Chicago Preview Part II

Wards 21-50

For Part I of our Chicago preview, covering the mayoral election and City Council Wards 1-20, click here.

Ward 21 (Washington Heights, Auburn Gresham, Morgan Park)

Preston Brown Jr. vs. Ayana Clark vs. Cornell Dantzler vs. Daliah Goree vs. Kweli Kwaza vs. Larry Lloyd vs. Ronnie Mosley

Chicago’s contentious redistricting process ended with the Latino Caucus getting little of what they wanted from the new districts, and the Black Caucus keeping most of their seats, but they did have to cede one from the South Side, owing to heavy population loss in the last decade. The solution was to combine the districts of Howard Brookins and Carrie Austin. The incumbent-on-incumbent battle implied by this redraw was never meant to be. Both had been in office for at least 20 years, but after rough reelections in 2019, neither were in the mood for another and hung it up instead of dealing with a district that was half new to them, which is how this double bunk turned into an open seat.

The frontrunner in this election is Ronnie Mosley, a political strategist who runs Homegrown Strategy Group, which counts among its clients the JB Pritzker for Governor campaign. Pritzker is, unsurprisingly, one of his highest profile endorsers, joining organized labor, state Sen. Jacqui Collins, and the Chicago Tribune. Mosley’s establishment support, as well as the money he’s raised, likely means he’s headed for, if not an outright win, then a commanding lead going into the runoff. That’s not terrible, but far from ideal.

As for alternatives, it seems like to compete with Mosley a candidate would probably need to enter this election with a profile, such as one of the candidates who nearly defeated this district's incumbents in 2019. As it happens, one of them, Austin’s, is running again. Preston Brown Jr. is in an odd position of being both a progressive reformer in reputation, both from his 2019 candidacy and from serving as a Bernie delegate in 2020, but as a more conservative candidate in policy, both from his laser focus on increasing the police budget and his unwillingness to take a side on many other policy questions—usually a bad sign. And yet, he’s backed by Rep. Justin Slaughter, one of the lead authors of the SAFE-T Act. Conclusion: who knows?

The only unambiguous progressive in the race is Ayana Clark, who has raised very little money. Firefighter Cornell Dantzler’s campaign would be totally dead in the water if it weren’t for the firefighters union funding him; as it is, it’s only mostly dead in the water. In a rare case of firefighter/cop union disagreement, the latter are backing cop Daliah Goree, who has dozens of civilian complaints on her record. Finally, Kweli Kwaza and Larry Lloyd are… both… definitely running. We can 100% verify that they will be on the ballot.

Ward 22 (South Lawndale)

Michael Rodriguez (i) vs. Kristian Armendariz vs. Neftalie Gonzalez

This is the heart of the Chuy García machine, and Michael Rodriguez is a loyal foot soldier. In this case, it’s fine. Rodriguez has a pretty progressive record, and neither of his opponents is a step up—nor does either one seem a particularly serious candidate, to be honest. Kristian Armendariz is…amateurish, and conservative cop Neftalie Gonzalez is…a conservative cop. Neither is raising much or collecting any endorsements. Rodriguez should win tonight without a runoff.

Ward 23 (Garfield Ridge, West Elsdon, West Lawn)

Silvana Tabares (i) vs. Eddie Guillen

This is a race between Cursed and Also Cursed. Sorry. At least it’ll be over tonight.

Incumbent Silvana Tabares is a product of the machine, running for another term with the support of the FOP in Mike Madigan’s home ward. Prior to running, Eddie Guillen was the chief of staff to state Rep. Angie Guerrero-Cuellar, who was appointed to succeed Madigan after his resignation (well, technically she was appointed to succeed the guy who succeeded Madigan, but that guy lasted three days before resigning because nobody vetted him until after he was appointed.) Guerrero-Cuellar—who Tabares had backed for that state House appointment—is supporting Guillen over her onetime political patron. It’s an incestuous machine mess where the opponent of the FOP-endorsed incumbent lists more police surveillance as a policy priority, in the form of the very dystopian-sounding acronym PODs (Police Observation Devices, which presumably just means cameras.) 

