2023 Chicago City Council Elections Preview Part Two
North side brawls!
Howdy everyone, Uncrewed here! Yesterday, we took a look at the first 25 Chicago City Council elections taking place this year. Now, we’re finishing things up with the final 25! Let’s get into it!
26th Ward:
Location: Humboldt Park area (northwestern Chicago)
Demographics: 67% Hispanic, 21% White, 12% African-American
With incumbent Alderman Roberto Maldonado retiring, three candidates have emerged to replace him: businessman/radio DJ Julian “Jumpin” Perez (who is a real mainstay on Chicago radio, having been a radio personality since the 80s), community organizer Jessie Fuentes, and 26th Ward Committeewoman Angee Gonzalez Rodriguez.
Perez enjoys the backing of the Chicago Tribune and the Fraternal Order of Police, Fuentes is backed by several local unions, Alderman Maldonado, and IL-03 Congresswoman Delia Ramirez, and Rodriguez is backed by 27th Ward Alderman Walter Burnett. This one’s going to be close between Fuentes & Perez, but I think Rodriguez takes just enough of the vote to force a second round between Fuentes & Perez.
27th Ward:
Location: Humboldt Park to Cabrini-Green (central Chicago)
Demographics: 49% African-American, 29% White, 15% Hispanic
Incumbent Alderman Walter Burnett is not facing any opponents and has secured another four year term on the City Council.
28th Ward:
Location: Garfield Park to University Village (western to central Chicago)
Demographics: 74% African-American, 11% Hispanic, 9% White
Incumbent Alderman Jason Ervin is only facing one opponent in his bid for a fourth term, construction consultant Shawn Walker. That’s only a recent development by the way, as Walker was initially thrown off the ballot and had to appeal to the courts to get back on, only getting back on the ballot about a week ago. Even without the ballot mess, Walker hasn’t really run a strong campaign, so Ervin’s the overwhelming favorite to win re-election.
29th Ward:
Location: Western Austin area (western Chicago)
Demographics: 65% African-American, 22% Hispanic, 12% White
Incumbent Alderman Chris Taliaferro is facing two challengers in his bid for a third term: community organizer Corey Dooley and nonprofit executive CB Johnson. Neither Dooley or Johnson have made that much noise, so Taliaferro is well positioned to win on Tuesday.
30th Ward:
Location: Belmont-Cragin to Irving Park (northwestern Chicago)
Demographics: 58% Hispanic, 33% White, 6% Asian
With incumbent Alderman Ariel Reboyras not running after nearly 20 years on the City Council, four candidates are running to replace him: community organizer Jessica Gutierrez (who is also the daughter of former IL-04 Congressman Luis Gutierrez), Chicago Transit Authority official Juan Pablo Prieto, Roosevelt University official Ruth Cruz, and progressive activist Warren Williams.
Gutierrez is backed by IL-05 Congressman Mike Quigley, Illinois Secretary of State Alexi Giannoulias, and several local unions, while Williams has been endorsed by the Chicago DSA and State Senators Robert Martwick and Robert Peters. Gutierrez should win this one outright on Tuesday, but I’d keep an eye out for Williams, who seems to be attracting a good amount of progressive attention in this area, which has been more open to electing more left-wing politicians as of late.
31st Ward:
Location: Hermosa area (northwestern Chicago)
Demographics: 77% Hispanic, 16% White, 5% African-American
Incumbent Alderman Felix Cardona is gunning for a second term, but first he has to get through real estate broker Esteban Burgoa Ontanon. Ontanon hasn’t really attracted that much attention, so Cardona is probably going to win easily.
32nd Ward:
Location: Bucktown area (northern Chicago)
Demographics: 74% White, 11% Hispanic, 9% Asian
Incumbent Alderman Scott Waguespack is not facing any opponents and has secured another four year term on the City Council.
