By Andrew R. Chow and Josiah Bates
Updated: August 6, 2019 4:01 PM ET | Originally published: March 8, 2019

Legal trouble for R. Kelly continues to mount with new federal charges in New York and Chicago that accuse him of forcing women and young girls to engage in illegal sexual activity. The R&B singer was arrested on July 11 in Chicago and is currently in federal custody. On Thursday, July 16, he entered a not guilty plea and a judge ordered him held without bail after a federal prosecutor said he’s “an extreme danger to the community, especially minor girls.”

He is facing multiple charges, including four counts of producing child pornography and five counts of enticement of a minor to engage in criminal sexual actively, according to the Northern Illinois U.S. Attorney’s office.

Kelly is also facing charges of sexual exploitation of children, forced labor and kidnapping, according to a statement by the U.S. Attorney’s office in Brooklyn. On Aug. 5, local authorities in Minnesota also filed charges of prostitution and solicitation.

“As alleged, R. Kelly, together with employees and members of his entourage, engaged in a racketeering enterprise that preyed upon women and girls who attended his concerts so that the victims could be available to engage in illegal sexual activity with him at a moment’s notice,” Richard Donoghue, the U.S. Attorney in Brooklyn, N.Y., who also filed charges, said in a statement.

These new developments are just the tip of the iceberg for a man who has previously denied all allegations of sexual misconduct while tangling with the law and feuding with accusers for more than 20 years. Earlier this year he was arrested twice and participated in an eyebrow-raising multi-part interview with Gayle King.

Here’s a comprehensive timeline following R. Kelly’s troubled personal history and career.

April 1994: Commercial breakthrough

R. Kelly, 27, achieves mainstream success when his single “Bump n’ Grind” hits number one on the Billboard 100. A month later, his protégé Aliyah releases her debut album, Age Ain’t Nothing But A Number, which was almost entirely written and produced by him.

July 1994: R. Kelly marries Aliyah

As Age Ain’t Nothing But A Number climbs into the top ten on the R&B/Hip-Hop Album charts, Kelly secretly marries Aliyah in Chicago. But while the marriage certificate falsely lists her age as 18, she is actually 15. The marriage is reportedly annulled months later, and in May 1997, Aliyah files suit in Cook County seeking to have all records of the marriage expunged. She says she had cut off all contact with Kelly. When Kelly asked about the marriage reports in 2016, he said: “Out of respect for her mother who’s sick and her father who’s passed, I will never have that conversation with anyone.”

December 2000: The investigation begins

Jim DeRogatis, a reporter for the Chicago Sun-Times, publishes an article that reveals that Kelly was sued in 1996 by Tiffany Hawkins, an aspiring singer. Hawkins alleges that Kelly “engaged in inappropriate sexual conduct” with her in 1991, when she was 15 and he was 24. Kelly countersues and later settles the initial lawsuit.

August 2001-May 2002: Allegations emerge

With Kelly established as a global superstar and the self-proclaimed “King of R&B,” a series of women sue Kelly for sexual misconduct. Tracy Sampson alleges that he had sex with her when she was 17 and claims that Kelly “often tried to control every aspect of my life.” Patrice Jones claims Kelly coerced her into having an abortion, while Montina Woods claims Kelly taped her during sex without her consent. Kelly reaches settlements with all three women. The cases never go to trial; Kelly admits to no wrongdoing.

Around this time period, DeRogatis receives two videos that allegedly show Kelly having sex with underage girls. He turns them over to the Chicago police.

June 2002: Kelly indicted on child pornography charges

After the police examine the second video tape turned over by DeRogatis, they indict Kelly on 21 counts of child pornography. Kelly is arrested at his vacation home in Florida; he posts bail and pleads not guilty. He says it’s not him in the video.

Singer Robert Kelly (aka R. Kelly) was arrested in June 2002 following his indictment in Chicago on 21 counts of child pornography.
Donaldson Collection—Getty Images

July 2003: Arrested in Miami

While shooting a music video, Kelly is arrested and charged with 12 additional counts of child pornography after lewd photographs are found in his home. But two months later, a Florida judge says the photographs were illegally seized, and those charges are dropped.

