How Michael Madigan’s departure accelerates a shift in Chicago politics from old-school machine to new-era progressives

Long before he became a congressman, federal judge or presidential adviser, a young Abner Mikva walked into the 8th Ward committeeman’s storefront office to volunteer for the 1948 election.

When Mikva had no political connections to speak of, the ward heeler responded with a now-infamous line that sums up the clout and cronyism of the city’s vaunted Democratic machine: “We don’t want nobody nobody sent.”

A look around the Chicago political landscape these days, however, shows the nobodies are faring quite well.

The last two Cook County Democratic Party bosses suffered embarrassing losses to political newcomers for county assessor and mayor. A congressional seat held for decades by a powerful establishment family now belongs to a progressive outsider. Several longtime white machine politicians have been defeated by first-time candidates of color.

And most notable of all: Illinois’ most powerful politician lost his decadeslong grip on the Capitol and state party, felled by a bribery investigation and sexual harassment scandal that led 19 House Democrats, many of them new to politics, to push him out.

The change is being driven by generational, ideological and demographic shifts, with federal law enforcement and organized labor providing major assists. The result is a move away from iron-fist bossism toward a more diffuse leadership structure that’s more diverse and practices an increasingly progressive style of politics centered on economic and racial equity.

Michael Madigan’s departure as party boss and House speaker is expected to accelerate that change, say more than two dozen Chicago elected officials and political operatives the Tribune interviewed. More independent candidates may be emboldened to run for office, leading to a more freewheeling legislature and City Council, and, perhaps, state party. In just the last two months, Illinois Democratic leadership already is more diverse — Emanuel “Chris” Welch is the first Black House speaker, and new state party chair, U.S. Rep. Robin Kelly, is the first African American and woman to hold the post.

But there’s decidedly less optimism among those interviewed about an impending end to political corruption in a city where patronage and graft undergo reinvention to stay ahead of the law, the greased palm remains a time-honored tradition and public corruption scandals get names like children.

“The machine isn’t just about certain personalities. It’s about a culture and really a way of life inside of city government and the relationship between the government and ordinary citizens and how they get their services,” said Mayor Lori Lightfoot, who in 2019 became the first Black woman and openly gay person elected Chicago mayor after running a campaign against public corruption. “A list of machine people is fading from the scene, but the culture they built is definitely not dead. In many ways, it’s still as virulent as ever.”

Major reforms around campaign finance, lobbying and transparency need to happen for Chicago’s politics to truly transform, said county Assessor Fritz Kaegi. Modest changes on the margins, he warned, could result in the machine simply giving way to a scattering of smaller fiefdoms still susceptible to corruption.

“The public has realized that Chicago’s old patronage model in all of its different manifestations was not working,” said Kaegi, a progressive who in 2018 ousted assessor and then-county Democratic Chairman Joe Berrios, an old-school patronage chief who oversaw an error-riddled and inequitable property tax assessment system. “No one in the public wants a boss overseeing a black box, and the answer is a more transparent government with a more level playing field.”

Critics of Chicago’s rising progressive reform movement contend it represents a new form of strongman politics, led by unions. Former Northwest Side Ald. Richard Mell said some progressive City Council members “can’t go against anything the teachers union wants.”

“Back in the day, I had my own organization, and that helped make me a more independent alderman,” said Mell, who represented the 33rd Ward for 38 years. “If a union tried to tell me what to do, I could tell them to get out of here, because I knew I could speak up for my residents and then my organization would get me the votes. That’s not really the case anymore.”

U.S. Rep. Jesus “Chuy” Garcia said those who wax poetic about the good old days when the precinct captains took care of everyone on the block aren’t mentioning the hundreds of thousands of Chicagoans who were ignored under that system.

“It (worked) if you were in a ward where you had the access and clout to the city services and all the jobs, but that philosophy completely ignores the racism within the party,” said Garcia, a first-generation Mexican American immigrant whose political profile skyrocketed after pushing then-Mayor Rahm Emanuel into a surprise 2015 runoff election. “It was good for those who were on the inside, but it left out people of color and women in a really bad way.”

The ‘machine tag’

The growing transformation of Chicago’s politics is illustrated by the dozens of new faces who have won office over the last decade.

More than two-thirds of Chicago’s 34 state House seats have turned over, as have nearly three-fourths of the city’s 18 state Senate seats.

It’s a similar story over at the City Council, where 35 of the 50 wards — 70% — have elected a new alderman since 2011.

Beyond the raw data, City Hall underwent a historic demographic shift after the 2019 election. For its entire history, the City Council had more white aldermen than any other race or ethnicity. A decade ago, there were 23 white aldermen, 19 Black aldermen and eight Latino members.

