Embattled R&B singer R. Kelly pleaded not guilty in a Chicago courtroom Tuesday to 13 federal charges, including child pornography and obstruction of justice.

The indictment was one of two federal cases issued against the singer last week, one in Illinois and the other in New York. Federal prosecutors in the Northern District of Illinois say that Kelly made substantial hush-money payments to silence the alleged victims — five girls — and members of their families.

Despite a history of allegations that stretches over a quarter century, this is the first time that Kelly was charged with federal crimes. In addition to the Illinois federal indictment, federal prosecutors in the Eastern District of New York unsealed a separate, five-count indictment of Kelly last Friday. Those charges include one count of racketeering related to kidnapping and four violations of the Mann Act, which refers to transporting girls over state lines for sexual trafficking. There are five alleged victims in the New York indictment, including three girls.

The alleged incidents referenced in the two federal indictments span 1998 to 2018. In total, the two federal indictments contain 18 counts, including child pornography, kidnapping, obstruction of justice and trafficking minors and women for sexual purposes.

During Tuesday's court appearance, Judge Harry D. Leinenweber also decided that Kelly will remain in custody as he awaits trial in Chicago. According to the Chicago Tribune,he will be taken by U.S. marshalls to face the New York indictment in Brooklyn; the Chicago Sun-Times reports that he will be transferred to Brooklyn sometime before Sept. 4.

Also charged in the Illinois indictment were two of Kelly's associates: his manager Derrell McDavid and an employee, Milton "June" Brown. Prosecutors say that Kelly and his associates paid out hundreds of thousands of dollars to collect copies of his child pornography videos that had begun circulating. In addition, prosecutors assert Kelly and others in his circle paid out cash, substantial gifts and foreign travel to alleged victims, their parents, other family members and witnesses to prevent them from testifying in court or otherwise coming forward publicly.

On Monday, celebrity lawyer Michael Avenatti — who says that he represents three alleged victims of Kelly as well as six other people, ranging from parents of alleged victims to three Kelly associates whom Avenatti calls "whistleblowers" — claimed that Kelly paid out $2 million to keep the alleged victim in a 2008 criminal trial in Chicago from testifying. In that case, Kelly was accused of making child pornography with a teenage girl. Neither the girl nor her parents testified in the case, though multiple family members, friends and even a basketball coach identified her on the witness stand. In June 2008, Kelly was acquitted on all counts.

Kelly also continues to face a range of criminal charges in Cook County, Ill., including aggravated criminal sexual assault and abuse.

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