On a recent Friday evening in December, Mueze Bawany, the sole challenger aiming to unseat 50th Ward incumbent Ald. Debra Silverstein, knocked on doors to tell voters what he was about.

Before Bawany could jump into his spiel, a woman at the door of a house on Lunt Avenue remarked she already knew who he was.

“It’ll just be nice to have new blood,” she told Bawany.

Bawany, a Chicago Public Schools teacher who immigrated with his family from Pakistan to the West Ridge neighborhood when he was 3 years old, is on leave to campaign full time against three-term incumbent Silverstein.

With endorsements from the Chicago Teachers Union, United Working Families and Chicago Democratic Socialists of America, Bawany is part of a wave of progressive candidates hoping to boost ranks in the City Council, in order to have significant sway over policy in the new term.

But with the departure or retirement of 16 incumbent aldermen this term, progressives aren’t the only ones who see an opportunity to influence the political tilt of Chicago’s legislative body.

“It is not surprising to me one bit that socialists, pragmatic folks, FOP, CTU — or anyone else for that matter — is trying to make the most of a historic opportunity,” said incumbent Ald. Raymond Lopez, one of the council’s most conservative members who faces two challengers, including from a progressive candidate endorsed by UWF. “Anyone with an interest would be foolish not to engage and try to make a friend or two, or win a seat, or six, if they have the opportunity and means to do so.”

The battle between moderate liberals and progressives is a historic opportunity to usher in a re-envisioned, independent City Council, said Delmarie Cobb, a veteran Democratic political strategist.

“This has the potential to really change things, and maybe get us back on the right course in terms of the city having a comeback,” said Cobb, who describes herself as a progressive. “Because certainly, we cannot continue to go in the direction that we’re going in as a city and thrive when we’ve got communities throughout the city that are dying on the vine.”

Progressive movement

In 2019, five self-identified Democratic Socialists made history with their election to the City Council. They joined 35th Ward Ald. Carlos Ramirez-Rosa, who was elected in 2015 as the first-ever and then-lone member of the Democratic Socialists of America in council.

Since then, one of the political organizations behind those candidates — United Working Families — says it’s seen a number of successes in getting issues socialists care about passed.

For instance, the city started a program that sends mental health providers to respond to 911 calls, a cause championed by socialist caucus member Ald. Rossana Rodriguez Sanchez, 33rd Ward, though the program doesn’t go as far as Rodriguez Sanchez and others envision.

“2019 was a banner year in terms of the gains that were made,” said Emma Tai, executive director of UWF. “Even with a pretty small legislative minority, we were able to really advance some monumental changes and some monumental shifts in public perception about what is the responsibility of city government.”

But the power of progressive aldermen has been limited. Even when the two separate, but similarly minded, progressive and socialist caucuses have voted together, they still only have 18 members, eight short of what it takes to pass legislation on the council.

“We need the mayor’s seat, we need committee chairs, we need 26, we need all of it …because we’re trying to pass legislation and we’re trying to wield governing power,” Tai said, referring to the fact that the council’s committee chairmen are chosen by the mayor and control when legislation can come up for a vote.

Tai said her political organization anticipates spending $500,000 on up to 18 aldermanic races, in addition to the mayor’s race where they’re backing Cook County Commissioner Brandon Johnson.

One of those aldermanic candidates is Victoria “Vicko” Alvarez, who’s running against the two-term incumbent, Lopez, in the 15th Ward.

Alvarez stepped down as chief of staff to Ald. Rodriguez Sanchez to run. She’s part of a cohort of progressive Latina candidates running in wards that neighbor hers on the Southwest Side. That also includes Jeylú Gutiérrez, a progressive candidate running in the open seat of the 14th Ward to replace long-serving Ald. Ed Burke, who is under federal indictment and decided not to run again.

Alvarez says this is a potential moment to change how her community is represented, bringing the concerns of progressives in her neighborhood front and center.

“All three of our wards have also been run by very conservative men,” Alvarez said. “Men who often have been able to put on a good facade of being quote unquote, good aldermen, when in reality, they’ve provided our neighbors the bare minimum of what a ward office can do.”

