What to know about R. Kelly’s new Chicago trial

The former R&B star is set to go to trial in Chicago — again — on Aug. 15. Here’s a rundown of what’s happening and why.

R. Kelly in courtroom
In this Sept. 17, 2019, file photo, R. Kelly appears during a hearing at the Leighton Criminal Courthouse in Chicago. Antonio Perez / Chicago Tribune via Associated Press
R. Kelly in courtroom
In this Sept. 17, 2019, file photo, R. Kelly appears during a hearing at the Leighton Criminal Courthouse in Chicago. Antonio Perez / Chicago Tribune via Associated Press

What to know about R. Kelly’s new Chicago trial

The former R&B star is set to go to trial in Chicago — again — on Aug. 15. Here’s a rundown of what’s happening and why.

WBEZ brings you fact-based news and information. Sign up for our newsletters to stay up to date on the stories that matter.

Singer R. Kelly is back in a Chicago courtroom this month, but a lot has changed since the R&B star’s 2008 trial in Cook County’s criminal courthouse — especially in the wake of his 2021 conviction in New York.

So what are the charges against Kelly? What’s at stake? Here’s everything you need to know as the trial gets underway.

When does R. Kelly’s Chicago trial start?

R. Kelly’s second Chicago trial will begin with jury selection Monday, Aug. 15.

What are the charges against Kelly in Chicago?

Kelly faces six child pornography counts and five counts of enticing a minor to engage in criminal sexual activity. He also faces two conspiracy counts — one to receive child pornography, and the other to obstruct justice.

How is this trial connected to the one in 2008, in which a jury acquitted Kelly?

The alleged obstruction-of-justice conspiracy revolves around Kelly’s 2008 state-court trial in Cook County. That case began in 2002, after a videotape allegedly depicting Kelly performing sex acts with a minor was sent anonymously to the Chicago Sun-Times. Jurors found Kelly not guilty, and they later said they did so because the alleged victim did not testify. Federal prosecutors now say Kelly and others pressured, intimidated and paid off witnesses in that case, including the alleged victim and members of her family. This time around, the alleged victim from the 2008 trial is expected to take the stand.

Why is Kelly being tried again after the Brooklyn conviction?

It may seem like piling on for federal prosecutors to take Kelly to trial all over again, six weeks after a judge in New York sentenced him to 30 years behind bars. But legal experts say this trial could vindicate further victims — and the failed attempt to hold Kelly accountable in 2008. Not only that, but Kelly has filed an appeal in the New York case. If this latest trial ends in a guilty verdict, it could help keep Kelly behind bars even if his earlier conviction is overturned.

Who else is going to trial along with him?

Also charged in this case are two of Kelly’s former employees: Derrel McDavid and Milton “June” Brown. McDavid is charged with Kelly in the obstruction-of-justice conspiracy and two child pornography counts, and McDavid and Brown are charged with Kelly in the child-pornography conspiracy.

Who is representing Kelly in Chicago?

Kelly’s lead attorney this time around will be Jennifer Bonjean, an aggressive lawyer with Chicago roots whose recognition soared after she helped free actor Bill Cosby from prison. She is a veteran of Chicago courts and is most well known here for her work in wrongful conviction cases.

How long will Kelly’s Chicago trial last?

U.S. District Judge Harry Leinenweber, who is presiding over the trial, told attorneys he wants it done in four weeks “come hell or high water.” Trial courtroom time is at a premium at the Dirksen Federal Courthouse, which is still operating under COVID-19 protocols.

If convicted, what sentence could the judge give Kelly?

If convicted on all counts, mandatory minimums would require a sentence of at least 55 years.