South Side alderpersons who aren't coming back. Illustrations by Bridget Killian, Dionne Victoria, and Ariandy Luna

At least a third of City Council will be newly elected in this year’s municipal elections. Between retirements and resignations, at least sixteen incumbent alderpersons will leave office at the end of their current term—a shake-up at a scale Chicago has not seen since 2011, when thirteen new alderpersons joined the council. The number of departures could grow depending on the outcomes of the election, but as it stands, City Council stands to lose a collective 264 years of experience in public office. 

“We’re at a generational change in the City Council. A lot of City Council members are older and have been there twenty years, and [are] simply deciding to move on,” said University of Illinois professor emeritus and former alderman Dick Simpson.

Several council members have alluded to their deteriorating relationship with Mayor Lori Lightfoot as their reason for leaving. Last year, on the Reader’s “Ben Joravsky Show,” outgoing 10th Ward Alderwoman Susan Sadlowski Garza said, “I’m tired of being ignored. I’m tired of not getting phone calls returned. I’m tired of letting the inmates run the asylum.” 

A former Lightfoot ally, Sadlowski Garza criticized the Mayor’s office, saying, “I’ve never met anybody who has managed to piss off every single person they come in contact with—police, fire, teachers, aldermen, businesses, manufacturing, and that’s it.” 

Lightfoot brought an adversarial relationship with some City Council members on day one, and some of this animosity lingers today. In her 2019 inaugural speech, she condemned aldermanic privilege for breeding corruption, saying, “these practices have gone on for decades…stopping it isn’t just in the city’s interest. It’s in the City Council’s own interest,” while addressing the alderpersons who were there to be sworn in. Aldermanic privilege gives Chicago alderpersons the ability to veto projects and control development in their ward but it has also been subject to abuse. “[It] set the tone for what would be a very antagonistic oppositional relationship,” former Inspector General Joe Ferguson told the Weekly.

The Weekly reached out to outgoing Alderpersons Leslie Hairston (5th), Susan Sadlowski Garza (10th), Ed Burke (14th), Howard Brookins Jr. (21st), Roberto Maldonado (26th), Ariel E. Reboyras (30th), Carrie Austin (34th), Tom Tunney (44th), James Cappelman (46th), Harry Osterman (46th), Sophia King (4th), and Roderick Sawyer (6th). None responded in time for publication.

While Mayors Richard M. Daley and Rahm Emanuel had strong majorities backing their legislation for much of their terms in office, Mayor Lightfoot received the same level of support from only nineteen alderpersons. Lightfoot has adapted to inconsistent support in City Council by making compromises, modifying the languages of bills, and delaying votes to make time to raise support. Despite these measures, Lightfoot’s tenure overseeing City Council has been contentious.

“Some people are more diplomatic about it, and some are less, but I don’t think there is anyone out there who’s going to look you dead in the eye and tell you Lightfoot is an easy person to get along with,” said Geoffrey Cubbage, a policy analyst from the Better Government Association. “You didn’t see the kinds of public fights with [Rahm Emanuel] that you see under Lightfoot, and it’s to the point that it spills out on the council floor.”

After twenty years in office, 44th Ward Alderman Tunney announced last August that he wouldn’t run for reelection. Tunny had previously described Lightfoot’s leadership style as “somewhat divisive” in an interview with the Sun-Times. “Her background as a prosecutor has some influence on the way she operates her office… It’s more like, ‘I’ve got all the answers, and we’re going my way,’” Tunney said. “As a chief executive, she’s got to work more behind the scenes and be more collegial and respectful.”

“I think you’ve got to accept that at least some of that is personality,” Cubbage said. “Some of that is just how this mayor manages relationships compared to how our previous mayor’s managed relationships.”

Whether the relationship between the mayor and City Council has gotten more contentious or not is up for debate. But where previous mayors like Daley or Emanuel would garner more support than needed to pass legislation, Lightfoot often makes do with the twenty-six required to pass legislation and compromises where she can.

A University of Illinois at Chicago report co-authored by Simpson argues that City Council has become more independent under Lightfoot. From June 2019 to March 2022, Lightfoot faced 131 divided roll calls (any vote in City Council that is not unanimous). Lightfoot has been met with twice as many divided roll calls as her predecessors Rahm Emanuel and Richard M. Daley. She has faced more delays and compromises on the legislation she has tried to introduce.

“Chicago has had thirty-plus years of one-person rule—a boss mayor and a rubber-stamp City Council—and I don’t think it’s done the city a lot of good. I think having a City Council that takes a little responsibility for its own actions and tries to do a little actual legislating—[one that’s] willing to say no to the mayor—I think that’s going to be a healthy thing,” Cubbage said. “Folks who don’t necessarily feel they have to do what the mayor says to do a good job [can] be very good for the city.”

