Defending R. Kelly: How His Legal Team Fell Apart

On Sept. 28, shortly after a jury found R. Kelly guilty of all nine charges brought against him — including sex trafficking, racketeering and the sexual exploitation of a child — Devereaux Cannick, a member of the disgraced R&B singer’s legal team, stood before TV cameras and supporters outside the courthouse and said that an appeal was on its way.

However, if Kelly’s legal team plans to file a successful appeal, while managing upcoming trials in Illinois and Minnesota, it will first need to solve its own problems of infighting and inexperience that have plagued it for the past two years.

In January 2019, Lifetime’s bombshell documentary series Surviving R. Kelly quickly turned mainstream opinion of Kelly from raunchy singer to warped predator. In the weeks following, he was dropped from his label, RCA Records, his music was largely pulled from radio and streaming services’ official playlists, and an Australian tour announcement was revoked within hours due to backlash. Weeks later, he was charged with aggravated sexual abuse in Chicago and in July 2019 was slapped with a federal indictment in New York stemming from racketeering charges.  

More commonly reserved for organized crime figures like the late Whitey Bulger and John Gotti, to prosecute Ponzi schemes and money laundering, the Racketeer Influenced and Corrupt Organizations (RICO) statute enabled federal prosecutors to group together Kelly’s more recent alleged crimes with allegations that were two decades old. It was a novel case, and Kelly’s defense team knew it. The idea of a musician-run sex trafficking ring and the use of racketeering laws “in this manner is an aberration,” Kelly’s lawyer Thomas Farinella told Billboard in an emailed statement after the guilty verdict. “The RICO ‘Enterprise’ was based on nothing more than a series of independent relationships and events the government patched together like different types of fabrics and passed it off as silk.” 

When the pandemic ground the courts to a halt, Kelly spent over two years behind bars awaiting trial, while his legal team failed to coalesce and eventually splintered. Two months before the New York trial’s Aug. 18 start date, the artist’s two lead Chicago-based attorneys, Steve Greenberg and Michael Leonard exited the case. The lawyers say they quit due to infighting and the uncooperative dynamics of the defense team. Their former co-counsel, attorney Nicole Blank Becker — who remains on Kelly’s legal team — recounts a different scenario: she says the two lawyers were fired by Kelly due to Greenberg’s “lies,” although court records suggest otherwise. 

Despite this alleged clean sweep, the remaining defense team’s performance during the trial was disastrous, according to sources close to the case. Power struggles between lawyers – fed, these sources say, by Kelly’s concern with “how he looked” to the public — shifted the defense’s strategy away from disproving racketeering allegations and toward breaking down victim abuse claims from victims.   

Discord Among the Defense   

Forty-eight hours before opening arguments, Becker sat in her Brooklyn hotel room, barefaced and visibly exhausted. Behind her sat two beds, one for sleeping; the other doubling as a desk, covered in files, pens, highlighters, sticky notes and binders.  

“It’s been f–king crazy,” she says of working for Kelly. “I guess it might be every lawyer’s dream, but it’s also insanity.”

Becker joined Kelly’s legal team in March 2019, despite having only three years’ experience trying state cases as a criminal defense attorney. She had spent 16 years prior as a prosecutor in Michigan advocating for victims of sexual assault but grew skeptical while working as the head of Macomb County’s sex crimes unit there. “We would deny more warrants than we would sign,” she says. “There is so much [bulls–t] out there.”  

Becker’s introduction to Kelly’s team came at the recommendation of disgraced former Detroit judge Vonda Evans, who knew the singer. “When the judge called me and she’s like, ‘With your history as a sex prosecutor, this is perfect for you,’ I was laughing at her,” says Becker. “Even when I went, I still thought it was a joke. But there was a part of me that [thought], if I don’t go and see if this is real — that they really want to talk to me — how will I ever know?”  

After meeting Kelly, Becker — who grew up with his music — says, “I was fortunate enough to truly see with my own eyes the other side of things.”  Becker’s new teammates included the Chicago attorneys Greenberg and Leonard who have tried dozens of federal cases and began representing Kelly in 2018 to “sue the people who stole all [Kelly’s] money,” says Greenberg. 

Before joining Kelly’s team, Greenberg’s most notable client was Drew Peterson, a retired police sergeant convicted of murdering his third wife after the disappearance of his fourth. While media reports claimed Greenberg was fired by Peterson for “poor performance,” Greenberg says this was a lie another one of the case’s attorneys, Joel Brodsky, fed to the media and showed Billboard documentation of work he performed after those reports came out. (One of the case’s other attorneys, Brodsky, wound up suspended for two years due to his “aggressive tactics and relentless vindictiveness.”) 