33rd Ward:
Location: Albany Park area (northwestern Chicago)
Demographics: 50% Hispanic, 31% White, 12% Asian
Incumbent Alderwoman Rossana Rodriguez Sanchez, a Democratic Socialist, is running for a second term. She’s facing two challengers: businessman Laith Shaaban and political aide Samie Martinez. Sanchez is backed by Governor JB Pritzker and the Chicago Teachers Union, while Martinez is backed by the Fraternal Order of Police and IL-04 Congressman/Mayoral candidate Chuy Garcia. In a bit of a revenge move following Sanchez unseating an incumbent in 2019, the political machine here is lining up behind Martinez and it may be enough to force Sanchez into a second round matchup with him. I think that’ll end up happening with Sanchez being the prohibitive favorite.
34th Ward:
Location: Greektown/The Loop (central Chicago)
Demographics: 57% White, 25% Asian, 9% African-American
Incumbent Alderwoman Carrie Austin had her district destroyed in redistricting, with her district shifting from a majority-African-American southwest side one to a majority-white district in The Loop. As such, she retired, and two candidates are running in this newly-drawn district: Cook County State’s Attorney Prosecutor Bill Conway (who you may remember from running against Kim Foxx in 2020) and Chicago Association of Realtors President Jim Ascot. Nearly the entire political establishment has lined up behind Conway, with Governor Pritzker, US Senators Tammy Duckworth & Dick Durbin, and the Chicago Tribune lining up behind him. As such, he’s the heavy favorite to win against Ascot.
35th Ward:
Location: Logan Square/Avondale area (northwestern Chicago)
Demographics: 53% Hispanic, 36% White, 6% African-American
Incumbent Alderman Carlos Ramirez-Rosa, a Democratic Socialist, is not facing any challengers and has secured another four year term on the City Council.
36th Ward:
Location: Montclare to Ukrainian Village (northwestern Chicago)
Demographics: 56% Hispanic, 33% White, 8% African-American
Incumbent Alderman Gilbert Villegas, who you may remember from his unsuccessful run for IL-03 last year, is running for a third term. He first has to get through three challengers though: teacher Lori Torres Whitt, community organizer David Herrera, and Humboldt Park Advisory Council President Jacqueline Baez, who was actually just arrested a few days ago for writing bad checks that total up to $7,000.
Villegas is backed by Governor Pritzker, US Senators Tammy Duckworth & Dick Durbin, and IL-04 Congressman/Mayoral candidate Chuy Garcia and Whitt is backed by IL-03 Congresswoman Delia Ramirez, Cook County Commissioner/Mayoral candidate Brandon Johnson, and the Chicago Teachers Union. This one’s probably going to a runoff between Villegas and Whitt, which Villegas should be the small favorite in.
37th Ward:
Location: Eastern Austin area (western Chicago)
Demographics: 67% African-American, 33% Hispanic
Longtime incumbent Alderwoman Emma Mitts is facing three challengers in her bid for a sixth term: Chicago city official Howard Ray, teacher Jake Tower, and police officer Corey Braddock.
Mitts is backed by Governor Pritzker, while Ray is backed by the Fraternal Order of Police and the Chicago Tribune. I expect Mitts to win this one, whether it be on Tuesday or in April. If she does have to go to a second round, I think Ray’s going to be the one joining her there.
38th Ward:
Location: Dunning/Portage Park area (northwestern Chicago)
Demographics: 57% White, 34% Hispanic, 7% Asian
Incumbent Alderman Nicholas Sposato, who’s become really well-known for his, um, controversial statements about race & LGTBQ issues (questioning why African-Americans traveled to the northwest side of the city during an Aldermanic meeting and saying that he identified as a vaccinated person) is running for his fourth term on the City Council. He has to get through four challengers first though: community organizer Ed Bannon, Illinois Pollution Control Board member Cynthia Santos, software engineer Franco Reyes, and truck driver Bruce Randazzo.