This wave of retirements leaves something for all nine Chicago mayoral contenders to consider. “Whoever is in the office of mayor needs to start to conduct themselves in a way that recognizes that our culture of governance involves [the] true collaboration of an independent legislature,” Ferguson said.

Chicago’s system of alderpersons acting as mini-mayors is unique compared to other American cities. It became the product of a city where segregation and immigrant enclaves created neighborhoods with localized cultural identities that all sought representation through the twentieth century. This hyper locality has its pros and cons. Chicagoans have greater local representation—alderpersons represent about 54,000 residents each, compared to 166,000 residents in New York and 264,000 in Los Angeles.

But it has also bred corruption and machine politics and created a system where alderpersons prioritize constituent services over lawmaking for the whole of the city—since constituent services are what they will be held accountable for on election days. “Older, longer-tenured alders tend to view themselves as there to be the touchstone for the delivery of services to their constituents in their ward. They don’t think they’re there to legislate,” Ferguson said.

It can be challenging for alderpersons to divide their attention between lawmaking in City Council and attending to their wards, especially with an office that can only be staffed by three additional employees, as allotted by the City’s budget. Former two-term 47th Ward Alderman Ameya Pawar recently commented that his office could not manage both legislating and the constituent concerns that came to his office without relying heavily on volunteer labor. “Talk to every single one of my former colleagues, and they’ll say that their office was either always underwater or on the verge of being underwater,” Pawar said to Crain’s Chicago. “It’s akin to playing Whac-A-Mole.”

When alderpersons already struggle with ward politics, serving as a City Council legislator can be a tall order. “They certainly don’t have enough staff to be legislators, to actually develop legislative proposals, so they need to rely upon the kindness of strangers to do work,” Ferguson said. “That expertise doesn’t exist, so the aldermen themselves have to generate it individually, and they only have a staff of three…constituent services eat that up almost entirely.”

“Before [Lightfoot], you had a rubber-stamp City Council site for Richard M. Daley and Rahm Emanuel, the most rubber-stamp Councils in Chicago history, and this council under Lightfoot has four different voting blocs,” Simpson said. During Lightfoot’s time in power, UIC researchers identified four significant voting blocs separate from City Council’s official caucuses that emerged—Moderate-Liberal, Progressive-Socialist, Conservative, and Chicago Machine. While Lightfoot receives the most support from the Moderate-Liberal bloc, most of whom serve as committee chairs, she finds the least from the Conservative and Machine blocs. “The aldermen are offering more legislation. The Progressive Caucus, in particular, has been active in proposing legislation that’s citywide and important in the ward,” said Simpson. “The question is: which way will it go?”

More recently-elected alderpersons also tend to be more progressive and active in City Council—missing fewer council meetings than their longer-sitting counterparts. “On one hand, you’re losing a lot of institutional knowledge and understanding of how things work. On the other hand, the habits that these alders had were not good habits,” Cubbage said. “I think we’re going to see a lot more active legislating. I think you’re going to see a lot of alders who are using [the] parliamentary process and are trying to have debates on the floor.”

New blood, new directions

Losing an experienced alderperson impacts residents less as the city has gradually rolled out a more democratized system for service requests and departments. When new alderpersons come to public office, they tend to rely more on standardized service models instead of being the point of contact for all city services. 

“The newer alders are trying to get away from that—both because they don’t have the kind of clout and relationships to do it the old-school way,” Cubbage said. “There are some reform-minded folks who’ve been elected in the last few cycles, who genuinely see it as better for the city if individual residents can get in touch with service departments and get services provided that way, rather than needing your alderman to go to bat for you.”

In the old-school vision of Chicago politics, losing long-time alderpersons meant losing years of institutional knowledge needed to keep up with constituent concerns and maintain the relationships between individual city departments. Oswaldo Gomez, a representative of Chicago’s first civilian oversight board, points towards the expansion of Chicago’s 311 system, a call center intended to respond to constituent concerns in a quick and more standardized manner, as a reason for why some alderpersons chose to call it quits this election cycle.

“I think a lot of aldermen were just not happy to see that the job became more stressful when it came down to legislating, and because of the expansion of 311 and City services being centralized away from them,” Gomez said. “They were used to providing garbage cans, getting people into City jobs—[they] don’t really do that, which was maybe rewarding for [them]. It’s not so fun and easy to pass or vote on legislation, and you actually have to be doing it and fighting for it.”

Historically, Chicago’s aldermanic system has been plagued by political patronage and corruption. Since 1973, Chicago has seen thirty-seven alderpersons convicted under federal charges, with more indicted over the years. 

