More trials? Consecutive sentences? What’s next for convicted R&B singer R. Kelly

For the second time in less than a year, Chicago-born R&B singer R. Kelly finds himself convicted of serious federal child-sex crimes and staring at a lengthy prison term.

Last September, a jury in New York found him guilty of racketeering conspiracy charges alleging his musical career doubled as a criminal enterprise aimed at satisfying his predatory sexual desires — a case that resulted in a whopping 30-year sentence.

The latest conviction came in U.S. District Court in Kelly’s hometown, where a jury on Wednesday found the “I Believe I Can Fly” singer guilty of sexually abusing his 14-year-old goddaughter on videotape back in the 1990s, as well as sexual misconduct with two other minors around the same time period.

The same jury acquitted Kelly on high-profile conspiracy charges, but he still faces anywhere from 10 to 90 years in prison when he’s sentenced Feb. 23 by U.S. District Judge Harry Leinenweber.

Among the unanswered questions: Will the judge order that Kelly serve his sentences in Chicago and New York consecutively? That would almost certainly assure the 55-year-old former superstar would spend the rest of his life in prison.

Also, what will become of four indictments still pending against Kelly in Cook County that were brought by State’s Attorney Kim Foxx in 2019 in the wake of the “Surviving R. Kelly” docuseries?

On top of all that, Kelly is also fighting efforts on multiple fronts to go after his money, which, according to court records, continues to flow from streaming services and other royalties.

Federal prosecutors in both Chicago and New York are asking that Kelly be forced to pay millions in restitution to victims and other penalties. Kelly also has a $4 million default judgment against him in a Cook County lawsuit filed by an accuser and is embroiled in an ongoing battle over the seizure of $30,000 in funds from his prison commissary account.

But the primary battle for his legal team now will be to try to mitigate the damage in his criminal cases and limit the total amount of time he must serve.

After the verdict was announced Wednesday at the Dirksen U.S. Courthouse, U.S. Attorney John Lausch said unequivocally that prosecutors plan to request Kelly’s federal sentences be served consecutively.

“When we have instances where defendants are convicted of committing horrific acts against other individuals, and it’s separate and apart from other horrific acts that he committed against other individuals, we’re asking for that (sentence) to be consecutive,” Lausch told reporters in the courthouse lobby.

Renato Mariotti, a former federal prosecutor in Chicago, said one of key factors at sentencing could be the alleged conspiracy by Kelly and his co-defendants to cover up his sexual misdeeds and rig his 2008 child pornography case in Cook County.

According to federal prosecutors, Kelly pressured his goddaughter and her family to deny any abuse and paid them thousands of dollars over the years to stay quiet.

The jury on Wednesday acquitted Kelly, his former business manager, Derrel McDavid, and ex-employee Milton “June” Brown on all charges related to those alleged conspiracies.

But Mariotti said prosecutors will almost surely try to bring the evidence in at sentencing as indicative of Kelly’s lack of respect for the law.

“You can bet your bottom dollar that John Lausch and his office believe that the obstruction occurred,” said Mariotti, who is now in private practice. “They wouldn’t have charged it if they didn’t. … Their view will be that this evidence is part of the history and characteristics of Mr. Kelly.”

Mariotti said that since the burden of proof is lower at a sentencing hearing as opposed to trial, prosecutors are also free to bring up “additional information and evidence” that was never charged in the indictment.

“R. Kelly is a particularly heinous defendant when you consider the wide range of conduct, the vulnerability of the victims in the case, and the damage (he) did,” Mariotti said.

Leinenweber, though, is not known as particularly harsh sentencing judge. In fact, the 85-year-old jurist, who has been on the bench for nearly four decades, often goes out of his way to be fair to criminal defendants, often departing downward from sentencing guideline ranges if he feels they’re too harsh.

“I would not be surprised if Judge Leinenweber rejects the government’s call for consecutive sentences and determines that 30 years is enough time for Mr. Kelly,” Mariotti said.

Mariotti said that doesn’t mean the Chicago prosecution was a waste of time or taxpayer money. He said Kelly has a chance in his appeal of the rather unusual racketeering case in New York as well as the extremely harsh sentence imposed by U.S. District Judge Ann Donnelly, which was well above what even prosecutors there were asking for.

“This conviction (in Chicago) offers a chance to give additional comfort to victims that Mr. Kelly will receive justice,” Mariotti said. It also significantly changes Kelly’s “bargaining position” when trying to negotiate a deal on the pending cases.

Evidence or testimony in one case could potentially be used against him in another, which “really counts in favor of (Kelly) trying to achieve a global resolution,” he said.

The Cook County cases made a splash when they were announced in early 2019 on the heels of the explosive “Surviving R. Kelly” docuseries. Reporters mobbed Kelly as he turned himself in to the Central Police District Station, and fans played his music while they waited for him to bail out of jail after bond court.

