R. Kelly’s summer of reckoning: Convicted singer faces potentially decades in prison in New York, jury trial in Chicago

It’s been nine months since Chicago-born R&B singer R. Kelly was last in a New York courtroom, where he was convicted by a jury after decades of allegations of sexual misdeeds.

On that day in late September, Kelly, dressed in a gray suit, remained stoic as the verdict came in: guilty of racketeering conspiracy and eight other counts alleging he used his organization to lure and trap girls, boys and young women to satisfy his predatory desires.

Now, as his time behind bars nears the three-year mark, Kelly is in store for another day of reckoning, one that could determine whether he will ever walk free again.

After several delays, Kelly is set to be sentenced in U.S. District Court in Brooklyn on Wednesday in a hearing that is expected to include emotional testimony from some of his victims and reveal disturbing new details about Kelly’s own troubled upbringing in Chicago, where he rose from busking at “L” stations to international superstar.

Federal prosecutors have asked U.S. District Judge Ann Donnelly to sentence Kelly to more than 25 years in prison, saying his racketeering conviction was part of a “long and pervasive history of enticing children to engage in sexual activity.”

“He lured young girls and boys into his orbit, often through empty or conditioned promises of assistance in developing a career in the entertainment industry or simply by playing into the minors’ understandable desire to meet and spend time with a popular celebrity,” prosecutors wrote.

Kelly’s lawyer, meanwhile, has asked for the mandatory minimum 10-year prison term in a court filing that so far has been kept from public view.

Attorney Jennifer Bonjean, who took over as Kelly’s counsel after his conviction, told the Tribune she filed the document under seal because it contained sensitive information about Kelly’s past — including sexual abuse he allegedly endured as a child — as well as details that could “implicate others” in wrongdoing. More details are expected to be revealed in court this week.

Prosecutors filed their response to the defense’s sentencing memo under seal, explaining that they did so because Bonjean filed hers that way, according to court records. Donnelly has ordered both sides to file paperwork by Sunday evening addressing whether they believe Kelly’s sentencing submission should be kept private.

Bonjean, who intends to challenge the conviction on appeal, said the judge’s role is to fashion a sentence “based on not just retribution, but based on rehabilitation and reasonableness.”

“This mob-justice mentality is not the way to go,” she said. “It’s not good for society and it doesn’t take into account the human being. … No matter how angry people are, R. Kelly is a human being.”

Regardless of the outcome, the legal woes for the Grammy-winning singer, whose hits include 1996′s “I Believe I Can Fly,” will not be over even with his sentencing.

Kelly also faces a pending trial in August in Chicago’s federal courthouse, where prosecutors allege he and two others fixed his 2008 trial in Cook County and paid people to buy back incriminating sex tapes. He’s also charged in four separate indictments alleging sexual abuse that are still pending at Chicago’s Leighton Criminal Court Building. Kelly also faces a solicitation case in state court in Minnesota.

While there has been no indication in court that plea negotiations on the other cases are in progress, a last-minute deal that would avert further trials is always a possibility. The odds of that outcome would only increase if Kelly receives a long sentence Wednesday.

Stark difference in sentencing requests
Kelly’s trial in New York took place over nearly two months amid strict COVID-19 protocols and involved some 50 live witnesses.

In all, the seven-man, five-woman jury found Kelly guilty of 12 individual criminal acts involving the racketeering scheme, including sex with multiple underage girls as well as a 1994 scheme to bribe an Illinois public aid official to get a phony ID for the 15-year-old singer Aaliyah so the two could get illegally married.

Steve Greenberg, one of Kelly’s lawyers, said he hopes the sentencing judge will consider that “someone who has been so severely sexually abused as a child will often become an abuser themselves.” Kelly is a sex addict, Greenberg said, not a pedophile who is pathologically inclined to abuse children.

“I think if there was any evidence he was a pedophile, then the judge would be justified in giving a longer sentence, but this is a man who’s already had his entire life ripped out from under him,” Greenberg said. “His career is in shambles. When this is all done he’s going to be singing in the subway again.”

Greenberg still represents Kelly in his pending Cook County cases, but is no longer an attorney of record in either of the singer’s federal prosecutions. He was ousted from the New York case amid internal tensions in the legal team, and the attorneys who ultimately defended Kelly at trial “had no idea what they were doing,” he said.

Bonjean, who was not involved in the New York trial, took over Kelly’s defense after the conviction and is expected to handle the sentencing hearing Wednesday. The judge likely will hear extensive arguments from Bonjean and prosecutors, and before she announces a decision, Kelly himself will have the chance to speak on his own behalf.

“He’s obviously here for sentencing based on the offenses that a jury found him guilty of,” Bonjean said. “But this one-dimensional sex predator monster (characterization) I think just doesn’t take into account the human being in the totality or the offense in totality.”

Kelly has a long history of sexual abuse by a sister and a family friend, Bonjean told the Tribune last week. He grew up poor, in a household that experienced domestic violence; he also witnessed the death of a close childhood friend, Bonjean said. He reads at an early elementary school level, which has made it easy for people around him to manipulate and exploit him, she said.

The difference between the competing sentencing requests could not be more stark for Kelly, who will turn 56 in January. Under federal rules, defendants must serve 85% of their sentence, so with credit for time already served, a 10-year sentence would mean he would be released when he’s in his early 60s.

But if the judge sentences him to closer to what prosecutors have asked for, Kelly would not taste freedom until he’s well into his 70s.

