Federal prosecutors in Chicago and Brooklyn on Friday unsealed indictments against R&B star R. Kelly that fleshed out what had been persistent rumors of sexual relations with underage girls — and a decades-long coverup of the singer’s alleged illicit appetites.

Wearing an orange prisoners’ jumpsuit, Kelly appeared at the Dirksen Federal Building in a cramped courtroom filled with reporters; he learned he will remain in custody at least until a detention hearing on Tuesday.

Kelly was arrested Thursday night as he walked his dog near his apartment in the Trump International Hotel & Tower. He faces charges of enticing a minor, child pornography and obstruction of justice in Chicago, and counts of racketeering and transporting minors across state lines in New York. Legal experts wonder if the 52-year-old singer might ever walk free again.

The indictments unsealed Friday come on top of charges of criminal sexual abuse leveled by a Cook County grand jury earlier this year. In the Chicago case, Kelly’s former business manager, Derrel McDavid and former employee Milton “June” Brown also were charged for helping the singer lure underage girls, and later intimidating them into silence to prevent Kelly from facing criminal charges.

In a memorandum filed in the Chicago case, seeking to keep Kelly from being released on bond while awaiting trial, prosecutors said Kelly beat child pornography charges at trial in 2008 by paying at least three people six-figure sums, sending associates out to gather up videos of the singer having sex with underage girls (to keep them out of prosecutors’ hands), and bullying witnesses and victims to keep them from cooperating with investigators.

“(Kelly) undermined the integrity of the state court trial, and his efforts obstructed the fair administration of justice. It further discouraged victims from cooperating with law enforcement for years, which allowed the defendant to get away with his conduct for so long,” prosecutors wrote. “Not anymore.”

After the singer’s court appearance Friday, Steve Greenberg, R. Kelly’s attorney, remained defiant.

“We’re going to wait and see what happens with the evidence,” Greenberg said. “We’re going to wait and see what proof they have. We’re going to challenge the proof. And we’re gonna press on because he didn’t do anything wrong.”

It was not immediately clear when Kelly might appear in court in the Brooklyn-based Eastern District of New York, or whether the new charges might affect his bond in Cook County. All told, the two cases involve 10 victims and 18 criminal counts. The charges in Chicago alone carry a combined potential sentence of 195 years in prison, prosecutors said. The New York indictment alleges Kelly abused girls as far back as 1999 and as recently as 2017, events that took place in Chicago, northern California and Connecticut.

The twin indictments were the latest blow to the Chicago-born singer, who more than a decade ago had continued to chart hits even as he faced down the child pornography charges stemming from a graphic video that appears to have resurfaced as evidence in his federal cases. Kelly had come under career-dampening criticism from activists in recent years, outcry elevated after the airing of the “Surviving R. Kelly” documentary series and emotional interviews with multiple women who said they met the singer as minors and had sex with him. The #MuteRKelly campaign targeted his performances and record company, prompting venues to cancel his concerts and his label to drop him.

In February, celebrity Los Angeles attorney Michael Avenatti brought a VHS tape to Cook County State’s Attorney Kim Foxx that, he claimed, showed Kelly having sex with a 14-year-old girl. Two weeks later, Kelly was charged in four sexual abuse cases involving four victims, three of them underage. Two weeks after posting bail on those charges, Kelly landed in jail again when he was unable to pay $160,000 in back child support.

“He is fighting on three fronts now— it might be more than that— and that is incredibly difficult and financially draining,” said former federal prosecutor Renato Mariotti, noting that Kelly also faces civil lawsuits in Cook County and criminal investigations appear to be ongoing in other jurisdictions.

Which of the cases might see Kelly stand trial first is hard to say. Federal cases tend to move more quickly to trial — Kelly’s waited six years between his 2002 arrest on the child porn charges and his trial in 2008 — but Kelly’s defense team will likely drive some of those decisions, said Steven Block, a former federal prosecutor who was head of the State’s Attorney’s Special Prosecutions Division until entering private practice last year.

Being indicted in two federal jurisdictions on the same day shows authorities are working together closely in the prosecution, Block surmised.

“For two U.S. attorneys to get involved at this point, after he’s already been charged in Cook County, means that they really believe they have the goods on him. This is not the kind of case where they’re going to want to swing and miss,” Block said. “What it says to me is, they have done a thorough investigation and they have developed flippers, insiders, people who have worked with him and are probably going to testify against him. Their witnesses are going to be witnesses who are not just the (underage) victims.”

The racketeering charges in the New York indictment allege Kelly’s entire musical career was part of a criminal enterprise to “recruit women and girls to engage in illegal sexual activity with Kelly.” Other participants in the “enterprise” are nameless “managers, bodyguards, drivers, personal assistants and runners for Kelly.”

Perhaps more daunting for Kelly is the evidence laid out in a government filing. Prosecutors in Chicago claim to have three videos of Kelly having sex with an underage victim, with other alleged victims claiming to have seen a fourth that is not in possession of the government.

Prosecutors also say the victim identified as “Minor 1” in the indictment is the same victim in Kelly’s 2008 trial. The girl is the niece of one of Kelly’s musical protégés, Stephanie “Sparkle” Edwards, and the daughter of a musician who played on his albums, and neither she nor her parents cooperated with investigators. Kelly’s Illinois indictment states the singer sent the girl and her parents overseas for a month to avoid investigators in 2002, and gave her a Yukon Denali in 2013 and “settlement” payments as recently as 2015.

Listing her in the indictment, even by a pseudonym, likely means she is working with prosecutors and will testify if Kelly goes to trial, something that didn’t happen in 2008, Mariotti said.

“They wouldn’t put her in the indictment if they didn’t think they were going to be able to put her on the stand,” Mariotti said.

A spokesman for the U.S. attorney’s office in Chicago said Kelly made his initial court appearance about 9 p.m. Thursday, where the details of his charges in Illinois were laid out. He did not enter a plea.

No decision as to when he’ll go to New York will be made until Tuesday’s detention hearing, according to a spokesman for the U.S. attorney’s office.

After spending the night in the Metropolitan Correctional Center, Kelly was back in front of a judge Friday afternoon.

His appearance before U.S. Magistrate Judge Sheila Finnegan concerned the charges he faces in New York, not Illinois. As he was led in by U.S. marshals, Greenberg gave him a pat on the shoulder. Kelly’s hands remained clasped behind his back throughout the hearing.

Prosecutors laid out the charges he faces in New York, noting the maximum penalties for each of the five counts he faces there; they stem from allegations of racketeering and violations of the Mann Act (transporting minors across state lines). The maximum penalty for convictions on all counts would be 80 years in prison, prosecutors said.

Finnegan asked if he understood the charges and penalties. Kelly replied: “Yes, ma’am.”

Addressing reporters in the lobby, Greenberg said he was “amazed” that Kelly “hasn’t had a complete breakdown in the face of all of this pressure.”

Greenberg said the racketeering charges against Kelly were “a scary use of that law” that is intended to curb organized crime.

“I think it’s abuse of the RICO laws, you know, saying that someone was a musician and that there (were) backstage parties and there were groupies,” he said. “That’s essentially what it is that they charged as a racketeering enterprise.”

McDavid, one of Kelly’s co-defendants in the Illinois case, also appeared in court Friday.

McDavid, who surrendered Friday morning, was charged with conspiring to obstruct justice, receiving child pornography and conspiracy to receive child pornography. His bail was set at $500,000.

Brown, Kelly’s other co-defendant in the Illinois case, is not set to appear in court until next week.