R. Kelly sentencing: Federal judge could add to singer’s prison time Thursday

Kelly is already serving a 30-year sentence for a federal racketeering conviction in New York. So the crucial question Thursday will be whether U.S. District Judge Harry Leinenweber feels the need to punish Kelly further.

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In this June 2019 file photo, singer R. Kelly appears at a hearing at Leighton Criminal Courthouse.

E. Jason Wambsgans/Chicago Tribune

The yearslong legal battle over R. Kelly’s sexual abuse of women and girls will reach a critical moment Thursday when the R&B superstar is set to once again be sentenced by a federal judge — this time in his hometown of Chicago.

Kelly is already serving a 30-year sentence for a federal racketeering conviction in New York. It’s likely to keep Kelly, 56, behind bars until his late 70s. Kelly’s defense attorney says he’s already more likely to die in prison than walk free again.

So the crucial question Thursday will be whether U.S. District Judge Harry Leinenweber feels the need to punish Kelly further by adding to the singer’s total sentence.

While Kelly attorney Jennifer Bonjean argues doing so could amount to improper double jeopardy, the feds say Kelly’s conviction last year in Chicago warrants an additional 25 years. And that would theoretically keep Kelly locked up until 2066, when he would turn 99.

“There is no reason that the consequences imposed for his heinous crimes here should be discounted due to the sentence imposed for harming different victims at different times in the New York prosecution,” the feds argued in a court memo earlier this month.

Thursday’s hearing should resolve the most serious of the criminal cases filed against the singer in 2019. Kelly still faces prostitution charges in Minnesota, but he will know how much time he’s expected to serve as a result of his convictions in federal court. Cook County prosecutors dismissed their own cases against Kelly last month.

That should leave Kelly’s attorneys to largely focus on his appeals, including the one already underway in the 2nd U.S. Circuit Court of Appeals centering on Kelly’s New York conviction.

The sentencing hearing comes five months after a federal jury in Chicago found Kelly guilty of three counts of producing child pornography and three counts of enticing a minor into criminal sexual activity. It will likely feature another hard-fought battle among lawyers, as well as commentary from some of Kelly’s victims.

Leinenweber is also expected to consider whether Kelly owes restitution to his victims, known in court as “Jane,” “Pauline,” and “Nia.” Prosecutors are seeking at least $11 million, though Bonjean has said the feds’ numbers are “outrageous” and without support.


R-Kelly attorney Jennifer Bonjean adjusts her glasses as she speaks to reporters after the R-Kelly verdict was announced at the Dirksen Federal Courthouse, Wednesday, Sept. 14, 2022. | Tyler Pasciak LaRiviere/Sun-Times

She also recently blasted prosecutors for arguing that Kelly has refused to accept responsibility for his crimes. She insisted they are “not in Kelly’s head and cannot say what he feels or thinks.”

“When federal and state prosecuting agencies stop indicting him, Kelly might be in a position to speak more freely about his regrets,” Bonjean wrote in a memo to the judge over the weekend.

Bonjean told the Sun-Times that she thinks Kelly “would love to be able to make a statement” to the judge Thursday, but confirmed that she would advise him not to for the reasons she mentioned in that memo.

Bonjean also argued in her filings that prosecutors could have combined the two federal cases against Kelly. The singer was prosecuted in New York for racketeering activity between 1994 and 2018, in which he recruited women and girls to engage in illegal sexual activity.

Bonjean said the allegations at issue in Chicago could have been included. “There was no reason for the government to engage in piece-meal prosecution except to attempt to enhance Kelly’s punishment,” Bonjean wrote in one memo.

Prosecutors say Bonjean’s argument is “completely unfounded,” and that Kelly’s claims of double-jeopardy “have no legal support.”

“Here, Kelly was convicted of sexually abusing minors who were not a part of the New York case and who did not testify at the New York trial,” they wrote in their own memo. They said his Chicago case “involves minors not accounted for in his New York sentence.”

Now in her early 40s, Nia said she met Kelly at age 15 in 1996. She said Kelly touched her breasts and masturbated in a hotel room after a concert in Minneapolis, and he once fondled her in a hallway in his Chicago recording studio.

Pauline, now in her late 30s, said she was introduced to Kelly by Jane when she and Jane were 14. She said her abuse by Kelly turned to sexual intercourse when she was 15 or 16, and she said she participated in numerous threesomes with Kelly and Jane.


A woman now in her late 30s, and using the pseudonym “Jane,” testified at the federal trial of R. Kelly at the Dirksen Federal Courthouse in Chicago.

L.D. Chukman for the Sun-Times

But the most serious crimes for which Kelly faces sentencing revolved around Jane, who is also now in her late 30s. The jury found that Kelly sexually abused Jane when she was a teenager, on camera, as his career skyrocketed in the 1990s.

A video of Jane’s abuse went public in the early 2000s. Not only did it become fodder for comedians, prosecutors say it was viewed by many people “because Kelly is Kelly.”

They wrote that the video of Jane’s abuse “has, in a despicable and insidious way, become part of the social record.”

“The very public consumption of [the video] is something that Jane grew up with and will live with for the rest of her life,” they wrote.

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