That’s no longer the case after the 2019 election, thanks largely to a surge in successful Latino candidates. The City Council now has 20 Black aldermen, 18 white aldermen and 12 Latino aldermen.

The chamber has become more diverse in other ways. In 2011, there was just one LGBTQ alderman and no democratic socialists. Now, there are six of each.

The 2019 city election helped drive the change when it became a referendum on Chicago’s traditional ward organization politics. A number of reformers ran pledging their independence amid a City Hall federal corruption probe.

Months before the election, federal agents raided the offices of Southwest Side political institution Ald. Edward Burke, a longtime Madigan ally, who was indicted on bribery and racketeering charges. Lightfoot immediately seized on the issue while many other top contenders with ties to Burke largely stayed quiet.

Lightfoot swept all 50 wards in a landslide runoff rout against Toni Preckwinkle, the Democratic county chair and County Board president. The Tribune reported that Preckwinkle was the intended recipient of a $10,000 contribution that federal investigators alleged Burke sought as part of an extortion scheme.

“I have no doubt whatsoever the circumstances of Burke and what happened absolutely propelled me forward,” said Lightfoot, who surged in the polls after the indictment. “That gave a jolt of life to my campaign.”

The Burke controversy played out in ward contests too.

Ald. Patrick O’Connor, already was in a tough reelection fight in the North Side 40th Ward, trying to win a 10th term after serving the previous eight years as the unpopular Emanuel’s City Council floor leader. O’Connor said four young progressive challengers painted him as part of the same old-school political problem as Burke.

“‘Machine’ is an idea people can use as a cudgel against an old white guy like me,” said O’Connor, who replaced Burke as chairman of the powerful Finance Committee. “I was down at City Hall trying to clean up the Burke mess ... and I was getting slammed up in the ward by opponents who had the time to walk the neighborhoods putting this machine tag on me.”

Andre Vasquez, who unseated O’Connor, said the machine mutated over time from taking on Republicans to securing “power in the hands of certain people and (keeping) it from others.” There was a racial component to that dynamic, said Vasquez, a one-time rapper who apologized during the campaign after O’Connor slammed him for homophobic and misogynistic lyrics.

“It was more passive-aggressive or implied,” said Vasquez, a democratic socialist. “I don’t want to denigrate the concerns people had about some of the things I said — but there were some things that were about the unpolished guy, the person of color, and whether I should be able to represent the so-called right people. That was insidious.”

The realignment away from white machine to young progressives of color played out in the 33rd Ward too.

The Northwest Side ward had become majority Latino years earlier, but charismatic white throwback Mell still lorded over one of the city’s most committed precinct organizations and unabashedly championed the machine practice of political patronage before stepping down midterm in 2013.

When Mell retired, Emanuel promptly named his daughter, then-state Rep. Deb Mell, to succeed him in a classic Chicago handoff. She fended off nepotism charges to win in 2015, but lost in 2019 to Rossana Rodriguez Sanchez, who called it the end of “44 years of a dynasty, one that was only working on behalf of people who were connected.”

Rodriguez Sanchez said she talked about affordable housing, the Chicago Police Department’s mistreatment of Black and Latino residents and fairness in the way city services are handled.

“There’s a better way to deal with tree trimming and streetlights that are out, a way that doesn’t count on who somebody knows,” Rodriguez Sanchez said. “People appreciate that.”

The upset wins by Vasquez and Rodriguez Sanchez followed a 2011 stunner in the 47th Ward. Veteran machine Ald. Eugene Schulter retired and joined ward resident Emanuel in backing a longtime precinct captain for the open seat, which was won by Ameya Pawar.

The then-30-year-old son of Indian immigrants walked the ward, stressing the need for an alderman to act like a legislator on citywide issues rather than just using ward-level services as political currency.

“I had to deal with questions from people, ‘Where is he really from, what are your roots,’ and some of that was clearly rooted in xenophobia and racism,” Pawar recalled of that first campaign. “But we obviously overcame that.”

Black aldermen win white wards

The waning of the Democratic establishment and a leftward ideological shift also has helped Black candidates emerge in new political terrain.

On the North Side, there are now two majority white wards represented by a Black alderman.

Under the traditional party slating system that dominated ward politics for decades, Black candidates like Matt Martin and Maria Hadden stood little chance of getting selected by political leaders in predominantly white North Side wards, and if they ran as outsiders they would have slim prospects of winning. Not anymore.

