Chicago Preview Part I
Mayor and Wards 1-20
We were going to start this with some fun pop cultural references, but in the process of that we looked up album names from the band Chicago and found that most of them are just the word “Chicago” followed by a number, and honestly that was when we gave up.
Mayor
Paul Vallas vs. Chuy García vs. Lori Lightfoot vs. Brandon Johnson vs. Willie Wilson vs. Kam Buckner vs. Sophia King vs. Roderick Sawyer vs. Ja'Mal Green
At this point in the election, we have the aid of a few (dozen) polls letting us know who is and isn’t making the April runoff. The problem is that the “is” list consists of one candidate and the “isn’t” list consists of four candidates, leaving one runoff spot and four contenders to fight for it. We’ll go through the field in three batches: the guy who’s making the runoff, followed by the four others who might join him, and then by the additional four who won’t.
See you in April:
Paul Vallas - As much as it pains us to say it, Paul Vallas is going to the runoff, and it’s not going to be close. In fact, at this point we’d consider it a massive upset if he didn’t come in first. Vallas was a budget director who Richard Daley promoted to Superintendent of Chicago Public Schools, where he quickly found the One Weird Trick to allow charters without affecting the budget of public schools: raiding the teacher’s pension fund and creating a billion-dollar budget crisis that continues to this day. Of course, by the time his decisions were catching up with the city, he was long gone, unsuccessfully running for mayor, and then fucking off to other cites where he innovated ever newer and bolder ways to privatize any parts of the educational system he could get his hands on. Vallas returned to Illinois to run for office in 2014 and 2019, failing both times, before announcing last year another attempt at the mayor’s office.
It’s not hard to point to why Vallas’s campaign has been successful: he’s the only white candidate, and the only candidate trying to appeal to non-Black conservatives. White conservatives like the Daley family and Rahm Emanuel had ruled Chicago politics for decades, but the 2019 wash-out of that breed of candidate in citywide office, and the 2021 collapse of the Madigan empire, convinced most people that that kind of candidacy was not viable anymore. That may in fact be true, and we’ll see for ourselves in the runoff, but the constituency for those kinds of candidates didn’t evaporate, just shrink, and now Vallas has it all to himself. Vallas has, to his credit, demonstrated an understanding that he’s only going to get this opportunity once in life, and he’s doing everything he can to realize the potential he has: angrily ending his dalliance with the Republican party, becoming pro-choice, and trying not to talk about what he actually did when he was running the city’s schools.
Four enter, one exits:
Brandon Johnson - Are we excited for Brandon Johnson? Yes? Maybe? We’re desperately hoping he makes the runoff, but much of that is fear of the alternatives. Brandon Johnson is a progressive, full stop. Even if he’s backed away from some of the police defunding language he used to use, Johnson has a pretty down-the-line progressive platform, and has proposed hefty new taxes on the wealthy.
Johnson’s campaign was functionally made by the Chicago Teachers Union, who had a falling out with Chuy García, and pumped $1 million into one of their own (though now on the Cook County Commission, Johnson was a CTU organizer for years beforehand and still is very tight with the union), quickly propelling him past the also-rans, at which point progressive orgs flocked to him. Since then, it’s been a dogfight for second place as Johnson jostles for voters without the racial bases enjoyed by his top competitors. There’s not much more to say really, other than we hope he makes the runoff, and if he doesn’t, then it better be…
Chuy García - Chuy García’s campaign has utterly baffled us, in several different ways. Before running for mayor he was the progressive voice of Chicago politics, building up a political machine while supporting the likes of Bernie Sanders and Delia Ramirez. In Congress, he was one of the most consistent progressive votes during the 2019-2020 session, and the prospect of Mayor García excited the city’s progressive class. But the last year has seen him slowly breaking with the left, most clearly in his endorsements against DSA incumbents in the Council, but also easily seen in his platform, which bears a striking resemblance to Lori Lightfoot’s, which is to say the status quo.