In the 50th Ward, Bawany is challenging Silverstein, who has represented the ward since 2011 when she defeated 38-year incumbent Bernard Stone and was herself part of a wave of 18 new faces to the council that year.

While she sees similarities to that era, “12 years ago we were fighting against a Chicago Machine that seems to have been largely forgotten by this newest generation of potential Aldermen,” Silverstein said in a statement.

“The new generation is focused on grandiose policy decisions when in reality most Chicagoans want their Alderman to focus on public safety and city services,” Silverstein said.

Silverstein, who has earned endorsements from labor unions like the Chicago Federation of Labor, said her experience is an asset. The two differ on how they would approach issues such as crime, with Silverstein pointing to more police as Bawany touts holistic approaches to address violence’s root causes.

Bawany sees the high number of vacancies on the council as evidence that the “tide is changing, that people in the city also want progressive policies.” A cornerstone of his campaign for alderman is giving residents more say in how the ward is run.

“We see this seat as a seat of service,” Bawany said, “and not a seat to wield power.”

Pragmatic PAC

A lesser-known, newly formed political group, dubbed the Get Stuff Done PAC, is trying to push the needle in what appears to be a more conservative direction.

Formed “to elect pragmatic candidates to the Chicago City Council” the group is led by former campaign adviser to Mayor Rahm Emanuel, Michael Reummler, who did not return requests for an interview on the PAC’s legislative priorities.

Late last year, he told the Chicago Sun-Times the PAC is meant to attract “people who are interested in coming to the City Council to be part of the solution and not lob bombs from the sideline.”

The PAC has raised a substantial $488,500 in one month since it officially formed. Donations in the tens of thousands have flowed from the Illinois Restaurant Association, Lettuce Entertain You and CEOs of investment firms, including a $250,000 donation from Michael Sacks, CEO at Grosvenor Capital Management.

Sacks declined to be interviewed for the story.

The PAC has not yet reported which candidates will benefit from that cash to the Illinois State Board of Elections, so it’s unclear which incumbents or challengers they’ll support in the election.

But 34th Ward candidate Bill Conway, a former prosecutor in the Cook County State’s Attorney’s Office and Navy veteran, is hoping his candidacy could get a boost from the PAC. Conway, whom Sacks has also donated to, said he filled out a candidate questionnaire seeking the PAC’s support, but hasn’t yet heard back.

In an interview, Conway emphasized he’s applied for a wide range of support and that he’s going to work collaboratively across the ideological spectrum if elected.

“It’s my understanding that they’re trying to elect candidates that are willing to get stuff done. And I don’t know if they will back me or not,” Conway said, adding his main priorities will be improving public safety, in part by addressing the root causes of violence, and revitalizing the city’s downtown business corridor.

The 34th Ward was redrawn in 2021, moving boundaries from the Far South Side to a puzzle piece that encapsulates pieces of the Loop, Greektown and near Fulton Market. The race for that ward became wide open after indicted Ald. Carrie Austin said she’d resign. Real estate agent and former healthcare worker Jim Ascot is also running.

Caucus power

In addition to the Democratic Socialist Caucus, four of the City Council’s other caucuses are aiming to grow their ranks: the Black Caucus, Latino Caucus, LGBTQ Caucus and the Progressive Reform Caucus.

While no group holds the 26-member majority needed to push through legislation on its own and caucuses do not always vote as a bloc, they form key allegiances that can share ideological goals. Some City Council members also sit on more than one caucus.

Currently the largest with 20 members, the Black Caucus is losing long-tenured members to retirements, aldermen throwing their hat into the mayor’s race and, in one case, a federal indictment.

But 28th Ward Ald. Jason Ervin, the Black Caucus’s chairman, anticipates the group will be able to maintain its ranks. In addition to continuing to address root causes of violence, such as poverty, Ervin said he aims for the caucus to keep a united front.

That strength was on full display during last year’s battle over remapping the city’s wards, he said.