“Having two Black aldermen win white wards, that’s a real encouragement,” said Ald. Roderick Sawyer, 6th, the son of the city’s second Black mayor, Eugene Sawyer. “With the segregation we’ve had in this city, if you would have told somebody that would happen 20 or 30 years ago, they’d look at you like you were crazy.”

Martin ran as a progressive in the 47th Ward, besting eight other candidates, including top Emanuel staffer Michael Negron. Hadden easily defeated 18-year veteran and Emanuel ally Joe Moore in the Far North Side’s 49th Ward.

A member of the council’s progressive, Black and LGBTQ caucuses, Hadden pledged independence during the campaign. In an interview, she described herself as “someone who’s a somewhat reluctant member of the Democratic Party.”

There was a racial element to Moore’s campaign, Hadden said, with a charter school organization that backed his candidacy putting out literature “that painted me as a Black, dangerous, anti-police candidate.” Hadden said she won because her story and policy ideas were more in step with residents of the diverse ward, which has a history of progressive politics.

“I think any system of control becomes less effective when it’s not serving people. Who does this serve and benefit?” Hadden said of political bosses’ control over the city’s politics. “And we’ve also seen a generational shift, with people our own ages supporting us, and that’s natural. We arguably haven’t seen as much of that as we should have in a country as young as ours, but it’s happening.”

Sawyer, 57, said he’s noticed a trend among young Black lawmakers. “They’re more progressive, more independent, and they buck the party politics in a way that would have been considered inappropriate a few years ago,” he said.

Still, the third-term alderman said Chicago’s Black political leaders have a tendency to hold onto their seats for too long and have done little to “build a bench” of newcomers for fear they could lose to them.

That’s led to a bunch of pent-up political ambition, but change is inevitable in the coming years. Outgoing Secretary of State Jesse White, 86, has held the office for 22 years; West Side U.S. Rep. Danny Davis, 79, has served in Congress for 24 years and was on the County Board and City Council before that; and South Side U.S. Rep. Bobby Rush, 74, has been in office for 28 years. Of the 15 City Council seats that have not turned over since 2010, more than half are held by veteran Black aldermen.

Lt. Gov. Juliana Stratton, Attorney General Kwame Raoul and Cook County State’s Attorney Kim Foxx represent the next generation of Black officeholders to rise through the party establishment to major offices. There also have been signs of new Black politicians making gains by running further to the left.

In the 5th Ward, which includes parts of Hyde Park and South Shore, activist William Calloway came up 176 votes shy of defeating longtime incumbent Ald. Leslie Hairston in 2019. And when a federal wire fraud indictment led 20th Ward Ald. Willie Cochran not to seek reelection representing Woodlawn and a portion of Englewood, democratic socialist and teachers union member Jeanette Taylor defeated eight other candidates.

“I didn’t come from the Democratic Party, I came from these people in these neighborhoods, who supported me,” Taylor said. “It’s my job to listen to them and stick up for them.”

She has been focused on protecting renters and longtime homeowners from gentrification driven by the Obama Presidential Center set to be built in nearby Jackson Park. Along with others in the new progressive wave of first-term aldermen, Taylor sees her role as extending beyond the typical ward caretaker duties of the old political structure.

“Some of my colleagues want to have tough conversations and fight for healthiness in the entire city, not just boost themselves up in their little area,” she said. “That’s what we need to do if we’re going to improve things for people all over Chicago.”

Growing Latino influence

On the Southwest Side, the machine’s decline, a surging Latino population and the rise of progressives are driving change.

As Madigan rose to power in the 13th Ward, close friend William Lipinski built a dominant ward organization in the neighboring 23rd, serving as alderman and congressman for 29 years before handing off the seat to his son, Dan, who served an additional 16 years in the House.

Progressive Marie Newman put an end to the family’s reign by focusing heavily on the younger Lipinski’s stature as a conservative congressional Democrat who opposed abortion and same-sex marriage. Drawing national attention, she outspent him 3-1.

“You have millions of dollars coming in from various sources around the country that’s not connected locally whatsoever,” Dan Lipinski complained in an interview. “That’s some kind of machine too.”

Newman made Madigan an issue, calling on the speaker to resign, while Lipinski did not. In an interview, Newman said Madigan stepping down was important to “prove that we are in a new day, that we are all moving forward.”

Madigan’s 13th Ward, the Lipinskis’ ancestral 23rd Ward and Ald. Burke’s 14th Ward encircle Midway Airport. The wards, once home to an array of white ethnic voters, are majority Latino today.