That would be comprehensible if it were in service of a Machiavellian drive for power, but he’s the mayoral candidate putting the least work into it. One of the reasons Johnson got the opportunity for so much labor support was that García didn’t even decide to run for mayor until so late that half the city’s political universe was convinced he wasn’t going to do it. Once in the race, García was late to fundraise, late to run ads, and just generally doesn’t seem to be putting his all into it. He’s either genuinely conflicted about leaving Congress for the mayorship, or so convinced of the inevitability of getting a runoff spot that he figures there’s no need to really get to work until then. To a greater extent than anyone else in the race, García’s fortunes are going to depend on his political network, and its ability to mobilize Latine voters. The reality is that if Latine turnout is high, he'll make the runoff, and if it’s low he’ll miss it.
Lori Lightfoot - Lori Lightfoot was truly not the worst mayor of Chicago, and may even have been the best mayor since the 80s. Of course, the bar is on the fucking floor, and she earns her title by being merely a bad mayor rather than an abjectly terrible one. Lightfoot has systematically alienated just about every force in Chicago politics, and if she weren’t in a position where her choices had real world consequences, that would have been enjoyable to watch. Lightfoot, almost immediately upon taking office, sided with the moderate faction of city government, and enjoyed popularity as a mayor who adopted mainstream liberal positions while attempting to fully sideline progressives from city government. After a year in office, Lightfoot’s career all but ended when protests broke out after the murder of George Floyd, and while it felt like half the mayors in America were trying to thread the needle between being pro-cop and pro-protests, Lightfoot did the opposite and fought with both. Within a year’s time, Lightfoot’s approval ratings were in the toilet, and her decision to pick a fight with the Chicago Teachers Union on top of everything was the final nail in the coffin.
Lightfoot’s been a dead candidate walking ever since. After spending a year wondering if she’d even put herself through the indignity of running for reelection, we’ve spent the last few months growing more and more scared of her. It’s not because she could win - she emphatically could not - but because she could make the runoff, and if she makes the runoff, Vallas is winning in a landslide. Even as it became more and more apparent that she had no chance of winning, most of her allies stuck by her, and she remained capable of holding onto a base of mostly Black, South Side voters. Five of the last seven polls have shown a Lightfoot/Vallas runoff, and, granted, some of those were garbage, but even in the polls where she misses 2nd place, it’s close.
Willie Wilson - anyone trying to describe Willie Wilson will eventually call him a character, and they’ll likely do it sooner rather than later. The businessman is much more serious of a candidate than your average charming eccentric, but everyone seems to think it would simply be too weird if he made the runoff for that to actually happen, even if polling says he’s in the hunt. Wilson is on his third campaign as mayor, after receiving 11% in both 2015 and 2019, campaigns where he got rounding error proportions of the non-Black vote, but above 20% of the Black voters, and above 30% in some parts of the city. Wilson left the Democratic Party in 2020 and ran for Senate as an independent, getting just 4% of the vote statewide, but over 20% in several heavily Black wards, an impressive result for an independent.
His political program is populist in the broadest sense of the word. His personal wealth, and repeated giveaways of money or gas in the poorest parts of the city, have built him a reputation, and it’s his reputation and the prosperity he promises that he campaigns on, rather than a political network or ideological cause. This is a man who asks rhetorically how many lives he single-handedly saved by giving away masks on his campaign website. Still, he understands, in many ways, that voters want actual candidates to speak to specific issues, and he has positioned himself firmly in the pro-cop side of politics, at one point memorably saying the police should be allowed to “hunt [suspects] down like a rabbit”. Wilson is definitely on the conservative side, but has historically only had appeal to Black voters, which has limited his potential. He may be consistently polling at the bottom of this tier of candidates, but he’s beaten his polls before, and with the field so tightly bunched up, even a decidedly factional candidate can make the runoff, possibly even if they fail to hit 20% of the vote.
There’s always 2027:
Kam Buckner - Kam Buckner was a nonprofit executive appointed to a South Side state house district in 2019. This will be his first election where he has any opponents. Buckner has put together a pretty progressive platform, jam packed with good government provisions and urbanist transit ideas. Progressives wound up looking towards Brandon Johnson, South Side political leaders mostly circled the wagons around Lori Lightfoot, and Buckner was left with some urbanists on Twitter as a political base.