After bitter fights with the Latino Caucus, the Black Caucus ultimately prevailed in securing a map that delivered 16 majority-Black wards. The Latino Caucus, which was calling for 16 Latino-majority wards to reflect its status as the largest minority in the city, ended up with 14 majority-Latino wards.

Ervin said the Black caucus succeeded in gaining more ground because it worked as a team.

“If it were up to ‘me, my and I,’ there was a possibility for us to come out of that situation with two to three less wards,” Ervin said. “…We were able to accomplish what we did because we worked as a collective and not as individuals.”

While the caucuses banded by political affiliation are growing, race continues to be a foundational draw for coalescing aldermanic power.

That’s evident in Chicago’s political history, from the infamous Council Wars era under Harold Washington, the city’s first Black mayor, to controversy over whether a white alderman who represented a majority-Black ward could join the Black Caucus’s ranks.

But it’s in the city’s political future too, says Connie Mixon, a political science professor and director of Elmhurst University’s urban studies program. She says race plays a unique role in city politics due to Chicago’s history steeped in both segregation and machine politics.

“Throughout our history, this segregation has resulted in less services and fewer benefits being provided to Black and brown communities within the city of Chicago,” Mixon said. “And so when we’re talking about city politics and what’s gonna shape city politics for the next decade, these racial tensions rise to the forefront.”

Ramirez-Rosa, a member of the LGBTQ, Latino and Progressive caucuses and chair of the five-member Democratic Socialist Caucus, said even if formal caucuses didn’t exist, he thinks Latino and Black aldermen would still have coalesced to protect their own group’s interests.

But Ramirez-Rosa said he sees the caucuses’ most important purpose is promoting policy agendas and issues that benefit their community.

“A caucus isn’t an end unto itself. It’s a means to an end,” Ramirez-Rosa said. “And in the context of the Democratic Socialist caucus, the goal that we’re seeking to achieve is democratic, good governance that is in the service of working class people, and not just a rich and powerful few.”

While the Democratic Socialist and Progressive Caucuses represent the only two political groups on the council, loose alliances on the other side of Chicago’s political spectrum have also formed. Though when asked whether a small group of more moderate or conservative aldermen, who tend to cast pro-police votes, will formalize the allegiance, one member laughed at the idea.

“Everybody’s scared to death to do that,” said 38th Ward Ald. Nick Sposato, who’s facing four challengers. “I mean, it’d be like you’re gonna have five white guys doing that?… I’d love to put together a somewhat of a moderate-slash-conservative caucus … It would be nice, but to get what done? I mean I think we’re all on an island. I think we’re all on our own. Life’s about building relationships. I just try to work hard with my friends.”

A more independent council

While aldermanic blocs attempt to increase their membership, which groups will be able to pull the levers of power also hinges on who will be Chicago’s next mayor.

With February’s mayoral ballot now set, eight candidates will be vying to unseat incumbent Mayor Lori Lightfoot after her first term.

A more right-leaning candidate could serve to further unite the Progressive and Democratic Socialist caucuses “in presenting an alternative to right-wing policies coming from the fifth floor,” Ramirez-Rosa said.

But a theme of aldermen’s desires for the next City Council is to see one that’s more autonomous — regardless of who holds the mayor’s office.

“What I’m hoping to see from this next City Council is more independence,” said 36th Ward Ald. Gilbert Villegas, who chairs the council’s Latino Caucus. “I think you saw a little bit of it rearing its head in the last six months, eight months. But we need to go further than that.”

While the City Council has historically earned the reputation of a “rubber stamp” council that goes along with the mayor’s priorities, a University of Illinois at Chicago report analyzing the council’s voting records over a nearly three-year period through March 2022 determined Lightfoot and the new council “buried” that designation.

Take for example Lightfoot’s annual budgets. While mayors have historically been able to pass their multibillion-dollar spending plans for 40 votes or more, Lightfoot’s proposals have received much fewer.

In 2020, her budget passed with just three votes to spare after progressive aldermen railed against it for its spending on police, and others voted against it because of its plan to increase property taxes. Lightfoot has painted her low budget votes as a badge of honor, arguing it exemplifies she won’t trade favors for votes.