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

  • R. Kelly turns himself in at 1st District police headquarters...

    Chris Sweda / Chicago Tribune

    R. Kelly turns himself in at 1st District police headquarters in Chicago on Feb. 22, 2019.

  • R. Kelly performs at Arie Crown Theatre in Chicago on...

    Scott Strazzante / Chicago Tribune

    R. Kelly performs at Arie Crown Theatre in Chicago on Oct. 25, 2012.

  • Singer R. Kelly appears at the Leighton Criminal Court Building...

    E. Jason Wambsgans / Chicago Tribune

    Singer R. Kelly appears at the Leighton Criminal Court Building in Chicago on June 6, 2019, where he pleaded not guilty to new charges.

  • Assistant State's Attorney Jennifer Gonzalez, center, responds to R. Kelly...

    E. Jason Wambsgans / Chicago Tribune

    Assistant State's Attorney Jennifer Gonzalez, center, responds to R. Kelly attorney Steve Greenberg, right, at Kelly's hearing at the Leighton Criminal Court Building in Chicago on May 7, 2019.

  • R. Kelly arrives for his child support hearing at the...

    Abel Uribe / Chicago Tribune

    R. Kelly arrives for his child support hearing at the Daley Center on March 6, 2019, in Chicago.

  • R. Kelly supporters Millord Edmond, 13, left, and his uncle,...

    Chuck Berman/Chicago Tribune

    R. Kelly supporters Millord Edmond, 13, left, and his uncle, Harlan Chambers, look into through the window of the Leighton Criminal Court Building, where singer R. Kelly pleaded not guilty to charges of child pornography in 2002.

  • R. Kelly appears before Judge Lawrence Flood at a hearing...

    E. Jason Wambsgans / Chicago Tribune

    R. Kelly appears before Judge Lawrence Flood at a hearing at Leighton Criminal Court Building in Chicago on May 7, 2019.

  • R. Kelly, center, arrives for his child support hearing at...

    Abel Uribe / Chicago Tribune

    R. Kelly, center, arrives for his child support hearing at the Daley Center on March 6, 2019, in Chicago.

  • Singer R. Kelly, right, appears at a hearing before Judge...

    E. Jason Wambsgans / Chicago Tribune

    Singer R. Kelly, right, appears at a hearing before Judge Lawrence Flood at the Leighton Criminal Court Building on March 22, 2019.

  • R. Kelly arrives to the Daley Center in Chicago for...

    Jose M. Osorio/Chicago Tribune

    R. Kelly arrives to the Daley Center in Chicago for a child support hearing on March 13, 2019.

  • Derrick Mosley, founder and president of the Bringing About Reform...

    Scott Strazzante/Chicago Tribune

    Derrick Mosley, founder and president of the Bringing About Reform organization, destroys R. Kelly compact discs in front of WGCI radio headquarters on South Michigan Avenue on Jan. 28, 2002. Mosley called others to come together for a day of repudiation to protest the embattled singer and the radio station for blatant disrespect toward the community.

  • R. Kelly follows his lawyer out of his studio Feb....

    Abel Uribe / Chicago Tribune

    R. Kelly follows his lawyer out of his studio Feb. 22, 2019.

  • Singer Robert Kelly enters court at 26th and California with...

    Chuck Berman/Chicago Tribune

    Singer Robert Kelly enters court at 26th and California with a phalanx of sheriff's deputies in 2002. A fan tried to shake Kelly's hand, but deputies pushed him away.

  • Singer R. Kelly leaves the Cook County Criminal Court Building...

    Michael Tercha/Chicago Tribune

    Singer R. Kelly leaves the Cook County Criminal Court Building after a hearing Aug. 21, 2007.

  • Jennifer Bonjean, defense attorney for the singer R. Kelly, speaks...

    Stephanie Keith/The New York Times

    Jennifer Bonjean, defense attorney for the singer R. Kelly, speaks outside the federal courthouse in Brooklyn on June 29, 2022, after R&B singer Kelly was sentenced to 30 years.

  • In this Dec. 21, 2007 file photo, R. Kelly arrives...

    Heather Stone / Chicago Tribune

    In this Dec. 21, 2007 file photo, R. Kelly arrives at the Cook County Criminal Courts building in Chicago to find out if the judge wants to revoke his bond or to deny permission to tour after missing a scheduled hearing.

