Diddy Trial: Everything You Need to Know — From RICO Charges to Cassie Tape to ‘Freak Offs’

Sean “Diddy” Combs is about to go on trial over accusations of sexual abuse. But what exactly are the charges he’s facing? Is Cassie Ventura testifying against him? And what in the world are “freak offs”? Before the trial starts, let’s get you up to speed.

The once-all-powerful hip-hop mogul was arrested in September, charged by federal prosecutors with running a large-scale criminal operation aimed at his own “sexual gratification.” For decades, the feds say, Diddy “abused, threatened and coerced women” into giving him what he wanted, including participating in drug-fueled sex parties.

Combs, who has denied all of the allegations, will finally head to trial next week to face a jury of his peers. Before he does, here are answers to all your Diddy trial questions.

What are the charges against Diddy?

Prosecutors have built much of the case against Diddy under the Racketeer Influenced and Corrupt Organizations Act, the “RICO” law used against mobsters and drug cartels. RICO, which allows the feds to target an entire illicit organization over many individual crimes, was designed to target organized crime, where bosses often insulate themselves from actual illegal acts.

In Diddy’s case, prosecutors say the star served as his own kind of crime boss, exploiting the “employees, resources and the influence of his multi-faceted business empire” to carry out a decades-long campaign of sexual abuse. That operation included numerous sexual and physical assaults, the feds say, but also forced labor, kidnapping, arson, bribery, witness tampering, drug crimes and more.

Separately, Diddy is also charged with violating a federal sex trafficking statute, which makes it illegal to use force, fraud, or coercion to compel someone to engage in commercial sex acts. He’s also accused of violating the Mann Act, an older statute that made it illegal to transport people across state lines for the purposes of prostitution.

What’s a “freak off”?

At the very center of the case against Diddy are allegations about so-called “freak offs” — drug-fueled orgies in which victims were allegedly coerced into having sex with male sex workers while Combs looked on.

Prosecutors say these “elaborate and produced sex performances,” which Combs “masturbated during,” were a regular occurrence and “sometimes lasted multiple days.” The rapper and his associates allegedly plied victims with illegal drugs, which prosecutors say was designed in part to “keep the victims obedient and compliant.”

According to charging documents, freak offs were “often electronically recorded,” sometimes without the knowledge of those being filmed — and the footage was then later used as a form of “collateral” to keep victims from speaking out.

The events were so complex that they required substantial logistical efforts by Diddy’s associates to pull off, the feds say — including booking hotel rooms, arranging travel, delivering large sums of cash to pay sex workers, cleaning up to “mitigate room damage,” and providing supplies. Among those supplies were “more than 1000 bottles of baby oil” — a headline-grabbing allegation when it was included in September’s initial indictment.

Who are the alleged victims?

Diddy has been hit with civil lawsuits by dozens of alleged victims, but the criminal charges against him formally center on just four people, identified in court documents as Victim-1, Victim-2, Victim-3 and Victim-4.

While technically still anonymous in filings, Victim-1 is strongly believed to be Cassie Ventura, Combs’ longtime girlfriend whose civil rape lawsuit in November 2023 helped to spark the rapper’s downfall. Prosecutors have said Victim-1 will testify in the courtroom under her real name, setting the stage for a potentially blockbuster moment at the trial.

The identities of the other three victims remain unknown, and prosecutors have sought to keep it that way. In a motion last month, they cited recent cases against R. Kelly, Ghislaine Maxwell and others in which judges allowed alleged victims to remain anonymous to avoid “harassment from the media and others” amid a case that has received an “exceptional amount of media coverage.”

At a hearing last week, the judge ruled that the three other victims could testify without revealing their names.

Who are the key players in the courtroom?

Diddy’s trial will be overseen by U.S. District Judge Arun Subramanian, a relatively new federal judge nominated by President Joe Biden in 2022 after a long stint as a litigator at a prestigious New York law firm. Subramanian, confirmed to the post in March 2023, has an understandably short track record so far — though he is also currently handling the Justice Department’s high-profile antitrust lawsuit against Live Nation and Ticketmaster.

Diddy’s lead attorney is Marc Agnifilo, a veteran defense attorney with an extensive background in handling the kind of complex, high-profile charges that Combs now faces. After prosecuting RICO cases against mobsters in New Jersey, Agnifilo worked for years under legendary New York criminal lawyer Ben Brafman, where he represented Martin Shkreli, the so-called “Pharma Bro” convicted of securities fraud in 2017, and Keith Raniere, the leader of the upstate New York sex cult NXIVM.

Combs is also represented by Teny Geragos, another Brafman alum (and daughter of celebrity attorney Mark Geragos) who joined Agnifilo when he left to start his own firm last year; and Alexandra Shapiro, a well-known appellate law specialist. Brian Steel, a veteran Atlanta defense attorney who rose to fame last year by winning Young Thug’s release from jail on gang charges, joined the team at the last minute last month.

