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A federal judge on Tuesday ordered R. Kelly held in jail without bond after a prosecutor warned that the singer accused of having sex with minors and trying to cover up the crimes would pose an extreme danger to young girls if set free.

“If he was attracted to middle school girls in 1999 then he’s still attracted to middle school girls,” Assistant U.S. Attorney Angel Krull told U.S. District Judge Harry Leinenweber. “That’s who the defendant is and that, your honor, makes him a danger today.”

Leinenweber said that under federal law Kelly would have to prove that he was not a danger to the public and Kelly’s attorney, Steve Greenberg, had failed to do so.

Kelly was arrested while walking his dog in Chicago last week and faces an array of sex-related charges in Chicago and New York . Appearing in court wearing an orange jumpsuit and shacked at the ankles, he said only two words, “Yes, sir,” when the judge asked him if he understood the charges. Two women who recently lived with Kelly, Azriel Clary and Joycelyn Savage, attended the court hearing Tuesday.

The ruling Tuesday means that Kelly, who pleaded not guilty to the charges contained in the Chicago indictment , will remain in custody to face a separate indictment in New York. He is charged there with racketeering, kidnapping, forced labor and the sexual exploitation of a child.

It was unclear when that hearing would be held and if he would have to be transported to New York for the hearing, or could appear via a video linkup from Chicago.

The decision to deny bond also raised the possibility that the 52-year-old Kelly could spend the rest of his life behind bars. Renato Mariotti, a former federal prosecutor in Chicago, said that “each of the federal indictments could take one to two years to go to trial.” Depending on delays in the case, Mariotti said Kelly’s stay in jail awaiting trial could go on a lot longer than that.

Krull portrayed Kelly as a predator who went to great lengths to find young girls and kept them under his control. She said that the evidence in the federal indictments against him is overwhelming. If convicted, the maximum sentence for the charges contained in the Illinois indictment is 195 years in prison and 80 years for the charges contained in the New York indictment.

Kelly, whose real name is Robert Sylvester Kelly, was first arrested on sex-related charges in 2002 after a video of Kelly having sex with 14-year-old girl was sent to the Chicago Sun-Times. After extensive delays, a Chicago jury acquitted him in 2008 in part because the girl did not testify at the trial,

Krull said Kelly was acquitted only because he paid off the victim and her family. She said the alleged victim in that video has since testified before a federal grand jury and confirmed it was her.

“Electronic monitoring can’t stop obstruction of justice, witness tampering…” Krull said. “He can entice victims to his own home.”

Kelly’s legal troubles mounted when he was arrested in February and charged with 10 counts in Illinois of sexually abusing three girls and a woman. He pleaded not guilty to those charges and was released on bail.

Then on May 30, Cook County prosecutors added 11 sex-related countsinvolving one of the women who accused him of sexually abusing her when she was underage. The federal charges filed last week are separate from the Illinois case.

Greenberg said preparing for trial will be a long process made even more difficult because Kelly does not know how to read and therefore someone must visit him in jail to read him the reams of documents the case will generate.

He said Kelly is no longer rich and has filed for bankruptcy.

“How could he flee?” Greenberg asked. “He has no money.”