When Zohran Mamdani won the primary race for New York mayor, the Democratic establishment's lukewarm response echoed the treatment of another charismatic, unconventional candidate decades earlier. This week, we bring you the story of Harold Washington, the greatest politician you've probably never heard of, and the backlash that ensued when he became Chicago's first Black mayor. Visit thisamericanlife.org/lifepartners to sign up for our premium subscription. * Prologue: As New York City’s Democratic establishment attempts to resist the candidacy of Zohran Mamdani, we look back at another mayoral candidate who upset the established political machine. (7 minutes) * Act One: A history of the brief mayoral career of Harold Washington and its lessons for Black and white America, as told by people close to him. (39 minutes) * Act Two: Ira revisits interviews with Chicago voters from the 1997 and 2007 rebroadcasts of this episode. In 1997, ten years after Harold Washington’s death, not much had changed in Chicago. By 2007, attitudes had begun to shift slowly, and another Black politician from Chicago was on the rise — Barack Obama. Ira also speaks to David Axelrod, an advisor to both Harold Washington and Barack Obama. (10 minutes) Transcripts are available at thisamericanlife.org This American Life privacy policy. Learn more about sponsor message choices.