CHICAGO — Prosecutors in Chicago have twice accused R. Kelly — the Grammy-winning, multi-platinum R&B superstar — of recording his sexual encounters with underage girls. 

Wednesday marked the first time that a jury in Chicago agreed. 

Robert Sylvester Kelly, 55, was convicted on six of the 13 counts brought against him in July 2019. The disgraced singer — originally from the city’s South Side — faces decades in prison at sentencing.  

“It had to be the way R. Kelly wanted,” Assistant U.S. Attorney Jeannice Appenteng said Tuesday during the prosecution’s rebuttal argument. “And, ladies and gentlemen, what R. Kelly wanted was to have sex with young girls.” 

The jury — made up of four white women, three Black women, three white men and two Black men — started deliberating shortly after 1 p.m. Tuesday, following four weeks of witness testimony. 

The jurors, however, acquitted Kelly of seven other counts in the indictment: one child pornography count, one count of sexual exploitation of a child, one count of aggravated criminal sexual abuse, as well as four conspiracy counts.

The federal jury’s decision to convict came 14 years after another jury — empaneled at the Cook County criminal courts building — acquitted Kelly of child pornography charges. That case stemmed from a VHS tape that purported to show Kelly engaging in sex acts with “Jane,” his 14-year-old “goddaughter.”  

Though he was found not guilty of charges in that case, federal prosecutors in the 2022 case said Kelly and his former business manager conspired to pressure Jane and her family to lie to a Cook County grand jury about the singer’s relationship with the teen girl. 

Kelly’s and his co-defendants — his former business manager Derrel McDavid and former assistant Milton “June” Brown — were acquitted of all conspiracy charges.

Kelly already faces a 30-year prison sentence stemming from his convictions on sex trafficking and racketeering charges in New York. He still faces two other pending criminal cases: one in Cook County and another in Minnesota. 

After McDavid learned of the jury’s decision, he shot up from his chair, raised both fists in the air and exclaimed, “Yes!”

McDavid quietly wept before hugging his attorneys, Beau Brindley and Vadim Glozman. McDavid also exchanged a hug with Kelly, who was seated just a few feet away from him throughout the trial.

As Kelly was being led out of the courtroom, Brown tried to offer him a hug, but he was stopped by the US Marshals. Kelly told Brown, “I love you, bro.”

Kelly’s sentencing date hasn’t yet been set. According to the United States Sentencing Commission, people convicted of federal child pornography charges received an average sentence of 23 years in prison in 2019.

The three defendants were charged in a 13-count indictment that was handed up in July 2019, about six months after the premiere of the Lifetime documentary series “Surviving R. Kelly.” 

Four of the counts against Kelly stemmed from four separate video recordings that, prosecutors said, showed Kelly engaging in sex acts with Jane, the prosecution’s star witness. He was convicted on three of those counts.

Jane did not take the witness stand at Kelly’s 2008 trial, and jurors in that case said that was a factor in their decision to acquit Kelly on child pornography charges. 

The singer has always publicly denied any allegations of wrongdoing, though, as is his right, he did not testify in his own defense in his 2022 trial. In 2019, the singer sat for a lengthy and often tense interview with Gayle King on CBS. Amid tearful screams, Kelly continued to maintain his innocence. 

This photo from Friday May 9, 2008, shows R. Kelly arriving for the first day of jury selection in his child pornography trial at the Cook County Criminal Courthouse in Chicago. (AP Photo/Charles Rex Arbogast, File)

Testifying under her pseudonym over the course of two days last month, Jane said she was first introduced to Kelly by her aunt, Stephanie “Sparkle” Edwards, when she was 13. At her aunt’s recommendation, Jane asked Kelly to be her “godfather” when she was 14, even though her parents — identified as “Susan” and “Brandon” — already selected Jane’s godparents. 

Kelly accepted, and their relationship soon turned sexual, Jane testified. Kelly engaged Jane in phone sex, asking her about her breasts and the color of her underwear. That quickly graduated to physical touching and, ultimately, intercourse. 

On the witness stand, Jane said she and Kelly engaged in sex acts “hundreds” of times while she was a minor. She also testified that she was indeed the girl seen in the video at the heart of Kelly’s 2008 trial.  

She and Kelly also had threesomes with other underage girls, including some of Jane’s friends from school, Jane said. Kelly often recorded the sexual encounters on a camcorder, and he kept the tapes in a gym bag that he and his handlers kept nearby. Other tapes were stored at Kelly’s home. 

After Jane testified, prosecutors played for jurors 17 different clips from Videos 1, 2 and 3 that allegedly showed Kelly and Jane engaging in sex acts. Video 1, prosecutors said, was the video at the center of Kelly’s 2008 child pornography trial.  

Before the videos were played, federal prosecutors asked U.S. District Judge Harry Leinenweber to order all members of the public and press out of the courtroom. The judge denied the request, though courtroom staff erected partitions around the jury to ensure that no one other than the judge, jury and attorneys saw the graphic footage. The audio from the clips, however, was broadcast throughout the courtroom. 

