Music critic Jim DeRogatis, who helped expose R. Kelly's abuse, has mixed emotions about singer's sentence

CHICAGO (CBS) -- A music critic who has spent years covering the alleged abuses of R. Kelly said he has mixed emotions about the disgraced singer being sentenced to only one additional year in prison in his Chicago sex crimes case, on top of a previous 30-year sentence out of New York.

Former Chicago Sun-Times reporter Jim DeRogatis said, while it's unprecedented for a prominent entertainer to effectively be sentenced to spend the rest of his life in prison, it's also somewhat of a slight for federal prosecutors.

"It's kind of an insult to the prosecution that laid out a tremendous amount of very harrowing evidence. Those videos, anyone who saw them will never forget them," DeRogatis said. "But you still have to look at it. No one in the history of popular music, where men have been mistreating women for a very long time, has ever been sentenced to life in prison, effectively, as Kelly is."

U.S. District Judge Harry Leinenweber on Thursday sentenced Kelly to a total of 20 years in prison for his child pornography and child enticement convictions in Chicago, but ordered only one year of that sentence would be served after he completes his sentence on racketeering and sex trafficking charges in federal court in New York. The remaining 19 years in the Chicago case will be served at the same time as his New York sentence.

Kelly, 56, could be eligible for release from prison when he's a little over 79 years old.

DeRogatis said he feels the judge's sentence sent a message to federal prosecutors that they should have consolidated the Chicago and New York cases into a single indictment, with one trial.

In September 2022, a federal jury in Chicago convicted Kelly of six counts accusing him of sexually abusing three women – who testified under the pseudonyms Jane, Pauline, and Nia – on video, while acquitting him of enticement charges involving two other accusers, Tracy and Brittany.

The same jury acquitted him of seven other charges, including obstruction of justice, accusing him and two associates of rigging his 2008 child pornography trial in Cook County by pressuring Jane and her family to lie to investigators about her relationship with him and about her being on a sex tape with him, and refusing to testify against him.

Jane had accused Kelly of sexually abusing her hundreds of times after becoming her godfather when she was only 14 years old. Prosecutors showed the jury three videos that they said showed Kelly having sex with Jane, including one that showed him telling her to lay on the floor while he urinated on her.

Nia had testified she first met Kelly in 1996, when she was only 15 years old, and that they had two sexual encounters, one at a hotel during his concert tour in Minnesota, and another later that year at his music studio in Chicago.

Pauline testified that Jane introduced her to Kelly when she was only 14 years old, and the three soon started having threesomes, before Pauline started her own sexual relationship with Kelly alone when she was 15. She estimated she had sex with Kelly more than 80 times and had 60 threesomes with Kelly and Jane between the ages of 14 and 16.

All three provided statements against Kelly at his sentencing on Thursday, urging the judge to sentence him to the rest of his natural life in prison.

DeRogatis said their testimony was "incredibly powerful."

"The main victim, from the 2008 case, her life was ruined," he said.

Nearly 20 years ago, DeRogatis helped break the first story with allegations against Kelly. In his book, "Soulless: The Case Against R. Kelly," he says he knows of 69 women who were allegedly abused by the singer over more than 30 years.

DeRogatis said dozens of women who have accused Kelly of sexual abuse or assault have never seen their cases go to court, and feel justice won't be served on their behalf, even with Kelly now facing 31 years in prison.

"I don't know how the dozens, dozens of victims who were never heard in court – not in New York, not in Chicago – how they ever feel like they will have justice," DeRogatis said.

"The damage this man wrought over 30 years – because his abuse goes from 1991 until the day he was arrested in 2019 – has left so many bodies, ruined lives," DeRogatis added. "I don't think Chicago has even begun to grapple with the enormity of his crimes, but 31 years in prison is a heck of a sentence, even if it only was one additional year added in Chicago."

Asked why it took so long for Kelly to finally be brought to justice, DeRogatis said for far too long, "Black women didn't matter."

"This is what I heard again and again and again from these young victims. The very first victim who stepped forward, Tiffany Hawkins, initially went to the Cook County State's Attorney, and they had no interest in pressing a case in criminal court, all the way back in '96, and so she turned to the civil courts."

DeRogatis has said he first became aware of allegations against the singer when he received a fax in 2000, around the time of Thanksgiving. He originally threw it on the slush pile of hate mail he received for writing about hip-hop, he said, "but there was a tone in that fax" that made it stand out.

"'Mr. DeRogatis, I'm writing to you hoping that you can help,'" he recalled the fax as saying in a 2019 interview with CBS. "'Robert has a problem. His problem is young girls.'"

He added that the fax described the case of Tiffany Hawkins, who "filed a lawsuit for having sexual contact with Kelly at age 15" after he allegedly picked her up from choir class.

DeRogatis estimates that "thousands" of people were aware of or witnessed the "damage" Kelly allegedly caused in the nearly 20 years that followed.

"It sounds like hyperbole when I say this … but if you go to Chicago on the South and West side and talk to two — if you talk to three black women, two will have stories," he said. "Not that they have been — but them or their sister or their aunt or their cousin or their mom has been at Kenwood Academy or the Evergreen Plaza shopping mall, or the rock n' roll McDonald's when Kelly was cruising."