Ward 24 (North Lawndale)

Monique Scott (i) vs. Vetress Boyce vs. Drewone Goldsmith vs. Traci Treasure Johnson vs. Larry Nelson vs. Creative Scott vs. Edward Ward vs. Luther Woodruff Jr.

Monique Scott was appointed last year after her brother Michael resigned from the city council. It’s not at all clear that she’ll have to fight to keep the job, because the field of challengers she faces is kind of weak. Luther Woodruff Jr. has a bit of money and the support of the Teamsters; Drewone Goldsmith has the FOP; nobody else stands out, though repeat candidates Creative Scott, Traci Treasure Johnson, and Larry Nelson might have residual name recognition. Monique Scott could still be forced into a runoff just by virtue of having seven challengers, and if that happens, we’re inclined to think you should hope it’s Woodruff, if for no other reason than he seems slightly more prepared to take on an incumbent head-to-head than the rest of the field.

Ward 25 (Lower West Side)

Byron Sigcho-Lopez (i) vs. Aida Flores

This contest should be an easy choice for anyone on the left. Byron Sigcho-Lopez is one of the founding members of the Socialist Caucus, and a consistent advocate for the working class and immigrants in all that he does. Sigcho-Lopez won an open seat by 8% in 2019, and since then just about every establishment force has had it out for him. They significantly redrew his district to remove Chinatown and neighborhoods near UIC, where he did well in 2019, and pushed the district much further west, into the heart of Chuy García territory. García did indeed field a candidate against Sigcho-Lopez: teacher Aida Flores, who ran in 2019 but finished a close 4th and missed the runoff. The building trades unions have gone all-in for her, as has Anna Valencia, the only Latine citywide official in Chicago. The race got nasty early as business interests flooded the zone with anti-Sigcho Lopez ads, to which Sigcho-Lopez responded by portraying her as a puppet of real estate interests (true) and as connected to the machine that he pushed out of office in 2019 (probably not as accurate). The candidates clearly hate each other, and at this point the contest has taken a larger meaning as a symbolic contest about the ideological direction of Hispanics in Chicago, who have recently grown significantly in political power.

Ward 26 (Humboldt Park)

Jessica Fuentes vs. Angee Gonzalez Rodriguez vs. Julian Perez 

The retirement of Ald. Roberto Maldonado gave progressives a golden opportunity on the Northwest Side, and community organizer Jessie Fuentes is here to take it. Businessman and DJ Julian Perez (Julian “Jumpin” Perez) is the FOP-endorsed conservative in the race, while local Democratic ward committeeperson Angee Gonzalez Rodriguez is…here to make a runoff possible. Fuentes has a serious financial advantage and an even bigger edge in endorsements, including from area progressive elected officials; her apparent frontrunner status has convinced Perez he needs to reach into the gutter in the final days of the campaign. Perez accepted an in-kind contribution from the FOP in the form of $10,000 worth of flyers highlighting Fuentes’s arrests for minor offenses as a teenager, more than a decade ago. It’s slimy, it’s desperate, and it’s so very FOP.

Ward 28 (Austin, Garfield Park, Near West Side)

Jason Ervin (i) vs. Shawn Walker

Shawn Walker is a perennial candidate and former Republican ward committeeman. Ald. Jason Ervin is a machine mainstay who leaves much to be desired, but at least he’s not a former Republican elected official.

Ward 29 (Austin, Montclare)

Chris Taliaferro (i) vs. Corey Dooley vs. CB Johnson

Chris Taliaferro is an establishment-y backbencher with a conservative streak. Unfortunately, his opponents either don’t appear to be running a serious campaign (Corey Dooley, whose platform is mostly platitudes about youth involvement) or any campaign at all (drug abuse prevention group founder CB Johnson, who has run twice before and even has Danny Davis’s endorsement, but doesn’t seem to be interested in actually campaigning.)

