Larry Jackson recently opened up about the intense and dangerous moments that surrounded his decision to sign Chief Keef, a teenage rapper from Chicago who was making waves in the music scene. At the time, this wasn’t just about music. Chief Keef was under FBI investigation, and there were alarming reports of a $50,000 hit placed on his life.
In an eye-opening interview, Larry Jackson, a former Apple Music executive, shared this untold story for the first time. He recalled how a friend with ties to the FBI warned him about the situation. “There’s a $50,000 hit out on this kid, and you may want to do something about it,” his friend told him.
Signing Chief Keef wasn’t a routine music industry move for Jackson. It was a life-or-death decision, with Jackson stepping into a role that went far beyond being an A&R executive. “That’s not something you learn in an A&R class,” he said. Jackson knew he had to take action to protect the young artist, who was just 16 or 17 years old at the time and caught up in the chaos of Chicago’s drill music scene.
One of Jackson’s most impactful decisions was writing a heartfelt letter to the judge handling Chief Keef’s legal troubles. “It was effective and persuasive. It kept him out of jail,” Jackson said. He didn’t stop there—he took on a mentor-like role in Keef’s life, acting as a father figure during an incredibly turbulent time. “This wasn’t just about the music; it was about his life.”
Despite all the challenges, Jackson worked closely with Keef on his debut album, Finally Rich. From selecting songs to sequencing the album and even mixing it alongside Chris Cheney, Jackson played a critical role in bringing the project to life. But what mattered most to him wasn’t the album’s success—it was keeping Chief Keef alive and out of prison. “The most important thing to me is that he’s still alive. And not in prison,” Jackson emphasized.
Finally Rich dropped in 2012 and became a game-changer for drill music. It debuted at No. 29 on the Billboard 200 chart, selling 50,000 copies in its first week. Over time, the album achieved RIAA Gold certification and solidified its place in music history with iconic tracks like “Love Sosa” and “I Don’t Like.”
This story highlights not just the rise of a music star but also the extraordinary lengths someone went to in order to protect a young talent from the dangers of his environment. For Larry Jackson, signing Chief Keef was more than a career move—it was a mission to save a life.
