Singer R. Kelly faces nine counts of enticing a minor, three counts of child pornography and one count of obstruction of justice in a federal indictment unsealed Friday in Chicago. Other criminal charges were unsealed in New York.

Derrel McDavid and Milton Brown, former members of Kelly’s entourage, also were named as defendants in the Chicago case.

The conspiracy count mentions five minors, saying Kelly “engaged in sexual contact and sexual acts” when they were under 18.

It also says four videos “depict Kelly engaged in sexual contact and sexual acts” with a girl under 18.

After videos of Kelly having sex with minors went missing, Kelly, McDavid and others had “hundreds of thousands of dollars” paid to get them back, according to the indictment.

McDavid pleaded not guilty in a hearing Friday at the Dirksen Federal Courthouse. His bail was set at $500,000. The indictment says McDavid was Kelly’s business manager between 1991 and 2014.

Brown was employed by one of Kelly’s businesses between 1997 and 2018, according to the indictment.

The U.S. Attorney’s Office said Kelly had an initial hearing on the Chicago charges at 9 p.m. Thursday. He didn’t enter a plea.

Kelly will spend at least the weekend in custody and a judge will hold a detention hearing Tuesday as it relates to the Illinois charges.

R. Kelly, wearing an orange jumpsuit, appeared in court Friday during a scheduled removal hearing on the New York charges, but a spokesman with the U.S. Attorney’s Office said no decision will be made on that matter until Tuesday’s detention hearing.

Kelly’s attorney Steve Greenberg taking questions from reporters pic.twitter.com/ccq4vjCknS — Sam Charles (@samjcharles) July 12, 2019

Federal prosecutors noted that, if convicted on all counts, Kelly would face 195 years in prison — an effective life sentence. Prosecutors also disclosed that none of the alleged conduct in the Illinois indictment overlaps with the allegations in the New York indictment.

“The defendant should be detained pending trial,” prosecutors wrote. “He poses a significant threat to minor girls in the community, to victims and witnesses in the case, and to the ongoing investigation.”

Read the indictments The 13-count indictment unsealed Friday (PDF) includes nine counts of enticing a minor, three counts of child pornography and one count of obstruction of justice.

A separate, five-count indictment (PDF) also unsealed Friday accuses Kelly and his entourage of acting as a criminal enterprise to “promote R. Kelly’s music and the R. Kelly brand and to recruit women and girls to engage in illegal sexual activity with Kelly.”

The U.S. Attorney’s Office in Chicago alleges that Kelly’s acquittal of child pornography charges in 2008 was the byproduct of a concerted effort by him and his entourage to conceal evidence and intimidate and bribe witnesses to prevent their cooperation with law enforcement.

“Defendant actively obstructed justice during the pendency of this trial,” prosecutors wrote. “Defendant threatened witnesses, he isolated the victim at issue in this case, and he paid hundreds of thousands of dollars to at least three separate people to collect and round up videotape evidence that would prove his guilt.”

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

The memo states the victim identified as “Minor 1” is the same girl who was the victim at Kelly’s 2008 trial, but who did not then cooperate with investigators. Prosecutors say they have “disturbing, explicit and crude” videos of Kelly having sex with a 14-year-old girl in his former home in Lake View. In two of the videos, Kelly and the girl mention the girl’s age — 14 — a total of 15 times. Two videos also show Kelly subjecting the girl to “sadomasochistic abuse” by urinating on her.

Prosecutors allege the girl and other victims have all testified to the existence of a fourth video that investigators have not located, in part because Kelly hired someone — who now is apparently cooperating with the government — to collect videos, and paid one of his victims $100,000 to return a tape. Kelly required other government witnesses involved in seeking out the tapes to take lie detector tests to prove they had turned over all copies to the singer.

Though not mentioned by name, the U.S. Attorney’s Office referenced Kelly’s former marriage to the now-deceased singer Aaliyah.

“The government’s ongoing investigation has revealed that defendant sexually abused many other young girls,” prosecutors wrote. “Indeed, as one example, in 1994 when defendant was 27 years old, he married a 15-year-old girl at a hotel in Rosemont, Illinois, knowing that she was a minor.”

