R. Kelly’s appeal argument calls reasons for long sentence too vague, but court warns he could wind up worse off

CHICAGO — Imprisoned R&B star R. Kelly’s attempt to win a new sentencing in Chicago’s federal court might well backfire, an appellate judge reminded his attorneys in court Thursday.

“If we agree with you, does your client realize he could be worse off?” Judge Amy St. Eve of the 7th Circuit U.S. Court of Appeals asked, noting that Kelly could be given a harsher prison term if he is resentenced. “… If he wins on this particular point, he has risks.”

Kelly’s attorneys were in court to argue that the disgraced R&B singer’s sex-crimes convictions should be thrown out and that the judge who sentenced him had no legitimate basis to give him 20 years in prison, which was higher than the suggested sentencing guidelines.

Much of the brief hearing was dedicated to discussing whether Kelly should be resentenced. But in the end, Kelly’s lead attorney Jennifer Bonjean noted, his fate really hinges on what happens on appeal in his New York federal case, a racketeering conviction that got him a whopping 30 years behind bars.

“That’s his life sentence,” Bonjean said during the 30-minute hearing at the Dirksen U.S. Courthouse. “If that sentence sticks, he will probably die in prison.”

Appellate arguments in the New York case are scheduled for next month.

A federal jury in Chicago convicted Kelly in 2022 on child pornography charges for explicit videos he made of himself and his then 14-year-old goddaughter, “Jane.” Kelly was also found guilty of inappropriate sexual relations with Jane and two other teenage girls, “Pauline” and “Nia.” The jury acquitted Kelly on separate charges of conspiring to rig his prior Cook County child pornography trial.

All but one year of Kelly’s 20-year sentence for the Chicago convictions is to be served concurrently with his New York sentence. The 57-year-old singer is in custody at a federal prison in North Carolina, records show.

The two-decade Chicago sentence was well above federal guidelines, but U.S. District Judge Harry Leinenweber’s comments during sentencing were “too vague to rely on,” Bonjean said, arguing he put too much emphasis on conduct for which Kelly was acquitted and did not precisely identify his reasons for giving Kelly such a hefty sentence.

“(It was) a little bit of stream of consciousness,” she said.

In response, Assistant U.S. Attorney Brian Williamson said sentencing judges have significant leeway to hand out prison terms longer than what federal guidelines suggest.

And Leinenweber justified the sentence in part by indicating that Kelly’s actions were “horrible, horrific and deserving of very very serious consequences,” Williamson said.

The arguments Thursday also briefly touched on Bonjean’s claims that the convictions should be thrown out because they were charged after the statute of limitations had expired.

Kelly abused the three girls in the 1990s, when the law allowed prosecutors to bring such charges until the victims turned 25. Congress in 2003 expanded the statute of limitations up until the victim’s death, but Bonjean argued lawmakers never intended that amendment to apply retroactively. Prosecutors could not have brought these charges any later than 2009, she said.

St. Eve again seemed skeptical, noting that no federal circuit has yet sided with Bonjean’s position.

Prosecutors argued that Congress expanded the statute of limitations long before it otherwise would have expired for Jane, Nia and Pauline. That’s a deadline extension, not a retroactive application of the law, they argued.

“This is a universal approach to changing that statute of limitations,” Williamson said. “It’s forward-leaning and backward-leaning.”

The brief arguments supplemented lengthy briefings that dove deep into Kelly’s claims.

Kelly’s briefings also argued that the charges against Kelly should have been split into separate groups: The child pornography counts, which had “dramatically stronger evidence” in the form of the videos of Kelly sexually abusing Jane, and the enticement counts involving Nia and Pauline.

The videos were such strong evidence of Kelly’s guilt that jurors likely didn’t completely consider whether prosecutors met their burden of proof on the separate accusations involving the two other girls, Kelly’s defense team argued.

Kelly also would have testified in his own defense on the charges involving Nia and Pauline, but didn’t do so, in order to avoid giving self-incriminating testimony about the other counts, according to Bonjean.

But prosecutors said jurors were explicitly instructed to consider each charge separately and they clearly did so, noting that while Kelly was convicted of abusing three teenage girls, he was acquitted of abusing two others.

Kelly, a Chicago native and onetime R&B superstar, had a stunning fall from grace after allegations of sexual abuse and misconduct reached a tipping point in 2019. Cook County prosecutors announced charges against Kelly early that year; a few months later, those were followed by the dual indictments in federal court.

Kelly’s trial in Chicago’s federal court featured 34 witnesses over five weeks. Jurors were shown clips from three separate videos made in the 1990s depicting Kelly abusing Jane, including the same tape from his Cook County trial as well as another where he instructed her to refer repeatedly to her “14-year-old” genitalia.

Jane testified for the first time at trial that not only was it her on the videotapes, but that Kelly had sexually abused her “innumerable” times when she was a minor, at his recording studio, his home, on tour buses and in hotel rooms.

Asked on the witness stand why, after two decades of silence, she finally decided to come forward and speak out, Jane said: “I became exhausted with living with (Kelly’s) lies.”

The jury’s split verdict came 14 years after Kelly’s infamous acquittal on similar charges in Cook County, which were based on a single video of Kelly allegedly abusing Jane in his former home. Jane had refused to cooperate in that case.

In a rare loss for federal prosecutors, the jury acquitted Kelly and two co-defendants on charges they conspired to retrieve incriminating tapes and rig his 2008 trial by pressuring Jane to lie to investigators about their relationship and refuse to testify against him.

Kelly was also found not guilty of filming himself with Jane on a video that jurors never saw. Prosecutors said “Video 4” was not played because Kelly’s team successfully buried it, but defense attorneys questioned whether it existed at all.

After Kelly’s federal convictions, Cook County prosecutors dropped their charges against him, in part to conserve resources given that he would already be serving significant prison time.

____