Ward 30 (Irving Park, Portage Park, Belmont Cragin)

Ruth Cruz vs. Jessica Gutierrez vs. JuanPablo Prieto vs. Warren Williams

The 30th Ward was the site of a major showdown in 2019, when 4-term incumbent Ariel Reboyras went into a tense runoff with Jessica Gutiérrez, daughter of Luis Gutiérrez, just weeks after he’d left Congress. The contest was fought more on the grounds of who was more of a machine politician, the 16-year incumbent and former city employee, or the nepotism case, as opposed to policy grounds. It was an election that Gutiérrez should have been able to win. At one point, Reboyras was even texting voters that her “daddy is trying to buy this election” in a very desperate finishing stretch. But Gutiérrez ultimately couldn’t pull it off, even with the family name, and, yes, money.

This time around Gutiérrez faces the promise of running as the only candidate every voter starts the race familiar with, but also the peril of a field without a past-his-prime politician to contrast herself against. Gutiérrez hasn’t rebranded herself as much as she’s slightly updated her image to reflect that she can no longer credibly call herself an outsider, speaking more about experience and commitment than last time, as well as trying to position herself both as the pro-cop candidate (“Crime is out of control, and I am a crime fighter”) and the pro-choice candidate. She still talks about fighting against the “failed” Latine leadership in the district, because in many ways she’s still fighting against Reboyras, who is backing college administrator Ruth Cruz. Cruz and Gutiérrez both have labor backing, the former basking in LiUNA! support, while the latter has Teamsters, Unite Here!, and a few others. The actual policy differences between the two are slight, but there’s something cynical about Gutiérrez’s approach that makes it harder to believe she’ll stick with the moderately progressive policies she’s supporting.

The labor split doesn’t end there. The Illinois Nurses Association and Cook County College Teachers Union are behind Warren Williams, a Bernie volunteer and founder of 30th United, a progressive political organization. Williams is endorsed by Chicago DSA, and, surprisingly, Robert Martwick, who represents the white and traditionally moderate northwest corner of Chicago. Williams, as a non-Latine candidate running in a majority Latine district, represents one of the tougher lifts for DSA, but his campaign has been well-run and on message in what seems like a very progressive district. Also running is ex-ICE contractor JuanPablo Prieto, who has split labor a fourth way (IBEW) but is probably not making the runoff.

Ward 31 (Belmont Cragin, Hermosa)

Felix Cardona Jr. (i) vs. Esteban Burgoa Ontañon 

Felix Cardona Jr. is an anti-gay bigot who is going to cruise to reelection because his only opponent, Esteban Burgoa Ontañon, barely exists. 

Ward 33 (Albany Park, Irving Park)

Rossana Rodríguez-Sánchez (i) vs. Samie Martinez vs. Laith Shaaban

Chuy García’s relationship with the Chicago left has gone from friendly to hostile in what seems like an instant, and it shows in Ward 33. Democratic socialist Rossana Rodríguez-Sánchez unseated machine Ald. Deb Mell in 2019 by a margin of just thirteen votes, and quickly established herself as one of the most stridently left-wing members of the Chicago City Council, joining the Socialist and Progressive Reform caucuses. Samie Martinez is running as the revenge of the machine—and Chuy endorsed him. Martinez, formerly the chief of staff to Ald. George Cardenas, has the FOP and the Chicago machine behind him and is running a standard big-city moderate Democrat law-and-order campaign. Endorsing him over a DSA incumbent is a great departure from the Chuy of just a year ago, when he was energetically backing a slate of progressive challengers to machine incumbents in the state legislature.

Sure, Rodríguez-Sánchez, like the rest of the Socialist Caucus and much of the broader Chicago left, drew Chuy’s ire by backing Brandon Johnson for mayor instead of Chuy. But he didn’t have to endorse Martinez to make this point. Laith Shaaban, a housing developer and investment adviser, is running a bland liberal/centrist campaign and carries the endorsement of the Chicago Tribune; Chuy could have gotten back at Rodríguez-Sánchez without endorsing the candidate of the machine and the FOP.

