Sources provided more detail about Tiffany’s settlement. The former associate said it came the day after Tiffany gave a seven-and-a-half-hour deposition to Kelly’s attorneys, Gerald Margolis and John M. Touhy. The case file did not include a transcript of the deposition. Although it was public record, the deposition had disappeared, and I never have found it. My source said it had been “hair-raising stuff about a predatory relationship based on perverted sexual acts,” including threesomes with underage girls. Demetrius Smith, Kelly’s longtime road manager and personal assistant, confirmed, “That deposition told the story of their relationship and mentioned other minors,” with hours of graphic detail. The sworn testimony stunned everyone in the room.
In exchange for $250,000 (one-fortieth of the $10 million she’d been seeking) Tiffany signed a nondisclosure agreement the next day, barring her from talking about any relationship or settlement with Kelly. Years later, I learned the star actually tried to compel the Hartford insurance company to pay the settlement. In December 1999, Hartford sued him for pressing that claim, “seeking a declaration that it owed no duty to defend or indemnify the insured under a homeowner’s policy in an underlying lawsuit asserting claims of negligence and intentional sexual battery.” Kelly appealed, and Hartford responded to the appellate court “that the underlying complaint against the insured sufficiently set forth factual allegations of sexual misconduct with a minor to exclude coverage under an ‘expected or intended’ exclusion.”
Hartford won the appeal, and Kelly paid Tiffany himself. A homeowner trying to have his insurer pay for illegal sexual contact with a minor has to stand as one of the strangest cases in the annals of the insurance industry, a business that has seen plenty of strange claims.
The Kenwood classmate believed Tiffany settled with Kelly for so little because “she just got tired of the case,” which dragged on for two years. She kept two-thirds of the money after legal fees, and she promptly squandered all of it, my sources said. “Tiffany just jumped once they started talking that money,” Smith added. Abdon compared it to Kramer leaping at the offer of free coffee for life in the Seinfeld episode about “Java World,” but I always wondered if there was more to the story.
Jovante Cunningham also appeared on Tiffany’s witness list, and she initially talked to me off the record, and only reluctantly. She, the Kenwood classmate, and Tiffany had been Aaliyah’s posse of three teenage girlfriends whom everyone called Second Chapter.
Jovante met Kelly at age fourteen and later worked for him as a dancer and backing vocalist. She knew a lot, she told me, but “if I would tell it, it would be in front of somebody’s huge television camera, and they’d have to be paying me a whole bunch of money.” Every time I told her the Sun-Times did not pay sources, she kept talking anyway. I got a quizzical look when one of the features editors overheard us on the phone. I had to speak especially loudly because my reluctant interview subject seemed to be shopping. “I like those shoes, I’ll take those,” she said at one point.
“I’ve seen him do things I can’t say,” Jovante said of Kelly. “I’m not at liberty to say who, what, where.” She did tell me she met Tiffany at a mutual friend’s house. “The first thing she said to me was, ‘I know R. Kelly!’ At the time, he was nobody. His first album hadn’t even hit yet. She said, ‘Let’s go over to his house,’ so we went over there. I don’t know if she was a recruiter for him or what.” She added that she believed Kelly made a mistake by settling with Tiffany—“I thought it would only encourage more girls to come forward”—and she said Kelly should have taken the lawsuit as a wake-up call.
“He should have learned from that and got some help. He definitely has something going on psychologically, and he needs to know there is repercussions. He has no value or respect for people as a whole. The brother got problems. The brother is ill. Robert’s thing was a fresh body. I don’t think it had anything to do with age. I think he goes for a fresh look, a fresh body, and it turns out to be a young body. There are a lot of different ways you could categorize it, but I’m not a psychologist, I’m just a person who witnessed some things who had her own opinion of it.”
Jovante finally got to talk to “somebody’s huge television camera” when she appeared nineteen years later in the Lifetime docuseries Surviving R. Kelly. In it, she tearfully said she witnessed R. Kelly having sexual contact with sixteen-year-old Tiffany in the studio, as well as with fifteen-year-old Aaliyah on a different occasion aboard his tour bus.