Sophia King - Ald. Sophia King is friends with the Obamas. She was able to pull an endorsement from the man himself in 2017 during her first reelection, but in something as high-profile as the mayoral contest, the Obamas are pretty clearly not getting involved. King isn’t particularly well known for her work in the Council and hasn’t built up a political network in the last 6 years. She’s been pretty clearly doomed for months now, and it’s hard to guess what the plan was for her, exactly. At least with Buckner, this is a free shot for him, but she had to give up her Council seat to run for mayor.
Roderick Sawyer - Roderick Sawyer got tired of the City Council after a dozen years and opted to try out running for Mayor, like his dad Eugene Sawyer. He pretty quickly gave up on that and has been vibing ever since. Good for him.
Ja’Mal Green - Ja’Mal Green is an activist who ran for mayor in 2019 but dropped out rather than defend his ballot signatures in court from Willie Wilson’s lawyer. This time he actually made the ballot, though the results are going to be similar for him. If there weren’t a close race with progressives desperately trying to get one of their own onto the runoff, his own activist-y, progressive campaign might have attracted a healthy number of protest votes, but as it is, nah.
The Chicago City Council is up once every four years, and only once every four years—no midterms, no special elections if someone leaves office. This is the only chance Chicagoans will get to pick their city council until 2027. Redistricting and a wave of retirements guarantee that Chicago is about to elect quite a few new aldermen to lead the city no matter who wins the top job. For our preview of Wards 21-30, click here.
Ward 1 (Logan Square and West Town)
Daniel La Spata (i) vs. Proco Joe Moreno vs. Sam Royko vs. Stephen Schneider
In 2019 Daniel La Spata pulled off an upset by not only defeating incumbent Proco Joe Moreno, but doing so by a 22% margin. The then-recently announced police investigation into Moreno’s filing of a false police report probably helped. La Spata, once in office, became a founding member of the Democratic Socialist Caucus. This year, despite some controversies on the campaign trail in 2019, La Spata has run a quietly diligent, low-drama campaign, even after his campaign office was vandalized. La Spata is the only socialist to represent any of the white, wealthy-relative-to-the-city North Side, contributing to the sense some business and moderate political leaders have that La Spata’s win was a fluke, which can be corrected this year.
You have to beat someone with someone, and what the anti-La Spata faction can’t agree on is who their someone should be. Proco Joe Moreno is both the most and least obvious choice. His legal problems are over…thanks to a guilty plea that isn’t likely to assuage many voters. His attempt to put the past behind him comes in the form of publicly quitting drinking, but expectations for his campaign remain low. Instead the leading anti-La Spata candidate will probably be commercial attorney and tough-on-crime crusader Sam Royko, son of famous Chicago newspaper columnist and virulent homophobe Mike Royko. Stephen “Andy” Schneider, a reporter, author, and neighborhood preservationist, was an afterthought for the entire campaign, right up until the Chicago Tribune endorsed him in the last days of the campaign, giving him an at least decent shot of making any potential runoff. A good night for La Spata will be winning outright, while a bad night would be falling below 50%.
Ward 4 (Near South Side, Oakland, and Douglas)
Tracey Y. Bey vs. Prentice Butler vs. Matthew “Khari” Humphries vs. Ebony Lucas vs. Lamont Robinson Jr. vs. Helen West
This ward is open thanks to Ald. Sophia King’s decision to run for mayor. King isn’t running in the left lane of the mayoral primary (she’s barely running at all, never having broken into the top tier of candidates.) She does chair the Progressive Reform Caucus, one of the two caucuses (along with the Socialist Caucus) that tries to check Lightfoot’s worst excesses. The race to succeed her is ideologically muddled—the CTU and United Working Families are backing Matthew “Khari” Humphries, an education policy staffer for…Lori Lightfoot, who both groups generally treat as an enemy. Meanwhile, a broad coalition is backing state Rep. Lamont Robinson, from machine figures to progressive alders and state legislators, as well as most non-CTU labor unions; King’s chief of staff Prentice Butler has his boss’s support. Local businesswoman Ebony Lucas, retired businesswoman Helen West, and entrepreneur Tracey Y. Bey round out the field, with enough money (and in the cases of Lucas and Bey, name recognition from previous runs) to potentially make a dent. However, this is Lamont Robinson’s race to lose; he’s already an elected official representing much of the ward, and he has a ten-to-one financial advantage over his closest competitor.