  • Musician R. Kelly, blue jacket, leaves the Cook County Jail...

    Zbigniew Bzdak / Chicago Tribune

    Musician R. Kelly, blue jacket, leaves the Cook County Jail on Feb. 25, 2019, after posting a $1 million bond.

  • Cook County State's Attorney Kim Foxx describes what happened to...

    John J. Kim / Chicago Tribune

    Cook County State's Attorney Kim Foxx describes what happened to alleged victims of R. Kelly after his bond hearing at the Leighton Criminal Court Building on Feb. 23, 2019, in Chicago.

  • R. Kelly leaves Cook County Jail after posting bond at...

    Zbigniew Bzdak / Chicago Tribune

    R. Kelly leaves Cook County Jail after posting bond at Leighton Criminal Court Building in Chicago on Feb. 25, 2019.

  • Singer R. Kelly addresses the media after walking out of...

    Abel Uribe / Chicago Tribune

    Singer R. Kelly addresses the media after walking out of Cook County Jail on March 9, 2019, after paying more than $160,000 in child support.

  • R. Kelly listens to Judge Karla Wright during his first...

    Joe Burbank/Orlando Sentinel

    R. Kelly listens to Judge Karla Wright during his first appearance hearing on felony child pornography charges June 6, 2002, at the Polk County Courthouse in Bartow, Fla. The judge approved Kelly's release from custody on $750,000 bail.

  • R. Kelly, performing at the Pitchfork Festival, in Chicago, on July...

    Nuccio DiNuzzo/Chicago Tribune

    R. Kelly, performing at the Pitchfork Festival, in Chicago, on July 21, 2013.

  • R. Kelly turns himself in to Chicago police Feb. 22,...

    Terrance Antonio James / Chicago Tribune

    R. Kelly turns himself in to Chicago police Feb. 22, 2019, on charges he sexually abused four victims, three of them underage, over a span of a dozen years.

  • R. Kelly stands behind his attorney, Steven Greenberg, as Greenberg...

    E. Jason Wambsgans / Chicago Tribune

    R. Kelly stands behind his attorney, Steven Greenberg, as Greenberg speaks to Judge Lawrence Flood at the Leighton Criminal Court Building on May 7, 2019.

  • R Kelly is taken into custody by Chicago police at...

    Chris Sweda / Chicago Tribune

    R Kelly is taken into custody by Chicago police at the 1st District police headquarters Feb. 22, 2019.

  • R. Kelly's attorney, Steven Greenberg, speaks the news media after...

    Zbigniew Bzdak / Chicago Tribune

    R. Kelly's attorney, Steven Greenberg, speaks the news media after Kelly pleaded not guilty at the Leighton Criminal Court Building in Chicago on Feb. 25, 2019.

  • R. Kelly performs at the Allstate Arena in Rosemont on...

    David Banks/for the Chicago Tribune

    R. Kelly performs at the Allstate Arena in Rosemont on June, 16, 2011.

  • R. Kelly's former business manager Derrel McDavid, from left, and...

    Terrence Antonio James / Chicago Tribune

    R. Kelly's former business manager Derrel McDavid, from left, and attorneys Beau Brindley and Vadim Glozman stand before the media at the Dirksen U.S. Courthouse in Chicago after verdicts were reached in Kelly's trial on Sept. 14, 2022.

  • "CBS This Morning" co-host Gayle King remains calm during her...

    Lazarus Jean-Baptiste / CBS

    "CBS This Morning" co-host Gayle King remains calm during her interview with the emotional R. Kelly in Chicago on March 5, 2019.

  • R. Kelly performs at Arie Crown Theatre in Chicago on...

    Scott Strazzante / Chicago Tribune

    R. Kelly performs at Arie Crown Theatre in Chicago on Oct. 25, 2012.

  • R. Kelly is led from the Leighton Criminal Court Building by Chicago police...

    Carl Wagner/Chicago Tribune

    R. Kelly is led from the Leighton Criminal Court Building by Chicago police officers to a waiting police car to be taken to the 10th District station on June 7, 2002.

  • R&B singer R. Kelly departs after his court appearance on...

    Barry Brecheisen/for the Chicago Tribune

    R&B singer R. Kelly departs after his court appearance on May 18, 2007, for child pornography charges at the Leighton Criminal Court Building.

  • Steve Greenberg, attorney for R. Kelly, files a motion before...

