Fighting a battle on two fronts to spring R. Kelly from jail, his lawyers in Chicago and Brooklyn have applied new labels to the serious indictments against him in both districts.

While his attorneys in Chicago called the allegations against him here “stale as used gym socks,” his attorneys in Brooklyn called the case there “nothing more than groupie remorse and a misdemeanor.”

Both made their arguments as Kelly was due for arraignment on the charges in New York on Friday. Federal prison records still listed Kelly as being held in Chicago’s Metropolitan Correctional Center as of Thursday.

Attorney Steven Greenberg filed his motion early Thursday asking U.S. District Judge Harry Leinenweber in Chicago to reconsider freeing Kelly as he awaits trial.

In his 12-page motion, Greenberg insisted that Kelly “no longer has the money or the entourage he once did to help him in his endeavors,” and he argued that home incarceration with close monitoring by court personnel and limited internet access would “make it virtually impossible to attempt to contact any witnesses without being caught.”

“The idea that Mr. Kelly has the means and wherewithal to obstruct any witness against him is frankly preposterous,” Greenberg wrote.

Though Greenberg wrote “the allegations are decades old and as stale as used gym socks,” Assistant U.S. Attorney Angel Krull said in court Wednesday “the vast majority of our witnesses have never spoken out publicly.”

Leinenweber ordered Kelly held in federal custody last month, increasing the chances that Kelly will never walk free again. He faces a combined 18 counts in the federal indictments for alleged crimes against 10 victims. He could go to prison for as many as 195 years for the Chicago case alone. Out east, he faces decades more.

But his lawyers in Brooklyn acknowledged in their letter that even if the judge in Brooklyn rules Kelly doesn’t have to be detained, his Illinois case would keep him locked up.

In addition to counts revolving around child pornography, enticing a minor into illegal sexual activity and racketeering, Kelly is accused in Chicago of a conspiracy to obstruct justice. Prosecutors say he thwarted his state court prosecution a decade ago with threats, gifts and six-figure payoffs.

The Chicago indictment describes alleged behind-the-scenes maneuvering designed to protect Kelly during that prosecution. It says Kelly and others intimidated the alleged victim and her parents into lying to police and a grand jury. They also allegedly paid hundreds of thousands of dollars as they tried to track down tapes of Kelly having sex with minors before prosecutors found them.

Nevertheless, federal prosecutors in Chicago have said they have three Kelly sex tapes in their possession and can present evidence of a fourth.