R. Kelly’s Chicago federal trial to put spotlight on brawling ‘26th & Cal’ legal tactics

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When Chicago-born R&B star R. Kelly walked out of the Cook County criminal courthouse a free man in 2008, it wasn’t just a stroke of luck.

Kelly’s stunning acquittal on child pornography charges nearly a decade and a half ago was the result of a carefully crafted strategy by a team of veteran Chicago criminal defense attorneys, who employed nearly every street-fight tactic in the 26th and California legal playbook.

Bury the court with paper. Delay the proceedings for years. Dirty up every witness you can. And when it comes to the prosecutors’ smoking gun, a videotape allegedly showing Kelly sexually assaulting a 13-year-old girl, relentlessly question its authenticity — and keep the victim on your side.

Kelly is going on trial again in Chicago, this time at the Dirksen U.S. Courthouse, where the “I Believe I Can Fly” singer stands accused of conspiring to rig the Cook County trial years ago by paying off the victim on the now-infamous videotape.

Also facing trial are Kelly’s former business manager, Derrel McDavid, and another associate, Milton “June” Brown, who, according to the indictment, schemed to buy back incriminating sex tapes that had been taken from Kelly’s collection and hide years of alleged sexual abuse of underage girls.

The trial, which gets underway with jury selection Monday, comes on the heels of Kelly’s federal racketeering case in New York, which involved similar allegations of sexual misconduct and resulted in a guilty verdict and 30-year sentence levied in June.

With the 55-year-old Kelly already facing what could be the rest of his life behind bars, some observers argued whether it makes sense to spend so many public resources to try Kelly again. Kelly also faces four pending cases in Cook County, which have largely been on hold since the federal indictments were revealed.

Sources said there were initial discussions of a plea deal earlier in the proceedings, but with Kelly appealing both his conviction and sentence in New York, they never really got off the ground.

Now, the trial about to unfold in Chicago seems ripe for intrigue. For one, Kelly’s new criminal defense attorney, Jennifer Bonjean, is a veteran litigator who relishes taking on what she portrays as an unchecked and overzealous government, representing controversial clients such as actor Bill Cosby and Gangster Disciples boss Larry Hoover.

McDavid, meanwhile, is represented by Chicago attorneys Beau Brindley and Vadim Glozman, who have shown in a flurry of pretrial motions that they intend to aggressively fight the charges, even if it means potentially throwing Kelly under the bus. Brown’s lawyer, Mary Judge, is also well-respected and a 25-year veteran of the Federal Public Defender’s Office in Chicago.

At the center of the trial is U.S. District Judge Harry Leinenweber, who at 85 is one of the senior statesmen of Chicago’s federal bench, with a well-worn reputation for fairness, an acute knowledge of the law and a fairly low tolerance for nonsense.

At a pretrial conference earlier this month, Leinenweber signaled he intends to run a tight ship, in part because the large ceremonial courtroom where the trial is being held is in high demand due to COVID-19 protocols still in place in the building. He said he wants to keep time-consuming sidebars to a minimum, and if a lawyer from either side tests positive for COVID-19, their colleagues will have to pick up the slack.

“We’re going to get it done in four weeks come hell or high water,” Leinenweber said. “I have a reputation of moving a case along.”

Not an easy legal climb

Winning an acquittal is always an uphill battle in Chicago’s federal court, where the U.S. attorney’s office has a nearly perfect record when it comes to celebrities, politicians or other high-profile defendants.

But Kelly’s path to victory could be even more unlikely, given that the evidence for the child pornography charges is significantly stronger than it was when Kelly was first indicted in Cook County in 2002.

Prosecutors are expected to present to jurors four videotapes depicting Kelly having sex with a minor — not just one. But potentially far more damaging to Kelly is that the girl depicted on the tapes, who refused to testify in 2008, is now cooperating with law enforcement, as is her mother.

The victim, now in her mid-30s, is expected to identify herself on the videos, and both she and her mother are expected to testify about efforts by Kelly and his team to keep them quiet — including flying the family to the Bahamas and Mexico and giving her father, who was a bassist in Kelly’s band, checks for hundreds of thousands of dollars.

Steven Greenberg, who was Kelly’s chief attorney until a rift in the defense team prompted him to leave the federal cases in 2021, told the Tribune in an interview last week that Kelly enjoyed “the super-presumption of innocence” in his trial in 2008, when he was still a famous musician with a string of recent hits.

But the public’s view of Kelly has changed significantly since then, starting with the #MeToo-era docuseries “Surviving R. Kelly” and ending with his high-profile trial in New York, which featured testimony from nearly a dozen victims of his alleged sexual and psychological abuse.

”Jurors are human, and while they say they can decide the case based on the evidence in the courtroom, anyone that claims they haven’t heard anything about R. Kelly is probably lying,” Greenberg said. “And anyone who says they don’t have some opinion about R. Kelly is probably lying.”

Bonjean posted to Twitter on Friday that it will be “difficult to find 12 people who can be fair given the media war on my client.”

“The government starts with an incredible advantage but we are going to fight like hell to get a jury that will follow the law,” she wrote.

Greenberg said the trial will likely pit the three defendants against each other, with McDavid trying to pin any wrongdoing on Kelly and his lawyers at the time “who orchestrated it.”

“And Kelly is going to say, if anything, it was McDavid and the lawyers,” Greenberg said.

When Kelly’s first criminal trial was unfolding in 2008, rumors abounded about the location of the alleged victim on the videotape, who was actually a potential witness for the defense. Behind the scenes, it was known that the girl had been living at Kelly’s south suburban mansion. She’d even been taken shopping for something to wear on the stand by the wife of an attorney on Kelly’s legal team. But she was never called to testify.

