How the case against Sean ‘Diddy’ Combs unfolded
“This is Sean Combs. To the public, he was Puff Daddy, or Diddy, a cultural icon, a businessman, larger than life. But there was another side to him…”
The case against Combs started like this. Because millions around the world knew him as the producer, the rapper, the Bad Boy record label founder. A one-time self-made billionaire and flamboyant host of the hottest A-list parties.
Following his arrest last year, he was known by another label – inmate 37452-054 at the infamous Metropolitan Detention Centre in Brooklyn, New York. He has now been found guilty of transportation for prostitution in relation to his former girlfriends, Cassie Ventura and Jane*, along with male sex workers.
Cassie and Jane*, who testified under a pseudonym, alleged they were forced and coerced into these “freak off” sex sessions, but jurors found Combs not guilty of the more serious charges of racketeering and sex trafficking.
He still faces up to 20 years in prison – but not life, which is the sentence those charges carry.
Over seven weeks, jurors tasked with deciding the fate of one of the most influential hip-hop producers of the last 30 years heard testimony from dozens of witnesses who spent time in his orbit, including former employees, police officers, male escorts, hotel staff, and fellow rapper and one-time love rival, Kid Cudi.
They also heard testimony from Cassie Ventura, the woman whose allegations against her former partner arguably lit the touchpaper that led Combs to the criminal courtroom.
In November 2023, just two months after Combs had been handed a “global icon” prize by MTV, and received the ceremonial key to New York by the city’s mayor, Cassie filed a bombshell lawsuit.
In a 35-page document, the singer accused him of coercing and forcing her into drug-fuelled sex sessions with male escorts – now known to anyone who been following the trial as “freak offs” – during the majority of their on-off relationship between 2007 and 2018. He blackmailed her with video footage, she said, violently assaulted her on several occasions, and raped her when she told him she wanted to end things for good.
The lawsuit was settled within 24 hours, for a sum of $20m, it was revealed during his trial. But it wasn’t the end. Four months later, in March 2024, federal agents raided properties belonging to the rapper in Miami and Los Angeles. In May 2024, CNN aired hotel security footage showing Combs punching and kicking Cassie and throwing her to the floor in 2016 – mirroring one of the allegations in her lawsuit.
“I was disgusted when I did it,” Combs said in a public apology video after the CCTV was aired. But this time, there was no denying or getting around what everyone could see in the footage.
‘Diddy was his own hobby’
Rob Shuter, a former publicist for Combs, admits it was an “incredible job” at times, and says the rapper had real charisma – echoing the sentiment of several witnesses who testified.
“There’s something about Puff… He’s one of the most charming people you will ever, ever meet.”
Shuter, from Birmingham, worked with several A-list music artists, but says Combs was his first mega star. He recalls an “absolute workaholic” who would call in the early hours and late at night, and says the Diddy brand was the star’s “own hobby”.
“All he did 24 hours every day, every year,” was think about the brand, he says. “And that’s what made him a superstar.”
Shuter is also candid about seeing excessive drinking and drugs – evidence of which was shown during the trial – and people “being oversexualised”.
Over the last few years, as allegations mounted, Shuter says he has had to reckon with his past. “Did I let things slip because he’s rich and famous and he paid me a lot of money?”
Cassie’s testimony
During the trial, after opening statements, a heavily pregnant Cassie took the stand.
“Within the first year of our relationship, Sean proposed to me this idea, this sexual encounter that he called voyeurism, where he would watch me… have intercourse and sexual activity with a third party, specifically another man.”
During her first day of evidence, she gave graphic details of these drug and drink-fuelled encounters, saying Combs would watch and masturbate, and often film.
Combs abused and degraded her, Cassie alleged, and was “too frequently” violent. He “would mash me in the head, knock me over, drag me, kick me… stomp me in the head if I was down”.
The freak offs could last for hours or even days – the longest for four days, she said. “Freak offs became a job where there was no space to do anything else but to recover and just try to feel normal again.”
But the defence argued that while others might not approve of Combs’s sexual proclivities, they did not make him a criminal. These were private moments never meant to be seen by anyone else, they said, and also argued that the videos showed both Cassie and Jane were happy to take part.
Jurors ultimately agreed that while the crimes amounted to prostitution offences, they did not amount to sex trafficking – or make Combs guilty of racketeering, or creating a criminal enterprise.
Cassie was 19 when she signed to the music mogul’s label, Bad Boy, and 22 when, during the first year of their relationship, Combs first proposed a freak off. She told jurors her “stomach churned” but she wanted to please him at first.
Soon, she found herself trapped with no real career of her own anymore. She said she was fearful of violence, and the consequences should Combs ever release any of the explicit footage.
His lawyers argued this case was about money. But Cassie had already received her civil settlement.
“Cassie has already received her money,” says attorney Lisa Bloom, who represents two accusers who have filed lawsuits against Combs – including singer Dawn Richard, who testified in the criminal trial.
“She [did] not have any financial motivation now to come forward… to testify against him in the criminal case, especially when she was [heavily] pregnant.”
Towards the end of her second day of evidence, Cassie broke down in tears when asked why she had put herself through it. “I can’t carry this anymore,” she told the court. “I can’t carry the shame, the guilt, the way he treated people like they were disposable. What’s right is right, what’s wrong is wrong. I came here to do the right thing.”
The court also heard from Jane, whose allegations were similar to Cassie’s, regarding freak offs – referred to as “hotel nights”, “debauchery” or “wild king nights” with her.
During the trial, explicit footage of freak offs was shown to jurors, but not the media or any members of the public in court. Some looked visibly shocked at what they were watching.
Following the verdict, Diddy fell to his knees. His team claimed it as the “victory of all victories”, despite the two guilty charges. Because although he is guilty of prostitution offences, the more serious charges he has been acquitted of carried potential life sentences. Jurors have given him his life, his lawyer Marc Agnifilo said in court.
His lawyers fought for bail before sentencing, but this was denied by the judge – who cited the defence’s own concessions of Combs’s violent past.
How much time he spends in prison will be determined at sentencing, which is currently set for October. Now, after nine months in prison already, the rapper who was once one of the most powerful men in the music business is facing more time behind bars – but not the life sentence it could have been.