Federal prosecutors in New York invoking what's known as the "RICO Act" to take down Kelly, who for decades seemed untouchable by law enforcement despite women telling horrid stories of sex abuse.
Using a law intended to crack down on organized crime, Kelly is now looking at decades in prison.
Chicago attorney Steve Greenberg said Monday that the 20 years or more that the government is likely to request will be tantamount to a life sentence for the 54 year old ex-R&B superstar.
Chicago singer R. Kelly found guilty in sex trafficking trial
A jury of seven men and five women found Kelly guilty of racketeering on their second day of deliberations.
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The charges were based on an argument that the entourage of managers and aides who helped the singer meet girls - and keep them obedient and quiet - amounted to a criminal enterprise.
RELATED: R. Kelly sexually abused underage Chicago boys, new court documents claim
"I've been practicing law for 47 years. During this time, I have pursued many sexual predators who have committed crimes against women and children. Of all the predators that I have pursued, however, Mr. Kelly is the worst, for many reasons. First, he used the power of his celebrity to recruit vulnerable underage girls for the purpose of sexually abusing them," Glorida Allred, the attorney for the alleged victims, said in a post trial interview.
Several accusers testified in lurid detail during the trial, alleging that Kelly subjected them to perverse and sadistic whims when they were underage.
For years, the public and news media seemed to be more amused than horrified by allegations of inappropriate relationships with minors, starting with Kelly's illegal marriage to the R&B phenom Aaliyah in 1994 when she was just 15.
His records and concert tickets kept selling. Other artists continued to record his songs, even after he was arrested in 2002 and accused of making a recording of himself sexually abusing and urinating on a 14-year-old girl.
Widespread public condemnation didn't come until a widely watched docuseries "Surviving R. Kelly" helped make his case a signifier of the #MeToo era, and gave voice to alleged victims who wondered if their stories were previously ignored because they were Black women.
At the trial, several of Kelly's accusers testified without using their real names to protect their privacy and prevent possible harassment by the singer's fans. Jurors were shown homemade videos of Kelly engaging in sex acts that prosecutors said were not consensual.
"Many of his victims had the courage to speak up and tell their truth under oath in a court of law. I am very proud of my clients who agreed to testify in this case. I thank them for trusting me, law enforcement and the jury to find the truth. My clients who testified, fought through their fear and relive their painful experiences with our Kelly and his enablers are Kelly's victims handled themselves with dignity and survived intense cross examination," Allred said.
Assistant U.S. Attorney Maria Cruz Melendez argued that Kelly was a serial abuser who "maintained control over these victims using every trick in the predator handbook."
R Kelly moves from Chicago jail to Brooklyn detention center ahead of trial
The defense labeled the accusers "groupies" and "stalkers."
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Defense attorney Deveraux Cannick questioned why the alleged victims stayed in relationships with Kelly if they thought they were being exploited.
"You made a choice," Cannick told one woman who testified, adding, "You participated of your own will."
Kelly, born Robert Sylvester Kelly, has been jailed without bail since in 2019. The trial was delayed by the coronavirus pandemic and Kelly's last-minute shakeup of his legal team.
When it finally started on Aug. 18, prosecutors painted the 54-year-old singer as a pampered man-child and control freak. His accusers said they were under orders to call him "Daddy," expected to jump and kiss him anytime he walked into a room, and to cheer only for him when he played pickup basketball games in which they said he was a ball hog.
The accusers alleged that they also were ordered to sign nondisclosure forms and were subjected to threats and punishments such as violent spankings if they broke what one referred to as "Rob's rules." Some said they believed the videotapes he shot of them having sex would be used against them if they exposed what was happening.
Among the other more troubling tableaus: Kelly keeping a gun by his side while he berated one of his accusers as a prelude to forcing her to give him oral sex in a Los Angeles music studio; Kelly giving several alleged victims herpes without disclosing he had an STD; Kelly coercing a teen boy to join him for sex with a naked girl who emerged from underneath a boxing ring in his garage; and Kelly shooting a shaming video of one alleged victim showing her smearing feces on her face as punishment for breaking his rules.
WATCH: R Kelly accuser, documentary producer speak out after conviction
R Kelly accuser, documentary producer speak out after Chicago singer's conviction
Some of the most harrowing testimony came from a woman who said Kelly took advantage of her in 2003 when she was an unsuspecting radio station intern. She testified he whisked her to his Chicago recording studio, where she was kept locked up and was drugged before he sexually assaulted her while she was passed out.
When she realized she was trapped, "I was scared. I was ashamed. I was embarrassed," she said.
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She said one of R. Kelly's employees warned her to keep her mouth shut about what had happened.
