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Why Has R. Kelly Been in Jail For the Past Year?

R. Kelly has been behind bars for more than a year in ongoing sexual abuse and obstruction of justice cases and we asked an expert why he hasn't been able to get out on bail as he awaits trial.

It’s been more than a year since R. Kelly was taken into custody in Chicago on 10 charges of aggravated criminal sexual abuse tied to allegations that the once high-flying singer sexually abused four women, three of whom were allegedly minors at the time. After the judge in the case set his bond at $1 million in Feb. 2019, Kelly pleaded not guilty and was released on $100,000 bail after two nights behind bars.

The singer was re-arrested on July 11, 2019, in Chicago by NYPD detectives and Homeland Security officers and indicted by a federal grand jury on federal charges that alleged additional sex crimes, with federal prosecutors in New York and Chicago indicting Kelly on 18 charges that included kidnapping, forced labor, child sexual exploitation and child pornography production and obstruction of justice. He was ordered held without bail and thus began more than a year of incarceration that has included a denial of bail three times — in October, April and again in May — as Kelly remains at the Metropolitan Correctional Center in Chicago while awaiting trial.


So why does the world-famous singer — who has denied the charges and who seemingly has the means to post bail — still remain behind bars? Billboard reached out to a veteran attorney with decades of experience working with musicians facing legal troubles to find out why Kelly remains incarcerated.

“There’s a huge push to get people released because of COVID-19, but just because you’re at risk in and of itself does not guarantee that you will be released, because it’s not the sole factor,” says Stacey Richman, a New York attorney who has worked on behalf of Lil Wayne, DMX and a number of other high-profile musicians over the years; Richman has no first-hand knowledge of Kelly’s case, but was speaking in general terms about federal bail issues.

The singer, who faces anywhere from 10 years to life in prison if convicted on the federal charges, has tried several times to earn pre-trial release, once in September 2019 citing hardships of incarceration — including only being allowed to see one of his two live-in girlfriends at a time — and then citing the spike in COVID infections and illnesses at the correctional institution where he is being held. The first request was denied in October after a judge said Kelly presented a flight risk and could potentially tamper with witnesses.

In denying Kelly’s third request to reconsider providing bail, a May 15 ruling from U.S. District Judge Ann M. Donnelly in New York said the singer’s claim that he is “entitled to bail because medical tests demonstrate that he is ‘likely diabetic'” did not pass muster.

Pointing to the COVID-19 pandemic, which has taken a high toll on the prison population across the country, the judge said that Kelly had “not presented compelling reasons for his release under section 3142 (i) in part because he is not uniquely at risk for contracting severe illness from COVID-19.” While being diabetic has been identified as a risk factor according to the CDC, “the same is not true of prediabetes, a condition that affects nearly one in three American adults.”

In another filing on May 1, Kelly’s lawyer Steve Greenberg revealed that his client also suffers from high blood pressure and cholesterol issues. In an email to Billboard, Greenberg wrote, “we have requested that he be released because of health concerns as well as the simple fact that we cannot prepare for trial while he is incarcerated, given that we are not allowed to meet with him,” adding that the bail issue is currently on appeal to the Second Circuit Court of Appeals.


Richman says the key factors likely keeping Kelly locked up can be found in U.S. criminal code 18 U.S.C. 3142, which provides two crucial criteria for obtaining bail in the federal system: can you assure the person’s return to court and are they a danger to anyone in the community? One of the things that stood out to Richman were claims of obstruction of justice tied to allegations of paying off potential witnesses and intimidation, which would clearly interfere with the judicial process.

In fact, citing U.S.C. 3142, which permits a court to order temporary release for a “compelling reason,” Donnelly wrote in the May 15 ruling that the seriousness of the alleged sex crimes, combined with the obstruction charge — which claims that Kelly “is alleged to have secured witnesses’ silence, and in at least one instance to have suborned perjury, through bribes, blackmail, threats and intimidation” — are reasons to keep him incarcerated. “This conduct strikes at the heart of the integrity of the trial process,” Donnelly wrote, noting that such conduct has been “a traditional ground for pretrial detention by the courts.”

Providing potential further evidence of the latter, on Wednesday (Aug. 12), New York prosecutors arrested three men they said were scheming to harass, threaten, intimidate and bribe some of Kelly’s alleged victims. Three criminal complaints were unsealed on Wednesday (Aug. 12) by the U.S. attorney general’s office for the Eastern District of New York detailing charges against Richard Arline, Jr., Donnell Russell and Michael Williams. Each of the men are charged with attempting to threaten or influence the Jane Doe witnesses in the case against Kelly.

They are alleged to have tried to influence, delay or prevent the testimony of one woman, with Arline, an allegedly longtime friend of Kelly’s, accused of contacting one of the singer’s alleged victims and discussing a $500,000 payment to keep her from cooperating with the government’s investigation. Russell, a self-described manager and advisor to Kelly, is charged with threatening to release sexually explicit photos of another alleged victim and to publicly reveal her sexual history if she did not “cease her participation and association with the organizers” of a “negative campaign” against Kelly. Williams is accused of setting fire to an SUV parked outside a residence in Florida where one alleged victim was staying.


“R. Kelly can’t control everyone and is not responsible for these three. He had nothing to do with any of this,” Greenberg said a statement about the indictments; Kelly has plead not guilty to the charges in the New York and Chicago cases.

Pointing to other high-profile defendants charged with serious sex crimes such as disgraced movie mogul Harvey Weinstein — who was granted bail in his ongoing case, and who Richman represented briefly — Richman says “just because you’re famous doesn’t mean you will get bail, and just because you’re famous doesn’t mean you won’t get bail… each situation is individualized.”

What’s clear to her about the Kelly case is the lurid nature of the allegations related to alleged sex crimes against women and girls and the “historic” aspect of alleged interference with the judicial process, which is what appears to have given the court pause in offering bail; Billboard spoke to Richman before the indictments against the three men were unsealed. “The differential between the New York State system and the federal system is part two — danger to the community — and one of the dangers to the community is interference with judicial process.”

Kelly is facing charges in New York of racketeering, coercion of a minor, transportation of a minor and coercion to engage in illegal sexual activity. The charges related to six different victims. The indictment alleges that for over two decades Kelly was the leader of a racketeering enterprise made up of managers, bodyguards, drivers, personal assistants and runners who recruited women and girls to engage in illegal sexual activity with the R&B singer. The sexual activity was often filmed and photographed by Kelly, according to the court filing by the DOJ. Kelly is also awaiting trial in Illinois regarding separate sexual abuse allegations.


In denying the singer bail, Connelly also said that Kelly’s team’s proposed arrangements for pre-trail release did not pass muster. Those included home confinement at Chicago’s Roosevelt Collection Lofts, where a motion from the singer’s team noted he would live with one of his reported girlfriends, Joycelyn Savage, whose parents have claimed is being held against her will by the singer, as well as electronic monitoring, which the ruling notes can easily be circumvented using technology. Connelly said that those suggestions were not “sufficient to eliminate the danger to the community,” especially since they are “powerless to stop a defendant from inducing others to interfere with witnesses.”

Additionally, in a July 8 motion, the prosecutors in the case requested that the judge grant their motion to impanel an anonymous and partially sequestered jury over concerns that they described as the “defendant’s past attempts to tamper with the judicial process.”

Additional reporting by Claudia Rosenbaum.