Sean “Diddy” Combs is currently incarcerated in Brooklyn’s Metropolitan Detention Center, awaiting trial on racketeering conspiracy, sex trafficking, and interstate transportation to engage in prostitution charges. The beleaguered mogul is facing 15 years to life in federal prison for allegedly heading a criminal enterprise of people who enabled him to drug and coerce women to participate in sex sessions he called “Freak Offs” with male sex workers he procured. His bail was denied twice, with New York’s Southern District citing his repeated witness tampering attempts. (His next court appearance is a Sept. 24th conference hearing.)
According to several criminal defense lawyers and other legal experts, SDNY prosecutors have a strong case against Combs based on considerable physical evidence and numerous witnesses set to testify about his alleged harm. They also expressed that Combs being the sole person arrested from his alleged enterprise hints at the possibility of his co-conspirators testifying against him.
Rolling Stone spoke to former federal prosecutors and legal experts who echoed SDNY lawyers’ comparison of Combs’ RICO case to singer R. Kelly’s federal trial. In 2022, Kelly was sentenced to 30 years for racketeering predicated on criminal conduct, including sexual exploitation of children, forced labor, and Mann Act violations involving the coercion and transportation of women and girls in interstate commerce to engage in illegal sexual activity. He still faces sex crime charges in Illinois and Minnesota. During Combs’ second bail hearing, a federal prosecutor noted that Kelly “was detained on all three grounds: Danger, obstruction, and risk of flight. Like this case, there was a pattern of obstruction that had occurred, and like this case, the sexual abuse that was alleged was violent and repeated.“ When Kelly’s indictment was unsealed in EDNY, it had five Jane Does. During Combs’ first detention hearing, his defense divulged that they were bracing for 12 victims, including potential Jane Does.
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During a Tuesday afternoon press conference, US Attorney Damian Williams told the press that they’re still investigating Combs in a case that attorney and former federal prosecutor Neama Rahmani tells Rolling Stone is already “strong.” “You’re talking about sex acts and sex trafficking involving force and duress,” he says.“ We have the Cassie Ventura video that was discussed in the indictment. Damian Williams spent a lot of time talking about [the seized “Freak Off” videos]. There’s also allegations that [Combs] tried to use force, drug these sex workers, [and] tried to dissuade them from testifying and coming forward.”
The indictment alleges that Combs’ criminal enterprise consisted of his business entities as well as employees and associates who helped facilitate his coercive sex sessions and keep women ensnared by Combs for a period beginning in 2008.
Kenya Davis, a partner with Boies Schiller Flexner LLP and former Assistant U.S. Attorney, says that the Southern District’s choice to construct the case as a racketeering organization allows them to efficiently lay out the full scope of the network’s alleged misdeeds. Her firm currently represents journalist and former record executive Drew Dixon, who filed a sexual assault and harassment suit against music executive L.A. Reid and a defamation suit against Russell Simmons. (The firm also represents a Jane Doe who filed a separate sexual assault suit against Russell Simmons). All three cases are open; Reid and Simmons have denied all allegations.
“You’re seeing more of these kinds of cases get a RICO charge on top of it because there are so many different elements that are at play that we can’t capture with one single count of trafficking or transportation,” she says, noting the complex network of people who allegedly enabled Combs’ behavior. She adds that Combs’ status as a music executive adds a distinct wrinkle to the alleged enterprise: “The fact that he [allegedly] ties the record deals or the release of one’s records, in the case of Cassie, to their participation in these sex acts [is a unique element of this case]. [As a victim], you really are having to decide whether or not you’re going to participate, and he’s able to hold that over your head.” Cassie’s November 2023 civil complaint alleges that after escaping Combs’ grasp, Bad Boy Management President James Cruz “tracked” her down and “told her that her single would not be released if she did not answer Mr. Combs’s phone calls.”
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Lauren Hersh is the head of the advocacy organization World Without Exploitation and a former prosecutor who served as Chief of Brooklyn’s Sex Trafficking Unit. She says that when it comes to Combs and Kelly’s cases, “the principles are really the same. You have a person who has tremendous power, tremendous access, and the ability to prey on vulnerable people.”
Davis says, ”You’re seeing a lot of the same elements in terms of coercion, the use of a recording career as a potential way to motivate people to participate, [as well as] having personnel around [as] bodyguards and the like to help the enterprise along because nobody can do this by themselves.” She also observes that both cases evoke the Mann Act, which she calls a “low-hanging fruit” of a charge because “all you have to show there is transportation for the purposes of some illicit sexual act.”
The US Attorney’s office successfully pushed to deny Combs bail. On Tuesday, they deemed him a “dangerous” flight risk who “poses an ongoing threat to the safety of the community.” During his initial bond hearing and subsequent appeal, Southern District attorneys revealed that Combs repeatedly reached out to victims and witnesses in the case: he contacted one witness 14 times, called another and recorded it on an accomplice’s device, and contacted Diddy-Dirty Money singer Kalenna Harper 58 times after their former groupmate Dawn Richards filed a civil suit against him on Sept. 10th. Soon after, Harper made a public statement asserting, “While I fully respect Dawn’s right to recount her experiences, I want to emphasize that her account reflects her personal perspective and should not be interpreted as a universal truth applicable to everyone involved.”