R Kelly 'Chocolate Factory': Witnesses describe life inside suburban Chicago mansion
Other testimony focused on Kelly's relationship with Aaliyah. One of the final witnesses described seeing him sexually abusing her around 1993, when Aaliyah was only 13 or 14.
Jurors also heard testimony about a fraudulent marriage scheme hatched to protect Kelly after he feared he had impregnated Aaliyah. Witnesses said they were married in matching jogging suits using a license falsely listing her age as 18; he was 27 at the time.
Aaliyah, whose full name was Aaliyah Dana Haughton, worked with Kelly, who wrote and produced her 1994 debut album, "Age Ain't Nothing But A Number." She died in a plane crash in 2001 at age 22.
In at least one instance, Kelly was accused of abusing a victim around the time he was under investigation in a child pornography case in Chicago. He was acquitted at trial in 2008.
"Today's guilty verdict forever brands R. Kelly as a predator, who used his fame and fortune to prey on the young, the vulnerable and the voiceless for his own sexual gratification. A predator who used his inner circle to ensnare underage girls, and young men and women for decades in a sorted web of sex, abuse, exploitation, and humiliation," said Jacquelyn Kasulis, the acting US Attorney for the Eastern District of NY.
Greenberg will defend Kelly in the next federal case in Chicago if it happens.
"The Chicago case could be resolved through a plea, it could be resolved through a trial or could be resolved by the government deciding that they don't want to put their alleged victims through it. It happens all the time in criminal cases where prosecutors and defense talk about a case reach an understanding and it's a compromise and in a compromise everyone is unhappy," said Greenberg.
In New York, dozens of witnesses provided excruciating details of abuse by Kelly over the decades; all wrapped up into a neat racketeering package.
ABC7 Legal Analyst and former Chicago federal prosecutor, Gil Soffer, said the New York charges against Kelly were "death by a thousand cuts" -- something the government was unable to pull off in previous investigations.
"You know, it's, this could simply have been prosecutors taking the time at the federal level to piece together all the different stories, they'd heard all the different accounts from all these different witnesses and come to the realization that it made for a compelling case and a winnable one, remember that we saw charges here not only in New York but also in Chicago, federally being brought at the same time. And so I think they just hit a critical mass of witnesses and evidence that convinced them. Now is the time and obviously this verdict proves them right," Soffer said.
If Kelly does come to Chicago next year for the charges, it would be after his May 4 sentencing in New York.
"The Chicago case, unfortunately for Robert, is far more serious," Greenberg said. "Because it involves child pornography charges and charges that he obstructed justice in his earlier trial from, from the 2000s which was in state court here. The Chicago case actually carries much more severe penalties than the New York case, but we're gonna fight for....we know the evidence in that case, we're prepared we could go to trial tomorrow."
After Chicago, there is a state case against Kelly in Minnesota where two criminal charges allege prostitution with a minor. That incident, according to authorities, is from 20 years ago in 2001. However, it's the New York conviction for racketeering and sex trafficking that federal prosecutors are heralding as a "powerful message" aimed at men who use fame and fortune to prey on the young and voiceless.
For the Brooklyn trial, U.S. District Judge Ann Donnelly barred people not directly involved in the case from the courtroom in what she called a coronavirus precaution. Reporters and other spectators had to watch on a video feed from another room in the same building.
The New York case is only part of the legal peril facing the singer. He also has pleaded not guilty to sex-related charges in Illinois and Minnesota. Trial dates in those cases have yet to be set.
"Where do we go from here? Continue to fight the fight," said Peter Fitzhugh, the special agent in charge for Homeland Security Investigations.
Cook County State's Attorney Kim Foxx released a statement on the verdict that said:
"This is the first step in a long journey towards justice and healing for many victims of these crimes. Without their bravery and courage, this outcome would not be possible. It is my sincere hope that today's verdict brings some form of closure and consolation, and sends a strong message to predators that one's celebrity status will not shield them from the law. The implications of today's verdict reach far beyond that of a megastar. There are other predators amongst us, that may be revered by the community, who will no longer be made to feel insulated from justice. While today's outcome may not have come as quickly as we'd like, I'm heartened to know that in this case, justice delayed was not justice denied. As a Black woman, mother, and survivor, my heart goes out to the victims of this case and countless others. I know firsthand how an already arduous task can be made even more difficult when compounded by race. As Cook County State's Attorney, my office stands ready to support those who experience sexual violence and to prosecute those who perpetrate it."
Chicago Mayor Lori Lightfoot tweeted that the verdict is "long overdue" and "sends a clear message that we must believe survivors and work to ensure they receive justice."
The Associated Press contributed to this article.
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