After fifty-four years in office, 14th Ward Alderman Edward Burke, the longest-serving councilor in City Hall, quietly chose not to seek reelection. Burke faces a looming corruption trial set for this November. Also, under federal indictment, 34th Ward Alderwoman Carrie Austin (34th) announced her intention to retire after twenty-nine years amidst worsening health issues and charges of bribery and lying to FBI agents. Last year, former 11th Ward Alderman Patrick Daley Thompson, a member of the Daley political dynasty, was forced to resign after being convicted of lying to regulators and filing false tax returns.

“Having a significant turnover is actually an opportunity for the City Council itself from within, to decide to be something different and to conduct itself as something different that I think is better for the interests of the city as a whole,” Ferguson said. “That takes us one step further from our deep roots in a political patronage culture operating within a city whose governance structure really hasn’t changed since the nineteenth century.”

All sixteen departing alderpersons are leaving with at least seven years of experience in their roles. Many retiring alderpersons commented on experiencing a great resignation of their own—a burnout spurred on by the exhaustion of COVID-19 and navigating the logistics of virtual meetings and digital voting. “Some of these folks have been in office for twenty-five, thirty years, and they weren’t spring chickens when they got in the technology shift…you had to adapt to new ways of doing things a lot faster,” Cubbage said.

Others have chosen to run for other offices or exit public service for the private sector. Alderpersons Sophia King and Roderick Sawyer are current candidates in the February mayoral race, leaving their seats open to new challengers in the 4th and 6th wards respectively. Former 12th Ward Alderman George Cardenas resigned last November after an unopposed election to the Cook County Board of Review, while former 24th Ward Alderman Michael Scott Jr. left office last June to work at Cinescape, a film studio in Chicago. 

However, many incumbents simply left office with a sense of exhaustion and hope to pass things on to the next generation. “The COVID times were particularly hard for all because it’s hard to deliver services and keep track of things run and learn Zoom,” Simpson said. “It was more difficult than the normal City Council times.”

Many stayed relatively quiet in their departure announcements—hoping to spend more time with friends and family or to simply hand over the reigns to the next generation. “I just thought it was a good time to let a younger person take over with bright ideas,” Alderman Ariel Reboyras (30th) said to the Chicago Sun-Times. In an email to his constituents, Alderman Harry Osterman (48th) said, “I am proud to have done my part to serve our community and move it forward. Now is the time for others to step forward and take on the responsibility to lead our community.”

Losing some of the city’s longest-sitting alderpersons does mean losing institutional knowledge and experience. But this wave of aldermanic retirements could also mean a generational and cultural shift for the council as more choose to become active legislators. 

“Because now there [are] more ‘nay’ votes [and] there are more people that are willing to be dissenters against the mayor, some aldermen have felt lost. They don’t really know what working with a new generation of aldermen is like because I think a lot of aldermen were used to a political culture of ‘we treat each other nicely. We all stick in our lane [and] make sure we get resources to our ward,’” Gomez said of the changing attitudes. 

“Now, there are very serious fights in City Council. I think a lot of aldermen were just not happy to see that the job became more stressful when it came down to legislating,” he added.

Over the years, community organizations have also gotten more involved in electoral politics, which has changed the dynamic with alderpersons needing their support.

“What’s changed in Chicago, in what is going to continue to be an incentive for community members, is this idea of, ‘I helped get you elected. And instead of wanting a garbage can from you, I want policy,’” Gomez said. “‘I want you to pass legislation that’s in my interest…and not only that, but I’m going to be watching you all the time. Whenever you want to pass legislation, I’ll be there with you, but if you don’t, we’re going to be calling you up, and we’re going to be pushing you when elections come around.’”

As older alderpersons step away from public office, they leave spaces for younger, often more progressive, alderpersons to take office. In 2019, five new alderpersons from activist and community organizing backgrounds were elected with the support of the Chicago Democratic Socialists of America, joining Alderman Carlos Ramirez-Rosa (35th) in City Council. Socialist newcomers, such as Alderpersons Jeanette Taylor (20th), Byron Sigcho Lopez (25th), and Rossana Rodriguez Sánchez (33rd), came from activist and community organizing backgrounds.

In the larger Progressive Caucus, alderpersons Andre Vasquez (40th), Felix Cardona Jr. (31st), Matt Martin (47th), Maria Hadden (49th), Michael Rodriguez (22nd), and Stephanie Coleman (16th) entered City Council in 2019 and became members of the larger Progressive Caucus, along with their socialist counterparts. 

Socialist and progressive City Council members have collectively pushed the Mayor and City Council to take stronger positions on funding social services, police reform, and economic justice.

