Facing decades behind bars after New York conviction, will R. Kelly ever stand trial in Chicago?

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R. Kelly appears during a 2019 hearing at the Leighton Criminal Courthouse in Chicago. - Antonio Perez / Chicago Tribune/Chicago Tribune/TNS

CHICAGO — A jury in New York has found R. Kelly guilty of racketeering and other federal charges, but the 20-year legal saga surrounding the disgraced R&B star is far from over.

With Kelly’s sentencing hearing more than seven months away, attention now swings back to his hometown of Chicago, where he faces five more indictments in both federal court and Cook County stemming from alleged sexual abuse.

But with Kelly already facing decades in prison, is it possible he may never go to trial in a Chicago courtroom at all?

What comes next depends on a lot of moving parts and behind-the-scenes maneuvering by prosecutors and the singer’s legal team — which itself has been in flux.

Among the possibilities: Kelly rolls the dice and goes to trial on a case that could add years of federal prison time; he works out a deal to plead guilty to some or all of the charges in exchange for leniency; or prosecutors maneuver to use some of the evidence against Kelly in Chicago to enhance his sentence in the New York case, rather than put him on trial again.

Adding to the complexity is that two of Kelly’s longtime associates, Derrel McDavid and Milton “June” Brown, are also charged in the Chicago federal indictment, so any deal struck by Kelly would not dispose of the case entirely.

There is also significant overlap between the allegations in the federal and county indictments that could lead to questions of double-jeopardy.

For example, Kelly’s most serious county charges — aggravated criminal sexual assault — relate to the alleged abuse of Jerhonda Johnson Pace, who was also a key witness for federal prosecutors in the New York trial.

Whatever happens, it’s clear the Cook County allegations are on the back burner for now. In an interview with the Chicago Tribune on Monday, State’s Attorney Kim Foxx said her office had agreed to stay in a “pretrial phase” with its cases as the federal matters play out.

Any decision about how to proceed with the county cases will be made in consultation with the victims, Foxx said.

“We will continue to work with the victims of our alleged crimes here in Cook County to determine what is the best course of action,” she said.

To begin sorting it all out, U.S. District Judge Harry Leinenweber is scheduled to hold a status hearing on Kelly’s federal case in Chicago later this month. The judge ordered that arrangements be made for Kelly to appear via a video link from the federal jail facility in Brooklyn, rather than by telephone.

The singer also has a decision to make about his legal team, which underwent a dramatic shake-up in the weeks leading up to the New York trial when Kelly gave Chicago-based attorneys Steve Greenberg and Michael Leonard the boot in favor of a far less-experienced group.

Greenberg and Leonard are still the attorneys of record for Kelly in Chicago, however. Greenberg told the Tribune this week that if prosecutors want to proceed on the remaining cases, “We’re going to be ready to defend them.”

Leonard said Friday it made little sense to rush anything without knowing what Kelly’s sentence will be in New York. If Kelly’s co-defendants demand a quick trial, the judge could decide to sever Kelly from the case and have a separate trial for the associates.

“There is a lot still up in the air in terms of the direction of the case,” Leonard said.

Kelly attorneys Deveraux Cannick and Nicole Blank Becker could not be reached Friday. Prosecutors in both Chicago and Brooklyn have declined to comment.

If the Chicago federal case does go to trial, it will likely focus on graphic videotapes Kelly allegedly made depicting him having sex with at least three girls when they were minors, court records show.

The 13-count indictment alleged that Kelly, both on his own and through associates, paid hundreds of thousands of dollars in cash, gifts and legal settlements to try to buy up copies of the sex tapes before they could get in the hands of investigators.

One of those tapes, which allegedly shows Kelly having sex with his 14-year-old goddaughter, was at the center of child pornography charges against Kelly two decades ago. But the girl at the time refused to testify, leading to a stunning acquittal by a Cook County jury in 2008.

The girl, identified in the charges as Minor 1, is now cooperating with federal investigators and is expected to be one of the key witnesses against Kelly should that case go to trial. She also is the alleged victim in one of the four sexual abuse indictments filed against Kelly in Cook County in 2019.

According to the federal indictment, Kelly and his associates ran a yearslong scheme to hide the abuse of Minor 1, including flying her parents out of the country to keep investigators from interviewing them and later making payments to her and her family to induce them to lie about the abuse to a grand jury.

The payments, gifts, and other benefits continued even well after Kelly’s 2008 acquittal, according to the indictment. As recently as October 2015, Kelly was still making monthly payments to Minor 1 through his businesses, often using the word “SETTLEMENT” in the transaction line, according to the indictment.

The lead charge in the indictment, producing child pornography, carries a mandatory minimum sentence of 10 years in prison and a maximum of 20 years behind bars.

Legal experts who spoke to the Tribune said that given the resources that went into the Chicago federal investigation, it’s highly unlikely prosecutors would walk away from the case just because Kelly stands convicted in New York.

But it also might make sense to work out a deal rather than sit a jury for another lengthy trial, particularly in light of the ongoing pandemic. What’s more, any sentence Kelly receives in Chicago could be ordered served concurrently with his New York case, and that sentence could be lengthy regardless of what happens in Chicago.

There have been even more creative resolutions to high-profile cases in Chicago. In 2018, for example, a Hillside man accused of attempting to detonate a car bomb in Chicago was convicted under what’s known as an Alford plea, a rarely used legal arrangement in which he acknowledged prosecutors have enough evidence to convict him but did not admit wrongdoing.

The move allowed Adel Daoud to resolve three separate indictments against him simultaneously, including separate charges alleging he tried to hire a hit man to kill an FBI agent and later attacked his cellmate with a knife in Chicago’s federal jail.

It also turned Daoud’s sentencing hearing into a mini-trial, with both sides calling witnesses to air out evidence before a judge that would have been presented to a jury.

Unlike Daoud, however, Kelly is facing charges in three jurisdictions.

Like the case in New York, the charges in Chicago and Cook County grew out of the Lifetime docuseries “Surviving R. Kelly,” which aired in early 2019 and highlighted the allegations against him on a nationwide scale.

In a highly unusual news conference after the series aired, Foxx made a public call for Kelly’s accusers to come forward, saying she was “sickened” by the allegations in the series. Their phone lines were flooded with tips after Foxx’s plea for cooperation, her office said at the time.

Less than two months later, Foxx announced that a grand jury had indicted Kelly four times over. He had sexually abused four people, prosecutors said, three of whom were underage at the time of the assaults.

The cases made blockbuster headlines and brought Kelly back to the Leighton Criminal Court Building for the first time since his acquittal in 2008.

But those cases were overshadowed a few months later, when federal agents arrested Kelly as he walked his dog outside the Trump Tower in downtown Chicago.

Foxx, meanwhile, told the Tribune she has been struck by the “incredible bravery” of the victims who have testified so far against Kelly.

“I think many people believed there would be no justice to the stories that surfaced again ... that seemed for many to be open and notorious behavior without consequence,” she said.

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(Chicago Tribune’s Megan Crepeau contributed to this story.)

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