R. Kelly appeals Chicago prison sentence that added a year; judge warns it could be worse

R. Kelly’s lawyer argued to an appeals court Thursday that the prison sentence given to him in Chicago last year was too high — but the argument prompted a warning from one of the judges.

If Kelly succeeds in undoing the 20-year prison sentence handed to him here, Judge Amy St. Eve asked, does the former R&B star “realize he could end up worse off?”

That’s because even though a judge gave him a 20-year sentence, that judge also ruled that 19 of those years could be served while Kelly is serving a 30-year sentence for a New York racketeering conviction. That effectively added just one year to Kelly’s time in prison.

If Kelly wins another sentencing hearing in Chicago, St. Eve noted Thursday, that could change.

Jennifer Bonjean, Kelly’s defense attorney, replied that such a move could be seen as “retaliatory.” Still, she acknowledged that the former superstar’s future largely depends on the pending appeal of his separate case in New York.

Kelly would still face prison time for his Chicago conviction if the New York sentence is undone. So he has appealed it to the 7th U.S. Circuit Court of Appeals sitting on the 27th floor of the Dirksen Federal Courthouse.

A federal jury in Chicago convicted Kelly in 2022 of three counts of producing child pornography and three counts of enticing minors into criminal sexual activity. U.S. District Judge Harry Leinenweber then handed Kelly the 20-year prison sentence in February 2023.

Kelly is currently being held in a medium-security prison facility in North Carolina. He is not due to be released until December 2045, when he would be 78.

Federal sentencing guidelines called for a sentence of up to 14 years in Kelly’s Chicago case. But judges are not bound by those guidelines, and Leinenweber exceeded them by six years.

A three-judge panel heard arguments in Kelly’s appeal Thursday. St. Eve was joined by judges Diane Sykes and Kenneth Ripple, but St. Eve handled nearly all of the questioning. It’s not clear when the panel will rule.

Bonjean argued that Leinenweber seemed to rely at sentencing on crimes for which Kelly had been acquitted — including a conspiracy to obstruct a 2008 state court prosecution that ended with a jury finding Kelly not guilty.

Assistant U.S. Attorney Brian Williamson said Thursday that Leinenweber found Kelly committed obstruction by a preponderance of the evidence. However, Williamson insisted that Leinenweber’s review of other factors in the case was enough to justify the higher sentence.

St. Eve told Bonjean that Leinenweber did not specifically say he was relying on the obstruction claims against Kelly to justify a harsher sentence. Rather, she said Leinenweber’s sentence seemed “grounded” in the factors mentioned by Williamson, like the nature of Kelly’s crimes and the need for deterrence.

St. Eve went on to note that, if Kelly’s sentence here is undone, Leinenweber “could start over and look at everything” — and hand down a sentence that would truly add more time to Kelly’s prison stay.

“Does your client realize that?” St. Eve asked Bonjean.

Bonjean said she’d discussed the risks with Kelly, but she added that such a result would amount to punishing Kelly for exercising his right to appeal. She also pointed to Kelly’s appeal in New York.

If the New York sentence stands, Bonjean said, Kelly “probably will die in prison.”