This American Life, Episode 869: "Harold"

Original Air Date: October 5, 2025
Host: Ira Glass

Overview:

This episode revisits the groundbreaking story of Harold Washington, Chicago’s first Black mayor, drawing fresh parallels to current political dynamics—specifically, the controversy surrounding Zoran Mamdani's bid for New York City mayor. Through archival material and new context, the episode explores how Washington’s election challenged entrenched race and power structures, transformed city politics, and left an indelible mark on Chicago and the nation.

Key Discussion Points & Insights

1. Parallels Between Harold Washington and Zoran Mamdani

• Opening Context (00:23): Ira Glass frames the episode by comparing Zoran Mamdani’s experience with the Democratic establishment in New York to Harold Washington’s relationship with the Democratic machine in Chicago.

  • Glass observes:

    "Harold's story is a parable about a Democrat whose very existence made the party have to question what it was all about, which seemed very much like Mamdani." (01:53)

• Caution in Comparison: While drawing similarities, Glass notes the different roots of controversy—race for Washington, ideology and religion for Mamdani (02:47).

2. Pre-Harold Chicago: Entrenched Segregation and Machine Politics

• Living Conditions and Machine Rewards:

  • Jackie Grimshaw speaks on systemic neglect:

    "My daughter started to believe that when buildings got old and died, like people got old and died, that you knew a building was old and was dying because it would burn up." (03:10)

  • Glass explains how machine politics benefited white wards, leaving Black neighborhoods behind. (03:38)

• Chicago’s “Colonies”

  • Harold Washington recounts Black aldermen reduced to little more than “garbage aldermen” due to basic service neglect.

    "You'd almost have to just be the garbage alderman ... I was tired of just being the garbage alderman." (03:57)

3. The Path to Power: Organizing and Opportunity

• Daily’s Death & Democratic Machine Weakness (08:23):

  • Judge Eugene Pincham recounts how even loyal Black aldermen were blocked from power in times of transition, articulating the systemic racism at play.

    "The only misqualification he had was he's black." (09:04)

• The Anti-Machine Momentum: Organizers register 130,000 new Black voters, outstripping Washington’s own skepticism (12:32).

4. The Debates: Washington’s Voice Resonates

• Primary Debates (13:12):

  • Washington’s authentic, direct debate style contrasts with boilerplate responses of his white opponents.

    "The precise question is, what would I do to improve the office of professional standards? ... I'll be the only one who answered the question." (14:17)

  • His intellectual vigor wins public support:

    "It was like watching Michael Jordan with a basketball." (15:13, Vernon Jarrett)

• Refusal to Mythologize Past Mayors:
  > "[Daley] was a racist from the core, head to toe and hip to hip." (17:01) > "I give no hoosanus to a racist, nor do I appreciate or respect his son." (18:04)

5. Race as the Central Conflict

• Community Reactions:

  • The divide in Chicago is palpable post-primary: jubilation in Black communities, somberness in white spaces.

    "There was such a somber feeling ... like somebody's family member, beloved family member, had died." (24:15, Monroe Anderson)

• Racial Hostility and Fear:

  • White flight, racially coded campaign slogans, and explicit slurs pervade the general election context.

    "Somebody spray painted on the church graffiti. It said, die, nigger, die." (25:54, Monroe Anderson)

  • Judge Pincham analyzes the double standard:

    "When the blacks try to get a black mayor, it's racism." (26:45)

6. Governing and “Fairness Over Patronage”

• High Community Expectations:

  • Lou Palmer expresses disappointment that Washington was “too fair,” refusing to use machine-style favoritism to uplift Black neighborhoods beyond others.

    "Harold was too fair. In fact, he would say in his speeches ... I'm going to be more than fair." (32:09)

  • Washington asserts:

    "No one ... is free from the fairness of our administration. [We] will find you and be fair to you wherever you are." (32:45)

• Systemic Resistance:

  • The “Council Wars”—white majority of aldermen block legislation, reducing mayoral clout.
  • Council Wars satirized as “Star Wars,” vividly illustrating obstruction and resistance to reform (38:56–40:51).

• Pragmatic Politics:

  • Jackie Grimshaw recounts Washington’s use of media and public demand to pressure recalcitrant city council members for city service funding (41:14).

7. Race Colors Every Move—Even Reform

• “Everything Was Seen Through Race”

  • Gary Rivlin:

    "But no one could ever see beyond his race." (42:28)

  • Washington’s own frustration:

    "All little silly business, you know. How many white folks did you convert today, Harold?" (43:22) "I do my job irregardless of race, color, creed, or sex." (44:01)

• Opposition Weaponizes Statistics:

  • Crime statistics are manipulated by opponents to play racial fears—Rivlin contends this was “playing the race card in a dirty way.” (44:52)

8. Legacy and Change after Washington’s Death

• Tentative Progress:

  • As he built cross-racial coalitions, even some former opponents in white wards came to respect Washington.

