Robert "Bobby" Jackson (January 13, 1875 - November 8, 1931), often known as "Boss Bobby" was a legendary Covenant-based criminal operating during Prohibition, although his business enterprises were focused around considerably more ventures than merely bootlegging.

Born a freedman to slave parents thanks to the Compromise of 1868, Jackson eventually rose through the criminal world of Covenant to become the city's undisputed master in the 1920's and early 1930's, having completely eliminated competitors in gambling, prostitution, racketeering and sales of illegal goods such as liquor (illegal in Arkansas, a dry state) and untaxed tobacco. Jackson also allegedly had "half the state of Arkansas" on his payroll, regularly giving police officers bribes to avoid cracking down on his enterprises and selling out his competition, and allegedly had the mayors of Covenant and Little Rock, as well as numerous state judges and lawyers, on his regular payroll - an impressive feat in a segregated Southern state for a black man at the time. Jackson helped repopularize riverboat gambling, muscled out competition in Hot Springs to establish the small town as a gambler's den for rich Southerners, and by his death at the age of 56 in 1931 of a heart attack, controlled a criminal empire that had contacts as far north as Memphis and St. Louis and as far south as New Orleans, earning him the moniker "the Negro King of the Mississippi."

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