The trial was held in the larger, ceremonial courtroom on the 25th floor of the Dirksen Federal Courthouse, which is typically used for naturalization ceremonies. The scope of the already high-profile case — three defendants charged in a 13-count indictment — on top of the court’s COVID-19 protocols necessitated the larger setting. 

The female in the video — Jane, according to her testimony — could be heard repeatedly referring to her genitals as “14 years old.” 

“I considered myself a submissive person and I wanted to give him what he wanted and what he required,” Jane testified. “He was an authoritative figure over me … I just went with the flow of whatever he said to do.” 

In one of the videos — “Video 1” at the center of Kelly’s 2008 trial — Kelly could be seen handing the 14-year-old girl money. That was done, Jane said, out of caution in case the tape was ever leaked to the public. 

“He wanted it to appear that I was a prostitute,” Jane said. 

Prosecutors said Kelly and his co-defendants were able to get rid of one of the tapes — “Video 4” — that showed Kelly engaging in sex acts with Jane and another government witness, Lisa Van Allen. Defense attorneys argued that the tape depicted Kelly having a threesome with Van Allen — who was of legal consenting age — and Kelly’s now ex-wife. Jurors acquitted Kelly of the child pornography count stemming from Video 4.

Kelly and McDavid were charged together in the fifth count of the indictment: obstruction of justice. Prosecutors alleged the two conspired to pressure Jane and her family to keep quiet about Kelly’s sexual relationship with the teen girl.  

In 2000, Jane told the Illinois Department of Children and Family Services that there was nothing inappropriate about Kelly’s and Jane’s relationship.  

“I denied it,” Jane said. “I was afraid that something bad would happen to Robert … I wanted to protect him so I did everything I could to keep it a secret.” 

“It was instilled in me not to admit that to anybody and that’s exactly what I did,” Jane said. 

Jane continued to deny any impropriety to her parents, as well.  

In late 2000, the Chicago Sun-Times was the first major media outlet to report on allegations that Kelly was engaging in sex acts with minors. The Sun-Times was later sent the VHS tape that eventually led to the state child pornography charges brought against Kelly in 2002. 

Jim DeRogatis, the former Sun-Times pop music critic who’s written extensively about Kelly over the last 25 years, was called to testify in the 2008 trial, though he declined to answer any questions on the witness stand. DeRogatis was subpoenaed to testify in the 2022 trial by McDavid’s attorney, though Leinenweber later quashed the subpoena. 

In early 2002, McDavid organized a meeting between Kelly, Jane and her parents at a hotel in Oak Park, prosecutors said. Before his death, Jane’s father was a guitarist who played for Kelly. At that meeting, Kelly admitted to Jane “that a tape was indeed leaked,” Jane said. It was then that Kelly confirmed to Jane’s parents that they were engaging in sex acts. 

“He wanted them on his team as far as handling the legal aspects about to take place,” Jane said. “I just remember my dad storming out and being upset.” 

Kelly then dropped to his knees and begged Jane’s father “for forgiveness,” Jane said. 

“He was just saying, ‘I can’t help you,’” Jane said of her father. 

McDavid, testifying in his own defense over three days, said he was not present at the meeting. Instead, he said, he was waiting outside in the car. McDavid also repeatedly told jurors that never gave credence to the early allegations against Kelly because of reassurances he received from the legal team that he hired for the singer. 

After that meeting, Susan said, she and her family decided to lie about Kelly and Jane engaging in sex acts out of fear. 

“We feared for our lives and we were intimidated and we just wanted to make sure my daughter was safe,” Susan said. 

Shortly after the meeting, Kelly paid for Jane and her parents to go on a weeks-long vacation in Mexico and the Bahamas. Susan said the trip was a way for Kelly to keep the family out of the reach of law enforcement and the news media. 

While she and her family were out of the country, Jane got a tattoo of Kelly’s first name “Robert” inside a heart. Upon her return home, she said, Kelly told her that the tattoo needed to be covered up. Kelly then assigned Brown to take Jane to a tattoo artist’s home, where the tattoo was obscured. 

Bonjean showed jurors a series of friendly text messages between Jane and Kelly, whose conversations lasted until Kelly was charged in 2019, seeking to demonstrate that the two remained friendly for years after the 2008 trial. 

The courtroom’s public seating was full each day of the trial, with supporters of Kelly showing up and staking out spots in line outside the courtroom each morning of the XX-day trial. The US Marshals, who provide courtroom security at the Dirksen Federal Courthouse, repeatedly reminded Kelly’s supporters to remain quiet during trial proceedings.  

Three counts in the indictment related to the efforts by Kelly, Brown and McDavid to recover videos 2, 3 and 4. Prosecutors said the three enlisted Charles Freeman, of Kansas City, to drive across the country in an effort to recover the illicit tapes stolen from Kelly’s collection. Freeman testified that McDavid ultimately paid him more than $600,000 for his efforts. 

