An upcoming Chicago hearing could answer questions about what’s next in R. Kelly trial

R. Kelly is scheduled to appear via video in Chicago court Wednesday, weeks after being convicted in Brooklyn. The hearing could answer some lingering questions.

R&B singer R. Kelly arrives at the Leighton Criminal Court in Chicago
This photo from Wednesday June 26, 2019, shows R&B singer R. Kelly arriving at the Leighton Criminal Court in Chicago for arraignment on sex-related charges. Amr Alfiky / Associated Press
R&B singer R. Kelly arrives at the Leighton Criminal Court in Chicago
This photo from Wednesday June 26, 2019, shows R&B singer R. Kelly arriving at the Leighton Criminal Court in Chicago for arraignment on sex-related charges. Amr Alfiky / Associated Press

An upcoming Chicago hearing could answer questions about what’s next in R. Kelly trial

R. Kelly is scheduled to appear via video in Chicago court Wednesday, weeks after being convicted in Brooklyn. The hearing could answer some lingering questions.

For the first time since being convicted of sex crimes and racketeering in a Brooklyn courthouse, singer R. Kelly is scheduled on Wednesday to attend a hearing in his pending Chicago federal case, albeit electronically.

The hearing could answer many questions hanging over the criminal case, including who exactly will be on Kelly’s defense team, whether the two sides have discussed a possible plea deal and if the government wants to continue with its case considering Kelly is already facing the potential of dying in prison thanks to his Brooklyn conviction.

A jury in New York found Kelly guilty of sex trafficking, and of heading a criminal organization aimed at allowing him to sexually abuse and exploit women and girls. The multiple charges in the federal case in Chicago are based on Kelly allegedly creating and obtaining child pornography, and committing criminal acts to keep it all secret. Kelly has pleaded not guilty to those charges.

At the last Chicago hearing in September, the Brooklyn case was still ongoing, and attorneys on both sides speculated that the outcome could determine what happens next in Chicago.

Attorney Steve Greenberg, who represents Kelly, told the judge he expected the verdict would have an “impact on how the government wants to proceed.”

Prosecutors didn’t offer any insight into their thinking, but did raise the question of whether Greenberg would continue to be Kelly’s attorney. Greenberg has long represented Kelly, but he was abruptly fired from the New York case before trial. He is still listed as Kelly’s defense attorney in the Chicago proceedings, but has been noncommittal on whether he will stay on.

During the September hearing, Greenberg guessed that if Kelly won his case in New York, he’d want to stick with the winning defense team. That obviously did not happen.

On the government’s side, Greenberg told WBEZ he thinks it’s a “good question” whether it would be worth the resources and potential stress on alleged victims to go through with a trial, if the New York conviction likely means Kelly will die in jail any way.

But former federal prosecutor Sergio Acosta said his impression is the prosecutors in Chicago believe strongly in their case and want to take it to trial. He also said it is likely Kelly will appeal his New York conviction.

“In most cases, you don’t want to give up and walk away from strong charges if there’s an appeal that could result in a reversal of a conviction,” Acosta said.

Another former federal prosecutor, Renato Mariotti, meanwhile suggested a possible middle ground, an agreement between Kelly and prosecutors that would get rid of any possible appeals and lump all of the federal charges together.

“When there are defendants who are facing criminal cases in multiple jurisdictions, there is usually an appetite from the defense for what’s called a global resolution. In other words, some sort of negotiated deal that ensures that all of their legal problems go away at once,” Mariotti said.

Kelly is being held in federal lockup in New York City, he has been ordered to appear in his Chicago case via video at 8:00 a.m. Wednesday.

He is scheduled to be sentenced in the New York case in May 2022.

Patrick Smith is a reporter on WBEZ’s Criminal Justice Desk. Follow him @pksmid. Email him at psmith@wbez.org.