Ward 5 (Kenwood, Hyde Park, and Woodlawn)
Marlene Fisher vs. Wallace Goode vs. Joshua Gray vs. Jocelyn Hare vs. Martina Hone vs. Kris Levy vs. Robert Palmer vs. Dialika Perkins vs. Gabriel Piemonte vs. Renita Ward vs. Desmon Yancy
Wards 5 and 6 both have 11 candidates on the ballot, a frankly baffling field size for districts of barely more than 50,000 residents. The closest Ward 5 has to a frontrunner is Desmon Yancy, Senior Director of Organizing and Advocacy for the Inner-City Muslim Action Network, by dint of the support he’s receiving from organized labor. Yancy appears to be straddling the progressive and more establishment elements of Chicago politics, but he should mostly be thought of as the SEIU’s candidate, considering he used to be an employee and they’re bankrolling him.
Attorney and judicial clerk Renita Ward has the Tribune endorsement, which makes sense for them, because she’s accomplished professionally, can raise money, and is offering absolutely zero in the way of policy (don’t worry though, she’s promised to work with people to eventually develop a position on policing if she’s elected). Gregory Piemonte, the only white candidate of note, is running for the second time after taking a surprisingly decent 25% of the vote in 2019 but just missing the runoff. In some ways he’s the most progressive candidate (the only one in support of taking cops out of schools, for instance) but we’d be remiss if we didn’t mention the mild crank energy his website gives off, or reiterate that a white candidate has long odds in a 60% Black South Side district.
Moving down a tier of viability, there’s Joshua Gray, a political consultant and former employee of retiring Ald. Leslie Hairston, running a self-financed campaign that isn’t getting much more traction than his 2018 Cook County Board campaign that ended with him taking less than 10% of the vote. Jocelyn Hare, on her second campaign for this district, still wants you to know she’s “not a politician”, and while she uses the most overtly progressive language of the candidates running, she’s also piled up red flags like: responding to candidate questionnaires by copy-pasting from her website, even when it creates answers like “What do you see as potential solutions to address the number of shootings in Chicago? Immediately: Install speed bumps to slow traffic;“ posting her absentee ballot with Willie Wilson bubbled in for mayor; and avoiding committing to specific policies when asked directly, by punting it all to community input. Martina Hone is the only candidate in the field who has held elected office before…in Virginia. She’s raising some of the best money in the field, and her whole deal is demanding more cops. Also trying out a tough-on crime campaign is Kris Levy (“I plan to crack down on the constant loitering” is some real 90s-era nonsense) whose top donor is a Republican.
IT administrator Marlene Fisher may be nudging her way out of the also-ran bracket through sheer effort, but when someone’s idea for fixing neighborhood disinvestment is a marketing campaign they probably shouldn’t be in government. Dialika “Dee” Perkins is a former boxer and current accountant who refreshingly supports several great policies like rent control and non-police response teams, but whose biggest proposal is cutting property taxes. Wallace Goode is a former member of the Robert Daley administration who is committed to cutting the size of government. Finally, Robert Palmer is only an election or two away from becoming a perennial candidate. We’re not going to bother looking up what his deal is—when he ran for IL-01 last year he came in 12th place overall and 15th in the 5th Ward.