On the prosecution side, the charges against Combs were filed last year by Damian Williams, the top federal prosecutor for Manhattan, who is known for bringing cases against cryptocurrency entrepreneur Sam Bankman-Fried, former U.S. senator Bob Menendez and New York Mayor Eric Adams. Following November’s election, President Donald Trump has since appointed Jay Clayton, a longtime partner at the law firm Sullivan & Cromwell, to fill that post.

Unlike the case against Adams — which was controversially dropped in early April — there has been no indication that Trump or Clayton plan to back away from Combs. The same attorneys under Williams (Meredith Foster, Emily A. Johnson, Christy Slavik, Madison Reddick Smyser and Mitzi Steiner) are all still on board, and the district attorney’s office has since added Maurene Comey — one of the lead prosecutors in the sex trafficking case against Ghislaine Maxwell, a top accomplice of Jeffrey Epstein.

Go read Billboard’s full story on all the lawyers involved in the Diddy litigation.

When does the trial start and how long will it take?

The proceedings will kick off on Monday (May 5) with jury selection. Jurors will be pre-screened with a questionnaire about their backgrounds and beliefs; Combs’ lawyers said in earlier filings that they want to ask their opinions of “people with multiple sexual partners.” After a broader pool is established, the two sides will spar in court over how to pick 12 jurors who can impartially decide the case.

Once a jury is selected, the trial will really get under way on May 12, first with opening statements by both sides, then with witness testimony. The trial is widely expected to last at least eight weeks, though that’s only an estimate. Back in 2021, the trial of R. Kelly — another major musical artist facing RICO charges over allegations of sexual abuse — took six weeks to complete.

How will the prosecution make its case?

If R. Kelly’s trial is any guide, prosecutors are likely to offer jurors mountains of evidence and hours of witness testimony aimed at painting a vivid picture: of an all-powerful man abusing his role at the top of an organization to coerce women into sexual activity against their will.

That will likely include not just the alleged sexual assaults, but all that happened before and after them, including threats, isolation, financial dependence and blackmail. “These are the tools of coercive control,” Nadia Shihata, one of the prosecutors in the Kelly case, told Billboard last year. “In the R. Kelly case, we called it the ‘Predator’s Playbook’.”

In court documents filed early in the case, the feds said they had interviewed more than 50 witnesses during their investigation, “many of whom saw or experienced the defendant’s abuse.” They also said they had pulled evidence from over 120 cellphones, laptops and other electronic devices.

One explosive piece of evidence that jurors will definitely see is the infamous 2016 surveillance video of him assaulting his former girlfriend Cassie Ventura in the hallway of a Los Angeles hotel. Though he initially apologized, Diddy’s lawyers have fought hard to keep it out of the trial, arguing the clip would “unfairly confuse and mislead the jury.” But prosecutors called that a “desperate” attempt to avoid “crushing” evidence, and Subramanian ruled last week that it could be played at the trial.

How will Diddy’s lawyers defend him?

Since the earliest days of the case, Diddy’s lawyers have signaled that they plan to build their narrative around the idea of consent — that the star’s sexual encounters with the alleged victims, while perhaps weird and unseemly, were ultimately still consensual.

At a bail hearing days after Combs was arrested, Agnifilo hinted at that argument, telling the judge that the star and then-girlfriend Cassie had brought sex workers into their relationship because “that was the way these two adults chose to be intimate.” And at a hearing just days ago, Agnifilo suggested that Diddy was a “swinger.”

“There’s a lifestyle called swingers, call it whatever you will, that he was in, that he might have thought was appropriate,” Agnifilo said, according to Reuters. “Part of the reason people think it’s appropriate is because it’s common.”

What happens if Diddy is found guilty?

Short answer: Lots of prison.

If Combs is convicted on the racketeering charge or either of the sex trafficking charges, he’s facing a potential life prison sentence; the trafficking charges alone have a mandatory minimum of 15 years, which would leave Diddy in federal prison until he was 70 years old. The Mann Act charges carry lesser penalties, with a maximum of 10 years in prison.

Recent RICO cases against alleged sex abusers don’t offer a rosy outlook for Diddy. In the R. Kelly case, the singer was sentenced to 31 years; Raniere, the NXIVM cult leader convicted of turning vulnerable women into sexual “slaves,” was sentenced to 120 years.

Even if acquitted on all charges — and court watchers aren’t optimistic — Combs is still facing a rough future. His reputation will be difficult to repair, and much of his once-formidable business empire is already crumbling. He’s also facing dozens of civil lawsuits, where he could still be held liable for monetary damages even if he’s cleared on the criminal charges.