Greenberg was also deemed “ineffective” counsel by a Cook County judge in a 2005 murder case, which led to a new trial and the defendant Albert Domagala’s conviction being downgraded from murder to aggravated battery. Greenberg is now representing Domagala’s nephew in a terrorism case and says he has a “tremendous” relationship with the family. 

East Coast attorneys Doug Anton — a sports and entertainment lawyer — andFarinella, a New York criminal defense attorney brought in by Anton, were also on the case. Anton, who left the legal team before Greenberg and Leonard’s departure, could not be reached for comment. 

According to Greenberg and Leonard, conflict arose early on between attorneys over who would steer the case and the division of labor. “It would make sense, based upon our experience of handling collectively more than 100 federal criminal cases, that we would row the boat,” says Leonard. “For good or for bad, we simply refused to dole out responsibilities in a manner that wasn’t consistent with people’s level of experience.”  

Factions formed among the lawyers and the infighting escalated. For example, Greenberg says, arguments broke out over cross-examination strategy. He claims, Becker and Farinella “were intent on slut-shaming.” Becker, on the other hand, says she was “ready for the truth to get out there” in order to clear Kelly’s name. 

When it came to decide which attorney would deliver the opening statement, a source says Nicole petitioned Kelly for the opportunity. “Nicole was telling him that, ‘Only I can tell your story, I need to do the opening. Robert, I know you so well,’” says the source, who adds, “He’s not sophisticated. He’s not very smart. So he’ll listen to these people.” 

Kelly and Becker had grown close too. According to a source close to the case, “[Becker] insisted she be given time to talk to [Kelly] about non-case related matters.” These conversations about Kelly’s personal and business matters were said to take place during time allotted to prepare for trial.  

Greenberg, who initially was supposed to deliver the opening argument says, he and Kelly “never had a single disagreement, except that he thought [Becker] should do the opening and we didn’t.” Greenberg says he tried to remain realistic with Kelly when it came to the defense’s strategy, but Becker, who he says spent more time nurturing a relationship with the jailed singer, prevailed.   

“When Kelly was talking about getting rid of us,” says Greenberg. “He was like, ‘Man, people are sending me stuff from the internet. You’re not doing this and you’re not doing that,’ and I’m like, ‘I don’t give a shit what the internet says. The internet ain’t on your jury.’”  

The source close to the case agrees with Greenberg’s assessment. “He was very focused on how he looked and how [witnesses] look — that they should be discredited, put in their place,” the source explains. 

Ultimately, it was this difference of opinion between lawyers that led to Greenberg and Leonard leaving the case. “Whatever you think of Kelly, Tom and Nicole played with his life in an effort to promote themselves,” Greenberg said. “They f—ed him over.” 

The details of the two attorneys’ withdrawal were messy. According to Becker, Greenberg and Leonard verbally “attacked” her, Kelly was “scared” of having Greenberg on his team and subsequently fired him because of his “lies.” But the public record shows Greenberg and Leonard filed a request to leave on their own volition and Judge Ann M. Donnelly accepted their withdrawal in early June.  

Becker takes issue with this, saying, “Nobody withdraws because they’re the lead in a case and can’t deal with those under [them]. That doesn’t even make sense. I felt what happens when people flat out lie and tell you the sky is orange when you know it’s blue,” she says, of Greenberg and Leonard’s narrative. “And the judge ate it up.” 

Greenberg, on the other hand, blames Becker for the defense team’s internal conflict. “She wanted to be the big star front and center all the time,” he says. He doesn’t have kind words for Farinella either. The attorney’s license to practice was suspended for two years in 2011. At the time, Farinella claimed he was “suffering from a mental infirmity” and therefore, could not “defend himself in disciplinary proceedings pending against him.” Because of these past issues, Greenberg describes him as “incompetent” and “incapable of doing any heavy lifting.” 

“My mental health problems from over a decade ago and the resulting disciplinary matter have nothing to do with this case or my ability to effectively and competently represent Mr. Kelly,” said Farinella, in a statement to the press in July. 

With the only lawyers with federal trial experience off Kelly’s New York case, Becker took charge. And early on at least, she seemed to be relishing in the attention. Many of Kelly’s supporters see her as a hero defending an innocent man being persecuted by bitter exes and the media. Before and after trial proceedings, fans would make a beeline for Becker and offer words of encouragement and admiration. Professionally, she tried to make the most of her role, emailing journalists who mentioned her in stories to request that they link to her firm’s website.  

