In 1906, fifteen-year old Elizabeth Gurley Flynn mounted a soapbox in Times Square to denounce capitalism and proclaim a new era for women’s freedom. Quickly recognized as an outstanding public speaker and formidable organizer, she devoted her life to creating a socialist America, “free from poverty, exploitation, greed and injustice.” Flynn became the most important female leader of the Industrial Workers of the World and of the American Communist Party, fighting tirelessly for workers’ rights to organize and to express dissenting ideas. Weaving together Flynn’s personal and political life, this biography reveals previously unrecognized connections between feminism, socialism, free love, and free speech. Flynn’s remarkable career casts new light on the long and varied history of radicalism in the United States.