What Today’s Insurgent Campaigns Can Learn From Harold Washington

Four decades ago, at the start of 1984, Harold Washington was finishing his historic opening year in office as Chicago’s first Black mayor. An outsider candidate who had been persuaded to run by the city’s social movements, Washington represented a major break from the past, and his 1983 victory served as an important milestone in the efforts of civil rights activists to gain footholds in electoral politics.

Today, as social movements increasingly take interest in running insurgent candidates for office, Washington provides a vital model for how grassroots forces can bring new constituencies into the electoral realm and upend the established practices of insider politics.

Once in office, the mayor—widely known in the city simply as “Harold”—faced entrenched opposition. And yet he was able to take significant strides in dismantling the city machine. Run for decades by Richard J. Daley, this machine long maintained a racist and inequitable system of distributing municipal resources.

Tragically, Washington died of a heart attack just months into his second term, in 1987. His sudden passing created a lasting trauma for progressive forces in the city and raised questions about what more he might have been able to accomplish had he lived.

The turbulent times of his election, governance, and untimely death are something that no one who lived through it can ever forget.

More recently, the 2023 election of a new progressive mayor in Chicago, Brandon Johnson, has both generated fresh hope and created revived interest in the lessons that might be drawn from Washington’s example in taking on Chicago’s old guard some 40 years ago.

As a filmmaker, Joe Winston has tackled topics ranging from conservative organizing in America’s heartland (as director of 2009’s What’s the Matter with Kansas) to the influence of the ultra-rich on our political system (as producer of 2013’s Citizen Koch). His latest film, Punch 9 For Harold Washington, is showing in coming months in cities including Denver, Atlanta, Nashville, and Chicago, and it has just been made available for both educational use and community screenings.

Recently, we spoke to Winston to discuss insights that Washington’ story can provide for social movements looking to bring new voices into electoral politics today. Our conversation has been edited for length and clarity.

Tell us about your background and how you got involved in this story.

My film, Punch 9 for Harold Washington, is about Chicago’s first African American mayor. When he was elected in 1983, I was a junior in a high school that was located just three or four blocks from Harold’s apartment. He was a huge figure in Chicago, and the turbulent times of his election, governance, and untimely death are something that no one who lived through it can ever forget.

As a documentary filmmaker, I realized years later that the story of Harold Washington has universal significance. As a trailblazing Black mayor in a city which was undergoing rapid demographic change, the kinds of coalitions that Harold had to build in order to win an election—and then subsequently to govern—had tremendous resonance. That was particularly true in the Obama era. Barack Obama came to Chicago as a community organizer partly because Harold Washington had taken office. And, subsequently, the white backlash to Obama’s presidency mirrored almost exactly what Harold Washington had to navigate as mayor of Chicago.

Before he decided to run for mayor in 1983, Harold almost had to be drafted by social movements. He made a number of demands that local organizers had to meet in order for him to run, including the demand that they register 50,000 new voters—which seemed like an impossibly huge number.

Right. Washington is a fascinating and complex figure. He was 61 years old when he first became mayor in 1983, and he had actually run for mayor before—in 1977, during a special election that was called shortly after the death of the legendary political boss Richard J. Daley. That election attracted a lot of candidates, and Washington only placed third. His experience of an underfunded, hastily put together campaign taught him that in order to beat an entrenched political organization like the Cook County Democratic Party machine, he needed more than a great campaign. He needed to be assured that there was a true groundswell and a broad coalition willing to support him.

Harold’s vision for Chicago was very detailed. He made it very clear that he was taking on an entrenched system of corruption that was harming the entire city.

By the time 1982 came around, Harold was serving in the U.S. Congress and he was reluctant to run for mayor again, unless he saw that there was a lot of infrastructure in place. And this time there was. There were a lot of people working in the neighborhoods who had opposed Mayor Daley on Vietnam, racism, development, and countless other issues. They knew what they wanted, and they mobilized the community. Depending on which figure you cite, they registered as many as 200,000 new voters for the 1983 mayor’s race—far more than he had demanded. And that convinced Harold Washington that it was his time to run again.

In your film, a Chicago politician named David Orr, who had served in the City Council when Washington was in office, says that was “the first time this coalition had come together.” What were the distinctive elements of the coalition that Washington created?