Becker has her fair share of critics, too. In the media, she’s accused of “weaponizing [her] womanhood against other women” and characterized by former colleagues as an inexperienced attorney wanting to be “the center of attention.” And, according to Becker herself, some even went so far as to suggest she is sleeping with Kelly. Of all this media attention, Becker said she blocks it out.  

“What’s the saying?” she told Billboard days before the trial started. “All press is good press.”    

Disorder in the Courtroom

On the morning of Aug. 18, journalists, photographers, fans and a few confused jurors gathered outside the Brooklyn Federal Courthouse hoping to get inside for opening statements.  

Kelly fans, some of whom took off weeks of work to attend the eight-hour days of trial, told brow-raising lies to security officers in hopes of bettering their chances to get inside the courthouse. “Are you a juror?” an officer asked a short, middle-aged woman in striped pants. “Yes, I’m on the jury,” she hesitantly replied in a slight southern drawl. She turned out to be a fan, who later that day delivered a fervent speech about Kelly’s innocence outside the courthouse to a dozen scoop-hungry cameramen and broadcast reporters forming a crescent around her and other Kelly supporters.  

“How many women have lied to you?” she asked, as the two women behind her slowly nodded their heads in agreement. “How many women have said, ‘Oh, I don’t want you no more, but now I’m gonna get you in trouble?’” 

It would almost seem that Becker took notes from these passionate fans when writing her opening statement. Instead of driving home the point that Kelly was not running a “criminal enterprise” — the bedrock of a racketeering charge — she spent most of her two-hour statement discrediting witness testimonies. She painted victims to be bitter exes out for revenge, called them “groupies” and “superfans” and stressed that Kelly and his “girlfriends” were all “like family” with “beautiful” relationships. 

Seemingly searching for words or just buying time, Becker addressed the jury as “ladies and gentlemen” over 100 times, while stumbling through an almost comical number of sustained objections from the prosecution, interruptions from Judge Donnelly, and other blunders of her own doing. “You ultimately will have to find Mr. Kelly guilty,” she said in her closing, before correcting herself, “excuse me — not guilty.” 

Things only got worse for the defense. It took the prosecution four weeks to make its case against Kelly, calling 50 witnesses, including former assistants, his doctor, tour managers, engineers, victims, an expert on interpersonal violence, records custodians, an Illinois clerk’s office employee and homeland security agents, among others. One by one, they delivered cohesive testimony, while the defense’s cross-examinations — which Becker said would be as simple as “one plus one equals two” — were sometimes so convoluted that reporters questioned whether it was a tactic to confuse jurors and witnesses. And while Becker remained at Kelly’s side every day, the two whispering to each other frequently throughout testimonies, she slowly faded into the background of the defense, with Cannick taking on key witnesses.  

Cannick, a trial lawyer with federal experience joined Kelly’s defense team on June 21 along with attorney Calvin Scholar, two weeks after Greenberg and Leonard’s departure. According to Greenberg, Cannick did not find Becker and Farinella cooperative. “I talked to Cannick a few times; I was trying to help them,” Greenberg says. “[Becker and Farinella] tried to freeze him out of discovery materials and he reached out to me to get them.” (Cannick did not respond to multiple requests for comment.)  

According to the anonymous source, Cannick grew frustrated with Becker and Farinella’s approach and work ethic, just as Greenberg and Leonard had. “It was two separate teams. He basically wouldn’t speak to them as the trial went on. Also, he wouldn’t give them any witnesses [to question], which was smart but makes it hard for one guy to try the case.” 

In some instances, Kelly’s legal quartet did sow doubt with the jurors. While cross-examining Kelly’s victims and former employees, they firmly established that in many scenarios, the women could have willingly walked out of his homes, studios and tour buses, undermining claims they were being held by Kelly against their will. Cannick drew attention to lies told by victims to their parents or Kelly himself, attempting to discredit their damning testimonies.   

But in other moments, Becker and Cannick resorted to victim blaming, claiming the women “knew what they were getting themselves into” — as Becker put it — and critiquing their dance moves and wardrobe choices as teenagers. Another time, Cannick berated a key witness, Jerhonda Pace, accusing her of lying to the jury about her age at first sexual encounter with Kelly. As he paced back and forth, raising his voice to theatrical levels and reminding Pace that she was under oath, it was his own math about her age that turned out to be wrong.  

When Cannick, who is Black, later suggested that Pace was lying about never having attended a party with loud music because she’s Black, he was quickly shut down. “Come on Mr. Cannick,” Donnelly said after the prosecution’s sustained objection. “Move along.” 

