Sly made what turned out to be a major financial blunder in 1984 when he sold his music publishing rights to Michael Jackson for $1 million. Though $1 million in 1984 was a decent sum of money, it was a fraction of what his rights would have been worth over the next 30 years. Tragically, in 2011 it was revealed that Sly was broke and living out of a van that he parked in various sections of South Central Los Angeles. Sly befriended a local family that was letting him use their house to take showers and eat meals.
Sly’s serious financial problems dated back to 1989 when he suddenly stopped receiving royalty checks from his business manager Gerald Goldstein. He launched a lawsuit that dragged on for more than three years. In January 2015, a Los Angeles jury awarded Sly $5 million in his breach-of-contract lawsuit. Half of the judgment was levied against a company called Even St. Productions which filed for bankruptcy protection in 2013. The other half was levied against his former managers who have vowed to appeal the decision.