869
October 3, 2025
Preview

Harold

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.

Prologue

Prologue

A look at the Chicago political machine in the days before our story begins. (5 minutes)

Act One

Yesterday

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. (46 minutes)

Many are activists and politicians, including Lu Palmer, Judge Eugene Pincham, Congressman Danny Davis, and then-Alderman Eugene Sawyer. There are people from his administration, including Jacky Grimshaw and Grayson Mitchell, as well as some reporters who followed his story, such as Vernon Jarrett, Monroe Anderson, Gary Rivlin, and Laura Washington, who later became his press secretary.

Harold Washington died on November 25, 1987. This show was first broadcast ten years later, in 1997.

Act Two

The Present and the Future

Ira Glass talks with David Axelrod, who served as an advisor to Harold Washington and Barack Obama. In 2007, when we last broadcast this show, Ira recorded an interview with Axelrod, who was riding on Obama’s campaign bus, during the Democratic Primary in Iowa. Axelrod explained that by 2007, the white Chicago wards that didn’t vote for Harold overwhelmingly came out for Obama. Then, WBEZ reporter Robert Wildeboer talks to some of those voters in wards where Harold did poorly in the 1980s, about what changed for them. And we hear an excerpt from "Dreams From My Father," where Barack Obama writes about what Chicago was like in the days after Harold’s death. (11 minutes)