Hankerson managed R. Kelly for the next 10 years and executive produced his first four albums. From the start, though, there was a problem: Kelly was a gifted songwriter and producer, but he was also rumored to be a sexual predator.

Tiffany Hawkins, one of his earliest alleged victims, met Kelly in 1991 at the age of 15. Enticed by promises of stardom, Hawkins claimed in a civil suit that she had sex with Kelly, and that he had her participate in group sex with other underage girls. When Hawkins turned 18, she says, Kelly dumped her. She attempted suicide. Numerous other young women would make similar allegations in the years to come; Kelly avoided conviction, often opting for out-of-court settlements.

How much did Hankerson know? It’s impossible to say. Still, if he had indeed heard or suspected anything—at least in 1991—it wasn’t enough to dissuade him from introducing Kelly to his 12-year-old niece, Aaliyah Haughton.

Aaliyah was the daughter of Hankerson’s sister Diane. Her talent was evident from a young age. Born in Brooklyn and raised in Detroit, she competed on Star Search in 1989 and, at Hankerson’s urging, performed onstage with Knight. (Hankerson and Knight had by this time reconciled.) With her parents’ approval, Aaliyah agreed to let Hankerson manage her, and he signed her to a recording contract with Blackground Records, a boutique label distributed by Jive Records that he founded with his son, Jomo, in 1993. (Jomo declined to comment for this story.)

Hankerson served as executive producer on all of her albums; he managed her publishing and royalty deals; he surrounded her with some of the most talented musicians of the era. For her debut, he paired her with Kelly, who produced and wrote most of the songs on Age Ain’t Nothing But a Number, released in 1994. The title track, written by Kelly, was a hit, but in retrospect, it was also a not-so-coded reference to their clandestine sexual relationship. Aaliyah was 14 when the song was released; Kelly was 27. On August 31, 1994, they were secretly married, with Aaliyah claiming to be 18 on the marriage certificate.

After Vibe published a story about Kelly in its December 1994/January 1995 issue and included a copy of the fraudulent certificate, the marriage went public; it was annulled shortly thereafter. Hankerson, reportedly furious, permanently separated Aaliyah from Kelly, but he didn’t cut his own business ties with him until years later, in 2000. Kelly, at the time the most popular R&B singer in the world, was too valuable.

In 1996, after striking a distribution deal with Atlantic Records, Hankerson moved Blackground—and Aaliyah—from Jive to Atlantic, gaining full control of her masters in the process. To replace Kelly, he recruited an emerging songwriting/production duo from Virginia Beach, Missy Elliott and Timbaland, to work on the next album. Released in 1996, One in a Million went double platinum on the backs of singles like the title track and “If Your Girl Only Knew,” which both became radio hits thanks to Timbaland’s innovative production style, Elliott’s memorable hooks, and Aaliyah’s effortlessly icy vocals. Hankerson quickly signed Timbaland to a solo deal, along with his collaborator Magoo, but Elliott defected to launch her own recording career, leaving Blackground short a songwriter once again.

Hankerson signed a Timbaland collaborator from Louisville, Kentucky, named Static Major, and over the next four years the pair turned out some of the best songs of the era, including Ginuwine’s “Pony,” in 1996; Aaliyah’s greatest single, “Are You That Somebody?,” in 1998; and “Try Again,” her first and only No. 1 hit on the Billboard Hot 100. By the turn of the millennium, she was an international star.

This was peak Aaliyah. Her music was tight, upbeat and complex, layering double and triple harmonic lines. Her voice, in isolation, was not among the all-time greats, but her whispery presence on a track was captivating. Her angular, syncopated dance moves spawned dozens of lesser imitators, and her fashion choices—the oversized jeans, the exposed midriff, the waist chain attached to the belly ring—became definitive late ’90s style.

Her self-titled third album launched in July 2001. Though it was pitched against the difficult headwind of widespread online file sharing, Aaliyah managed to go platinum twice, thanks to singles like “Rock the Boat” and “More Than a Woman.”