    E. Jason Wambsgans/Chicago Tribune

    Steve Greenberg, attorney for R. Kelly, files a motion before Judge Lawrence Flood requesting law enforcement officials preserve all communications between prosecutors and attorney Michael Avenatti at the Leighton Criminal Court Building on April 1, 2019.

  • R. Kelly stands behind his attorney, Steven Greenberg, as Greenberg...

    E. Jason Wambsgans / Chicago Tribune

    R. Kelly stands behind his attorney, Steven Greenberg, as Greenberg speaks to Judge Lawrence Flood at the Leighton Criminal Court Building on May 7, 2019.

  • City inspectors from the Department of Buildings arrive at the...

    Jose M. Osorio/Chicago Tribune

    City inspectors from the Department of Buildings arrive at the studio space for musician R. Kelly on Jan. 16, 2019.

  • R. Kelly performs "I Believe I Can Fly" with a...

    Mark Lennihan/AP

    R. Kelly performs "I Believe I Can Fly" with a choir behind him Feb. 25, 1998, during the 40th annual Grammy Awards at New York's Radio City Music Hall. Moments later, Kelly won Best Male R&B Vocal Performance for the same song.

  • Singer R. Kelly appears in court on Sept. 20, 2002,  for...

    Ovie Carter/Chicago Tribune

    Singer R. Kelly appears in court on Sept. 20, 2002,  for a status hearing on child pornography charges.

  • Singer R. Kelly and his attorney, Steve Greenberg, left, appear...

    E. Jason Wambsgans / Chicago Tribune

    Singer R. Kelly and his attorney, Steve Greenberg, left, appear at a hearing at the Leighton Criminal Court Building on March 22, 2019.

  • R. Kelly performs at the Allstate Arena in 2003.

    Scott Strazzante/Chicago Tribune

    R. Kelly performs at the Allstate Arena in 2003.

  • Singer R. Kelly walks into court at the Daley Center...

    Erin Hooley/Chicago Tribune

    Singer R. Kelly walks into court at the Daley Center for a hearing on his child support case on March 13, 2019, in Chicago.

  • Jennifer Bonjean, defense attorney for the singer R. Kelly, arrives...

    Stephanie Keith/The New York Times

    Jennifer Bonjean, defense attorney for the singer R. Kelly, arrives for his sentencing hearing at the federal courthouse in Brooklyn on June 29, 2022.

  • Latoya Williams, left, of Chicago, and other fans, come out...

    Antonio Perez/Chicago Tribune

    Latoya Williams, left, of Chicago, and other fans, come out to support R&B star R. Kelly as he arrives at the Cook County Criminal Courts Building for closing arguments in his child pornography trial on June 12, 2008

  • R. Kelly's attorney, Steve Greenberg, waves to news media as...

    John J. Kim / Chicago Tribune

    R. Kelly's attorney, Steve Greenberg, waves to news media as he records them before a bond hearing for R. Kelly at the Leighton Criminal Court Building on Feb. 23, 2019, in Chicago.

  • R. Kelly's attorney Steve Greenberg speaks to media following a...

    Antonio Perez / Chicago Tribune

    R. Kelly's attorney Steve Greenberg speaks to media following a hearing for his client R. Kelly at the Leighton Criminal Court building, Sept. 17, 2019.

  • Joycelyn Savage, center, and Azriel Clary, right, attend a bond...

    John J. Kim / Chicago Tribune

    Joycelyn Savage, center, and Azriel Clary, right, attend a bond hearing for R. Kelly at the Leighton Criminal Court Building on Feb. 23, 2019, in Chicago.

  • In this courtroom sketch, Assistant District Attorney Nadia Shihata presents...

    Elizabeth Williams / AP

    In this courtroom sketch, Assistant District Attorney Nadia Shihata presents her rebuttal statement to the jury during R. Kelly's sex trafficking trial on Sept. 24, 2021, in federal court in New York. R. Kelly is seen in the upper left hand corner inset and is seated lower right.

  • R. Kelly appears during a hearing at the Leighton Criminal...

    Antonio Perez / Chicago Tribune

    R. Kelly appears during a hearing at the Leighton Criminal Courthouse on Sept. 17, 2019.

  • Singer R. Kelly performs at United Center on May 14,...

    John Bartley/for the Chicago Tribune

    Singer R. Kelly performs at United Center on May 14, 1999.