The famous Harold Washington Coalition was made necessary by the ethnic makeup of Chicago at the time. The city was about 40% African American, 40% white, and 20% other ethnic groups, primarily Puerto Rican and Mexican. So no single ethnic group in Chicago could win a majority on its own. Washington and his allies understood this. They formed an alliance that joined African American with white liberals—and they also brought in the Hispanic community, which previously had not been very politically active. That gave them just the numbers they needed to overcome the entrenched machine and white resistance.

One of the exciting things about the Washington campaign of 1983, that would be echoed in the Obama campaign of 2008, is that both brought in people who were new to electoral politics, people in groups who were energized by a sense of new possibilities. Washington not only formed an electoral coalition of these different groups, but he translated it into a governing coalition.

One thing that seems to make Harold Washington different from other politicians is that he seemed to reject polite politics and to embrace polarizing subjects. When he talked about the legacy of Richard J. Daley, whom many people in Chicago still loved, Harold didn’t pull any punches. Instead, he denounced Daley as a flat-out racist. It seems he had a strategy of energizing his base, while also somehow reaching out to the middle over time. That’s different from how most politicians think about messaging. What do you think?

A lot of the messaging that Harold Washington used was being carried out over Black radio and newspapers—publications like the legendary Chicago Defender—that most white Chicagoans didn’t pay any attention to. So when Washington defeated two white Democrats in the Democratic primary, the major news media was shocked. They didn’t think this guy had a chance, because they hadn’t been paying attention to what was being discussed in the media consumed in Black neighborhoods.

These days, media targeting looks different, but certainly Washington was a great political communicator. He could be very blunt and populist in his appeal to voters. But he was smart enough and understood policy well enough to really engage them. He didn’t have to waffle on the issues, although he certainly had to try to be polite. There would have been plenty of opportunities for a Black politician to be much more negative about the power structure that existed in the city at the time. To this day, Black politicians always have this onus on them: They are always expected to reach out, and Washington was certainly subject to those burdens.

It seems like Washington did things to intentionally agitate and engage his base, which did push away some people. But he wasn’t concerned about that, because he had a strategy to build a majority. Do you think that’s correct?

Well, I would take issue with that a little bit. The truth is that when we’re telling his story, we are focused on the political combat that he engaged in. By the time he ran, he already had opponents who were saying the worst possible things about him. When he was running in the general election against a Republican opponent, his opponent’s slogan was “Before it’s too late.” Everybody in Chicago knew what that meant: It was a blunt, racial appeal. So in some cases, I think Harold Washington was really just fighting back. I don’t think he intended to push away a single voter. In fact, winning over white voters was the thing he worked the hardest at.

Harold was very determined not just to put a new face on the old system, but to overthrow the system completely.

Harold’s vision for Chicago was very detailed. He made it very clear that he was taking on an entrenched system of corruption that was harming the entire city. He put through programs that not only helped African Americans, but actually benefited a lot of white neighborhoods, which themselves had been neglected.

One of the ways that he ended up beating the deadlock in City Council was by putting forward a bond issue on infrastructure and then going directly to the public to say, “Your City Council members are blocking this.” He appealed to the common interest of people throughout the city of having their roads repaired.

Yes, that was one of his great victories.

In the film you show how, once Harold came into office, he made an attack on the patronage system in Chicago politics his central fight. But because this system was so deep-seated in city politics, his attack created massive resistance from the City Council. It probably made it more difficult for him to accomplish things in the short run than if he tried to make peace and cut deals. Why do you think he took on this strategy?

The battle that you’re describing is the crux of the Washington story. Harold was very determined not just to put a new face on the old system, but to overthrow the system completely. It was an enormous challenge, and it led to a stalemate known as the “Council Wars,” which stymied much of his governance for his first three years.

The saddest part of the Harold Washington story is that he simply did not live long enough to consolidate his coalition into something that could outlast him.

Many of his allies did not want him to do this, because it was incredibly difficult. But Washington knew exactly what he was doing. He himself had come up through this very same system, having served as a precinct captain as a young man. His father had tried to work his way up from the bottom ranks of the Democratic Party, too, and was rebuffed by the Daley machine. So, for Harold, this was the fight of his life. He felt the system was wrong, and that it needed to be changed.