Ward 34 (Near West Side, the Loop)

Jim Ascot vs. Bill Conway

We’re beginning to appreciate that at least many of the most cursed races are guaranteed to be over tonight. This is one of them. The guy to root for here is developer Jim Ascot—not because Ascot is particularly good (he’s a developer running in one of Chicago’s richest wards, come on) but because his opponent is Bill Conway. Conway is a former prosecutor who ran, very unsuccessfully, as the tough-on-crime Blue Lives Matter primary challenger to Cook County State’s Attorney Kim Foxx in 2020; he’s also the son of the Carlyle Group’s billionaire CEO, William Conway. This ward is entirely new, having relocated from the South Side due to the Loop’s rapid population growth over the last decade, and Conway would make a depressing first alderman.

Ward 36 (Belmont Cragin)

Gilbert Villegas (i) vs. Jacqueline Baez vs. David Herrera vs. Leonor Torres Whitt 

Longtime readers may remember that machine Ald. Gilbert Villegas suffered a truly humiliating blowout loss to now-Rep. Delia Ramirez, a progressive and at the time a Chuy ally, in the primary for IL-03 last year, even losing his seat on the state party committee at the same time. Progressives and Chuy have grown apart in record time; Chuy is backing Villegas for another term, less than a year after backing Ramirez in that primary. The Northwest Side’s progressive political class isn’t as ready to call a truce with Villegas; Ramirez, state Sens. Omar Aquino and Cristina Pacione-Zayas, and state Rep. Lilian Jiménez are all behind Leonor “Lori” Torres Whitt, a CTU organizer and CPS teacher running a progressive campaign that looks to finish what Ramirez started last year.

Ward 37 (Austin, Humboldt Park)

Emma Mitts (i) vs. Corey Denelle Braddock vs. Howard Ray vs. Jake Towers

Longtime machine Ald. Emma Mitts faces a weak and scattered field of opponents. FOP endorsee Howard Ray wants to “implement a proactive crime strategy called ‘The Formula’ that has numerous components to prevent crime” and “create a Sports ministry,” according to his website, which is unnervingly committed to the pointed use of the third person to refer to Howard Ray. Corey Braddock and Jake Towers are certainly on the ballot.

Ward 38 (Dunning, Portage Park)

Nicholas Sposato (i) vs. Ed Bannon vs. Bruce Randazzo vs. Franco Reyes vs. Cynthia Santos

Ah, Nick Sposato. Truly, the man is a living parody of a racist Chicago Italian—except he’s real, and nobody even ran against him in 2019. Once a member of the Progressive Reform Caucus for some reason, Sposato left the Democratic Party and embraced Donald Trump during his presidency. Now he’s your standard lame-ass boomer edgelord, telling a radio station “You can identify as whatever you want these days, can’t you? I identify as a vaccinated person,” and claiming that racial disparities in traffic stops exist because “white people just know how to talk their way out of a ticket.” He’d like you to know that he is very angry at “commie, lefty loons.” One time he decided to brandish a knife during a city council meeting to make some sort of point about how it would be bad to approve a police misconduct settlement. You get it—he’s gotta go.

Bruce Randazzo, a phantom candidate, and Cynthia Santos, a former city staffer who appears to have written her entire website herself, aren’t going to win. (What they might do is help nudge Sposato below 50%.) Franco Reyes is a liberal software engineer who would be a step up from Sposato just by virtue of being pro-choice and pro-LGBT, but the rest of his platform seems okay as well; he’s more of a real candidate than Santos or Randazzo. Sposato’s chief opponent, however, is Ed Bannon, a nice-seeming guy who holds consistently progressive policy positions and also does not seem the type to wave a knife around at work. Progressive organizations and the Chicago Tribune are in rare agreement here, both backing Bannon.

Ward 39 (Forest Glen, North Park, Albany Park)

Samantha Nugent (i) vs. Denali Dasgupta

Samantha Nugent is a pretty standard machine alderperson who loves CPD and doesn’t have much else in the way of ideas. Researcher Denali Dasgupta is backed by CTU and United Working Families, in a race that’s a pretty simple ideological battle between the center and the left. Though technically possible thanks to a registered write-in candidate, a runoff is incredibly unlikely here; this race will be decided tonight, and it’ll help set the tone for the April runoffs.