  • R. Kelly performs at Pitchfork Festival in Chicago on July...

    Nuccio DiNuzzo / Chicago Tribune

    R. Kelly performs at Pitchfork Festival in Chicago on July 21, 2013.

  • In this courtroom sketch, the front of the courtroom is...

    Cheryl Cook / AP

    In this courtroom sketch, the front of the courtroom is blocked off as a sexually graphic video clip is played for the jury during R. Kelly's trial in federal court Aug. 19, 2022, in Chicago.

  • Singer Robert Kelly, known as R Kelly, leaves court with a...

    Chuck Berman/Chicago Tribune

    Singer Robert Kelly, known as R Kelly, leaves court with a phalanx of sheriff's deputies on June 26, 2002. He pleaded not guilty to charges of child pornography.

  • R. Kelly follows his lawyer out of his studio Feb....

    Abel Uribe / Chicago Tribune

    R. Kelly follows his lawyer out of his studio Feb. 22, 2019.

  • In this courtroom sketch, Kitti Jones, right, speaks during R....

    Elizabeth Williams / AP

    In this courtroom sketch, Kitti Jones, right, speaks during R. Kelly's sentencing in federal court in New York on June 29, 2022. Kelly and his attorney Ashley Cohen are seated, background left. The former R&B superstar was convicted of racketeering and other crimes.

  • Demonstrators rally in response to the R. Kelly allegations, Jan....

    Brian Cassella/Chicago Tribune

    Demonstrators rally in response to the R. Kelly allegations, Jan. 9, 2019, outside his recording studio in the West Loop.

  • Singer R. Kelly, center, appears at a hearing before Judge...

    E. Jason Wambsgans / Chicago Tribune

    Singer R. Kelly, center, appears at a hearing before Judge Lawrence Flood at Leighton Criminal Court Building in Chicago on June 26, 2019.

  • A courtroom sketch of R&B star R. Kelly during his...

    Cheryl A. Cook/for the Chicago Tribune

    A courtroom sketch of R&B star R. Kelly during his child pornography trial with attorneys Ed Genson (right,) and Sam Adam, Jr. (rear,) at the Cook County Criminal Courts Building, May 20, 2008.

  • In this courtroom sketch, R&B singer R. Kelly appears before...

    Tom Gianni sketch/AP

    In this courtroom sketch, R&B singer R. Kelly appears before Cook County Associate Judge Lawrence Flood with his attorney Steve Greenberg, Feb. 25, 2019, at the Leighton Criminal Courthouse in Chicago. Kelly's attorney entered not guilty pleas on the singer's behalf.

  • Camera crews are set up outside the federal courthouse in...

    Stephanie Keith/The New York Times

    Camera crews are set up outside the federal courthouse in Brooklyn on June 29, 2022, for singer R. Kelly's sentencing hearing.

  • City inspectors from the Department of Buildings and Chicago Fire...

    Jose M. Osorio/Chicago Tribune

    City inspectors from the Department of Buildings and Chicago Fire Department enter the from back door alley entrance to the studio space for musician R. Kelly on Jan. 16, 2019.

  • R. Kelly's defense attorney Jennifer Bonjean speaks to the media...

    Terrence Antonio James / Chicago Tribune

    R. Kelly's defense attorney Jennifer Bonjean speaks to the media at the Dirksen U.S. Courthouse in Chicago after verdicts were reached in Kelly's trial on Sept. 14, 2022.

  • Attorney Michael Avenatti is flanked by Jerhonda Pace and Angelo...

    Zbigniew Bzdak / Chicago Tribune

    Attorney Michael Avenatti is flanked by Jerhonda Pace and Angelo Clary after R&B superstar R. Kelly pleaded not guilty at Leighton Criminal Court Building in Chicago on Feb. 25, 2019. Pace was featured in the documentary "Surviving R. Kelly" and said she began a sexual relationship with R. Kelly when she was 16 years old.

  • A man motions for photographers to get out of the...

    John J. Kim / Chicago Tribune

    A man motions for photographers to get out of the way as Joycelyn Savage and Azriel Clary exit after a bond hearing for Savage's boyfriend, R. Kelly, at the Leighton Criminal Court Building on Feb. 23, 2019, in Chicago.

  • Cook County State's Attorney Kimberly Foxx announces charges against R&B superstar...