Trial attorney Phillip C. Hamilton, managing partner at Hamilton-Clarke, LLP, who is not involved with Kelly’s case, questions the defense’s approach to witnesses. “Trial is theater,” says Hamilton. “The jury is now sympathizing with witnesses because of the way that you are ineffectively beating them up. I’m not really hearing any sympathy for R. Kelly here, and as a defense attorney, not [encouraging sympathy] is damn near malpractice.”    

Where Do You Go From Here?

When it came time for the defense — which does not hold the burden of proof — to argue its case, witnesses were few and arguments were flimsy. The defense rested its case after only two and a half days, with five witnesses total. Phil Lee, a former videographer for Kelly who was working on a documentary about the singer that was never completed, says a woman called him on behalf of Kelly’s legal team just days before closing statements, asking him to come to New York and testify for the defense. “She was asking if I would be willing to come out and talk on Rob’s behalf,” says Lee. “It did seem like a last-ditch effort of desperation.” 

As did Cannick’s closing argument, which consisted of a bizarre list of comparisons with Kelly, including Trump-era vice president Mike Pence, who is reported to call his wife “mother” while Kelly’s victims would call him “daddy;” fellow “sex symbol and playboy,” Hugh Hefner and slain civil rights’ activist Martin Luther King Jr.  

“Somewhere I read of the freedom of speech,” Cannick said, loosely quoting King’s “I’ve Been to the Mountaintop” speech. “Somewhere I read of the freedom of assembly,” he continued nonsensically. “That’s all Robert is trying to do.”  

During the trial, prosecutors had to prove, beyond a reasonable doubt, that Kelly used his employees and enterprise to systematically carry out illegal acts. According to numerous attorneys, this would have been the easiest charge for the defense to knock down. Of the charges against Kelly, racketeering carries the most serious sentence, greater than the penalties for violations of the Mann Act — a law meant to punish human trafficking — which Kelly was also charged with.  

“Most of the people that will testify are not going to see themselves as criminals or members of an enterprise. They’re going to see themselves as stage managers and lighting people [with] no criminal objective. All of that gives you a great chance to win this case,” says Leonard. Instead, the grotesque testimonies and evidence of alleged sexual and physical abuse overshadowed the sparse efforts to disprove that Kelly was knowingly running a criminal enterprise.   

“[His defense] didn’t file a single motion to restrict the government’s presentation of evidence,” adds Greenberg. “If a girl was held in a room for three days because R. Kelly wanted to have sex with her, what difference does it make if when he ultimately had sex with her, they did it backwards, forwards, upside down or inside out? It doesn’t make any difference because the allegation was that she was being held in that room.”  

Instead, the defense’s cross-examinations focused whether or not there was food inside tour buses and studios, what witnesses wore during sex with Kelly, voluntary “twerking” and proving there weren’t “buckets of urine” in Kelly’s bedroom — not breaking down the government’s claims that Kelly was the head of an ongoing criminal enterprise. “It’s not the documentary,” says Leonard, of the charges. “It’s a RICO case.”  

In a joint statement to Billboard after the verdict, Becker and Farinella — who both deny Greenberg’s allegations — said, “Unfortunately, we are unable to respond at this time, but there will be an appropriate time and manner in which the truth will be told in the future.”

While sentencing for Kelly’s New York charges won’t happen until May 4, 2022, the next major milestone in his legal saga comes Oct. 20 in Chicago. That’s when a conference hearing for his federal charges on aggravated criminal sexual abuse will determine the next steps in that case. Greenberg and Leonard are still set to defend Kelly in Chicago, but as a result of the legal turmoil their relationship has suffered, Greenberg says his relationship with the singer needs “a lot of work” and that he no longer thinks he’s the right person to represent Kelly. “I haven’t talked to Robert in months. He completely refused to speak to us,” he says. Still, Greenberg says he will likely visit Kelly in New York in coming weeks to work out the next steps for the upcoming case.   

“The Chicago case probably won’t ever go to trial,” he adds. “We’ll work out a concurrent plea or something like that. He’s going to get launched. [Judge] Donnelly is going to make sure he never gets out of jail.”

It’s a drastic change from 2018 when Kelly first hired Greenberg and their focus was reclaiming the singer’s money. “You know [Kelly’s] last public performance was at my house?” he says, from his Hawaii hotel room. “Like two weeks before he got arrested on these charges.” It was a going away party for Greenberg at his home in Highland Park, Ill., and Kelly sang with a band for three hours, “hung out” with Greenberg’s mom and even brought along his pet Pomeranian, Believe, named after his 1996 hit single “I Believe I Can Fly” that lasted 42 weeks on the Hot 100 chart.  

Greenberg says, “I was very fond of him.”