Sposato is backed by the Fraternal Order of Police (which is somewhat big here as a lot of police officers live in this part of northwestern Chicago) and Bannon is backed by the Chicago Tribune and State Representative Will Guzzardi. Sposato should win, but if his controversial statements finally catch up to him, I expect Bannon to force him into a second round matchup.
39th Ward:
Location: North Park area (northern Chicago)
Demographics: 50% White, 24% Hispanic, 21% Asian
Incumbent Alderwoman Samantha Nugent faces businesswoman Denali Dasgupta in her bid for a second term. Nugent is backed by Governor Pritzker, the Fraternal Order of Police, and US Senator Dick Durbin, while Dasgupta is backed by the Chicago Teachers Union and IL-03 Congresswoman Delia Ramirez. Nugent is the favorite here, but Dasgupta has racked up some impressive endorsements.
40th Ward:
Location: Lincoln Square area (northern Chicago)
Demographics: 48% White, 22% Hispanic, 19% Asian, 11% African-American
Incumbent Alderman Andre Vasquez, a Democratic Socialist, is facing two challengers in his bid for a second term: attorney Christian Blume and community organizer Jane Lucius. Lucius has the backing of the Fraternal Order of Police, but neither her or Blume have been able to muster much of a campaign. Vasquez is heavily favored on Tuesday.
41st Ward:
Location: Norwood Park/O’Hare Airport area (northwestern Chicago)
Demographics: 74% White, 14% Hispanic, 9% Asian
Incumbent Alderman Anthony Napolitano is running for his third term on the City Council, but he first has to get through attorney Paul Struebing. Struebing has attracted some impressive endorsements, earning the backing of several local unions and the Chicago Tribune. However, Napolitano is backed by the Fraternal Order of Police (which is big in a cop-heavy district like this) and the Firefighters Union. Napolitano should win again easily, keeping his claim of the most recent Republican to win a Chicago City Council election alive (though he is an Independent now, he was a Republican for years, which makes sense in this district that barely voted for Biden).
42nd Ward:
Location: Downtown Chicago
Demographics: 70% White, 17% Asian, 7% Hispanic
Incumbent Alderman Brandon Reilly is not facing any challengers and has secured another four year term on the City Council.
43rd Ward:
Location: Lincoln Park/Gold Coast area (northern Chicago)
Demographics: 79% White, 9% Asian, 7% Hispanic
Appointed incumbent Alderman Timmy Knudsen is running for a full term after being appointed back in September. He has to get through five challengers though: businessman Steve Botsford, businesswoman Wendi Taylor Nations, Sheffield Neighborhood Association President Brian Comer, attorney Rebecca Janowitz, and businessman Steve McClellan.
Knudsen is backed by Illinois Secretary of State Alexi Giannoulias and Chicago City Clerk Anna Valencia, Botsford is backed by the Fraternal Order of Police, Nations is backed by former Alderwoman Michele Smith (who preceded Knudsen on the City Council), and Comer is backed by the Chicago Tribune. This one’s going to be really close. I think ultimately though, Knudsen advances to a runoff with either Nations or Botsford. If I had to choose between the two, I’d say Nations joins Knudsen.
44th Ward:
Location: Wrigleyville area (northern Chicago)
Demographics: 77% White, 10% Asian, 8% Hispanic
Political Aide Bennett Lawson is not facing any challengers and has won his first term on the City Council.
45th Ward:
Location: Jefferson Park area (northwestern Chicago)
Demographics: 59% White, 26% Hispanic, 11% Asian
Incumbent Alderman Jim Gardiner is running for a second term, but faces five challengers in his quest to do so: environmentalist attorney Megan Mathias, businessman James Suh, community organizer Susanna Ernst, businesswoman Marija Tomic, and socialist activist Ana Santoyo.
