When authorities arrested the R&B singer known as R. Kelly outside of his condo in downtown Chicago on federal sex crime and obstruction of justice charges, Kelly was already out on bond awaiting trial on sexual assault and abuse charges in Cook County Circuit Court. Then the next day, federal prosecutors in New York City unsealed another indictment against him. Altogether, Kelly is facing a total of three dozen criminal charges in three separate jurisdictions.

Legal experts say the rare stacking of cases is bad news for Kelly and has created an unusually fuzzy picture for how the pending cases will proceed, especially the two federal cases in Chicago and New York which are both being prosecuted by offices that are part of the U.S. Department of Justice.

Former federal prosecutor Renato Mariotti said it is typical for federal investigators from separate jurisdictions to go after the same suspect, but in most cases, it’s decided within the Department of Justice which U.S. attorney’s office will handle the case before an indictment is filed, rather than having cases in separate jurisdictions.

“In my experience, districts work independently of each other and usually … there would be a kind of an internal discussion and one would decide to go forward,” Mariotti said. “It would sometimes be contentious, both offices would sometimes want to handle the same case, but eventually, some decision was made.”

Similarly, Mariotti said, he has worked on a federal investigation that overlapped with a case in state court. But in his experience, they waited for the state case to wrap up before deciding on whether to bring federal charges.

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The new federal indictments against Kelly come as the state cases against him are still in the preliminary stages. Mariotti said one potential reason for that could be the obstruction of justice charges against Kelly.

Federal prosecutors in Chicago said Kelly used bribery and coercion to cheat the system and get a not-guilty verdict when he went to trial in Cook County in 2008 on child pornography charges.

“One thing that may have been on their mind is: ‘If we don’t act now, he may obstruct justice in another state trial,’” Mariotti said.

Andrea Lyon, a longtime attorney and professor of law at Valparaiso University, said based on past practice, it is most likely the state cases against Kelly will be put on hold so that one of the federal cases can proceed first, although she cautioned that “is not written in stone in anyway.”

Tandra Simonton, a spokeswoman for the Cook County State’s Attorney, said the cases in Cook County Circuit Court are still moving forward as usual, and prosecutors have not made any decisions about the timing of the cases or how they will affect one another.

Lyon also said it was difficult to predict which of the federal cases would take priority, because there’s so little precedent for having simultaneous federal cases against the same defendant.

“I can’t tell you politically what happened in this case, but obviously, they didn’t have an agreement or maybe they had an agreement to do both [federal cases],” Lyon said. “I can’t answer the question. You know it’s kind of a black box in [the U.S. Attorney’s Office]. You really don’t know how they do what they do.”

Assistant U.S. Attorney Joseph Fitzpatrick, a spokesman for the U.S. Attorney’s office in Chicago, said as of now all of the cases are moving forward in parallel, without any internal decisions about the order in which they’ll be tried. Fitzpatrick agreed it is “rare” for federal prosecutors in separate jurisdictions to indict the same person at the same time, but did not comment on whether there were any internal discussions or debates about how to proceed.

Richard Kling, a professor at Chicago-Kent College of Law, said Kelly’s defense team could have a say in how the cases proceed.

“The biggest impact I think is going to be the state of Illinois speedy trial right,” Kling said.

The right to a speedy trial in Illinois means a case has to go to trial within 160 days if a defendant demands it.

That means Kelly’s attorneys could force the Cook County cases to move forward on an accelerated timetable.

But Lyon was skeptical that would be in Kelly’s best interest.

“The disadvantage to the defense is you can’t get very well prepared if you’re trying a case that fast, especially with allegations that are this old and with witnesses all over the place,” Lyon said.

Kelly’s attorney Steve Greenberg said he has “no clue” which of the cases against Kelly will be resolved first. He said he does not have enough information in the federal cases to make a decision about what would be best for Kelly.

Whatever order the cases are tried, Mariotti said the concurrent cases put Kelly in a unique predicament.

“When you are facing multiple criminal trials, you can do something that could maximize your interests of winning the first trial, let’s say take the witness stand,” Mariotti said. “But then that transcript can get used, portions of it can be used against you at other trials, so it really ups the difficulty level for the defense team.”

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