Sean "Diddy" Combs Trial: Cassie Ventura Faces Cross-Examination

The high-profile trial of Sean "Diddy" Combs continues today with Cassie Ventura returning to court for cross-examination by Diddy's legal team. Yesterday marked the fourth day of proceedings, where Ventura, Combs' former partner of 10 years, continued her testimony against the hip-hop mogul.

During yesterday's court session, Ventura testified about a 2016 attack at a Los Angeles hotel, which was captured on CCTV and played in court. She described how Combs threw a vase at her, leaving her with a black eye and fat lip. She also testified that Combs told her to hide her injuries from his son.

Perhaps most shocking was Ventura's testimony about what she called "freak offs" - sessions where she claimed Combs paid male escorts up to $6,000 to have sex with her while he watched. She identified several of these men by name and stated that these encounters occurred "hundreds of times," with drugs being present at all of them.

The 55-year-old Combs has pleaded not guilty to charges of sex trafficking, racketeering conspiracy, and transportation to engage in prostitution. He has remained jailed in Brooklyn since his September arrest and faces a minimum of 15 years to life in prison if convicted.

This trial comes at a critical time for Combs' business empire, estimated to be worth around $1 billion. His flagship Ciroc vodka brand has reportedly seen sales plummet 32% year-on-year in 2025, while Bad Boy Records' catalog value has collapsed to just 10% of its peak worth.

Combs built his fortune through strategic investments in music, fashion, beverages, and media. His business portfolio includes partnerships with Diageo for Ciroc vodka and DeLeón tequila, and he recently moved to establish what could become the country's largest Black-owned licensed cannabis company in a deal worth up to $185 million.

The trial is expected to continue through mid-July, with a verdict potentially reshaping the future of Combs' business ventures and legacy in entertainment.