Sean ‘Diddy’ Combs’ assistant testifies about how rapper viewed ex Cassie Ventura

Sean “Diddy” Combs former personal assistant pulled back the curtain on the music mogul’s long-term relationship with singer Casandra “Cassie” Ventura — and what was allegedly happening.

According to James, who spent years with Combs during his peak Bad Boy Records days, the public romance between Combs and Ventura might not have been as nice as it seemed. 

During a drive through Manhattan in an Escalade, James recalled a conversation where Combs spoke fondly of Kim Porter, the mother of four of his children, calling her, “Kim is doing good, that’s my queen.”

But when it came to Ventura, who started dating Combs at 19 and became his musical protégé, the tone allegedly shifted. James testified that Combs described her as “moldable,” and reportedly said, “Got her right where I wanted her — she’s young.”

That comment landed hard in the courtroom, but James wasn’t done. 

He described a moment in 2007 when he, Ventura, and her then-best friend, model Kerry Morgan, were taking a cigarette break outside Combs’ Miami mansion. According to him, Ventura looked around and said, “Man, this lifestyle is crazy?”

That was the moment James said he asked her a simple but loaded question, why not leave?

Her response? “I can’t get out,” James recalled. “Mr. Combs oversees so much of my life.”

The assistant went on to testify that Combs not only controlled Ventura’s career but also her bank account. “He paid for her apartment,” James said. “He also gave her an allowance.”

James is now the third witness to testify in the second week of the high-profile trial, which has gripped the music industry and made national headlines. 

Combs was arrested in September 2024 and currently faces charges of racketeering, sex trafficking, and transportation to engage in prostitution. He has pleaded not guilty to all charges.