Ward 40 (Lincoln Square)

André Vasquez (i) vs. Christian Blume vs. Jane Lucius

André Vasquez was one of Chicago DSA’s success stories…until he had a falling out with the organization after he broke with them to support Lori Lightfoot’s second budget. No longer a member of the Socialist Caucus, Vasquez is still a generally progressive voice on the council. He endorsed Chuy García for mayor this year, differentiating him from many of his progressive colleagues and all of his former Socialist Caucus colleagues, but he’s still more aligned with them than with the alternative. And his opponents, Christian Blume and FOP-endorsed Jane Lucius, are both clearly to his right. They’re also both clearly going to lose.

Ward 41 (Edison Park, Norwood Park)

Anthony Napolitano (i) vs. Paul Struebing

Anthony Napolitano and Nicholas Sposato are aldermen for neighboring districts, and kindred spirits in clearly being Republicans but not wanting to admit it for electoral reasons. Attorney Paul Struebing, purely by virtue of being a basically normal Democrat, is obviously a way better choice here. If this were a partisan Democratic primary, he’d have all but won by now. Unfortunately, it’s a nonpartisan primary in a district where Biden only outpolled Trump by 2%. It’s an uphill task, but Struebing is doing his best by focusing on nuts and bolts issues like street design, and has raised a fair bit of money. Hopefully that keeps him from totally flopping.

Ward 43 (Lincoln Park)

Timmy Knudsen (i) vs. Steve Botsford vs. Brian Comer vs. Rebecca Janowitz vs. Steven McClellan vs. Wendi Taylor Nations

Timmy Knudsen has been on the Council for all of 5 months. He was appointed by Lori Lightfoot (bad), considered using his discretionary ward dollars to hire a private security firm for the ward (bad), and was a cryptocurrency lawyer before the appointment (bad). Steven Botsford is a real estate developer who worked for California Rep. Tony Cárdenas, doesn’t consider himself a Democrat, and whose pitch for himself begins with paragraphs, plural, about how talented he is at drafting bipartisan legislation. The man also has some phenomenally dipshitted opinions, our favorite being that cash bail should only be available to violent offenders. Once again, he believes that the only people who should be allowed to buy their way out of custody are the specifically ones that are the most likely to be a danger to others. His campaign is primarily self-funded, because even in one of the richest parts of Chicago his particular brand of bullshit is a little much. Wendi Taylor Nations has the endorsement of Michele Smith, the last Alder to actually be elected in this district, and her crime platform beginning with a statement that the city needs to be “confronting” beliefs about the police that aren’t positive enough is really all you need to know about where she sits ideologically. Brian Comer is a neighborhood association president who, for absolutely baffling reasons, was endorsed by the Chicago Tribune.

We’re 40something Council races in, we need to take a second to complain about how the Chicago Tribune endorsements are such dogshit. They would be the worst major city newspaper for political endorsements if the Washington Post would stop endorsing Republicans for offices in DC. In a district with actual serious candidates, the Tribune chose a man who refuses to put a policy platform on his website and who gave, in his endorsement interview, two concrete plans to reduce crime: 1) paying DePaul college students a $42,000 bonus in exchange for a 4 year commitment to being a police officer (to counteract “social media”) and 2) that he “commit[s] to gathering those new voices and leading a focused group, inviting existing alders, to march to Kim Foxx’s office to say enough is enough”. What? It’s one thing to consistently endorse against the left (and the Tribune can’t even get that right, not that we mind when they endorse candidates like Óscar Sánchez), but it’s genuinely confusing that the Tribune ed board will listen to several candidates with similar opinions and choose the one who phrased their opinions in the most nonsensical, poorly-thought-out way of the entire group.

