How will R. Kelly’s Chicago cases proceed after New York sentence?

The charges against R. Kelly came down like an avalanche: First, four indictments in Cook County. Another in Minnesota. Then a one-two punch of federal cases in Chicago and Brooklyn.

Three years later, the Chicago native, reputed sexual predator, and R&B legend received his first prison sentence: 30 years, handed down Wednesday in the New York case.

Soon enough, Kelly will be back in a federal jail in his hometown, with decisions to make about how to proceed on his other cases. The kind of hard time he got in New York could well change the calculus on how his lawyers and prosecutors in Chicago proceed.

“The law is like physics, for every action there’s a reaction,” said attorney Steve Greenberg, who represents Kelly in his Cook County cases. “And only the individual can decide what their risk tolerance is or what consequence they’re willing to stomach.”

Kelly is slated for trial in Chicago’s federal court in August on charges related to child pornography and obstructing justice. But given that he could be behind bars for decades anyway, attorneys might be more inclined to strike a plea deal, averting at the last minute the stress and public spectacle of a second trial — particularly if the deal included an agreement that his sentences in the New York and Chicago cases would run concurrently, multiple legal experts told the Tribune.

“On the other hand, some people would say that from Kelly’s perspective, there’s no downside to going to trial now. He basically got a life sentence and if that sticks, it’s not like he’s getting any more time,” Greenberg said.

Prosecutors in Chicago may also be eager to secure a conviction for Kelly as a backup, in case he successfully appeals his New York case, former federal prosecutor Steven Block told the Tribune.

“It would ensure that he remains incarcerated,” Block said, noting also that the New York case involves different victims than the Chicago indictment.

“The prosecutors are likely thinking about this case as vindicating the rights of victims who are not part of the New York case, and that is probably a very compelling reason for them to proceed,” he said.

Greenberg also said that the possibility of a successful New York appeal would probably factor in to any deal that Chicago prosecutors would be willing to strike.

“If (prosecutors) make an offer, it’s going to be a number where they feel if this was the only case, it’s enough time,” Greenberg said.

Any plea would require Kelly to publicly admit wrongdoing, Block noted, which he might not be inclined to do.

“We’ve seen nothing at all to indicate he’s prepared to accept any responsibility or take a plea,” Block said. “He’d have to be prepared to get up n court and admit to the conduct that he’s charged with. He’s given no indication that that’s something he’s interested in doing.”

Kelly was convicted last year in Brooklyn federal court on racketeering charges that accused him of using his stratospheric fame to lure in vulnerable victims and sexually abuse them. Kelly’s team has vowed to appeal, saying the government overstretched when they charged him under the RICO act.

The Chicago federal indictment, while not as sprawling as the New York case, includes mention of potentially damning evidence: Multiple videos depicting Kelly having sex with an underage girl.

He also taped himself during sexual acts with two other minors, and had sexual contact with two more, the indictment alleges. When police and a Cook County grand jury began to investigate, Kelly and his collaborators paid off witnesses, schemed to buy back the videotapes, and persuaded one girl and her father to lie to authorities, according to the charges.

While Cook County prosecutors brought him to trial for child pornography in 2008, the allegedly underage girl on the video did not testify, and Kelly was acquitted.

If Kelly’s August trial in fact takes place, it is expected to reveal further details about the way the first Cook County case against him was put together, allegedly sabotaged, then fell apart.

Complicating matters, Kelly’s Chicago federal case also charges two of his former associates, Derrel McDavid and Milton “June” Brown, who may want to take the case to trial regardless of what happens to their famous co-defendant.

Meanwhile, the Cook County cases have largely been put on hold. State’s Attorney Kim Foxx’s office was the first to charge Kelly in the most recent wave of court cases, hitting him with four indictments for sexual abuse in 2019. One of the cases was later upgraded to more serious sexual assault charges.

But a few months later, Kelly was hit with the federal indictments. Foxx has said her office agreed to keep the case in a pretrial posture while the federal cases move forward. Kelly’s attorney has moved to dismiss one of the indictments, saying it violates Kelly’s right to double jeopardy since it charges some of the same conduct for which he was convicted in New York. That request has been pending for months.

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Regardless of what happens in the remainder of Kelly’s cases, one thing is almost certain: His devoted fan base will stick by his side. In person and online, his supporters

One of those avid fans, Christopher Gunn, appeared in federal court Friday after being charged with threatening the New York prosecutors who handled Kelly’s case. Among other alleged threats, a video on his YouTube channel featured a photo of the U.S. Attorney’s office in Brooklyn, and he told his viewers to “get real familiar with this building” because “If Kellz goes down, everybody’s going down,” according to the charges.

“On Wednesday, Kellz, or R. Kelly, went down,” Assistant U.S. Attorney Peter Madrinian said in court, arguing that Gunn would be a danger to the public if released. “The defendant said what he would do if that happened.”

Gunn’s attorney noted that he was not arrested for months after the video was posted, and there was no evidence of a weapon or ammunition when he was taken in.

Ultimately, Kim ordered Gunn released to home detention, but Madrinian said prosecutors in New York would want to appeal that order in an effort to keep Gunn in custody.

mcrepeau@chicagotribune.com

jmeisner@chicagotribune.com