Larry Jackson’s Reflections on Signing Chief Keef

Larry Jackson recently reflected on the unique and powerful position he was in when he signed Chief Keef amid FBI investigations and death threats.

In a candid interview, the former Apple Music music executive shared the extraordinary circumstances surrounding his decision to sign Chief Keef, revealing that his motivations extended far beyond music. At the time Chief Keef, who had emerged into the mainstream as a teenage rapper from Chicago, was under investigation by the FBI and reportedly the target of a $50,000 hit.

“This is the first time I’ve ever told this story,” Larry Jackson began, describing how a friend connected to the FBI alerted him to the dangerous situation. “There’s a $50,000 hit out on this kid, and you may want to do something about it.”

For Jackson, signing Chief Keef wasn’t a typical A&R decision. “That’s not a job from a traditional vocational perspective of an A&R executive. That wasn’t in an A&R class,” he said. The threats and legal troubles Keef faced prompted Jackson to take a more active role in the young artist’s life, stepping in not just as a label representative but as a mentor and protector.

“I personally wrote a letter to the judge,” Jackson revealed, explaining how his intervention kept Keef out of jail. “It was effective and persuasive. It kept him out of jail.”

At the time, Keef was only 16 or 17 years old and already entangled in the challenges of life in Chicago’s drill scene. Jackson’s involvement went deeper than helping Keef avoid incarceration.

“I kind of stepped up in a father figure role,” he said. “This was so much deeper in terms of a vision for not just the music, for his life.”

Despite the chaotic circumstances, Jackson played an instrumental role in shaping Finally Rich, Keef’s debut album.

“I went in and picked the songs for the album. I came up with the intro, came up with the interludes. I mixed the album with Chris Cheney. I sequenced the album,” Jackson recalled. However, his greatest pride came from ensuring Keef survived the turbulent period. “The most important thing to me is that he’s still alive. And not in prison.”

Upon its released in 2012, Finally Rich became a landmark album in the rise of drill music, influencing the modern rap landscape. The project debuted at No. 29 on the Billboard 200, selling 50,000 copies in its first week. It has since achieved RIAA Gold certification, with standout tracks like “Love Sosa” and “I Don’t Like” becoming cultural staples.

Check out the clip in the post above.