Prosecutors said they have three of the alleged videos. Those, they said, were filmed at Kelly’s former Lake View residence.

Mayor Lori Lightfoot said she doesn’t have enough information to comment on specifics of the R. Kelly indictment.

But that didn’t stop the former federal prosecutor from lumping Kelly together with financier Jeffrey Epstein, who was arrested July 6 on charges of sex trafficking.

“I want to make sure that our children are protected. And unfortunately--as we we’ve seen, not just with Mr. Kelly, but others [like] Mr. Epstein, who have been in the news-- we need to make sure that people who are predators, people who don’t value our children other than for illicit purposes, see justice,” the mayor said.

“Mr. Kelly, as Mr. Epstein, is entitled to a presumption of innocence. But if they have harmed our children, I hope that they will see and feel the full measure of the law.”

Kelly, 52, was arrested while walking his dog about 7 p.m. Thursday in Chicago. He was held overnight at the Metropolitan Correctional Center in Chicago.

Kelly’s attorney Steve Greenberg said Friday the charges appear “to largely be the same as the conduct previously alleged against Mr. Kelly in his current state indictment and his former state charges that he was acquitted of. Most, in not all of the conduct alleged, is decades old.

“Mr. Kelly was aware of the investigations, and the charges were not a surprise,” Greenberg said.

Please see the attached statement regarding @@rkelly pic.twitter.com/dkVV8tpCFW — Steve Greenberg (@SGcrimlaw) July 12, 2019

A separate, five-count indictment was unsealed Friday in the Eastern District of New York. In that indictment, Kelly and his entourage were accused of acting as a criminal enterprise to “promote R. Kelly’s music and the R. Kelly brand and to recruit women and girls to engage in illegal sexual activity with Kelly.”

Cook County State’s Attorney Kim Foxx said the federal indictment “demonstrates the collaborative efforts of our criminal justice system.”

“My office was pleased to work together to secure these charges and will continue to work with our colleagues in the pursuit of justice for all victims. And let us be clear: this is not just about surviving R. Kelly. For most victims, it’s about surviving a less famous abuser, a trusted adult, or a total stranger,” Foxx said.

Six weeks ago, Cook County prosecutors filed a new series of sexual assault charges against Kelly, who was first charged in state court in February. The criminal sex abuse case against him there involves four women — three of them minors at the time — with the illegal acts he’s accused of dating from 1998 to 2010.

In May, Cook County prosecutors upgraded charges in one of those cases, this one involving someone described as a victim and identified by the initials “J.P,” to aggravated criminal sexual assault.

The state charges came weeks after celebrity Los Angeles attorney Michael Avenatti said he had a VHS tape he said showed Kelly having sex with a minor girl. That tape appears to be the basis for the charges against Kelly involving a girl who had sex with the singer in his former home in Olympia Fields sometime between 1998 and 2001, when the girl would have been 14 to 16 years old.

Kelly has pleaded not guilty to all charges.

Former Sun-Times music journalist Jim DeRogatis, who has reported on allegations against Chicago native Kelly for nearly two decades, wrote in February in The New Yorker that the FBI and IRS offices in the Eastern District of New York were investigating the singer and that a human-trafficking investigation by the federal Department of Homeland Security also was underway. The U.S. attorney’s office in Manhattan also was investigating Kelly, DeRogatis reported.

He also wrote then that officials in Fulton County, Georgia, where Kelly had a residence until recently, were investigating. Kelly has been free since posting $100,000 bail in February and living in an apartment in Trump Tower.

Kelly was acquitted of child pornography charges in 2008 after a trial in Cook County that centered on a videotape prosecutors said showed the singer having sex with a girl who was as young as 13.

Kelly had been dogged by allegations he had sex with underage girls before he was charged with the child pornography counts in 2002. The singer has come under more scrutiny since January, when the TV documentary “Surviving R. Kelly” aired on Lifetime. The six-part series featured interviews with women who said they had sex with Kelly when they were minors. It detailed allegations that the singer kept several women in cult-like captivity.

Kelly has denied the allegations of having sex with minors and of keeping two women who live with him against their will, as have the women, Azriel Clary and Joycelyn Savage.

Contributing: Ashlee Rezin