Monday’s verdict prompts the obvious question: How does this decision change or shape the landscape for his remaining cases?
"It's a bit two-fold," says trial attorney Phillip C. Hamilton, managing partner at Hamilton-Clarke, LLP. "Chicago is looking at what the prosecutors in the Eastern District were able to pull off. You don’t often see one person getting charged with being the head of a criminal enterprise when it’s not like a mafia or the MS-13. If they were able to get him on that, that means the sentiment towards R. Kelly that once existed when we heard the kind of activity occurring but he was still doing his thing in the industry, has clearly changed. Chicago federal prosecutors are thinking 'we can get him, he’s no longer invincible.'"
Kelly could also choose to plea instead of going to trial. "His attorneys in Chicago should start having some more fruitful discussions about what a plea could look like," adds Hamilton. "He might also be thinking that if he'll knock out any case with an appeal, it would be the New York one and want to go hard in terms of fighting the Chicago federal case. He has all kinds of calculations so it really all depends on what he wants to do with the case in New York. Does he want to appeal or use it in some way to leverage the federal prosecutors in Chicago to maybe talk about a global deal? We'll see."
But the chances of him prevailing on an appeal are "pretty low" in federal court, according to criminal defense attorney Isabelle A. Kirshner, partner at Clayman & Rosenberg, LLP. "The likelihood of his case getting overturned is minimal. The likelihood of him getting a lifetime sentence is pretty significant so he may think, 'why spend all this money on another trial and get dragged around the country into different jails so let me just wrap this up now and plea.'"
Alternatively, adds Kirshner, local jurisdictions in Illinois and Minnesota may choose to drop some or all state cases as Kelly already faces so much time in prison and to save resources as these high-profile prosecutions can get expensive.
However, his federal case in Chicago isn't going anywhere.
"All the time, money and resources that have gone into prepping that case for them just to say, 'ok well you’re good in New York so we won’t move forward here,' I just think it’s unlikely," argues Hamilton. "In their mind they think he should’ve gone down with the state case back in 2008 so they'll want to get him now."
The first allegations of R. Kelly using his superstardom to sexually abuse teenage girls surfaced decades ago but it wasn't until 2019 that the Chicago-born artist -- who was previously acquitted in a 2008 child pornography case -- was placed behind bars where he awaited trial in Brooklyn. Now, his sentence will be determined by Judge Ann M. Donnelly on May 4, 2022.
Chicago's federal trial has been postponed on multiple occasions, and while a new date has not been set, the next conference hearing for that case is Oct. 20. If all parties decide to move forward with a trial, it could begin before he is sentenced in New York, Hamilton points out.
"I don't know if the judge in Chicago would want to wait till June to start this," he says. "I’m not saying it’s impossible but if they do want to move forward I think there’s a chance it'll start before May."