Why the Sean Combs trial is about more than ‘Diddy vs. Cassie’

Advisory: This report contains descriptions of physical and sexual violence.

Over its first two weeks, the highest-profile witness to testify in the criminal trial of hip-hop tycoon Sean Combs has been his ex-girlfriend, singer and model Cassie Ventura. In often-intense moments on the stand, she told the jury that he raped and abused her. As a result, the media attention and online chatter about this trial so far has frequently been framed as “Diddy vs. Cassie.”

And if people know just one thing about the relationship between Combs and Ventura, it’s probably a widely seen video in which he can be seen attacking her in a California hotel in 2016. Combs was seen kicking and dragging her, and throwing a vase at her — footage that has been key evidence so far for prosecutors arguing that Combs used force and fear as a means of control. (After CNN aired that video in May 2024, Combs published a video apology that has since been removed from social media.)

The government’s case is about much more than just the video.

Because this is a federal trial, with charges of racketeering, sex trafficking and transportation to engage in prostitution — all of which Combs has pleaded not guilty to — the prosecutors have a very particular job.

“What they really need to show from a prosecution perspective is that there was a criminal organization in play here that committed a number of illegal acts over time,” says former prosecutor Jennifer Beidel. She now practices in Michigan as a government investigations and corporate compliance lawyer, used to work in the same federal office that is currently prosecuting Combs: the Southern District of New York.

“So simply finding that Cassie Ventura was the subject of domestic violence, while that’s obviously awful and a very important thing from a state court level, doesn’t satisfy the federal standard,” she says.

What are the charges Combs faces?

In the sex trafficking and transportation to engage in prostitution charges, the government is accusing Combs of coercing women into participating in commercial sex acts with him and with male sex workers. He also allegedly arranged for women and sex workers to be flown to him across state lines. That’s a big part of what Cassie Ventura testified about. She said she felt forced to participate in Combs’ so-called “freak offs,” and that she could not safely leave. Combs’ defense team is arguing that Ventura chose to stay in a toxic relationship. The government’s indictment includes at least one other alleged victim who will testify against Combs under a pseudonym.

Racketeering is the most complicated charge to understand. Jennifer Beidel says back in the day, the feds used to use racketeering charges — also known as RICO — to fight organized crime.

“RICO is traditionally a statute that was designed to prosecute the mob and other organizations that were essentially hiding their conduct through legitimate organizations,” Beidel says. “RICO over time has been applied more broadly. Mob prosecutions were pretty effective, at least in New York, for example, and there aren’t as many today. So it’s expanded into other areas where you might have an otherwise legitimate business that is also engaged in criminal misconduct, and maybe using that legitimate business to hide that criminal misconduct.”

Prosecutors are arguing that while Sean Combs had a legitimate business empire — spanning music, clothing brands, alcohol and media properties — he was using those businesses to fuel and hide criminal activities. Think of this charge as being like money laundering, but instead of money, Combs is accused of laundering actions. According to the federal indictment, those included kidnapping, arson, bribery, forced labor and abusing and coercing women. The other government witnesses who have testified about those alleged activities include the musician Scott Mescudi — better known as Kid Cudi — who said on the stand Thursday that he believes that Combs broke into his house and was involved in setting fire to his car after finding out that Mescudi and Ventura had been dating.

Cassie Ventura’s story is still at the center of the prosecution’s case

Beidel says the prosecution might have had no choice but to present Cassie Ventura as a witness very early on — she’s eight and a half months pregnant. But it may have a broader strategic benefit as well, since Ventura was involved with Combs for over a decade.

“Ventura covers a pretty long time frame and wide range of conduct,” Beidel explains. “Somebody who testifies in that way is much more understandable to a jury than when you put on maybe 10 witnesses for the same amount of time, when each of them has one little nugget, and the jury has to put that together. So you have sort of a narrator to start out with where they’re getting the story in their head to some degree.”

The Southern District of New York has an extremely high success rate for convictions — well above 90%. The jury has seen and heard evidence including the hotel video, that is viscerally affecting. But with charges as broad as the ones aimed at Combs, a big question remains: Will the prosecution be able to convince jurors that he was the head of a criminal organization? The court estimates that the trial will continue until late June at least.

This story includes reporting by Isabella Gomez Sarmiento.