Gardiner is backed by the Fraternal Order of Police, Mathias is backed by IL-05 Congressman Mike Quigley and the Chicago Tribune, and Suh is backed by State Representative Theresa Mah. Let’s get one thing out of the way before I make my prediction, Gardiner is a walking controversy magnet. In his four years on the Council, Gardiner has:
Been accused of abusing his power for having an innocent man arrested for supposedly stealing a phone (which the man just found, didn’t steal it at all)
Been investigated by the feds for taking bribes
Sent text messages to fellow Alderman Scott Waguespack calling Waguespack’s Chief of Staff (a woman), “Waguespack’s b*tch”
So, yeah, a lot of terrible things to do in just four years. As such, I doubt he gets out of this year without at least facing a second round runoff. If he does advance to the second round, I expect Mathias to join him.
46th Ward:
Location: Uptown area (northern Chicago)
Demographics: 56% White, 20% African-American, 12% Hispanic
With incumbent Alderman James Cappleman retiring, six candidates are running to replace him: political aide Kim Walz, community organizer Angela Clay, union organizer Roushaunda Williams, environmentalist Marianne Lalonde, judge Patrick Nagle, and real estate agent Michael Cortez.
Walz is backed by Governor Pritzker, US Senator Dick Durbin, and IL-05 Congressman Mike Quigley, Clay is backed by the Chicago Teachers Union and 47th Ward Alderman Matt Martin, Williams is backed by Chicago City Clerk Anna Valencia and several local unions, and Lalonde is backed by IL-04 Congressman/Mayoral candidate Chuy Garcia. This one’s definitely going to a second round, probably between Walz and either Clay, Williams, or Lalonde. If I had to guess, I’d say Clay joins Walz in April.
47th Ward:
Location: Ravenswood area (northern Chicago)
Demographics: 72% White, 13% Hispanic, 9% Asian
Incumbent Alderman Matt Martin is not facing any challengers and has secured another four year term on the City Council.
48th Ward:
Location: Edgewater area (northern Chicago)
Demographics: 54% White, 16% African-American, 16% Asian
With incumbent Alderman Harry Osterman retiring, an astounding 10 candidates have emerged to replace him: businessman Joe Dunne, community organizer Nick Ward, real estate agent Andre Peloquin, political scientist Larry Svabek, businessman Andy Peters, businesswoman Leni Manaa-Hoppenworth, attorney Isaac Freilich-Jones, Illinois State Government official Nassir Faulkner, progressive activist Brian Haag, and political aide Roxanne Volkmann.
Dunne is backed by Alderman Osterman and several local unions, Ward is backed by the Chicago Teachers Union and the Democratic Socialists of America, Manaa-Hoppenworth has been endorsed by State Representative Theresa Mah, and Freilich-Jones is backed by the Chicago Tribune. This one’s definitely going to a second round, probably between Dunne and Ward.
49th Ward:
Location: Rogers Park area (northeastern Chicago)
Demographics: 39% White, 29% African-American, 23% Hispanic
Incumbent Alderwoman Maria Hadden is facing two challengers in her bid for a second term: businesswoman Belia Rodriguez and businessman Bill Morton. Outside of Morton being endorsed by fellow businessman/Mayoral candidate Willie Wilson, neither candidate has attracted that much attention. Hadden is the major favorite to win on Tuesday.
50th Ward:
Location: West Ridge area (northern Chicago)
Demographics: 41% White, 28% Asian, 18% Hispanic
Incumbent Alderwoman Debra Silverstein is running for a fourth term against teacher Mueze Bawany. This one looked pretty interesting on paper a while back, with Bawany getting the endorsements of the Chicago Teachers Union and several Aldermen, but that kind of went out the window when his old tweets emerged. In these tweets, Bawany said “F*ck Israel and f*ck all you Zionist scum.” He also called someone a cracker, which led to this amazing out of context picture from a Silverstein ad:
Anyway, Silverstein should win this one on Tuesday relatively easily.
And that’s all for this preview of the 2023 Chicago City Council elections! I hope you enjoyed reading this two-part preview and I’ll be back in April to cover the runoffs. Until then, stay excellent!