It’s interesting that, before running for mayor in the 1983 election, Harold was serving as Congressperson in Washington, D.C. Prior to that, he had been in the state government. So he had figured out how to operate inside of the machine system, even if he eventually came to hate the machine. How do you look at Harold’s political evolution?

Washington came up through the machine in a ward organization during the Daley years. Then he found his place in the state legislature, where you’re kind of at arm’s length from the Cook County machine. Those legislators had a little bit more latitude. For a couple of decades, Washington managed to stay within his lane, deciding which votes he could take and which ones he needed to skip in order to get good work done. In the state legislature, Harold passed the first holiday in the country commemorating Dr. Martin Luther King, for example. But he broke with the machine in the late ‘70s. At that point, his opponents tried to run somebody against him, but Harold beat them. So by 1980 or so, Harold was completely independent; he had his own power base, and he was able to become a U.S. congressman. The machine itself was weakened after the death of Richard J. Daley in 1976, and that set the stage for Harold to later become mayor.

There was a history of reform candidates in Chicago who couldn’t get much done. Because they were always on the outside, they didn’t know the machine’s internal workings. You could say that one part of Harold’s genius was that he really knew the system, and this is what allowed him to take it apart.

I think that’s absolutely correct. It’s quite remarkable that he was so schooled in this system of politics and power, but then he chose to take it on. It’s rare, but that is part of what made him the right person to do the job.

In your documentary, there’s a scene where they talk about disrupting the patronage system, and Harold decides to fire everyone who doesn’t show up for work and isn’t in the office. Would you say that he had a vision of using the power of the institutional bureaucracy in a way that might be different from other politicians?

At the time that Washington was elected mayor of Chicago, the city employed something close to 40,000 people, with various positions directly appointed. When Washington took office, most of these people had been employed by his opponents. So the machinery of bureaucracy was working against him. This was kind of the mirror image of what former President Donald Trump would talk about as the “deep state.” There really was a deep state in Chicago of bureaucrats who had been appointed to patronage jobs. The reason that they were in the Department of Housing was not because they knew anything about housing, but because they had turned out 1,200 votes in their precinct in the last election. Harold and his allies realized this was a system that could not continue.

A variety of people, including Barack Obama in Dreams from My Father, have made the point that the coalition that put Harold in office ended up being overly dependent on the charisma and the personality of one individual. So when Harold died suddenly, the machine was able to come back and co-opt parts of his coalition.

The saddest part of the Harold Washington story is that he simply did not live long enough to consolidate his coalition into something that could outlast him. Harold died of a sudden heart attack in 1987. He collapsed at his desk, having won re-election just a few months prior. This was an enormous trauma for the Black community in Chicago, as well as for all progressives, inside and outside of Chicago.

Politically, it set off complete chaos. The fracturing of the Washington coalition was an immense tragedy. And it did unfold with horrifying speed—basically in one week’s time. Part of the problem was that a lot of City Council members, and even a number who were in the Washington coalition, had come up through the old system of patronage and corruption. They were really much more comfortable with that. It was only Harold Washington’s immense popularity and force of personality that kept them in line. So it became pretty easy for the operators of the Chicago machine to bring around just enough Black members to form a new majority and take power again.

“You know, I need people to be on the outside pushing this. Change is hard. And I want to see protests out there.”

There’s that old line from Will Rogers: “I’m not a member of any organized party. I’m a Democrat.” Progressive coalitions are always tricky to hold together. And the Washington coalition had not been together very long. Daley’s son came in as mayor soon after, and the son ended up ruling longer than his father had.

In terms of their reliance on a single leader, do you think there were alternatives that movements could have pursued?

It’s clearly a tremendous weakness for a movement to be dependent on any one person. Black Lives Matter groups and younger activist groups have taken this to heart. But at the same time, the forceful leadership and the cohesiveness that Washington applied was crucial to getting so much to change so fast. Harold destroyed a decades-old system of patronage and corruption very quickly, and change like that is hard to make happen. Having your leader die on you, four years after getting elected, is a crippling wound. There is no simple answer. There’s just a continuing need to nurture new political talent. And we must have an understanding that these movements take time.

