Some of the similarities in the cases brought against Sean “Diddy” Combs this week and Robert Sylvester Kelly several years ago are evident at a glance: Both are world famous, powerful and influential musicians who were accused of sex crimes by federal prosecutors in New York City.

But Combs’ case echoes R. Kelly’s in another way: In each, prosecutors relied on a novel use of the Racketeer Influenced and Corrupt Organizations Act, or RICO, to indict them on allegations of using that power and fame to wield the resources, businesses and people who answered to them to commit crimes – and attempt to cover them up.

“There are certainly parallels in these cases,” said Nadia Shihata, the former federal prosecutor who tried the 2021 case against Kelly in the Eastern District of New York, one of two that sealed the R&B singer’s downfall.

“Obviously the conduct in each case is somewhat different. But there is this idea of a superstar using the employees and entourage at his disposal to facilitate really serious sexual violence crimes,” she told CNN, “and to use coercion and control of victims to coerce them into engaging in sexual activity that they otherwise would not have.”

Kelly is now serving 30 years for the New York case following his conviction on racketeering and sex trafficking charges and 20 years for another case out of the Eastern District of Illinois, where he was convicted on charges of child pornography and enticement of a minor.  Kelly has since appealed both convictions, and in July petitioned the US Supreme Court to overturn his Illinois conviction, claiming the charges should have been barred by the statute of limitations.

Combs, meanwhile, was indicted in the Southern District of New York on three counts: racketeering conspiracy, sex trafficking and transportation to engage in prostitution. He has pleaded not guilty and faces up to life in prison if convicted.

A key distinction between the two is the cases against Kelly involved victims who were underage, whereas Combs has not been accused of wrongdoing against minors – and it’s possible that will evolve into a defense strategy, experts said, wherein Combs’ attorneys argue his purported victims were willing participants.

Regardless, the charges against Combs are “very, very serious charges,” said civil rights attorney and CNN Legal Analyst Areva Martin, which have “an eerie similarity” to those against Kelly in New York – “another music icon, who is now serving a 30-year prison term for very similar allegations that were filed against him in New York and then an ultimate conviction at trial.”

Wielding a business empire

The RICO statute, which dates to 1970, was created to prosecute organized crime that affects interstate commerce. Any racketeering case centers on a so-called “enterprise,” or the group carrying out the alleged misconduct – think, the Mafia.

But the use of RICO to prosecute Kelly was “a pioneering use of the RICO statute against a single individual,” and the Combs case “follows the same legal architecture,” according to CNN’s Chief Law Enforcement and Intelligence Analyst John Miller. He described the strategy as a “creative adjustment to target individuals whose own empires of wealth and companies had been leveraged to allow them to get away with a continuing pattern of serious crimes.”   

“The R. Kelly case, the investigation by (Homeland Security Investigations), the prosecution as a RICO case was an unusual federal prosecution, with an unusual structure,” Miller said. “And it really became a model, not only for the P. Diddy investigation, but likely for the Southern District and how they put this together.”

When the Eastern District of New York indicted Kelly under the RICO Act – the Illinois indictment did not rely on the statute – it placed him at the head of an enterprise made up of the singer and his entourage, including his managers, bodyguards, drivers and personal assistants.

The enterprise’s goal, the EDNY indictment said, was not only to promote Kelly and his music, but to also “recruit women and girls to engage in illegal sexual activity with Kelly.”

Specifically, EDNY prosecutors said Kelly would choose girls and women from the crowds at his concert, and then direct others within the enterprise to bring them backstage. The enterprise would then arrange for the girls and women to visit Kelly, and that’s when the sexual crimes would take place, including the production of child pornography.

Now, across the East River, SDNY prosecutors allege Combs was the leader of his own enterprise, encompassing various businesses and employees, including security and household staff and personal assistants. Some of its aims were legitimate – to promote Combs as a musician and to operate his sprawling business empire, which the indictment says spanned record labels, a studio, a clothing line, a marketing agency and a business for alcoholic spirits.

But the enterprise also engaged in a variety of crimes, like sex trafficking, forced labor, kidnapping, arson, bribery and obstruction of justice, the indictment alleges. And for a decade, Combs “abused, threatened, and coerced women and others around him to fulfill his sexual desires, protect his reputation, and conceal his conduct.”

Combs’ enterprise “enabled” this behavior, the indictment says, by paying off victims, manipulating their career opportunities or obtaining drugs to maintain their compliance. Members of the enterprise also witnessed acts of violence by Combs against the victims, it says. Rather than intervene, they worked to conceal it.

One advantage of a RICO conspiracy is it enables the SDNY to widen the scope of its prosecution, said Neama Rahmani, a former federal prosecutor and the president of West Coast Trial Lawyers.

He pointed to the 2016 caught-on-video attack of Combs’ former girlfriend, Casandra “Cassie” Ventura, which was outside the statute of limitations to be prosecuted when CNN published footage of the attack in May – and for which Combs apologized. It was unclear whether Ventura reported any of the allegations of abuse to police and a federal lawsuit was later settled.

The SDNY’s indictment describes an incident that appears to match the assault, including it as evidence to support the racketeering conspiracy charge.

“You can bring in a lot of conduct as relevant conduct, or predicate acts that aren’t federal,” Rahmani said, adding, “It brings in a lot of evidence, it brings in a lot of crimes – and frankly, it brings in a lot of people.”

It remains to be seen whether anyone else will be indicted in connection with the allegations in the Combs case.

The key distinction

Whereas Kelly’s victims included underage girls, prosecutors in the SDNY have not accused Combs of victimizing minors – a significant divergence in their cases.

The indictment against Combs outlines a number of alleged victims, women and sex workers among them, but does not say how many there are. Combs’ attorney has asserted the case centers on just one victim – the sex trafficking charge is based on allegations involving a single, unnamed victim – while federal prosecutors have insisted there are multiple.

This distinction, the question of consent, could emerge as a key element of Combs’ defense, said Rahmani, describing it as “substantively, the only defense.”

“He’s not going to argue that it didn’t happen, or it was someone else,” Rahmani said. “Obviously, consenting sex between adults is legal, as long as there’s no force, fraud or coercion – that’s what makes it trafficking – or any kind of commercial element – that’s what makes it prostitution.”

“The only chance he has of winning this case is if witnesses testify and jurors believe that it was consensual.”

Miller agreed: Kelly’s underage victims could not give consent, he noted, “whereas the crux of the Combs’ defense is going to be that these were wild parties with willing participants involved in sex, drugs, and hip hop, and that everybody was having a good time until they weren’t.”