Abdon and I knew we couldn’t tell Tiffany’s story without one more interview. We had to talk to Lena McLin about Kelly’s visits to Kenwood Academy. Several students told us other teachers there warned them the star frequently returned to “cruise” young girls. Abdon reached out to McLin when I told him I didn’t have the stomach to pose the questions that needed to be asked of the then-seventy-year-old gospel legend.
“Robert comes back all the time. He considers me his mother and mentor,” McLin told Abdon in a scolding tone. “I don’t know what he did outside of school, but in the school, there was no hanky-panky. If they were involved in that, the sad thing is, it takes two to tango.” She admitted she disliked Kelly’s raunchier songs, but she lauded his potential. “He has a very decent moral spirit inside that’s dying to come out. It comes out in ‘I Believe I Can Fly.’ It comes out in the angel song he did with Céline Dion. It will eventually grow. It may be a little baby now, but it will eventually get real big.”
As Abdon and I learned more about Tiffany, the question of what really happened with Aaliyah loomed. Tiffany’s lawsuit included the marriage certificate that had been published in Vibe, as well as a four-page petition filed by an attorney for Aaliyah in Cook County Circuit Court in July 1997 seeking, with legalistic overkill, to “expunge, obliterate, erase, and/or otherwise wholly strike from all public records all marriage documents associated with Plaintiff’s August 31, 1994 marriage.” Abdon checked, and the marriage certificate was indeed no longer available in the public records. The petition noted that the marriage had “been declared invalid by the Circuit Court of Wayne County, Michigan,” but Abdon found that through an order by that court in October 1994, any annulment or divorce in Michigan had also been expunged, obliterated, erased, etcetera.
We thought we’d hit another dead end, until a source provided a copy of a document signed by Kelly, Aaliyah, and her parents, Michael and Diane Haughton, on September 29, 1994, less than a month after the marriage between the then-twenty-seven-year-old producer and his fifteen-year-old protégé. The agreement stipulated that in consideration of payment of $100 by Kelly to Aaliyah—two sources later told me the amount Kelly actually paid “off the books” was $3 million—the two would sever all personal and professional contact and pledge to avoid any public comment about their relationship or the separation agreement, “due to the nature of the music industry and its ability to engender rumors and disseminate personal information, both true and untrue.”
In the agreement, Kelly admitted no liability or wrongdoing, and Aaliyah and her parents discharged him from any future legal claims due to “a decline in her ability, reputation, or marketability . . . emotional distress caused by any aspect of her business or personal relationship with Robert . . . [or] physical injury or emotional pain and suffering from any assault or battery perpetrated by Robert against her person.” Hankerson and an attorney for Kelly, Arnold E. Reed, were named as monitors to assure the two complied with the terms of the agreement.
When Abdon and I reviewed these pages with Don Hayner, the law school grad turned city editor, he thought the assault and battery clause could be boilerplate for any divorce agreement. We did not note it in our story. Only years later did the possible significance strike me, after other women began telling me Kelly allegedly physically assaulted them if they broke “his rules.”
Unlike many who worked with him, Aaliyah’s career thrived after she split with Kelly. She left Jive, the label founded by Clive Calder, and signed with Virgin Recor
ds. “In 1994, Hankerson and the Haughtons came to Calder’s office,” Geoff Edgers of the Washington Post reported a quarter-century later. “There was no talk of reprimanding Kelly. Instead, the family demanded that Jive let Aaliyah go. ‘And they basically tell me that they want a release from the contract,’ Calder said, saying they thought Aaliyah would never get the proper promotion if she was on the same label as Kelly. Calder agreed to let her leave, but only after securing a percentage of her future album sales on a new label.”
Aaliyah released her second album, One in a Million, on Virgin in August 1996. A radical departure from the slick R&B sounds Kelly crafted for her debut, many of her new, percolating grooves were written and produced by then-rising hip-hop talents Missy Elliott and Timbaland. With them, Aaliyah “helped invent a style that might be called avant-garde R&B,” Kelefa Sanneh wrote in the New York Times, while in SPIN, Jon Caramanica contended these sounds were “the nexus of street-savvy R&B and elegant pop.”