  • Patrick O’Connor recounts:

    "He got a great reception. People that really didn't vote for him ... respected the fact that he came out there..." (46:13)

  • Vernon Jarrett remarks:

    "He was chubby, warm, friendly ... going into some lower class white neighborhoods, having their streets paved for the first time, and they were slowly beginning to lose their fear." (48:32)

• Permanent Shifts in City Governance:

  • Fairer distribution of services, new political standards, and enduring anxiety among white voters are traced (49:11–51:31).

• Incremental White Attitudinal Change (2007 Follow-up):

  • Twenty years on, many voters who once opposed Washington express changed attitudes—though racist sentiments linger, willingness to support Black candidates grows (53:23).

9. The Broader Political Legacy: From Harold to Obama

• Barack Obama’s Chicago:

  • Obama (audio from Dreams from My Father):

    "It's hard to forget the sense of possibility that he sparked in people." (56:02)

  • David Axelrod measures electoral changes:

    "Obama carried all but one ward on the northwest side of Chicago ... the precinct in which St. Pascal's Church sits." (56:53)
    "I said to Barack that night, I think Harold's smiling down on us tonight."

• Cautionary Lessons:

  • Both Lou Palmer and Obama highlight the peril of pinning change on one leader, noting that the movement waned after Harold’s death.

  • Obama’s reading:

    "[T]here was no political organization in place, no clearly defined principles to follow. The entire of black politics had centered on one man who radiated like the sun. Now that he was gone, no one could agree on what that presence had meant." (59:20–60:08)

  • Ira Glass draws a parallel to criticisms of the Obama-to-Trump transition—without a strong movement or organization, lasting change is at risk.

Notable Quotes & Memorable Moments

• "I recall telling people time and time again that I was tired of just being the garbage alderman." —Harold Washington (03:57)
• "There are no good qualities of past mayors to be had. None, none, none, none. ... [Daley] was a racist from the core, head to toe and hip to hip." —Harold Washington (17:01)
• "When the blacks try to get a black mayor, it's racism." —Judge Eugene Pincham (26:45)
• "Harold was too fair. In fact, he would say in his speeches ... I'm going to be more than fair." —Lou Palmer (32:09)
• “Everything was seen through the prism of race, even though often it had nothing to do with race, often it had more to do with reform.” —Ira Glass (42:13)
• “If we have to beat them across the head and knock them down and make them take it, we're going to give it to them.” —Harold Washington (19:03)
• "All little silly business, you know. How many white folks did you convert today, Harold?... I do my job irregardless of race, color, creed, or sex." —Harold Washington (43:22, 44:01)
• "I blame Harold for this. ... Harold was put on a pedestal, and I think that was a major mistake. We lifted him to almost God status." —Lou Palmer (58:41)
• "[Obama] carried the precinct in which St. Pascal's Church sits. ... I said to Barack that night, I think Harold's smiling down on us tonight." —David Axelrod (56:53)

Important Timestamps

• 00:23–02:47: Setting up the episode’s parallel between Mamdani and Washington
• 03:10–06:22: Life in Black Chicago under the machine; Harold’s voice, wit, and frustration
• 08:23–10:46: The political machine’s treatment of Black politicians
• 13:12–14:50: Washington’s debate performance—turning point
• 17:01–19:03: Washington on Daley, racism, and redemption
• 24:15: White and Black Chicago’s divergent reactions to Washington’s win
• 25:54: Racist backlash at St. Pascal’s Church
• 32:09–37:07: Washington’s fairness as governing principle and the tension it created
• 38:56–41:14: "Council Wars" and efforts to pass evenhanded city improvements
• 42:13–45:53: Race overshadowing reform, weaponization of statistics
• 46:13–48:32: White attitudes shift as Washington reaches out
• 51:24–54:34: Evolving white voter attitudes decades after Washington’s tenure
• 56:02–57:49: Barack Obama connects his path to Washington’s legacy
• 59:11–60:10: Movement’s collapse after Harold, organizational lessons
• 62:55: Closing, Harold’s second victory celebration

Tone & Style

The episode blends direct, unflinching accounts of racial strife with sharp political analysis, historical storytelling, humor, and moving personal anecdotes. Archival voices, satire (“Council Wars”), and reflective narration from Ira Glass and others keep the tone engaging, clear-eyed, and—at times—deeply emotional.

Conclusion

The episode serves as a riveting history lesson, a cautionary tale about expecting individual leaders to create systemic change, and a meditation on cycles of racial progress and backlash in American politics. The legacy of Harold Washington looms over subsequent decades of politics, his impact profound but also a warning: true change demands more than just one leader—it requires a movement, an organization, and commitment beyond the allure of any singular, charismatic figure.