Harold was not the first Black mayor of a major U.S. city after the civil rights movement of the 1960s. Before 1983, you had Black mayors in places like Cleveland, Washington D.C., Detroit, Atlanta, and Los Angeles. And yet many people talk about Harold Washington as a model in a different way. Why do you think that is?

I think what was really special about Harold was that as a trailblazing Black mayor of a major U.S. city, he neither presided over a city which whites had abandoned, like Cleveland, Detroit, or St. Louis, nor was he looking to just put a new face on the old system. Harold was someone who came into office promising revolutionary change, as a Black mayor in a city where Black people were a substantial ethnic group and not the majority. So I think that makes him tremendously important. What he was able to accomplish was a real civil rights movement candidacy and governance, but one in which he did have to reach out beyond African Americans to form coalitions to make it happen.

We are in a moment where there has again been a lot of interest in social movement circles in running insurgent electoral campaigns—something that’s been on the rise at least since Bernie Sanders’ presidential run in 2016. We’ve seen things such as the rise of The Squad in Congress coming out of that. What do you think are the lessons that Harold Washington offers for activists who are looking to bring social movement energy and issues into electoral politics today?

The fact that Washington had to build a coalition beyond his base is really crucial. The fact that he couldn’t just depend on his ethnic group identification to carry him to victory. And the fact that he did it through bread and butter issues. He understood infrastructure and development and redistribution—and how all these things would actually get done in ways that could broaden his appeal. He had programs for the whole city, and I think he provides a really valuable example of how politicians can broaden their coalitions.

It’s also crucial that Harold Washington’s candidacy came from a movement. Although voters later might remember his qualities as a politician—his charisma and his political skills—he wasn’t out there by himself. There was an entire movement behind him that had goals and also had the ability to mobilize people.

I wanted to present a documentary of a unique person and place that could inspire people to want to do governance better—and maybe give some tips on how to do that.

Washington is somebody who was not only brought up in bare-knuckle, Democratic Party politics, but also in the social movements. In the 1940s he went to Roosevelt College, which was a rare integrated institution of its day that admitted Blacks, Jews, and women. He was surrounded by really smart people who were doing things like lunch counter protests very early, 25 years before you were seeing the events that we celebrate from the 1960s.

In terms of bringing social movements into governance, what are the mechanisms of accountability or inclusion that make grassroots groups part of a governing project?

David Orr, who was a close ally of Washington’s, told us an interesting story we didn’t end up having room for in the film. He said that Harold had a meeting with him shortly before his death, where he was talking about his reelection, having secured his position and working majority on the council. He finally had the ability to enact the programs that the two of them and many others have been fighting for. And then Harold turned to Orr, who was much younger than him, and said, “You know, I need people to be on the outside pushing this. Change is hard. And I want to see protests out there.”

This meeting was never documented. But certainly Washington was somebody who was aware of the tension between grassroots advocacy and insider governance. There were staff people who were brought into his administration that came from activism, instead of conventional politics. And there were lots of others who stayed on the outside and kept pushing. Had Harold been around longer, that tension would have always been there. But he embraced it. He understood the usefulness of having both of those forces pushing for change.

Harold Washington’s story is pretty well known. In making your film, did you feel like there was an aspect that hadn’t been told already?

There have been a lot of films about political campaigns. They make for good stories because there’s a natural beginning, middle, and an end. There’s a winner and a loser. But we had always wanted to dig deeper into governance, which is less sexy and much harder to project. To me, a lot of the stories about inspirational candidates fall short, especially for the left. Really, the election is only the beginning. There’s so much that has to happen after that. I wanted to present a documentary of a unique person and place that could inspire people to want to do governance better—and maybe give some tips on how to do that.

Because he died unexpectedly, and relatively young, there’s a huge sense of lost potential that surrounds Harold Washington. And there is the idea that by the start of his second term he had finally subdued his opposition and got the position where he could start really accomplishing things. Of course, all of that was cut short.

There’s a tendency to say that Harold’s accomplishments were completely vaporized when Daley took over. But when you look more closely at it, I think that’s not true. When Washington disassembled the political patronage machine, no one was able to put it back together in quite the same way. People had to govern differently. They were forced to be more inclusive and to distribute services equally to all areas of the city. I don’t think that would have happened without Harold.