Federal prosecutors referred to Cali in court filings in 2014 as the underboss of the Mafia's Gambino family, once one of the country's most powerful crime organizations. News accounts since 2015 said Cali had ascended to the top spot, though he was never charged with leading the gang. His only mob-related conviction came a decade ago, when he was sentenced to 16 months in prison in an extortion scheme involving a failed attempt to build a NASCAR track on Staten Island. He was released in 2009 and hasn't been in legal trouble since then.