The collaboration between Kelly and Aaliyah became history. “Whenever R. Kelly comes up,” a Virgin executive told me, “she doesn’t even speak his name. When she came over to this label, we were all told on the sly, ‘Don’t ever bring up R. Kelly’s name.’ It’s just one of those weird topics.”
One in a Million eventually sold more than three million copies in the United States, and Aaliyah also started a film career. In March 2000, she costarred in Romeo Must Die, a streetwise retelling of Shakespeare’s tragic love story. She played the daughter of a gangster in love with kung-fu master Jet Li, an ex-cop investigating the murder of his brother, a member of the Chinese mob. The affair was, of course, star-crossed.
Everyone I interviewed said the affection between Kelly and Aaliyah had been genuine. “He loved Aaliyah,” Demetrius Smith said, while he and others described her feelings for Kelly as a teenage crush turned to infatuation. Young, naive, and sheltered by her family, Aaliyah experienced independence for the first time while working on Age Ain’t Nothing but a Number. All but one of my sources said she and Kelly began having sexual contact during her first recording sessions. Some said he surprised her with the marriage ceremony in a third-floor room at the Sheraton Gateway Suites in suburban Rosemont, and that Aaliyah looked nervous and scared. “She thought it was all an elaborate game,” one source said. Another claimed, “She knew she’d regret it—her family wasn’t there!—but she just got swept up in the excitement.”
Demetrius Smith gave me the most detailed account, later repeated in his book, The Man Behind the Man. After a gig in Orlando while on tour with Salt-N-Pepa, Kelly told Smith they had to return to Chicago immediately before the next show in Miami because Aaliyah had run away from home and needed to see him. When they got back to Chicago, Aaliyah told Kelly she was pregnant. Kelly’s accountant, Derrel McDavid, and attorney, Gerald Margolis, convinced him he should marry his protégé, Smith claimed. Neither of them would comment. Smith, Kelly, and Aaliyah obtained the Cook County marriage certificate at city hall in suburban Maywood, using fake IDs Smith bought for Aaliyah in what he called “Jewtown,” slang for Chicago’s famous Maxwell Street Market, which started as a Jewish ghetto but became a hotbed of electric blues and a thriving bazaar where black vendors sold everything from “discount” color television sets and stereos to bootleg CDs and videos.
Aaliyah lied about her age, signing the marriage certificate as an eighteen-year-old, she admitted in the court documents Abdon and I obtained. Several other sources confirmed she told Kelly she was pregnant, but the legal filings made no mention of that.
After the wedding, Smith and Kelly flew back to Florida while Aaliyah stayed at the hotel in Rosemont, but Smith said that within a day, she left and went home to Detroit, telling her parents and uncle Barry Hankerson what had happened. “Aaliyah was a baby. She knew nothing. Aaliyah was just a sweet child, man,” Smith said. Others disagreed and said some members of her family knew about the relationship. What is confirmed in the legal documents is that the family immediately set about undoing the marriage and keeping it quiet so as not to damage either star’s career.
“We never had any trouble with Aaliyah when that was done,” a family member told me. “It was never her trying to see him, call him, or get to him. We didn’t want any money. The issue with the family was to move on, and to totally undo what Robert Kelly did. We just thought, ‘This guy is stupid. He’s like a big, dumb fifteen-year-old hisself.’ At that time, we didn’t think about pedophilia. It was just, ‘How dumb can you be, boy? You’re lucky we are the family!’ We embraced her and she cried and she said she never wanted to see him again. We were apprehensive, and we watched her, but we never took away the freedom of the telephone or the mobility to leave the house. She just never saw him again.”
Smith agreed. “Rob made a mistake, that’s how the family looked at it.” Although Hankerson stayed on as Kelly’s manager, “Barry just started backing up after that. He was trying to save his family and his career. Barry is a smart man, and he’s compassionate and a good man who realizes that we are all born to sin.” The relationship between Kelly and Hankerson was never the same, however, and Derrel McDavid began to play a bigger role in overseeing the singer’s career long before Hankerson quit in early 2000.
Instead of Dan Klores Associates, in 2000, Kelly employed as his publicist Regina Daniels, the wife of the owner of the South Side’s biggest record store, George’s Music Room, which boasted a wall-size mural of Kelly. Midway through our reporting, I called Daniels to ask her about Kelly and Aaliyah. She gave me a statement that exceeded what anyone in the Kelly camp had been authorized to say, and sources told me her employers later chided her for it.
