Chief Keef
Chief Keef

In 2012, Chief Keef skyrocketed to fame with his now-classic track “Don’t Like” and became one of the most notorious figures in Chicago’s Drill music scene. At just 16 years old, he signed a $6 million deal with Interscope Records, a move that would take Drill music mainstream with his debut album, Finally Rich.

However, in a recent interview, former Interscope A&R and current Gamma CEO Larry Jackson revealed shocking details about what Chief Keef was facing before his breakthrough deal. Speaking to NPR, Jackson disclosed that Sosa was on the FBI’s watch list and had a $50,000 bounty on his head at the time.

Behind the Scenes of Chief Keef’s Rise

“With Chief Keef, he wasn’t just a vision,” Jackson shared. “This is the first time I’m telling this story, but I got a call from a friend who was in touch with the FBI. They told me this kid [Chief Keef] was on a watch list. Then they called me back and said there’s a $50,000 hit out on this kid. You may want to do something about it.”

Jackson confirmed that Chief Keef had already signed with Interscope Records when he learned about the rapper’s dire circumstances.

A&R Turned Father Figure

Beyond the business, Jackson revealed how he became a mentor and father figure to the young rapper:
“He had gotten into some trouble. I personally wrote a letter to the judge. My letter was effective and persuasive. It kept him out of jail… So I kinda stepped up in a ‘father figure’ role,” Jackson explained.

He emphasized that his vision for Chief Keef extended beyond music:
“It’s so much deeper than, ‘Oh, let me just sign this guy because everybody wants him.’ No, this was about a vision for his life, not just his music.”

This bond has endured, with Jackson noting that he and Chief Keef remain close to this day.

Finally Rich and the Birth of Mainstream Drill

Chief Keef’s debut album, Finally Rich, dropped under Interscope in December 2012. It featured collaborations with major artists like 50 Cent, Wiz Khalifa, Young Jeezy, and Rick Ross. The album played a pivotal role in bringing Drill music into the mainstream, cementing Chief Keef’s legacy in hip-hop history.

Larry Jackson’s Legacy and Industry Insights

Larry Jackson’s influence extends far beyond his work with Chief Keef. Now the co-founder of entertainment powerhouse Gamma, Jackson has shaped the careers of countless artists while navigating the ever-evolving music industry.

On a recent episode of Popcast, Jackson sat down with hosts Jon Caramanica and Joe Coscarelli to discuss his journey, including the high-stakes rivalry between Kendrick Lamar and Drake and how his experiences at labels like Interscope inform his current strategies in today’s streaming-dominated landscape.

Final Thoughts

Chief Keef’s rise to fame was anything but ordinary, marked by challenges that went far beyond the music industry. Thanks to Larry Jackson’s guidance, Sosa was able to overcome significant hurdles and become a transformative figure in hip-hop.

With Finally Rich standing as a testament to Drill music’s breakthrough and Jackson continuing to innovate in the industry, their story highlights the profound impact of mentorship, resilience, and vision in shaping the future of music.

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