Ward 6 (Chatham and Greater Grand Crossing)
Sylvester Baker Jr. vs. Kirby Birgans vs. Tavares Briggs vs. Patrick Brutus vs. Paul Bryson Sr. vs. Barbara Ann Bunville vs. Kimberly Egonmwan vs. William Hall vs. Aja Kearney vs. Sharon Pincham vs. Richard A. Wooten
Like Ward 4, this seat is open because of a hopeless mayoral campaign. If there’s a frontrunner, it’s pastor and Rainbow PUSH alum William Hall, who has a huge financial advantage and near-unified support from progressives and organized labor. Barbara Ann Bunville is the first of three cops running here, and she’s the one with the FOP’s endorsement (they passed over Richard Wooten and Sylvester Baker Jr.) Kimberly Egonmwan seems to be a phantom candidate, Sharon Pincham and Patrick Brutus are acting like phantom candidates despite raising more than enough for a website and some media hits, and Kirby Birgans and Tavares Briggs are close to flat broke. That leaves Bunville, Aja Kearney, and Paul Bryson as the strongest non-Hall contenders. Kearney, who worked her way up in Democratic politics from Young Democrats clubs to working as a political staffer, has a couple of unions in her corner. Bryson is running on the fact that he’s a longtime aide to outgoing Ald. Roderick Sawyer and not much else.
Ward 8 (Avalon Park, Calumet Park, Montclair)
Michelle Harris (i) vs. Sean Flynn vs. Linda Hudson
Michelle Harris has been on the Council since she was appointed by Richard Daley in 2006, and, like most appointed Alders, has been steadfastly aligned with the city and state party establishment ever since. She’s perhaps best known for her 2021 bid for party chair, which she narrowly lost—as the pick of both JB Pritzker and Mike Madigan—to Robin Kelly. Harris is perhaps Lori Lightfoot’s most powerful ally on the Council, and she has remained as such even after Lightfoot’s popularity has tanked. Harris is powerful and has easily turned back challengers in the past, but drafting her would be a powerful blow to the machine, and she represents a district that, while generally machine-friendly, isn’t like some on the city’s fringes where conservative representatives are all but guaranteed (it also has the highest share of Black residents of all wards).
Harris is being challenged by Sean Flynn, chief of staff to Ald. David Moore, a member of the Progressive Reform Caucus and noted Rahm/Lightfoot opponent. Previously, Flynn was an aide to Ald. Leslie Hariston, also of the PRC. Presumably, Moore would follow in his bosses’ footsteps and take a place on the progressive side of the council’s divide. At the very least, it’s hard to imagine him being more devoted to upholding the status quo than Harris. Flynn, unfortunately, has not been taking his campaign as seriously as he could be, raising little money and so thoroughly mailing in his application for the endorsement of the Chicago Tribune it instead went to tax assistant Linda Hudson, running a campaign that isn’t especially progressive, but is at least critical of the close relationship Harris has had with the city’s moderate mayors. Hudson ran in 2019 and lost to Harris 64-17.
Ward 9 (West Pullman and Roseland)
Anthony Beale (i) vs. Cameron Barnes vs. Cleopatra Draper
Longtime South Side Ald. Anthony Beale faces a rematch with Cleopatra Draper, who used the surname Watson when she ran four years ago. Organized labor is split between Draper and Beale, while progressive groups are split between Draper and nobody—many progressive groups are sitting this race out. Also in the race is Cameron Barnes, who resigned his job as the national youth director of the Rev. Jesse Jackson’s Rainbow PUSH Coalition to run. Connections to Jesse Jackson on the South Side never hurt—just ask the South Side’s newly-elected congressman, Jonathan Jackson, son of the reverend.
Ward 10 (Hegewisch, Riverdale, South Deering, East Side)
Yessenia Carreón vs. Peter Chico vs. Ana Guajardo vs. Óscar Sánchez vs. Jessica Venegas
Ald. Susan Sadlowski Garza is a Progressive Reform Caucus member and Lightfoot antagonist hailing from a generally conservative ward, a Hispanic enclave along the Indiana state line in the predominantly Black South Side. The race to succeed her is…a mess. The favorite is union organizer Ana Guajardo, who has the support of Sadlowski Garza as well as Chuy García and most of the labor movement. Community and environmental organizer Óscar Sánchez has CTU, DSA, United Working Families, and, oddly, the Chicago Tribune in his corner. Cops Peter Chico and Jessica Venegas are running tough-on-crime campaigns straight out of the 90s; perhaps unsurprisingly, the FOP endorsed both. This one is probably headed to a runoff.
