She 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 as a prostitute.

In addition to allegedly acting as a mistress to members of the Chicago Mob, she served as a courier to pass messages between mobsters.

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.

She 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.

[8] However, organized crime king Lucky Luciano wrote in his memoir that Siegel once owned an interest in the Hialeah Park Race Track and viewed the local flamingo population as a good omen.

[11][12] In 1951, she was subpoenaed to testify before the Kefauver hearings, where she denied having any knowledge of organized crime despite being described by Time magazine in March of that year as the "queen of the gangsters' molls".

[18] According to Andy Edmonds' biography Bugsy's Baby: The Secret Life of Mob Queen Virginia Hill, her death was suspicious despite it being an apparent suicide.