February 2003: Kelly returns to the top of the charts

Kelly releases his fifth album Chocolate Factory, which features the single “Ignition (Remix).” Chocolate Factory debuts at number one, selling over 532,000 copies in its first week of sales.

2003-2008: Delays and postponements

A series of improbable events causes the trail to drag on for years. In 2006, Judge Vincent Gaughan falls off a ladder and sustains injuries. The following year, Kelly undergoes emergency surgery for a burst appendix and the lead prosecutor gives birth, leading to more delays. A trial date is set for that September, but Gaughan postpones it once again.

July 2008: Kelly found not guilty

After one day of deliberations, Kelly is found not guilty on all counts. The girl believed to be on the tape refuses to testify, and jurors say that they cannot be certain of her identity.

R&B star R. Kelly, 41, waves to supporters as he leaves the Cook County Criminal Courts Building after he was acquitted of child pornography charges Friday, June 13, 2008, in Chicago, Illinois.
Chicago Tribune—MCT via Getty Images

2009-2017: Continued success

Kelly’s career continues in full force. Three more albums hit number one on the Billboard 200, and he is asked to perform at major stages and events, including Whitney Houston’s memorial service, the 2010 World Cup, the 2011 Grammy gala and Coachella 2013. He releases an autobiography in 2012.

July 2017: Buzzfeed publishes an exposé

DeRogatis publishes another investigation into Kelly’s wrongdoings, this time on Buzzfeed, which alleges that Kelly is keeping women against their will in an abusive “cult.” The women interviewed — described as “former members of Kelly’s inner circle” — say that Kelly lives with six women “controls every aspect of their lives: dictating what they eat, how they dress, when they bathe, when they sleep, and how they engage in sexual encounters that he records.”

Kelly’s lawyer says that the singer “unequivocally denies such accusations.” Jocelyn Savage, a woman whose parents told the police that she is being held captive, releases a video on TMZ in which she denies being held against her will.

The piece spawns an activist hashtag, #MuteRKelly, online, as the #MeToo movement picks up steam.

May 2018: Another lawsuit

Faith Rodgers files a lawsuit against Kelly in New York that accuses the singer of sexual battery. She later says that Kelly tried to silence her through threats of retaliation.

A Kelly concert at the University of Illinois in Chicago is cancelled due to protests, and his music is removed from Spotify’s playlists. The following month, he releases a 19-minute song called “I Admit” in which he denies many of the accusations against him.

January 2019: Surviving R. Kelly is released

Surviving R. Kelly, a six-hour docuseries on Lifetime, explores allegations against Kelly stretching back to the early 1990s. More than 50 interviews are conducted with siblings, journalists and accusers, who say that they were lured into sexual relationships with Kelly as underage girls and mentally and physically abused by him.

The series prompts Kim Foxx, the Cook County State’s Attorney, to make a public plea for accusers to come forward. Amidst protests both online and in person, Kelly is dropped by Sony music. Kelly’s lawyer vehemently denies the claims in the documentary, saying, “It just didn’t ever happen.”

February 2019: Indicted again

Foxx indicts Kelly on 10 counts of aggravated criminal sexual abuse in connection with four women, three of them underage. The lawyer Michael Avenatti says he turned in another tape to Foxx in which Kelly allegedly sexually assaults a minor. Kelly is arrested and then released on $100,000 bond; he pleads not guilty to the charges.

In this photo taken and released by the Chicago Police Dept., Friday, Feb. 22, 2019, singer R. Kelly is photographed during booking at a police station in Chicago, Il. R. Kelly, the R&B star who has been trailed for decades by allegations that he violated underage girls and women and held some as virtual slaves, is being charged with aggravated sexual abuse involving four victims, including at least three between the ages of 13 and 17.
AP

March 2019: Public denial and re-arrest

In an interview with Gayle King on CBS This Morning, which aired March 6, Kelly jumps out of his seat, screams and curses, yelling “I’ve been assassinated” and “I’m fighting for my f-cking life.”

