It is not just Sean “Diddy” Combs’ legacy that is on the line, it is the entire myth of the mogul himself. The 55-year-old music titan, once untouchable in hip-hop circles, is now facing the music in federal court as his ex-girlfriend, singer Cassie Ventura, lays bare more than a decade of alleged abuse, manipulation, and psychological control.

Cassie Ventura and Diddy | Credit: X

On 15 May, Cassie returned to the Manhattan courtroom for a heated cross-examination, following two days of emotionally charged testimony about her time with Combs. His legal team tried to flip the script, painting her as a willing participant and, at times, the aggressor in their volatile relationship.

Awkward moment Cassie name-drops Whitney Houston, quips at Diddy lawyer when asked ... - https://t.co/2OGn7BFxDG #GoogleAlerts

— MOIZ ESUFALLY (@moizesufally) May 16, 2025

But Ventura did not flinch. When shown early emails and texts where she professed love and craved his attention, she told jurors that she genuinely cared for Combs at the time. Her message? This was not about bitterness, it was about survival.

Among the most jaw-dropping revelations? Cassie said Combs overdosed on painkillers after a wild night in February 2012. She claimed it happened shortly after they left a sex club and before he threw a party at the Playboy Mansion a partu she skipped. According to her, he overdosed alone, and she had to rush him to the hospital.

Then there were the “freak offs” — the now-infamous term used to describe drug-fuelled sexual encounters allegedly orchestrated by Combs. Cassie claimed they were not optional but expected. She described them as a disturbing part of her reality, something she called a “job.”

Ventura also spoke about their mutual drug use, saying they would often call each other “get-high partners.” However, she added that Combs grew hostile if he found out she was using drugs with anyone else. His reaction, she said, could turn explosive.

During testimony, she also referenced an alleged incident involving Suge Knight, where she initially said she had stayed home while Combs went to confront Knight. The defence pointed out a previous statement where she said she was in the car, crying. Cassie responded that it may have been a misunderstanding, standing by her memory.

When questioned about her brief relationship with Kid Cudi, Cassie admitted she had to use a burner phone to hide the romance from Combs, fearing his temper. “It would have been too dangerous to tell him,” she told the court.

"Cassie Told Diddy She Was 'Always Ready' for Freak-Offs, Messages Show"
https://t.co/PmNsApB48W

— HM HR RHONDA SUZANNE BELCHER (@hm_suzanne) May 16, 2025

Oh, and Michael B. Jordan? Cassie confirmed Combs suspected a connection between her and the actor post-breakup, and although she was not around to witness his reaction, she noted that he had tried to contact her afterwards.

Cassie also acknowledged feelings of jealousy toward Kim Porter, Combs’ long-time former partner and mother of four of his children. Defence attorneys presented texts from Cassie in which she admitted feeling like a “side piece” around the holidays.

The courtroom took a dramatic turn when Combs' team questioned her about the fallout of her 2023 lawsuit, asking if she realised what it did to his career. Cassie responded carefully, saying, “That’s a lot.” No further explanation needed.

As this trial barrels forward, the lines between celebrity, power, and accountability are getting blurrier by the day. But one thing’s clear: this is not just a court case, it is a reckoning.