R. Kelly entered his plea during an arraignment hearing held in Brooklyn Federal Court on Friday morning

By Maria Pasquini
August 02, 2019 12:45 PM

R. Kelly has pleaded not guilty to charges of racketeering and violating federal laws prohibiting sex trafficking.

The singer, 52, entered his plea during an arraignment hearing held in Brooklyn Federal Court on Friday morning, after having been transported in custody from Chicago, where he is being held without bond.

Kelly — who “appeared sullen” — only addressed the court briefly, made his plea through his attorneys, according to the Associated Press and Variety.

Scheduled for back-to-back hearings, the singer was also denied bail, as government attorneys argued that Kelly was a flight risk, the outlet reported. Kelly’s lawyers Steve Greenberg and Douglas Anton didn’t immediately address the ruling.

The five-count indictment from the U.S. Attorney’s Office for the Eastern District of New York includes charges of racketeering and violations of the Mann Act, which “prohibits transporting people across state lines for the purpose of prostitution,” the New York Times previously reported.

Sketch of R. Kelly in court in New York Friday
Aggie Kenny/AP/Shutterstock

The indictment, which was previously obtained by PEOPLE, claimed that Kelly and his team — including managers, bodyguards and assistants — “traveled throughout the United States and abroad to perform at concert venues…and to recruit women and girls to engage in illegal sexual activity with Kelly” as far back as 1999.

Kelly is alleged to have required the women under his watch to follow “numerous rules” in which they “were not permitted to leave their room without receiving permission, including to eat or go to the bathroom,” were “not permitted to look at other men” and “were required to call Kelly ‘Daddy,’” the documents claimed. The indictment also accused Kelly of “engaging in sexual activity with girls under 18 years old,” failing to disclose “a sexually transmitted disease Kelly had contracted” and producing child pornography by requesting underage girls send him photographs.

Following Friday’s court date, Kelly will be returned to Chicago ahead of a separate hearing scheduled for September, the Chicago Tribune previously reported.

RELATED: R. Kelly’s Crisis Manager Announces He’s Stepping Down After Saying He ‘Would Not’ Leave His Daughter with the Singer

Kelly’s court date comes less than a month after the singer (né Robert Kelly) was arrested on federal charges including child pornography, racketeering and obstruction of justice — per two indictments out of Chicago and New York City.

The Chicago indictment also accused Kelly of using physical abuse, violence and blackmail to “prevent victims from providing evidence to law enforcement.”

R. Kelly at court in Chicago in May
TANNEN MAURY/EPA-EFE/REX/Shutterstock

In June, Kelly pleaded not guilty to 11 felony sexual abuse counts after he was charged by Cook County prosecutors in Chicago in May. The charges included five counts of aggravated criminal sexual assault, and they stemmed from one accuser who claimed Kelly abused her in 2009 and 2010 while she was underage.

In February, he was also hit with 10 counts of aggravated criminal sexual abuse against four alleged victims, three of which were specially referred to as under the age of 17. He pleaded not guilty to all of the charges.

An arrest warrant was issued for Kelly in February after the first charges were announced, and he surrendered to Chicago police hours later. Three days later, Kelly was released from jail after paying 10 percent of his $1 million bail amount, the Cook County Sheriff confirmed to PEOPLE at the time.

The singer faces a maximum prison sentence of over 200 years, according to Reuters.

Kelly, who was also the subject of the bombshell documentary Surviving R. Kelly earlier this year, has maintained his innocence throughout his legal troubles.

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