Capitalizing on newfound popularity after his mayoral run, Rep. Garcia looked to expand his influence in those wards. He successfully put up young high school counselor Aaron Ortiz to knock Burke’s brother, Dan Burke, from his state House seat in 2018.

The following year, Edward Burke defeated a Garcia ally to hold on to his council seat. But last year, Ortiz defeated Burke for 14th Ward Democratic committeeman, a position Burke held for 52 years. Ortiz, 29, said he has focused heavily on outreach to Latino stretches of the ward he said had been neglected for decades.

Ortiz was not among the 19 House Democrats who called for Madigan to step down, but nonetheless he said the departure allows the party to “begin recognizing that our politics is a lot more than just one old, white man.”

The Southwest Side’s Latino growth largely has been driven by Mexican American immigrants. Garcia said because of citizenship issues, it’s taken a longer time to turn that population growth into power. From his political base in Little Village’s 22nd Ward, Garcia has backed County Board and state legislative candidates in the area but has had more mixed results endorsing candidates across the city.

“We’ve had less voting power than the Puerto Rican community, for example, because they are all citizens,” Garcia said. “So, the fight has been longer and slower, but the fact that we’ve been able to elect progressives on the Southwest Side shows the politics are changing.”

The Puerto Rican power structure concentrated on the Northwest Side is more in flux. Berrios, the former assessor and county party chair, is out. Longtime state Rep. Luis Arroyo resigned last year amid a federal bribery charge. And retired U.S. Rep. Luis Gutierrez unsuccessfully backed his daughter for alderman.

A likely player is recently elected county Circuit Court Clerk Iris Martinez, a former state senator who also is now the top Democrat in the 33rd Ward that Richard Mell once controlled. Martinez joined other women in the state House and Senate in criticizing Madigan’s leadership.

“Nobody disagrees, nobody dares speak up. You come into the meeting, it’s pre-scripted and there you go,” Martinez said of the state Democratic Party under Madigan. “Those days should be over.”

The desire for a far more progressive agenda has helped a political transformation on the Northwest Side, where three democratic socialists have won seats.

Independent Vermont U.S. Sen. Bernie Sanders’ first presidential campaign, the fight for a $15 minimum wage and national movements pressing for racial and economic justice have helped reframe political priorities within the party and inspire a younger generation of activists to seek office. The tenure of Emanuel, dubbed “Mayor 1%,” helped galvanize that political energy in Chicago, as protesters took to the streets by the thousands in the wake of the historic 2012 teachers strike, the 2013 closing of 50 schools and the 2015 release of the graphic video showing Laquan McDonald killed by police.

The city’s two most progressive unions, the Chicago Teachers Union and Service Employees International Union, have been at the forefront of harnessing that grassroots activism into political power, helping fund young progressive candidates eager to take down incumbents and push the city’s political discourse.

Among them is 35th Ward Ald. Carlos Ramirez-Rosa, the council’s first democratic socialist, elected in 2015.

Even before Sanders’ campaign and Emanuel’s election, Ramirez-Rosa said a progressive movement started percolating during Mayor Richard M. Daley’s tenure, as middle-class life became more difficult to attain at a time when corporate interests wielded increasing influence at City Hall.

“When I ran for alderman the first time, I was going door to door talking to folks about taking on corporations, a $15 living wage, health care and well-funded public schools,” he said. “I was hearing from people who were graduating from college and realizing they would never be able to pay off their student loans or buy a house, from working-class families who absolutely didn’t think City Hall was acting in their best interests, and that anger was already there.”

Chicago, ready to reform?

Madigan’s power over the state party and House began to slip when sexual harassment allegations within his operation led him to publicly part ways with veteran political operatives and his longtime chief of staff. Then came the emergence of a federal probe that has implicated Madigan in a jobs-for-legislation bribery scheme with Commonwealth Edison. Madigan has not been charged and has denied wrongdoing.

The scandals, paired with defeat of some Democrats and Gov. J.B. Pritzker’s graduated income tax proposal last fall, left the governor and U.S. Sens. Dick Durbin and Tammy Duckworth calling for Madigan to step aside as party chairman. Then 19 House Democrats, all of them taking office since 2010, refused to give him the votes needed to remain as speaker.

Some self-styled progressives were more cautious about speaking ill of the speaker while he was still politically alive.

For all her talk of the need to dismantle the machine, Lightfoot never called for Madigan to step down as either speaker or party chair. In an interview, the mayor explained that she lives “in a world where Springfield matters.”