Back to the actual election: Rebecca Janowitz and Steven McClellan ran in 2019 and got about 7% of the vote between them, which would normally mean they can be discounted here, but normally a highly failed candidate doesn’t come back and dump $750,000 of her own money into this election like Janowitz just did. That’s close to $1,500 per ward resident, and likely around $5,000 per voter, in case you're keeping track. She’s running on two plans: one to “protect and expand abortion access”, and one to fight crime. Both are roughly what you would expect from a rich white lawyer. And yet, running against a crypto lawyer appointed by Lori Lightfoot, a bipartisanism enthusiast, a proxy for the district’s previous, deeply moderate alder, and whatever the fuck is going on with Brian Comer, she may just be the best of the bunch. The SEIU, Robert Peters, Jan Schakowsky, and Toni Preckwinkle have all endorsed her, and she belatedly got the Girl, I Guess endorsement as well.

Ward 45 (Jefferson Park, Irving Park)

Jim Gardiner (i) vs. Susanna Ernst vs. Megan Mathias vs. Ana Santoyo vs. James Suh vs. Marija Tomic

Jim Gardiner was elected as the reactionary, white suburban backlash candidate before it was cool—2019. He took down Ald. John Arena in an upset, with backing from the cop unions and running on a platform that you would recognize as what every conservative cottoned onto in the post George Floyd era. The old 45th was a tug of war between Irving Park, a thoroughly urban, somewhat progressive neighborhood, and, to its northwest, the much more conservative Jefferson Park. Redistricting shifted the 45th north, making it even whiter, more Republican (about ⅓, quite high for Chicago), and, of course, conservative. Despite all that, Gardiner may still lose. He is: under FBI investigation for bribery and battling a civil suit for using his position to arrest a ward resident under false pretenses, but at least the Chicago Board of Ethics investigation into him using his office to retaliate against political enemies finished because he paid the fine before the new investigation into him harassing opposing volunteers began. He’s also been in non-legal trouble as well, such as the time troves of misogynistic text messages from him were released, and he responded by apologizing to the one man he insulted, and only that one man.

In a different part of Chicago, Gardiner might be dead in the water for his behavior, but for the territory he represents we’ll merely call him vulnerable. And if you thought that the cop unions would stop contributing to him merely because he’s under investigation for actual crimes, you’d be severely mistaken. Susanna Ernst, cofounder of the Jefferson Park Neighborhood Association, presents herself moderately but is actually on board with spending more on social services and, refreshingly, doesn’t want to bring every conversation around to crime. She supported John Arena for Council and Robert Martwick for Senate, which puts her solidly on the good side of Democratic politics in this part of the city. Megan Mathias is Ernst if Ernst weren’t a bit better than she was letting on; she’s endorsed by the Chicago Tribune, Rep. Mike Quigley, and the Chicagoland Chamber of Commerce.

Ana Santoyo is something you don’t see too often in Chicago: a PSL candidate. The Party for Socialism and Liberation is a Marxist-Leninist group that split from Workers World Party during the Bush years, and is probably America’s most active communist group. They run candidates separate from Democratic Party and consistently put up a candidate for president but not necessarily local offices, perhaps going about it backwards for a party with domestic policy ideas such as a 30 hour workweek, and foreign policy ideas such as “give North Korea nukes”. If we were them, we’d just be choosing campaigns that would let us focus on the former over the latter, is all. Since Santoyo is doing that, her platform is pretty good, but it’s not going anywhere in this part of Chicago.

Business owner James Suh has the makings of a reactionary candidate as a small business owner who likes to brag about disarming a robber and carrying a gun, but his actual policy stances are much more in line with Mathais/Ernst than Gardiner, and better than Marija Tomic, the only candidate to really attempt to straddle the Gardiner lane of cops and tax cuts with the non-Gardiner stance of not being an insane asshole towards everyone she meets. 

