The case that gets underway Monday in federal court in Chicago, however, is in some ways a do-over of a state child pornography trial held 14 years ago in Cook County.
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While at the time, he was acquitted, legal experts say the circumstances now are much different.
In 2008, Kelly walked out of the Cook County Criminal courthouse a free man after a jury acquitted the Chicago singer on charges that he produced a video of himself having sex with a girl who was no older than 14. At the time, the alleged girl and her parents denied it was her on the tape and refused to testify.
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When R Kelly walks into Chicago's Dirksen Federal Building Monday, there will be one major difference. This time, the girl, who is now in her 30s, is talking. The charges against Kelly are also much broader.
"He's charged, with among other things, conspiring to obstruct that earlier trial. That's a different charge, of course, by definition. And there are other victims, so we're going to see a lot more witnesses," said ABC7 legal analyst Gil Soffer.
In all, it is expected that four women, who were minors at the time, will testify against Kelly. Four different videos have also been entered into evidence.
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If convicted in Chicago, the sentence could be even more severe that the one imposed in New York.
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"He could face an even longer term here, upwards of 50 years because these charges are broad and they include enticing a minor to come into the state for purposes of producing child pornography," Soffer said. "And producing child pornography, there is a lot of heft to these charges."
Publicly Kelly has denied the charges against him. What strategy his defense attorneys choose to pursue is the question.
"We'll have to see what the defense does," Soffer said. "Will they simply try to cast down on everything by calling all the minors, now adults, who are going to testify, liars? They may. The tough argument to make."
Jury selection begins Monday and the trial could last up to four weeks. Not only are there four different victims in this case, but there are also two other men charged as co-defendants along with Kelly. Derrel McDavid, who is charged with helping Kelly to fix the 2008 trial, and Milton Brown, who is accused of receiving child pornography.