County prosecutors hit Kelly with four separate indictments. One alleged he sexually assaulted underage Jerhonda Pace, who was a teenage superfan when they met during his 2008 trial at the Leighton Criminal Court Building at 26th and California.

Another involved new footage of Kelly allegedly sexually abusing his goddaughter, who was at the center of that trial as well as the recent federal case in Chicago. At that trial, she testified under the pseudonym “Jane.”

A third case centered on a woman identified as H.W., who accused Kelly of having sexual contact with her when she was just 16. And a fourth indictment involves an adult accuser, L.C., who said Kelly sexually abused her in 2003 when she came to braid his hair.

But all that was quickly overshadowed when federal prosecutors brought their one-two punch of indictments, and the county cases have languished ever since.

At first, the judge on Kelly’s Cook County cases, Lawrence Flood, repeatedly said the federal matters should not impede the progress of the county cases.

”I understand there’s two other matters in federal court, New York and in Chicago,” he said from the bench in December 2019. “That’s not really the concern of this court. These victims are entitled to their day in court just as the other people in the other cases.”

After saying that, he set the date for Kelly’s first Cook County trial in September 2020. That did not happen, at least partially because the COVID-19 pandemic hit.

Last year after Kelly’s conviction in New York, Foxx told the Tribune that county prosecutors agreed to remain in a “pretrial posture” while the federal cases played out.

And at a hearing for Kelly in August, Flood deliberately set the next court date for early October, when the Chicago federal trial would be over and he could get an update on how the county cases would proceed.

The allegations in two of the county indictments overlap significantly with Kelly’s federal cases. Pace was a central witness in the New York trial last year. And the video on which Cook County prosecutors based one of their cases was also at the center of his Chicago federal trial.

Greenberg filed a motion alleging that the Cook County indictment involving Pace should be thrown out, citing a provision in Illinois law that prohibits a state prosecution if the defendant has been convicted in a different jurisdiction for “the same conduct.”

Prosecutors have pushed back, saying the allegations in the New York trial were distinct from the Cook County case, even though they involve the same victim. Now that Kelly has been convicted on federal charges related to the videos, his defense might try to get that county case thrown out too.

But given the overlap, prosecutors may decide on their own to drop those cases, sparing the accusers from having to take the witness stand again. And given that Kelly might be facing the equivalent of life in prison, they might choose to drop all the county charges — or try to negotiate a plea, though Kelly so far has appeared resistant to pleading out.

Foxx said last year after Kelly’s conviction in Brooklyn that the decision about how her office would proceed would be made in consultation with the victims.

In a statement released this week Foxx said her office “has long combined efforts with our federal partners, and we are pleased that our collaborative efforts resulted in this conviction. We will continue this collective work in the pursuit of justice for all victims.”

“As we review next steps in the prosecution of these cases, the Cook County State’s Attorney’s Office will continue to prioritize public safety and support all victims of crime and we will remain a compassionate trauma informed resource for survivors as they regain their power and heal,” the statement continued.

If the cases that overlap with Kelly’s federal charges are dismissed, that would leave two other indictments still remaining: The cases involving L.C. and H.W.

The alleged incident involving L.C. occurred while Kelly was out on bond on Cook County child pornography charges. Lanita Carter has since come forward publicly, saying that she went to braid Kelly’s hair in 2003 but that he greeted her with his pants down and performed a sex act on her.

Carter appeared in the Lifetime documentary series, “Surviving R. Kelly Part II: The Reckoning,” recounting her accusations in emotional and vivid terms.

Carter said in the series that she reported the attack to police and ultimately appeared before a Cook County grand jury. She said grand jurors disbelieved her story and that charges were rejected. Carter came forward again after Foxx made an unusual public plea in early 2019 for Kelly’s accusers to reach out and cooperate with investigators.

In the case centered on H.W., prosecutors allege Kelly’s manager approached the girl as she celebrated her 16th birthday at a restaurant, gave her Kelly’s card and told her to contact him. After that they had repeated sexual contact, beginning in June 1998.

Afternoon Briefing

Daily

Chicago Tribune editors’ top story picks, delivered to your inbox each afternoon.

H.W. has also filed a civil suit alleging that she was “star struck” when Kelly’s associate told her to contact the singer. She thought she would get a role in a music video, the suit said. Instead, the two had regular sexual contact during which Kelly “represented to (H.W.) that this behavior was appropriate,” the suit said.

It was only years later that H.W., then an adult, realized from therapy that her “great shame, guilt, self-blame, confusion, depression” and other emotional distress had resulted from Kelly’s sexual abuse, the suit said.

The lawsuit filed by H.W. took a twist in early 2020, when neither Kelly nor his attorneys showed up for a court date, apparently due to a miscommunication or mixup. As a result, a Cook County judge determined that H.W. should win her suit by default and ordered Kelly to pay her $4 million, a judgment he is appealing.

jmeisner@chicagotribune.com

mcrepeau@chicagotribune.com