Ward 46 (Uptown)

Angela Clay vs. Michael Cortez vs. Marianne Lalonde vs. Patrick Nagle vs. Kimberly Walz vs. Roushaunda Williams

After nearly losing to progressive scientist Marianne Lalonde in 2019, conservative Ald. James Cappleman got the message and retired this cycle. You almost have to feel a little bad for Lalonde, because despite a progressive platform and proven campaigning ability, she’s not the candidate progressives have rallied around this time. That would be housing activist Angela Clay, backed by DSA, CTU, United Working Families, the SEIU, and…you get the picture. The entire Chicago left is quite excited to elect Angela Clay. Roushaunda Williams has the support of City Clerk Anna Valencia and the more establishment-oriented wing of the labor movement, while Kim Walz has some politicians and a whole lot of money. Patrick Nagle is the most overtly conservative candidate in the race, and this is probably the wrong ward for that. Finally, Michael Cortez is a phantom candidate.

Any combination of the first four candidates could end up in a runoff; Clay is the one to root for, and if not Clay, Lalonde.

Ward 48 (Edgewater)

Joe Dunne vs. Nassir Faulkner vs. Isaac Freilich Jones vs. Brian Haag vs. Leni Manaa-Hoppenworth vs. Andre Peloquin vs. Andrew Peters vs. Larry Svabek vs. Roxanne Volkmann vs. Nick Ward 

Artist and restaurant worker Nick Ward is the final DSA-endorsed candidate running tonight, and doing so in the whiter, wealthier North Side, often tricky territory for progressives. Ward has scored two major union endorsements, CTU and SEIU, putting him in a good position to make it to the runoff, but he’s had a few bumps on the campaign trail, most notably the revelation that someone on his campaign was lying about being Latina (she was immediately let go), on top of which his fundraising has been generally meh. In other situations these setbacks would be relatively minor, but here there’s just so much competition.

Most obviously, there’s real estate developer Joe Dunne, who is backed by outgoing incumbent Harry Osterman, as well as organized labor, with the exception of the unions that are backing Ward. Former Mike Quigley staffer Nassir Faulkner is running a fairly generic campaign, seemingly without the support of Quigley, which is a little sad. Isaac Freilich Jones has the Chicago Tribune endorsement and not much else. He bills himself as a progressive without really trying to prove it, considering he’s running against a DSA endorsee. A self-proclaimed progressive who’s at least trying to back up that claim is Leni Manaa-Hoppenworth, who cofounded Indivisible Illinois, and remains active in running her local chapter to this day. She kind of, sort of, wants to defund the police a little, supports just cause eviction laws, and has serious interest in expanding public transit and the housing opportunities near it. Andre Peloquin and Larry Svabek are running liberal, but light on policy, campaigns, worrying the former’s case because he’s a realtor, and in the latter’s case because he keeps talking about how much he’s going to be using data, without devling into any specifics, rarely a good sign. Finally, three candidates are probably out of the running: Andrew Peters is fresh off getting crushed 45%-8% in an overlapping state house district, Brian Haag barely has a campaign at all, and Roxanne Volkmann simply doesn’t have any money. 

Ward 49 (Rogers Park)

Maria Hadden (i) vs. Bill Morton vs. Belia Rodriguez

Maria Hadden has been a solid progressive on the council since her landslide defeat of Ald. Joe Moore in 2019, and that landslide four years ago appears to have done a good job of warding off potential challenges from the right. Business owner Belia Rodriguez is backed by a landlord PAC, while Bill Morton is the president of the Rogers Park Chamber of Commerce, but neither appears to be putting up much of a fight; if they’re trying, it certainly isn’t showing in their fundraising.

Ward 50 (West Ridge)

Debra Silverstein (i) vs. Mueze Bawany

Debra Silverstein is one of the last moderate holdouts in the liberal eastern half of the Far North Side, representing a ward that’s more suburban than anything on the lakefront but a far cry from Jim Gardiner country. CTU member Mueze Bawany is running against her with his union’s endorsement, as well as most progressive groups; he also had Chicago DSA in his corner until he had a falling-out with the group and distanced himself from the word “socialist” entirely (after embracing it up to that point and touting DSA’s endorsement.) Weird, and sorta sounds like his fault, but ok. Still better than Silverstein, still going to be one of the best votes on the council if he wins. As one of the relatively few high-profile races to be decided tonight, this could serve as a narrative-setter if Bawany wins or if Silverstein crushes him.