Convicted in New York, R. Kelly Faces Another Federal Trial In Chicago

R. Kelly Chicago
This photo from Friday May 9, 2008, shows R. Kelly arriving at the Cook County Criminal Courthouse in Chicago. On Monday, a New York jury found Kelly guilty of racketeering and sex trafficking. Charles Rex Arbogast / Associated Press, File
R. Kelly Chicago
This photo from Friday May 9, 2008, shows R. Kelly arriving at the Cook County Criminal Courthouse in Chicago. On Monday, a New York jury found Kelly guilty of racketeering and sex trafficking. Charles Rex Arbogast / Associated Press, File

Convicted in New York, R. Kelly Faces Another Federal Trial In Chicago

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R. Kelly’s conviction in a Brooklyn federal courthouse on Monday does not mark the end of the singer’s legal reckoning for his alleged sexual crimes against women and underage girls. Far from it.

A New York jury found Kelly guilty of racketeering and sex trafficking on Monday. Now, he faces pending criminal charges in federal court in Chicago, Cook County court and state court in Minnesota. 

Most of those charges have to do with alleged sexual abuse. Up next is the federal case in Kelly’s hometown of Chicago. A judge could set a trial date for that case at a scheduled hearing in October.

The federal cases in Chicago and New York are distinct and separate cases with no shared victims. But legal experts said the two cases have several overlapping elements, from potential witnesses to the type of alleged criminal behavior. And they said the verdict in New York, and the way the six-week trial played out, could have an impact on what happens inside the federal courthouse in Chicago.

Attorney Sergio Acosta, a former federal prosecutor who worked several cases where defendants went on trial in other jurisdictions before he prosecuted them, said he is sure prosecutors and defense attorneys have been studying the strategy and actions of the other side since the Kelly trial started.

“You want to see what the tactics were, how [the other side] went about it, what was successful, what wasn’t successful, and then try and adapt your case to prepare for that,” Acosta said. “Both sides are going to do that, they’re both going to go to school on that first trial.”

Victim questioning

One thing that stood out from the lengthy Brooklyn trial was the aggressive way Kelly’s defense team went after the singer’s victims during cross-examination. The defense attorneys were even admonished by the judge in the trial for asking witnesses about their sexual histories.

Defense attorney Steve Greenberg, who was abruptly fired from Kelly’s New York defense team before trial but still represents Kelly in the Chicago federal case, said it was clear from the way the trial played out, that strategy was a mistake.

“I think they missed the boat in the New York case [because] they tried to sort of victim blame … when really the sex wasn’t at issue, but it played right into the government’s hand by allowing the sex to become the focus of the case,” Greenberg said. “The focus of the case should have been…that they don’t have any evidence that he was running a criminal enterprise. … So while everyone is focused on the sex, and maybe there was some underage sex and there was some kinky sex, and there was some weird stuff going on, that’s not what he was on trial for.”

Greenberg said the goal in a Chicago trial would be to keep the focus off of the sexual elements of Kelly’s alleged crimes as much as possible.

But Renato Marrioti, another former federal prosecutor, said the charges in the Chicago case will make that almost impossible.

In New York, federal prosecutors proved to the jury that Kelly was the head of a large criminal organization based around sexually abusing and exploiting women and girls. Mariotti said that racketeering case was complex and unusual, with some murky legal questions.

In contrast, the Chicago case is based around Kelly allegedly creating and obtaining child pornography, and committing criminal acts to keep it all secret. Mariotti said it is a much stronger, simpler case than the one tried by prosecutors in New York.

“I have obviously not viewed or seen these images and movies, but I suspect they depict sexual activity with underage individuals, and the prosecutors feel pretty confident that they can prove that right? And so where do you go with that? If you’re on the defense side,” Mariotti said. “It’s very difficult to defend, because there’s not a lot of legalism to it, the jury is not going to have a lot of sympathy for that either. And either you’re the guy who made a video or you weren’t. And so it’s a purely a factual question.”

“A convicted felon”

Greenberg agrees that the case in Chicago is much more straightforward. And he said there really will not be much overlap between the case laid out in New York and the case in Chicago.

Greenberg believes that is a problem for Kelly, and a mistake by the defense attorneys who replaced him in the New York case.

“I think that there could have been [overlap] and this smart way to have handled the New York case would have been to ensure that there was some overlap, so that a double jeopardy claim could have been raised in Chicago. But New York counsel didn’t do that,” Greenberg said.

Still, Greenberg said he expected there will be some witnesses who testified in Brooklyn who will again take the stand in Chicago. He said the defense team was studying transcripts to see how they had been questioned and good ways to approach them. But he said the utility would be limited.

“I don’t think that there’s going to be much overlap because the charges are so fundamentally different, what the witnesses are going to be testifying about is going to be completely different, even if they’re the same witnesses,” Greenberg said.

Greenberg declined to say which witnesses he expected to repeat, saying the information was privileged.

One potential impact of the guilty verdict in Brooklyn is all-but ensuring Kelly does not take the stand in his own defense.

Kelly chose not to testify at the trial in Brooklyn, and now that he has been convicted, it’s extremely unlikely he will be a witness in the Chicago trial. That’s because Kelly testifying would allow prosecutors to talk about his conviction.

“It would certainly impact his ability to take the witness stand because he would be a convicted felon … And that’s something that you can bring up to impeach a witness when they take the stand,” Acosta said.

Tainting The Jury Pool?

If Kelly does not take the stand, jurors will not be told about the Brooklyn conviction during the trial in Chicago. 

But that does not mean they won’t have heard about it.

It’s one other way the New York trial could affect Chicago - tainting the prospective jury pool. The court will have to find 12 people who will not be swayed by the fact that Kelly was just convicted of crimes involving sexual abuse of women and underage girls, and using his power to try and cover up those crimes.

“You try to screen out jurors who might either know about the conviction or have feelings about it,” Acosta said. “You want to find people who are going to be, you know, fair and open minded and not be prejudiced. Really against any side. But here, what we’re talking about is prejudice against the defendant, because he’s been convicted.”

But Mariotti said he doesn’t think it makes things that much more difficult than they already were.

“R. Kelly was always going to be a difficult person to find jurors for,” Mariotti said. “The courts are able to find the appropriate jurors … because the goal is not to find 12 people who have never heard of R. Kelly or don’t have any opinion about the man, the goal is to find 12 people who can be open minded and fair.”

“You don’t want to give up and walk away”

Perhaps the biggest question posed by the guilty verdict in Kelly’s Brooklyn case is whether there will be a Chicago trial at all.

At a telephonic court hearing last week, Greenberg speculated that the outcome in New York could change the government’s plans back in Chicago. U.S. attorneys on the call did not offer any insight into their thinking.

Greenberg told WBEZ he thinks it’s a “good question” whether it would be worth the government 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 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, meaning the government has an obligation to keep pressing forward in Chicago.

“If he prevails on appeal, you don’t want to have given up the opportunity to pursue justice in your case as well,” Acosta said. “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.”

Mariotti suggested a possible middle ground, some sort of agreement between Kelly and prosecutors that would get rid of any possible appeals and lump all of the federal charges together.

“Whenever there’s a conviction, it certainly changes the landscape,” Mariotti said. “And 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.”

A status hearing in the Chicago case is scheduled for Oct. 20.

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