The next day, CBS airs King’s interview with two women who live with Kelly. They deny that they are being held against their will and denounce their parents, who believe they are being brainwashed. Kelly himself is in the room for the interview, according to King.

The day that the first part of the interview airs, Kelly is arrested once again for failing to pay his ex-wife more than $160,000 in child support.

The same day, Detroit authorities open an investigation into a woman’s claims that Kelly had sex with her in 2001 in Detroit when she was 13 years old.

May 2019: More charges

Kelly is charged by Cook Country prosecutors with 11 new sex-related counts, including some that carry a maximum sentence of 30 years in prison. The counts describe alleged sexual assault and abuse against a victim under 17. On Twitter, Kelly’s lawyer writes that the charges are related to an previous case and are not being brought by a new accuser. “These are the same conduct, just charged differently, same alleged victim, same time frame, same facts. We expect the same results,” he writes.

July 2019: Federal charges

Kelly was arrested on July 11 on new federal charges stemming from incidents in New York, Connecticut, Illinois and California, according to the U.S. Attorney’s office in Illinois. He faces 13 counts of producing and receiving child pornography and telling minors to engage in criminal sexual activity. The charges say that Kelly engaged in sexual activity with five minors. He is also charged with conspiring to threaten victims and hide evidence from law enforcement.

On Tuesday, July 16, U.S. District Judge Harry Leinenweber ordered Kelly to be held without bond after federal prosecutors said that if he was released he might try to flee and that he was a risk to minors, according to the AP.

Assistant U.S. Attorney Angel Krull reportedly told the judge Kelly was “an extreme danger to the community, especially minor girls.”

The charges against Kelly in New York include sexual exploitation of children, forced labor and kidnapping, according to a statement by the U.S. Attorney’s office in Brooklyn.

Kelly’s lawyer, Steve Greenberg, said the singer was arrested while walking his dog.

“Mr. Kelly was aware of the investigations and the charges were not a surprise. He has already assembled a team of outstanding federal litigators. He and his lawyers look forward to his day in court,” Greenberg said in statement posted to Twitter on Friday.

Greenberg also said in his statement that Kelly looks “forward to his day in court” and believes that he will be vindicated from “what has been an unprecedented assault by others for their own personal gain”

Two other members of his music business, Derrel McDavid, 58 and Milton Brown, 53, face charges of receiving child pornography as well.

According to the indictment from federal prosecutors in Brooklyn, Kelly and his associates, who included bodyguards, managers, drivers and assistants, would recruit women at concerts and other venues to travel with the singer,.

The women were given strict instructions, which included them being required to refer to R. Kelly as “Daddy.” They also were not allowed to leave their rooms, eat or drink without Kelly’s permission, according to the indictment. The women also had to wear baggy clothes when they were not with Kelly, unless otherwise instructed, according to the indictment.

They also couldn’t look at other men while in public and were told to keep their heads down, the indictment alleges.

Along with these charges, the indictment from prosecutors in Illinois alleges that Kelly engaged in illegal sexual activity with multiple minors around 1998 and 1999 and that these incidents were filmed. He’s also alleged to have intimidated victims and their families from speaking with the police about his actions, the indictment says.

Kelly is also accused of forcing victims and their families take lie-detector tests to make sure they had no copies of the videos he made.

The indictment also alleges that Kelly arranged for a victims and her parents to travel internationally so they wouldn’t be able to talk to the police before he was indicted back in 2002.

Kelly is accused of making payments to his alleged victims’ families that estimated be over $100,000, the indictment says. One of the victims was also given a GMC truck in 2013, according to prosecutors.

August 2019: Minnesota charges

Kelly was also charged with prostitution and solicitation on Aug. 5 in Minnesota, stemming from an allegation that he paid a 17-year-old girl $200 to dance naked with him in 2001, the AP reported.

Hennepin County Attorney Mike Freeman said that Kelly solicited the girl after meeting her before a concert in Minneapolis.

Both charges are felonies and each carry up to five years in prison. Freeman said his office investigated after receiving information via a Chicago tip line, according to the AP.

Write to Josiah Bates at josiah.bates@time.com.

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