Entertainment / Sean Combs Diddy's Jurors Have One Main Question to Answer Was his entourage actually a 'criminal enterprise?' Jury selection starts Monday By John Johnson Posted May 5, 2025 6:20 AM CDT Copied Sean Combs arrives at the Beverly Hilton Hotel on Saturday, Jan. 25, 2020, in Beverly Hills, Calif. (Photo by Mark Von Holden/Invision/AP, File) See 1 more photo Jury selection starts Monday in the trial that could determine whether Sean "Diddy" Combs spends the rest of his life in prison. What's ahead: Criminal enterprise? The 55-year-old isn't merely accused of sexually abusing multiple victims over the years, he's accused of using his vast operation to facilitate that abuse. A key question for the jury to decide is whether he ran a "celebrity entourage" or a "criminal enterprise," as the New York Times explains. Racketeering: The above is why charges against Combs include not just sex trafficking but racketeering conspiracy—and why the exhaustive indictment against him reads like one that might refer to a Mafia boss, notes the AP. One difference might be the "freak offs," described as marathon, drug-fueled orgies in which women were allegedly coerced into sex acts with male sex workers. The charges also include transporting individuals over state lines for prostitution. Key witness: At least four victims identified by federal prosecutors are expected to testify, reports CNN. The crucial one is expected to be Cassie Ventura, a former girlfriend. Combs publicly apologized after video surfaced of him physically assaulting her in 2016. Trial: It's expected to last eight to 10 weeks. Combs has pleaded not guilty and has rejected a plea deal for a lesser sentence. (More Sean Combs stories.) See 1 more photo Report an error