivotal moment in the trial, and photos showed her steeling herself for what was to come.
Meanwhile, Diddy sat at the defense table, occasionally making gestures toward family members — his face mostly unreadable.
Behind the Settlement: Cassie’s Earlier Lawsuit Against Diddy
Last year, Cassie filed a separate lawsuit accusing Diddy of sexual abuse and violence.
That case was settled privately — just 24 hours after it was filed — for an undisclosed amount. But the floodgates had opened.
Since then, more women have come forward with similar accusations.
Judge Denies Diddy’s Claims of Racial Bias
Earlier this year, Diddy’s legal team tried to argue that the case was racially motivated — that no white man had ever been prosecuted in a similar way.
But Judge Arun Subramanian rejected that claim, saying there was no proof that race played a role in the prosecution.
He also denied a request to suppress key evidence in the trial.
Cassie’s Husband Alex Fine: From Trainer to Life Partner
Before becoming her husband, Alex Fine was Diddy’s personal trainer — an awkward origin story, given the current courtroom drama.
Cassie and Fine are now expecting their third child, and he’s remained at her side throughout the proceedings.
A Male Escort’s Testimony: “I Was Paid to Sleep with Cassie”
Daniel Phillip, a male escort and stripper, took the stand to back up Cassie’s claims.
He testified that Diddy paid him to sleep with Cassie while Diddy watched.
Sometimes the encounters lasted 10 hours, and Phillip said he often waited alone in hotel rooms while the couple retreated together.
Phillip claimed he didn’t always get paid, but was initially just “excited” to be part of a world filled with celebrities.
Defense Tries to Discredit Witnesses
Diddy’s lawyers focused on poking holes in Phillip’s testimony.
They accused him of being jealous of Cassie and tried to highlight contradictions in his earlier statements.
Still, Phillip stuck to his story — describing Diddy’s bizarre behavior and the transactional nature of the “Freak Off” encounters.
The Trial Continues: More Shocking Details Surface
As the trial moves into its next phases, more disturbing details are emerging.
Prosecutors allege Diddy once stomped a woman’s head, dangled someone from a balcony, and even tried to set a car on fire.
Security footage from a 2016 hotel incident — allegedly showing Diddy assaulting Cassie — has been played multiple times in court.
Witnesses said Cassie looked terrified, huddled in a corner with her hoodie pulled up.
The Jury: Who Will Decide Diddy’s Fate?
Twelve jurors — eight men and four women — are now hearing the case.
They come from a range of racial backgrounds, with six alternates ready to step in if needed.
Their verdict will determine whether one of hip-hop’s most influential figures walks free — or goes down in one of the most high-profile trials in recent memory.
Prosecutors Say Diddy Tried to Tamper from Behind Bars
And finally, federal prosecutors claim Diddy attempted to interfere with witnesses while in custody.
They allege he used jailhouse calls to influence victims and create “narratives” to shape public perception.
Despite his team’s efforts to paint him as misunderstood, the judge refused to release him on bail — citing concerns about obstruction and intimidation.