By the time Hill was eight, she moved to Marietta, Georgia with her mother and siblings after her parents separated. Hill attended Roberts Grammar School, where she completed eighth grade, then dropped out. In November 1931, Hill, then 15, married 16-year-old George Randell. In 1933 Hill left Georgia for Chicago with Randell, with the hopes of breaking into show business. Once in Chicago, Hill separated from Randell, divorcing him the following year. Hill found a job as a waitress at the mob-run San Carlo Italian Village exhibit during the 1933 Century of Progress Chicago's World Fair, and supplemented her income working as a prostitute. She came to the attention of a wealthy bookmaker and gambler, Joseph Epstein, who became her financial advisor and reputed lover (although Epstein was known to be gay), and ultimately, Hill entered into the Chicago Outfit crime organization. In addition to being sexually passed around the Chicago mob, she was used as a courier to pass messages between mobsters. One contemporary commentator described Hill as:   ... more than just another set of curves. She had ... a good memory, a considerable flair for hole-in-the-corner diplomacy to allay the suspicions of trigger-happy killers and a dual personality, close-lipped about essentials, and able to chatter freely, and apparently foolishly about inconsequentials. Even law enforcement eventually concluded that she was a "central clearing house" for intelligence on organized crime and enjoyed an independent power base within the Mafia. Eventually Hill became associated with Charles Fischetti, a cousin and bodyguard of Al Capone. It was Fischetti who sent Hill to New York to keep tabs on Luciano family capo Joe Adonis, which she did by becoming his lover. Hill told people that she was a Southern-belle society girl who had gone through four rich husbands, all divorced or dead, and that she had received $1 million each from their estates, but authentic socialites saw through the ruse. Hill built up an entourage of hangers-on and Latin gigolos hanging out on Broadway and frequently picked up the check. While in New York, Hill was introduced to another Luciano associate, Benjamin "Bugsy" Siegel, and they ended up in a hotel together that night. Later Siegel's and Hill's separate life paths brought them both to Hollywood, and they began a torrid affair. There were rumors that she and Siegel were secretly married in Mexico after Siegel divorced his wife Esta in 1946, but there has not been any evidence to prove the theory.