Defense attorneys, meanwhile, painted Freeman — one of several government witnesses to testify with immunity — as a con artist who approached Kelly’s camp and demanded money in exchange for him not publicly releasing the tapes. Freeman also testified in Kelly’s 2008 trial. 

On the witness stand last month, Freeman often sported a grin as he, at times, struggled with questions from Bonjean and McDavid’s attorney, Beau Brindley, who pointed out alleged inconsistencies between Freeman’s trial testimony and previous sworn statements he made to a Cook County grand jury and a federal grand jury. 

“Is this funny? You having a good time?” Brindley asked during Freeman’s second day of testimony last month. 

“Yes, I am,” Freeman replied before he leaned back in the witness chair and took a sip of iced tea. 

Freeman also testified that Brown was sometimes the one who gave him money. Brown’s name was invoked the least of the three defendants during the trial, and Brown’s attorneys sought to portray him as a lowly assistant to Kelly who knew to just do his job and not ask questions. 

Though prosecutors said they were able to recover videos 1, 2 and 3, the fourth video was never recovered. Lisa Van Allen — another government witness with immunity who also testified in the 2008 trial — testified that Video 4 contained footage of her having a threesome with Kelly and Jane, who was 14 at the time the video was made. 

Van Allen said she stole the tape once she learned Jane’s real age, and she sent it to Keith Murrell, a friend of hers who lived in Kansas City. Murrell testified that he watched the video, and he did not see anything that would suggest any of the people depicted were under age. 

Kelly was the lone defendant in the final five counts in the indictment, all of which related to alleged sex acts he committed against five different girls who were younger than 18 at the time. Four of them — Jane, “Nia,” “Tracy” and “Pauline” — testified at length about meeting Kelly while they were in their teens and the sex acts they engaged in. 

The fifth victim, identified as “Brittany,” did not testify during the trial and prosecutors never explained why.

Jurors convicted Kelly on the counts related to Jane, Nia and Pauline, but acquitted him on the counts related to Tracy and Brittany.

The initial indictment against Kelly, brought in July 2019, listed five victims, identified as Minors 1, 2, 3, 4 and 5. However, Kelly’s superseding indictment, filed in February 2020, listed the victims as Minors 1, 3, 4, 5 and 6. 

During Van Allen’s cross-examination, McDavid’s attorney Beau Brindley suggested that she was originally “Minor 2,” but prosecutors removed her as a victim when they learned she was actually 18 years old when she and Kelly first met. A central theme of the Kelly’s defense was that several complaining witnesses and victims — namely Van Allen and Tracy — were actually of legal consenting age when they engaged in sex acts with Kelly. 

Tracy, who met Kelly while she was an intern at Epic Records, testified that she and Kelly engaged in sex acts in 1999 when she was 16. However, Tracy brought a lawsuit against Kelly in 2001 that alleged the encounters occurred in 2000, when Tracy was 17 — the legal age of consent in Illinois.

Bonjean pressed Tracy on the inconsistencies, and Tracy said her attorney in the lawsuit — Susan Loggans, who’s represented several women in lawsuits filed against Kelly — may have made a mistake when drafting the complaint.

During McDavid’s direct examination, Brindley sought to demonstrate that the early allegations against Kelly were part of a smear campaign orchestrated by his former manager, Barry Hankerson. 

Jurors, however, were not allowed to hear any testimony about Hankerson’s niece, Aaliyah, the R&B phenom who illegally married Kelly in the mid-1990s when she was 16 years old. Kelly also produced Aaliyah’s debut album, “Age Ain’t Nothing But a Number.” Aaliyah died in a plane crash in 2001. 

McDavid, on several occasions, told jurors that he never gave credence to the early allegations against Kelly. The attorneys who he hired for the singer in advance of the 2008 trial repeatedly told him that Kelly was innocent, McDavid said. 

However, during Kelly’s trial last year in federal court in New York, the singer’s former tour manager, Demetrius Smith, testified that Kelly told him that he was worried Aaliyah might be pregnant with his child. Smith said McDavid pushed Kelly to marry the singer as a way to protect himself from legal liability. 

Kelly was sentenced to 30 years in prison last June following his convictions on sex trafficking and racketeering charges.  

“R. Kelly used his fame, fortune and enablers to prey on the young, the vulnerable and the voiceless for his own sexual gratification, while many turned a blind eye,” Breon Pace, U.S. Attorney for the Eastern District of New York, said in a statement after Kelly was sentenced. “Through his actions, Kelly exhibited a callous disregard for the devastation his crimes had on his victims and has shown no remorse for his conduct.” 

Bonjean, who also represented Kelly in that case, said the singer will appeal both his conviction and sentence. 

Kelly, meanwhile, still faces pending criminal charges in Cook County and Minnesota. Those cases have largely remained on hold during the pendency of the federal cases.