Larry Jackson, former Interscope executive and current CEO of gamma., revealed that Chief Keef was placed on an FBI watchlist with a $50,000 bounty on his head during his teenage years. This revelation came during Jackson's interview with The New York Times' Popcast.

Jackson discovered this information through an FBI contact who warned him about the threat to Keef's life around the time Interscope signed him in 2012. In response, Jackson took on a protective role, even writing a letter to a judge that helped keep the young rapper out of jail.

The relationship between Jackson and Keef developed beyond typical business dealings, with Jackson assuming a mentorship role. "This was so much deeper in terms of a vision — for not just the music but for his life," Jackson explained. Their close relationship continues to this day.

Interscope signed Chief Keef for $6 million following his breakout hit "I Don't Like" in 2012. While he released his debut album "Finally Rich" that same year, the label dropped him in 2014 due to legal issues.

Prior to his signing, Keef faced serious legal troubles. At age 16, he was involved in a shootout with police and faced multiple charges, including aggravated assault with a firearm on police officers. Earlier, in 2011, he was arrested for heroin manufacture and distribution, resulting in house arrest as a minor.

Now 29, Chief Keef (born Keith Farrelle Cozart) has largely avoided legal issues since his last arrest in 2017 for cannabis possession in South Dakota.

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