Ward 11 (Bridgeport and McKinley Park)
Nicole Lee (i) vs. Anthony Ciaravino vs. Steve Demitro vs. Don Don vs. Elvira Jimenez vs. Froylan Jimenez vs. Ambria Taylor
The 11th Ward is best known as the home of the Daley machine, the patronage-and-corruption outfit ran by the Daley family and its allies—but there’s no Daley on the ballot in 2023 because the last one standing, Ald. Patrick Daley Thompson, went and got himself convicted of tax fraud last year. That’s where Nicole Lee comes in.
Appointed by Lightfoot after Daley Thompson’s conviction automatically removed him from the council, Lee is a career corporate executive—and the daughter of Gene Lee, a longtime aide to the Daley machine in its heyday. Lightfoot-approved and Daley-connected, Lee is a continuation of the Daley machine whether or not she says so. However, she’s also the first Asian woman on the Chicago City Council, and this ward was redrawn to be majority-Asian. That could help her against her two main challengers, socialist teacher Ambria Taylor (backed by CDSA and some labor unions) and conservative police officer Anthony Ciaravino (backed by the FOP); both are white. Businesswoman Elvira “Vida” Jimenez and CTU leader Froylan Jimenez are also running noteworthy campaigns, making it even less likely that anyone will get a majority in the first round. If someone does, we think it’ll be Lee.
Ward 12 (Brighton Park)
Anabel Abarca (i) vs. Julia Ramirez
Anabel Abarca was appointed to succeed Ald. George Cardenas when he resigned to take a seat on the Cook County Board of Review, and she’s the first of two Cardenas chiefs of staff on the ballot as the more conservative candidate in a city council race. (See Ward 33 for the other one.) Abarca has some labor backing, as well as the Chicago Tribune, but Chicago progressive groups, the left flank of the labor movement, and erstwhile progressive leader Chuy García all agree on social worker Julia Ramirez. With only Abarca and Ramirez on the ballot in Ward 12, one of the two women will win tonight.
Ward 13 (Clearing and Garfield Ridge)
Marty Quinn (i) vs. Paul Bruton
Marty Quinn, a quiet and largely forgettable city councilman, would be able to sail to reelection most years in his practically suburban district where Trump won 37% of the vote, and where moderates would seem to reign supreme. However, this is not just any ward—it’s the home of disgraced former Speaker of the Illinois House Mike Madigan, who has chaired the ward committee for 53 years, and maintained it as the core of his political machine—which, even after his fall from grace and indictments, has remained incredibly strong. Quinn faces full-time father Paul Bruton, running to “fight Chicago’s legacy of corruption.” Quinn is still the odds-on favorite, but after Madigan allies suffered losses in this part of the county in 2022, a single-issue anti-Madigan campaign may have a shot.
Ward 14 (Archer Heights, Gage Park, Chicago Lawn)
Jeylú Gutiérrez vs. Raul Reyes
Ald. Ed Burke is finally on his way out after more than a half-century in office, though whether the true motivation is his age (79), an unfavorable redistricting cycle, or the federal indictment hanging over his head is anyone’s guess. In addition to being a crook, Burke has been a huge pain on the city council since the days of Harold Washington, when he was a leader of the conservative, almost entirely white council majority which opposed Washington, Chicago’s first Black mayor, at every turn. Good riddance.
Only two candidates made the ballot in Ward 14, so this ward will be decided tonight. Raul Reyes is proudly running as Burke’s chosen successor. He has Burke’s endorsement and years of work for Burke’s political organization under his belt. (The FOP is also supporting him.) Jeylú Gutiérrez, a staffer for Cook County Commissioner Alma Anaya, is the non-Burke option, making her superior by default.
Ward 15 (A squiggly mess across the Southwest)
Raymond Lopez (i) vs. Victoria Alvarez vs. Gloria Ann Williams
Given the retirements this year, Raymond Lopez may be the only competition this year for Ald. Nick Sposato and Ald. Jim Gardiner in the category of “worst incumbent on the ballot.” Willie Wilson’s only supporter in the Council began his career as a Lipinski political staffer, won election to city council with the backing of cops, realtor money, and the Daley machine against a much less conservative opponent, and is now running for reelection with $250,000 from a tobacco CEO & sports team owner. If you’d want to see what Lopez is up to on any given day, just turn on Fox News and wait until he shows up to complain about Democrats being too soft on crime.