“Rob did date Aaliyah, yes, he did, and he did have a relationship with Aaliyah, yes, he did, and past that, unfortunately, it didn’t work out and that was really that. Did they have a relationship? Yes, they did. I’m not gonna sit here and bullshit you or nobody else about it. Yes, they did. Did they get married? Well, there was a marriage certificate, so that pretty much kinda means something happened there. Was I there? No, I wasn’t, but there was a relationship. It ended with, ‘Maybe we’re over our heads, maybe this is too much, maybe we need to go our separate ways. I love you, I always will, I wish you the best, and maybe we just jumped in way too deep into this thing.’ And she went her way and he went his.”
Daniels chastised me for even asking about the relationship. “Robert has done enough else in his career that if people can’t say nothing else other than whether or not he screwed Aaliyah, then they can kiss my ass!” Her tone made it clear she meant me.
According to Smith, the sudden end of Kelly’s relationship with Aaliyah crushed him. The singer finished his tour, returned to Chicago, and checked into the Hotel Nikko, where he spent more than a month sleeping in the closet. Whenever Kelly got depressed, Smith said, he tried to get his friend to sing “Hard Times,” the song he’d written as a teen about his mom and the early days. When Kelly finally emerged, he wrote a new song called “Trade in My Life” that eventually appeared on the R. Kelly album in November 1995, with backing from a gospel choir led by Kirk Franklin.
“We both know that we made a vow / Said we’d always be together / That our love would endure, yes / But now you’re gone and I’m all alone,” Kelly croons. The song ends with him posing the same question the heavenly voice asked a few years later in the “I Wish” video: “What does it profit a man to gain the world and lose his soul?”
As Abdon and I continued reporting, we scoured police and court records and found that by late 2000, R. Kelly had had three brushes with the law, the first only nine days after he married Aaliyah. On September 9, 1994, at the end of his tour with Salt-N-Pepa, he headlined the Budweiser Superfest at Madison Square Garden. The singer and his crew stayed at the posh Michelangelo Hotel near Times Square, and the day after the show, police arrested two of his bodyguards in a hotel room on charges of raping and sodomizing a twenty-two-year-old woman. The hotel’s guest-services agent c
onfirmed that a rape had been reported, according to New York Newsday, which added that police sought a third suspect.
We could find no resolution of the case, but sources told me the incident actually involved Kelly and an underage girl with a fake ID, who later withdrew her charges when the star paid her a cash settlement. Kelly posted bond for the bodyguards after they spent a night on Rikers Island. Tour manager Demetrius Smith said the pair had rushed to Kelly’s room as the girl fled, and they stayed to talk to police while Kelly left the hotel. “He paid them, but then treated them like shit. They took that case for him, but after that, he had no respect for them.”
In the summer of 1996, Kelly himself was arrested along with four of his bodyguards after they got into a fight with some local players on the basketball court at a health club in Lafayette, Louisiana, hours before a scheduled performance at the Cajundome. One of the three men who pressed charges had been beaten so badly, he needed 110 stitches on his face, according to police. They charged Kelly with second-degree battery, a felony punishable by up to five years in prison, and he spent the night in jail, missing the concert. In the morning, an attorney posted $11,500 bail. Kelly claimed the men had taunted him and his entourage with racial slurs. The district attorney in Lafayette eventually determined that Kelly had not started the fight, and he reduced the charge to simple battery. The singer drew a sentence of one year of unsupervised probation, and he ended a civil claim by the men with a cash settlement.
Finally, one night in the spring of 1998, Chicago police arrested Kelly for disorderly conduct as he sat in his new Lincoln Navigator blasting loud music outside the Rock ’N’ Roll McDonald’s on North Clark Street. According to a report in the Sun-Times, police said Kelly became loud and abusive when officers asked him to turn down the music. A city ordinance prohibited music so loud it could be heard seventy-five feet from a vehicle. As a crowd gathered to watch, Kelly refused to produce a driver’s license, and officers arrested him. He went limp as they carried him to their squad car.
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