Dick Devine, who headed the Cook County state’s attorney’s office back then, told the Tribune his team strongly suspected at the time that the young victim and her family were being “taken care of” to keep them from cooperating, but they could not prove it.

”We did try to figure out what was going on and see if there were any links we could establish,” he said in an interview last week. “But as you can imagine, the people involved did not want to cooperate at all, and did not. So we reached dead ends in many of the things we were pursuing.”

The prosecution team was “very frustrated” that the central witness and her parents were not in place, Devine said. But he said “they did their best, they tried a good case, but it simply wasn’t enough in light of the gaps that were there, at least according to the jury.”

Devine said that they brought the case knowing it would be tough to win, and at one point rejected an offer from Kelly’s camp to have him plead guilty and get a slap on the wrist.

The trial, he said, was “kind of a slugfest day to day,” with the throngs of R. Kelly fans outside the courthouse, the aggressive moves from his defense team, and the strong suspicions of witness tampering.

”It’s part of our legal history, and I don’t think the best part, but one we’re living with,” Devine said.

Details of the case

The federal charges Kelly is now facing fall into two overlapping categories. Some allege he repeatedly molested underage girls and would make videotapes of their sex acts. The obstruction charges allege that, when he got wind that authorities were investigating, he bought back incriminating tapes and paid off witnesses so they wouldn’t cooperate with law enforcement.

According to a recent prosecution filing, the evidence will span a 23-year period from 1991 to 2014, when Kelly rose to the height of his fame before becoming the butt of late-night comics’ jokes.

Jurors are expected to hear evidence about four videos made by Kelly during that time depicting him sexually abusing an underage girl: his goddaughter from the original tape, who is identified in the charges only as Minor 1. Other witnesses are also expected to testify that Kelly had sexual contact with them when they were underage, and that he often taped those encounters as well.

Some of the evidence the jury is expected to hear is well-documented territory in Kelly’s history of sexual conduct: The tripods and camcorders at his recording studios, tour buses and hotel rooms; the gym bag of VHS tapes containing child pornography he allegedly carried around; the threats of civil suits followed by nondisclosure settlements.

Prosecutors allege that beginning in 2001, Kelly and his entourage became aware of multiple videos missing from Kelly’s “collection” and that he and McDavid orchestrated a scheme of payoffs to get them back and keep others quiet about Kelly’s relationship with Minor 1.

In addition to Minor 1, two other women who were underage at the time of the alleged conspiracy are expected to testify that Kelly struck up a sexual relationship with Minor 1 when she was as young as 13 and videotaped himself assaulting her in his home, at his studios, on tour buses and in hotel rooms.

In one video that jurors are expected to see, Kelly is having sex with Minor 1 at his home on George Street in Chicago while she is wearing a “distinctive” necklace — the same necklace that she is wearing in a passport photo taken about the same time, according to prosecutors.

In the early 2000s, Chicago police attempted to locate Minor 1 for questioning but Kelly’s team had her flown to the Bahamas and Mexico for weeks to get away from law enforcement, according to prosecutors.

When they returned to Chicago, Kelly’s team “isolated” Minor 1 from her family, monitoring her phone calls and moving her around to different hotels, according to prosecutors. That lasted until her parents agreed to deny that it was Minor 1 on the videotape, prosecutors said.

Another woman, identified as Minor 5, is expected to testify that Kelly began having sexual contact with her when she was 14 or 15. He would often tape their sex acts, as well as sex acts involving her and other underage girls, according to prosecutors.

When police began to investigate the videotape in late 2001, Minor 5 initially identified Minor 1 as the girl on the footage. But later on, Kelly persuaded her to lie to the grand jury and say she did not know of any sexual relationship between Kelly and Minor 1, according to prosecutors.

After her first sexual contact with Kelly, Minor 5 is expected to testify that he told her: “We all have secrets now.”

Trial drama expected

However the evidence shakes out, Kelly’s trial is the most high-profile event at the typically buttoned-down Dirksen U.S. Courthouse in the 2 ½ years since the onset of the pandemic.

Kelly’s die-hard followers — some who live-tweet events in his case and post social media videos that garner millions of views — are expected to show up in droves to support him, just like they did at his first Cook County trial and his Brooklyn trial.

And the scenes could be just as theatrical inside the courtroom. Recent weeks have seen a flood of pretrial motions, each seemingly more bombastic than the last.

Prosecutors want to bar Kelly’s defense from presenting expert testimony that Kelly has an IQ of about 79, saying his alleged intellectual deficiencies are irrelevant to whether he videotaped himself molesting underage girls. Kelly’s defense wants to prohibit prosecutors from calling an expert witness to testify about child sex abuse and grooming.

Most dramatically, perhaps, McDavid’s legal team has argued in a series of strongly worded motions that prosecutors botched the chain of custody for the key videotape involving Minor 1, and accused the former lead prosecutor on the case, Angel Krull, of having inappropriate contact with the alleged victim as well as Jim DeRogatis, the Chicago journalist whose reporting decades ago was the first to bring the accusations against Kelly to light.

Krull, it has been revealed, communicated with DeRogatis using a burner email account under the alias “Demetrius Slovenski” and the username piedpiper312, a reference to one of Kelly’s own nicknames for himself. In text messages in 2019, Krull had Minor 1 stored in her contacts under the name “Boss Baby,” at one point telling the woman that a pregnancy photo of her is “beautiful and glowing.”

As of Friday evening, Leinenweber had made no rulings on the pending requests.