The R&B singer was in a Chicago courtroom on Tuesday (July 16) for his bond hearing, wearing an orange jumpsuit and shackled at the ankles.
Kelly's attorney, Steve Greenberg told the Chicago Sun Times that his client can be trusted not to flee if released from custody.
The New York indictment alleges Kelly recruited women and girls to "engage in illegal sexual activity", as well as having sex with women younger than 18, producing child pornography by asking minors to send him photos and not disclosing a sexually transmitted disease.
U.S. District Judge Harry Leinenweber made the ruling Tuesday after R. Kelly was arrested last week, he faces charges in both IL and NY. The Chicago crimes can give Kelly 195 years in prison, with some charges holding a mandatory minimum of 10 years. Two of tapes were not part of the 2008 case, they said. The singer "has a unique ability to influence and intimidate witnesses and victims, and that continues to this day".
"Unlike his most famous song, 'I Believe I Can Fly, ' Mr. Kelly doesn't like to fly", Greenberg said.
The indictment, obtained by PEOPLE, stated that Kelly and his team - including managers, bodyguards and assistants - "traveled throughout the United States and overseas to perform at concert venues ... and to recruit women and girls to engage in illegal sexual activity with Kelly" as far back as 1999. Leinenweber's decision reportedly resulted in the inability for Kelly's lawyers to prove why a defendant facing child pornography charges shouldn't be detained while pending trial. Kelly was being held after turning himself in to face ten counts of aggravated sexual abuse.
"There's no evidence that he's a risk to minors at all at this point", Greenberg continued, adding, "The man's entitled to be held in a humane situation".
The singer has faced accusations of abuse, manipulation and inappropriate encounters with girls and young women for more than two decades, and has been on trial before. They were unclear in what order the cases would be tried.
Kelly's legal troubles mounted when he was arrested in February and charged with 10 counts in IL of sexually abusing three girls and a woman. She said the alleged victim in that video has since testified before a federal grand jury and confirmed it was her.