“Things have become much more politicized in recent years, and that’s in large part because of the organizing happening over the last decade, not only in terms of electing folks but in terms of lots of other progressive organizing that has been happening outside of City Council,” Chicago Democratic Socialists of America organizer Sean Estelle said. “Now, we see champions—socialists and progressives, and more—that are actually trying to articulate a vision of politics and what the aldermanic office can do.” 

Chicago DSA has endorsed ten aldermanic candidates this election cycle—five of whom are running to represent their wards for the first time. While these newcomer candidates began campaigning before their incumbent chose to retire, these vacancies created new opportunities for them to come to the forefront.

New alderpersons coming in and older alderpersons calling it quits could be a sign that the remnants of Chicago’s political machine are losing their hold on the city. 

But cultural changes may not be enough without structural changes to City Council’s operations. Some of those reforms, such as naming committee chairs without the mayor’s blessing, are in the power of the City Council itself. But according to Ferguson, many others require charter reform.

Unlike other major cities, Chicago lacks a charter, which functions like a constitution for the city and can create external accountability when the city government violates its own code. Each of the other twenty-four largest cities in the United States has charters and periodically reviews them. Instead, Chicago leaves many governance issues up to council tradition or discretion, making it difficult to challenge those in power when they do not do what is in the city’s best interest. According to Ferguson, many structural improvements that could improve City Council require charter reform.

“That has resulted in a system of governance that is largely been driven by transactional power politics, that in the absence of this sort of guiding constitution, largely has been inhabited historically by the political machines that have sort of filled that void,” Ferguson said. “The customary culture and practice of the City Council is acquiescence to the mayor, who’s the head of the political machinery, and as a result, we don’t have checks and balances. We don’t have standards. We don’t have hearings in our city council. The city council actually has the authority to name its own committee chairs, to decide which committees it has to decide, when the committees meet on what subjects, [and] when they’re going to vote on things. Right now, that’s all controlled by the mayor.”

“City Council doesn’t have subpoena power to require officials to come in…There is nothing that obligates the executive branch, all the functions controlled by the mayor, to provide information and cooperation to the city council, which is why a lot of things get passed without the City Council ever seeing all of the underlying information or being able to do the analysis themselves,” Ferguson added.

An influx of new alderpersons who see the City Council as independent can serve as a greater legislative check on the mayor’s office, but it may not be enough to tip the balance. There could be significant changes in how City Council operates. Still, depending on how the ward elections turn out, we may not see these outcomes until Chicago’s next aldermanic elections in 2027.

The 2023 aldermanic elections have brought some of the youngest candidates to the races. 10th ward candidate Óscar Sánchez is campaigning to bring a co-governance approach to the alderman’s office. 12th ward candidate Julia Ramirez and 26th ward candidate Jessie Fuentes hope to expand violence prevention and social programs. In the 22nd ward, twenty-five-year-old Kristian Armendariz is running for the first time. Community organizer Warren Williams has run a platform in the 30th ward prioritizing mental health care, accessible transit, and community building.

“If there are twenty people who want a different council and a different form of relationship with the mayor, that still means there’s still a lot of traditionalists, and that means we probably have a period of chaos ahead of us as they sort themselves out within the body itself—a different form of council wars,” Ferguson said. “There are a lot of different directions this can go, but it’s a moment ripe with potential.”

The Council Wars under Mayor Harold Washington saw Chicago’s mostly white political machine unite against their reform-minded, first Black mayor—twenty-nine alderpersons led by Alderman Edward Burke and former Alderman Edward Vrdolyak voted down all legislation Washington tried to push forward.

Compared to the Daleys, the Council Wars were when City Council was most independent from the mayor. Still, the power struggle stalled legislation until 1986, when a court ordered the city to redraw its map to reflect its racial demographics better. Once Mayor Washington finally had the twenty-five supporters needed to break a tie, the stalemates ended. “There’s a lot of different directions this can go, but it’s a moment ripe with potential,” Ferguson said.

We have yet to see what impacts this exodus might have on the future of Chicago politics. But over the course of Lightfoot’s term, Chicagoans have seen City Council become more independent from the mayor. There is an opportunity to reset how things operate for the new candidates running in the thirteen wards without an incumbent. For the three appointed by Lightfoot last year when their predecessor retired, their seats are vulnerable. An influx of new alderpersons may bring new ways of pushing forward legislation and changing the culture of the City Council—to become genuine legislators that Chicagoans want them to be.

“They could really change the balance of power in the halls of government for Chicago. You’re talking about a decade, almost a century, of the mayor having the first and most important decision-making. All of a sudden, there’s a lot of legislators that don’t want [that],” Gomez said. “I think that separation is going to continue to happen.”

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Reema Saleh is a journalist and graduate student at the University of Chicago studying public policy. She last interviewed author Ling Ma on her short story collection Bliss Montage.

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