Davis says that Combs contacting witnesses “hit my heart as a former prosecutor” because “when you’re dealing with someone who’s powerful, people are reluctant to be a part of these cases. They don’t want to participate. And the control comes from this level of influence.” She adds, “It represents for us who do this work a consciousness of guilt. Why are you calling somebody 50 times if you didn’t do anything? If they say something about you that’s not true, you can claim defamation.”
The end of the Combs indictment contains a “forfeiture” section. While some readers speculated that it meant Combs’ bank accounts and assets had been immediately frozen, Rahmani clarifies that this isn’t the case, and the section is meant to reveal the prosecution’s desire to seize any assets that they can prove funded his criminal enterprise. Davis says that there are two reasons that prosecutors seek forfeiture: to keep a defendant from giving away the proceeds of their enterprise to other people and to reroute the funds for potential restitution to victims.
But both Rahmani and Davis say Combs’ vast portfolio of business interests would make it difficult to trace the funds or how he potentially profited from his enterprise. “Was he able to get albums out of people and not pay a fair price for them because he had tapes to blackmail them with?” Davis asks. “We don’t know how he was able to use the enterprise to get these proceeds.”
During the U.S. Attorney’s press conference, Williams was coy about several aspects of the investigation and told reporters, “I’m not taking anything off the table” with regard to further charges. Rahmani says that he feels Williams’ call for “anyone with information to come forward” may encourage more potential witnesses to reach out to prosecutors. “Every month, it seems like we’re getting a new lawsuit,” Rahmani says. “So those people that maybe were hesitant to come forward…I wouldn’t be surprised if we start hearing more, especially now that criminal charges have been filed.” During Combs’ second bail hearing, Judge Andrew Carter revealed that the court had begun receiving calls from potential witnesses after the mogul’s arrest.
Some have speculated on why the six weapons Homeland Security retrieved during their raids of Combs’ homes (including three AR-15s with scratched serial numbers) weren’t charged in the indictment. Elizabeth Geddes, a former federal prosecutor in Brooklyn who delivered the closing arguments in the EDNY R. Kelly trial, explains that those weapons are out of the Southern District’s jurisdiction. “Possession of a defaced weapon, while that can be a federal crime, and they could have charged that federally if it happened in their district, it is not a predicate racketeering act, so they could not have charged it as part of the racketeering case,” Geddes says. “Not all federal crimes can be included as racketeering acts. It’s a pretty limited number of crimes, and weapons possession is not among them.”
Geddes also says that she found it “a little surprising” that the Combs indictment didn’t “more specifically describe other victims.” She notes that SDNY prosecutors crafted their case to resemble a “Glecier-format” RICO conspiracy, a more succinct indictment that allows them to withhold certain case details and has the benefit of affording more protection to witnesses. “By proceeding that way, they don’t have to list out every single different predicate racketeering act that they’re planning to prove up at trial. They can just list broad categories of crimes [without] alleging the particular instances, or the particular victims,” she said. This “gives confidence to their witnesses, and future witnesses,” that they’ll be protected.
Davis says that Combs’ alleged obstruction of justice may have caused the prosecution to come forward before they had finished their grand jury testimony and gotten sufficient evidence for certain charges. She also contends that other people mentioned in the indictment as part of Combs’ alleged criminal enterprise may be in the process of cooperating against him. “What you’re going to see is a lot of cooperating witnesses, either people who have come in and rolled over or people who have decided to cooperate with the government as they start to think about their own exposure and liability in the case.”
The prosecution can add additional charges in a later superseding indictment, and they also have the latitude to offer Combs a plea deal for the existing charges and inform him that they will add in other charges if he refuses the deal.
And as the case sprawls, it could rope in more defendants. Rahmani says that “Diddy’s parties were the worst kept secret,” and there’s a possibility that other prominent people may be held to account if they were involved in his sex acts. “Unfortunately, rich and powerful men taking advantage of women [is] something that’s far too common,” he says. “If I participated in the sex acts, I would be especially concerned. That judgment day may be coming.”
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Both Hersh and Davis agree that the Combs case could represent a reckoning for the entertainment world. Davis says that the industry as a whole needs to be more accountable in calling out their peers. “I hear people say stuff like, ‘I was around. I saw a black eye. I saw this, I saw that.’ But you didn’t say anything. And now you want to tell your story and maybe even profit from it,” she laments. “This does not have to be a defining part of our culture for hip-hop or for Black people. It’s not how the majority of us operate in this world. There are plenty of artists who have had nothing to do with this kind of stuff, and they’ve been successful. So this notion that you have to pay this price in order to be a part of the industry…I pray that that notion ends with a case like this.”
Hersh says that “when powerful people operate with complete impunity, they tend to prey on our most marginalized.” But she also notes that “we are finally at the moment where there is accountability for really powerful people. And we’re also in a moment where, although the powerful people have long told victims that they will not be believed, society and the justice system is saying, ‘I believe you.’ I think that’s very powerful.”