    Jose M. Osorio / Chicago Tribune

    Cook County State's Attorney Kimberly Foxx announces charges against R&B superstar R. Kelly as Chicago police Superintendent Eddie Johnson looks on at her office in Chicago on Feb. 22, 2019. Kelly was indicted on 10 counts of aggravated criminal sexual abuse.

  • R. Kelly turns to exit during a hearing at the...

    Antonio Perez / Chicago Tribune

    R. Kelly turns to exit during a hearing at the Leighton Criminal Court building, Sept. 17, 2019.

  • R. Kelly performs at the Chicago Theatre on April 26, 2006.

    Brian Kersey/for the Chicago Tribune

    R. Kelly performs at the Chicago Theatre on April 26, 2006.

  • The building that houses the R. Kelly recording studio on Jan....

    Brian Cassella/Chicago Tribune

    The building that houses the R. Kelly recording studio on Jan. 10, 2019.

  • R&B singer R. Kelly, center, is surrounded by deputies as...

    Charles Bennett/AP

    R&B singer R. Kelly, center, is surrounded by deputies as he leaves court Nov. 1, 2002, in Chicago. A judge ruled that Kelly, who had been free on bond since he was indicted in June on child pornography charges, can leave the state to appear at a concert in New York later in the month.

  • Jacquelyn Kasulis, the acting U.S. attorney in Brooklyn, New York,...

    Spencer Platt/Getty

    Jacquelyn Kasulis, the acting U.S. attorney in Brooklyn, New York, in the case against R&B star R. Kelly, speaks with the media on Sept. 27, 2021, after a federal jury announced that it found Kelly guilty of racketeering and sex trafficking charges.

  • Najee Ali with anti-R. Kelly signs, laughs at the jeers...

    Antonio Perez/Chicago Tribune

    Najee Ali with anti-R. Kelly signs, laughs at the jeers and put downs by two women shouting in defense of Kelly outside the Cook County Criminal Courts Building, May 9, 2008, in Chicago.

  • Singer R. Kelly walks into court at the Daley Center...

    Erin Hooley/Chicago Tribune

    Singer R. Kelly walks into court at the Daley Center for a hearing on his child support case on March 13, 2019, in Chicago.

  • Cook County State's Attorney Kim Foxx on called  any accusers...

    Brian Cassella/Chicago Tribune

    Cook County State's Attorney Kim Foxx on called  any accusers with allegations of wrongdoing against singer R. Kelly to come forward, Jan. 8, 2019.

  • R. Kelly, center, appears at the Daley Center in Chicago...

    Antonio Perez / Chicago Tribune

    R. Kelly, center, appears at the Daley Center in Chicago on May 8, 2019, for a hearing in his child support case.

  • Demonstrators rally in response to the R. Kelly allegations, Jan....

    Brian Cassella/Chicago Tribune

    Demonstrators rally in response to the R. Kelly allegations, Jan. 9, 2019, outside his recording studio in the West Loop.

  • Musician R. Kelly turns himself in at 1st District police...

    Chris Sweda / Chicago Tribune

    Musician R. Kelly turns himself in at 1st District police headquarters in Chicago on Feb. 22, 2019.

  • R. Kelly, center, who was charged with child pornography, leaves...

    Abel Uribe/Chicago Tribune

    R. Kelly, center, who was charged with child pornography, leaves the Leighton Criminal Court Building after appearing in front af a judge Feb. 7, 2003.

  • R. Kelly stands before the judge during a hearing at...

    Antonio Perez / Chicago Tribune

    R. Kelly stands before the judge during a hearing at the Leighton Criminal Court building, Sept. 17, 2019, in Chicago.

  • Singer R. Kelly walks out of Cook County Jail, accompanied...

    Abel Uribe / Chicago Tribune

    Singer R. Kelly walks out of Cook County Jail, accompanied by his attorney, Steven Greenberg, right, on March 9, 2019, after paying more than $160,000 in child support.

  • R. Kelly's former girlfriends Azriel Clary, left, and Joycelyn Savage,...

    Antonio Perez / Chicago Tribune

    R. Kelly's former girlfriends Azriel Clary, left, and Joycelyn Savage, right, leave following Kelly's hearing at the Leighton Criminal Court building, Sept. 17, 2019.

  • R&B star R. Kelly, 41, arrives at the Cook County...