Pressed on the issue, Lightfoot brought up a west suburban House campaign last fall. A Madigan-backed Democratic challenger circulated flyers against a Republican lawmaker, claiming he supported using tax dollars to bail out Chicago Public Schools. The ads, copies of which a Lightfoot spokeswoman provided, featured an image of a smiling Lightfoot with her hand held out amid a flurry of money aboard a train and a bus.

“This is a guy who ran racist literature against me — against me, a Democrat … and put my face on something that I had nothing to do with,” Lightfoot said of Madigan, noting the mail piece went out in an overwhelmingly white district. “That’s racist to the core. And they thought that was OK in 2020.”

Lightfoot’s comments came after Madigan stepped down as speaker, but before he resigned his House seat and stepped away as party leader. Madigan, who has declined interview requests, called the mayor last year to express his regrets about the flyer, aides for both confirmed.

“Speaker Madigan acknowledged the mail piece and apologized at the time,” Madigan spokeswoman Eileen Boyce said. “For decades, Speaker Madigan prioritized increasing diversity in the Illinois House and in elected offices across the state, fought for representation in redistricting and is an outspoken supporter and ally of the Black Caucus and its critical initiatives, including criminal justice reforms.”

Rep. Garcia, too, has spent his political career railing against the machine but reached a detente with Madigan, endorsing the party leader and allies 13th Ward Ald. Marty Quinn and 23rd Ward Ald. Silvana Tabares. Madigan backed Garcia’s candidates for several open state legislative seats. Garcia called it a practical decision but insisted his hard work won him the growing influence that drove Madigan to deal with him.

“My organizing strategy for political engagement enhanced the ability for the traditional power brokers to recognize that the Latino community needed to be advanced, and that our winning of seats was inevitable,” Garcia said in an interview. “So, there was a constructive dialogue with the speaker in terms of what’s happened on the Southwest Side.”

Even with Madigan gone, the unions are likely to continue to hold deep influence over the party, and if campaign fundraising falters, billionaire Gov. Pritzker still has the resources to drive political loyalty.

Former Cook County Clerk David Orr said the real reform fight doesn’t stop with Madigan, but rests with “nuts-and-bolts” changes to lobbying, zoning, redistricting and campaign finance among other issues.

“The key will be the battle now between those who would like to say, ‘OK we’re done now because we got rid of Madigan’ and those who say, ‘No, that’s just the beginning, We’re not done at all unless we have other major reforms,’” said Orr, who founded the political action committee Good Government Illinois.

Lightfoot has been criticized by progressives for not governing like one. After winning with her reform mantra, “Bring in the Light,” she’s had mixed results on ethics overhauls.

The mayor drew pushback from aldermen when she attempted to water down an ordinance the council passed outlawing elected officials from serving as City Hall lobbyists.

On her first day in office, Lightfoot issued an executive order aimed at curtailing aldermanic privilege, the local power that council members held over city decisions in their wards such as approving driveway permits or business signage. Lightfoot, however, largely has been hampered in her plans to do away with aldermanic privilege on zoning, a difficult practice to police since there is an informal tradition of aldermen deferring to colleagues on building issues within each others’ wards.

Lightfoot said her administration is working on a new land use plan for the entire city that could further loosen the grip of aldermen over zoning decisions. But the mayor, who is up for reelection in 2023, said that process could take a couple of more years.

“There have been too few instances where you see aldermen self-regulating against the bad behavior of their colleagues and instead being deferential no matter what,” she said. “That is absolutely a vestige of the machine system. And there are still aldermen who are absolute bullies — they bully employees and bully their colleagues to assert themselves and their authority. It puts a shadow on the entire City Council.”

One factor that could speed up Chicago’s shift away from machine politics is the redrawing of the city’s ward maps and the state’s legislative and congressional districts following the 2020 census. The once-a-decade process has been closely controlled behind the scenes by Madigan at the state level and machine aldermen in the city, but it’s likely to spill more into public view this time, various elected officials agreed.

Chicago’s Black population has shrunk and its Latino numbers are increasing, though questions linger about how well a census run by former President Donald Trump’s administration will document that trend. Some long-protected ward boundaries also could be in for major change with fewer old machine bosses left.

Lightfoot is a longtime proponent of redistricting reform, to the point where she represented Republican-backed lawsuits on the issue as an attorney at Mayer Brown. As it stands now, the mayor said she did not intend to introduce her own fair map, instead preferring to partner with aldermen.

“I am not going to support an effort that is behind closed doors where people divvy up the spoils of the city, and I’m hopeful the majority of alderman understand we’re in a very different time and a very different place than 10 years ago,” Lightfoot said of the last ward redistricting. “You know, 10 years ago, I couldn’t have been elected mayor, right?”