Jane Byrne never intended to get into politics. But after her life was turned upside down by a tragic accident, she volunteered for John F. Kennedy’s presidential campaign and eventually caught the attention of the powerful boss of Chicago Democratic machine politics, Richard J. Daley. She became his protégée and held various positions, working her way up in city government. But after Daley’s death, Byrne called out corruption where she saw it, lost her job, and turned against the machine that shaped her. Her 1979 mayoral campaign as an anti-machine underdog appealed to many Chicagoans, including those in the city’s most marginalized communities. Though Byrne ultimately had a mixed record in office, her journey to get to the fifth-floor office of City Hall ended with her becoming not only Chicago’s first female mayor, but also the first woman to become mayor of a major U.S. city.