    Michael Tercha/Chicago Tribune

    R&B star R. Kelly, 41, arrives at the Cook County Criminal Courts Building for his child pornography trial on May 20, 2008, in Chicago. The charges against Kelly stem from a 15-minute videotape that law-enforcement officials say he made with the alleged victim between Jan. 1, 1998, and Nov. 1, 2000.

  • A courtroom sketch shows defense attorneys Ashley Cohen, from left,...

    Cheryl Cook / Chicago Tribune

    A courtroom sketch shows defense attorneys Ashley Cohen, from left, and Jennifer Bonjean with singer R. Kelly at the Dirksen U.S. Courthouse in Chicago on Sept. 14, 2022.

  • Singer R. Kelly walks into court at the Daley Center...

    Jose M. Osorio/Chicago Tribune

    Singer R. Kelly walks into court at the Daley Center for a hearing on his child support case on March 13, 2019, in Chicago. Kelly had been jailed earlier this month for failure to make about $160,000 in outstanding child support payments.

  • R&B star R. Kelly arrives at the Cook County Criminal...

    Chuck Berman / Chicago Tribune

    R&B star R. Kelly arrives at the Cook County Criminal Courts Building, Thursday, Dec. 20, 2007, in Chicago. Kelly was threatened with arrest after failing to appear in court Wednesday. (Chuck Berman/Chicago Tribune)

  • Attorney Michael Avenatti addresses reporters after a bond hearing for...

    John J. Kim / Chicago Tribune

    Attorney Michael Avenatti addresses reporters after a bond hearing for R. Kelly at the Leighton Criminal Court Building on Feb. 23, 2019, in Chicago.

  • R&B star R. Kelly, 41, leaves the Cook County Criminal...

    Scott Strazzante/Chicago Tribune

    R&B star R. Kelly, 41, leaves the Cook County Criminal Court Building after his child pornography trial recessed for the day on May 28, 2008, in Chicago. The charges against Kelly stem from a 15-minute videotape that law enforcement officials say he made with the alleged victim between Jan. 1, 1998, and Nov. 1, 2000.

  • R. Kelly, nominated for five Grammy Awards in 1997, records at...

    Charles Cherney/Chicago Tribune

    R. Kelly, nominated for five Grammy Awards in 1997, records at Chicago Trax Studio on Jan. 22, 1998.

  • Attorney Gloria Allred, right, walks out of federal court alongside...

    John Minchillo / AP

    Attorney Gloria Allred, right, walks out of federal court alongside Lizzette Martinez, left, on June 29, 2022, in the Brooklyn borough of New York. R&B star R. Kelly was sentenced to 30 years in prison in a federal sex trafficking case in New York.

  • Attorney Gloria Allred, who represented several of Chicago-born R&B singer...

    Angela Weiss/Getty-AFP

    Attorney Gloria Allred, who represented several of Chicago-born R&B singer R. Kelly's victims, speaks before the sentencing hearing in New York on June 29, 2022.

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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.

Jacquelyn Kasulis, the acting U.S. attorney in Brooklyn, New York, in the case against R&B star R. Kelly, speaks with the media on Sept. 27, 2021, after a federal jury announced that it found Kelly guilty of racketeering and sex trafficking charges.
Jacquelyn Kasulis, the acting U.S. attorney in Brooklyn, New York, in the case against R&B star R. Kelly, speaks with the media on Sept. 27, 2021, after a federal jury announced that it found Kelly guilty of racketeering and sex trafficking charges.

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.

In this courtroom sketch, Assistant District Attorney Nadia Shihata presents her rebuttal statement to the jury during R. Kelly's sex trafficking trial on Sept. 24, 2021, in federal court in New York. R. Kelly is seen in the upper left hand corner inset and is seated lower right.
In this courtroom sketch, Assistant District Attorney Nadia Shihata presents her rebuttal statement to the jury during R. Kelly’s sex trafficking trial on Sept. 24, 2021, in federal court in New York. R. Kelly is seen in the upper left hand corner inset and is seated lower right.

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.

R. Kelly stands before the judge during a hearing at the Leighton Criminal Court building, Sept. 17, 2019, in Chicago.
R. Kelly stands before the judge during a hearing at the Leighton Criminal Court building, Sept. 17, 2019, in Chicago.

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.”

jmeisner@chicagotribune.com

mcrepeau@chicagotribune.com