Six weeks later, at the age of 22, Aaliyah was dead. She’d been shooting the music video for “Rock the Boat” in the Bahamas when her plane crashed immediately after takeoff. Carrying eight people and luggage, the plane was overloaded. Its pilot, Luis Morales, had obtained his license by falsifying his flight logs. An autopsy revealed traces of cocaine in his system.

Hankerson was devastated, retreating into a long period of grief. He made no public statements about her death. According to those who worked with him, he never really recovered.

In February 2002, seven months after Aaliyah’s death, Chicago Sun-Times reporter Jim DeRogatis received an anonymous videotape in the mail, showing a man who looked exactly like R. Kelly urinating into the mouth of a underage girl. DeRogatis, who had already been investigating Kelly’s reputation as a statutory rapist, immediately turned the tape over to the police. In a published transcript with the victim’s mother, DeRogatis later speculated on the identity of his source, using initials instead of full names: “I’m sure that tape came by B.H.,” he said. “He’s tired of seeing young girls get hurt.”

Hankerson had split with Kelly, acrimoniously, sometime in 2000. When I talked to DeRogatis recently, nearly 14 years after the infamous tape first leaked to the public, he recalled Hankerson fondly. “I always found him to be a man with a conscience who felt wrong by his niece,” he told me.

For a brief period after Aaliyah’s death, it looked like Blackground might survive. The label still had Timbaland and Static Major. Hankerson had managed Braxton since 1997, and, in 2003, he inked her to his label as well. He signed Aaliyah’s possible replacement, a 12-year-old named JoJo aimed at the Radio Disney demographic. And he had the unreleased, unmixed vocals of Aaliyah’s outtakes—more than a dozen potential songs on two-inch reel-to-reel tapes. All they needed was a producer.

According to Hankerson’s eventual business partner, Rell Lafargue, COO of independent music publisher Reservoir Media, Hankerson never found one. He couldn’t find the sound he thought the music deserved. And the wound left by Aaliyah’s death remains raw: “Barry can’t be in the room when the new music is playing,” says Lafargue. Grief turned to despondency; despondency turned to inertia. Inexplicably, Blackground stopped releasing music, and artists stopped getting paid. As the music business moved from CDs to MP3s, and MP3s to streaming media, Blackground didn’t participate.

Soon the lawsuits started. In 2007, Braxton sued Blackground, claiming a breach of trust and misrepresentation and accusing Hankerson of “fraud, deception, and double-dealing.” In 2009, Timbaland sued as well, alleging that the label had refused to provide financing for his third album with Magoo and that Hankerson was interfering with his career as a producer. (Timbaland and his lawyers declined to comment for this story.) In 2013, JoJo filed her own suit, alleging that Blackground had refused to release her third album for more than six years, despite the fact she had delivered numerous audio masters to Hankerson.

That same year, Jeffery Walker, a former producer for Blackground, sued the label after being sent a tax bill from the IRS for more than $200,000 of reported income he says he never received. Walker’s lawyer claimed that Hankerson’s son Jomo had endorsed the checks himself, then cashed them in a Blackground account. The case is ongoing.

All the other lawsuits were settled out of court, with the parties signing confidentiality agreements. Speaking with the Fader earlier this year, JoJo, who’s now signed to Atlantic, described this period in her career: “I’m not entirely clear on what I’m not supposed to talk about, because I want them to leave me alone. It was such a strange and scary time. Threats and a lot of drama.” (JoJo declined to comment for this story.)

The pattern in these lawsuits was similar. Hankerson’s lawyers would contest every filing and push for changes of jurisdiction, generally seeking to delay things as long as possible. “They use every available means to crush you into a powder,” said Kelli Hooper, a lawyer who formerly represented Walker. “That’s what Blackground does.” Once the legal tactics were exhausted, the cases entered the discovery process, where Hankerson might be deposed under threat of perjury. At this point, Blackground would unexpectedly settle. “Concerns about testifying under oath may have led to settlement in this case,” said one lawyer employed by a Blackground plaintiff, “and perhaps others.”