Dolly Fine was one of San Francisco’s last great madams and a defining figure of the city’s wide-open 1930s nightlife. Tall, blonde, impeccably dressed, and deeply embedded in the city’s underworld, Dolly ran one of the most profitable and professionally managed houses in town—right as Frisco’s long tradition of tolerated vice was beginning to crack under public scrutiny.

Before diving into Dolly’s reign, we take whirlwind tour of some of the city’s legendary madams, from Gold Rush pioneers like Irene McCready and Ah Toy to fan favorites Tessie Wall and Jessie Hayman. These women helped define San Francisco’s peculiar relationship with sex, money, and moral flexibility—a relationship that lasted for decades, until reformers, headlines, and political embarrassment forced the city to look too closely at its own reflection.

Dolly Fine’s story sits squarely at that breaking point. With ties to Prohibition-era smuggling, early gangster life, and a past that police later dredged up with relish, Dolly faced the full force of the Atherton investigation and a changing civic mood. Though she survived the Grand Jury and continued operating, the ground was shifting beneath her feet. Part One sets the stage for her dramatic fall—her arrest, flight, and nationwide manhunt—stories that will unfold in Part Two.
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