Rocky time behind bars
Kelly’s last moments of freedom came on the evening of July 11, 2019, when federal agents and Chicago police officers approached him as he walked his dog outside the Trump Tower in downtown Chicago.

That night, federal prosecutors in both New York and Chicago unveiled stunning indictments against the singer, who was already free on bond in the Cook County cases brought five months earlier.

There would never be bond granted for Kelly in his federal indictments, despite months of pleadings from his legal team arguing everything from exposure to COVID-19 to physical assaults from inmates who targeted him because of his fame.

His time in federal custody has indeed been remarkably turbulent. In his earlier days at Chicago’s Metropolitan Correctional Center, die-hard fans would demonstrate outside the downtown jail. That reportedly spurred prison authorities to put the building on lockdown.

Enraged by such a lockdown, fellow detainee Jeremiah Shane Farmer slipped into Kelly’s cell in August 2020 and beat him repeatedly in the head, according to records. Farmer stopped only after a security officer pepper-sprayed him.

In a handwritten court filing, Farmer, a Latin King gang member who was sentenced to life for his role in a 1999 double murder, later said he attacked Kelly “due to the most blatant corruption in Farmer’s case and being (on) lockdown for Robert Kelly protest.”

Kelly suffered a serious concussion that left him with headaches and pain for months afterward, his attorneys said.

A year later, while Kelly was in the middle of his New York trial, the Tribune reported that unsealed court records revealed a Bureau of Prisons official in Wisconsin was under investigation for allegedly accessing Kelly’s recorded phone calls and emails at the MCC. The official apparently leaked them to a popular YouTube personality, who racked up hundreds of thousands of views touting her inside scoops on Kelly’s life in lockup.

No one has been publicly charged in the probe. As part of Kelly’s federal proceedings in Chicago, Bonjean has requested access to materials related to the investigation. In a court filing last month, she wrote she has “a good faith basis to believe that the stolen information was also provided to a government informant who may have shared said information with government witnesses at the behest of the government.”

Ahead of Kelly’s New York trial, he was transferred to the Metropolitan Detention Center in Brooklyn, where he has been in custody ever since. It was at that facility that Kelly was diagnosed with COVID-19 earlier this year, according to his attorneys. The omicron variant surge that swept through the country last winter did not spare the Brooklyn jail, which saw a spike in cases.

At some point soon after his sentencing, Kelly will be back in his hometown, likely detained once again at the MCC on West Van Buren Street, three years after he first arrived.

A Chicago trial
At Kelly’s trial in New York last summer, a small band of die-hard Kelly fans made their presence known on many trial days, setting up camp in a park across from the Brooklyn courthouse, where they carried signs, chanted about government overreach and blasted Kelly’s music.

It’s expected to be a far different scene when Kelly’s trial begins Aug. 15 at the Dirksen U.S. Courthouse, however. Despite decades of allegations of sexual misconduct, Kelly has maintained a robust fan base in his hometown, and a much larger contingent of supporters is likely to converge on Chicago’s Loop to get a glimpse of the action.

The trial itself will unfold in the courthouse’s large ceremonial courtroom on the 25th Floor, the only room large enough to accommodate Kelly and his two co-defendants — longtime manager Derrel McDavid and Milton “June” Brown — as well as attorneys, jurors, reporters and spectators.

Last week, U.S. District Judge Harry Leinenweber sent out notice for a special jury pool to be summoned that will weed out those who are obviously unable to sit for what is expected to be at least a monthlong trial.

Security is expected to be beefed up to accommodate any crowds, though unlike in his infamous trial in 2008, Kelly is in custody and won’t be entering and leaving the courthouse through the lobby every day.

Among the allegations Kelly was convicted of in New York was grooming Jerhonda Johnson Pace, an underage “superfan” who caught the singer’s eye as she attended his trial at the Leighton Criminal Court Building at 26th and California.

Pace was the first prosecution witness to testify at trial, telling the jury that despite knowing she was only 16, Kelly repeatedly sexually abused her over the course of several months, forcing her to wear baggy clothes and call him “Daddy” as part of an escalating campaign of physical abuse and control.

Among other evidence seen by the jury was a videotape depicting the singer spanking a young woman and forcing her to parade naked in front of him. Audio excerpts of the recording were later ordered released to the media by the judge.

“Keep your eyes closed,” Kelly can be heard saying at one point. “Eyes open? Guess what — we start over.”

Kelly’s instruction was followed by the sound of a series of slaps, and the woman could be heard sobbing. Afterward, she is heard weeping as Kelly makes her say, over and over, “I’m a stupid (expletive) daddy, I want you to fix me.”

Kelly’s lawyer, Bonjean, has argued that Pace’s testimony should not be given added weight because it was clear from the trial record that she misrepresented her age to Kelly.

“The trial record refutes any suggestion that Defendant did anything in altering the behavior of Jerhonda. Quite the opposite. Jerhonda, a sophisticated 16-year-old, took great pains to get close to Defendant, including by misrepresenting her age,” the defense filing stated. “Defendant did nothing to seek out Jerhonda.”

In their filing asking for a sentence of more than 25 years in prison, prosecutors in New York said that being charged in Cook County had no effect on Kelly’s sexual misdeeds.

“If anything, the defendant’s acquittal after his state trial appears to have emboldened the defendant with a belief that he was untouchable,” prosecutors wrote in their 31-page sentencing memo, “and, over the next decade, the defendant’s crimes continued unabated.”