Lopez won with less than 60% of the vote in 2015 and 2019, doing much better in the district’s Black-majority southern leg than the rest of the district, which is majority Latine. Redistricting cut down slightly on that leg of his district, but added a mostly white, Trump-supporting neighborhood to the east, giving him what is presumably a safer district, or at worst a wash.
Lopz has two opponents, though only one is running a real campaign: Victoria “Vicko” Alvarez. Alvarez, the Chief of Staff to DSA-affiliated Ald. Rossana Rodríguez-Sánchez, does not have DSA backing, but they’re seemingly the only group on the left who hasn’t endorsed her. Alvarez’s solidly progressive campaign also has United Working Families and the CTU, two groups known for providing real organizing and financial heft to candidates, though the latter, at least, seems to be letting non-mayoral races fall to the side as they go for broke to elect Brandon. Lopez remains a favorite here, but the potential for an Alvarez upset remains. It’s even possible we see a runoff if things are close enough today.
Ward 16 (Englewood, West Englewood)
Stephanie Coleman (i) vs. Carolynn Crump vs. Eddie Johnson
Carolynn Crump is a Chicago cop who’s already lost one election as a cop backlash candidate, and after losing 71-29 to state Rep. Sonya Harper she’s chosen Ald. Stephanie Coleman as the next standard-issue Democrat she wants to lose to. Eddie Johnson is a phantom candidate, and while he could theoretically force a runoff, we expect Coleman to easily clear 50%.
Ward 18 (Ashburn)
Derrick Curtis (i) vs. Heather Wills
Derrick Curtis is one of Lightfoot’s top allies in the Council, and, like Michelle Harris in Ward 6, has a target on his back for it. Unlike with many other races this year, there’s no particularly fantastic or terrible record to highlight on the incumbent’s behalf, political machines engaging in a proxy war, or any other adornments. Rather, it’s a simple ideological battle, with moderates and progressives both striving to put a win on the board. The latter, mostly in the form of the SEIU, are supporting Heather Wills, a community organizer who would be a great Alder if it weren't for one thing: her pro-car, anti-transit oriented development stances that are, unfortunately, pretty important when it comes to city politics. Still, Wills is better on the majority of issues and we hope for good things out of her admittedly underdog campaign.
Ward 19 (Mount Greenwood, Beverly, Morgan Park)
Matthew O'Shea (i) vs. Michael Cummings vs. Timothy Noonan
This ward is a collection of conservative white neighborhoods on the Southwest Side, so the field is kind of depressing. Ald. Matthew O’Shea is one of the council’s conservative bloc; when he opposes Lori Lightfoot, it’s usually from the right. Because he’s not a total seething lunatic, the FOP has endorsed a challenger, Michael Cummings, a retired cop with dozens of complaints on his disciplinary record. Timothy Noonan is a community activist who opposed school closures, likes public transit, and generally seems like a nice, well-meaning liberal. Rough ward for that message, but hope springs eternal.
Ward 20 (Washington Park, Woodlawn, New City)
Jeanette Taylor (i) vs. Jennifer Maddox vs. Andre Smith
Jeanette Taylor was a community organizer known for a hunger strike protesting the planned closure of a South Side high school. Then, in 2019, she pulled off an impressive upset victory in an open South Side ward and became a founding member of the Chicago City Council’s Socialist Caucus. It’s odd that DSA’s lone South Side Alderperson is having an easier reelection than some of her colleagues in relative leftist strongholds on the Northwest Side, but it’s true: FOP-endorsed cop Jennifer Maddox and perennial candidate Andre Smith aren’t quite token opposition, but we would’ve expected stronger opposition to a socialist with a flawless record of being a thorn in Lori Lightfoot’s side and a tireless fighter for a more progressive, more equal Chicago.