A City that Works’ Guide to the 2024 November Election

Recommendations for competent governance and sensible ideas

As we hope everyone knows, we’re a few weeks away from this year’s election, and early voting is already open in Illinois. If you live in Illinois, we encourage you to vote. Strictly as a matter of principle, we think anyone who can vote should. Civic responsibility is important, and voting is a very simple part of fulfilling that responsibility.¹ Beyond that, if you’re someone willing to subscribe to a Substack about the public finance and governance challenges of Chicago, you’re more informed than the average voter - and consequently you should have a particular interest in ensuring that our institutions are governed well. Please vote.

With that said, here’s our official slate of recommendations for the races you’ll find on your ballot in Chicago. Consistent with the primary guide - and with everything else this publication stands for - by and large we are prioritizing the candidates that we view as competent, prudent, and sensible choices who will be able to govern effectively over activists and other more ideologically extreme candidates.

Moreover - as was the case last time around, please note that we’re not necessarily making a recommendation in every race. Particularly for state house and senate, there are a bunch of races between an incumbent Democrat who’s heavily favored to win and a Republican whose campaigns are varying degrees of seriousness. It’s not a valuable use of anyone’s time to go through a bunch of races which are effectively done deals. Instead, we’re choosing to focus on races we expect to be at least somewhat competitive.

As always, please feel free to reach out at citythatworksnewsletter@gmail.com with any thoughts, questions or concerns.

President: Vote Kamala Harris

We’re incredibly skeptical that this is going to move the needle for anyone in the presidential race, and there’s a good argument in favor of sticking to Chicago-based politics, given that that’s the primary focus of this newsletter. That said, there are a number of dimensions along which a Harris administration is likely better for the City of Chicago, including more federal grant money for police department spending² and building infrastructure projects like the Red Line extension. We also don’t want to leave the impression that we think there’s no difference between the candidates or that you should do something stupid like leaving that section blank. At any rate, we will both be voting for Kamala Harris.

State’s Attorney: Vote Eileen O’Neill Burke

The race to replace Kim Foxx as Cook County’s chief prosecutor is likely the highest profile countywide race on the ballot. Eileen O’Neill Burke, our recommendation in the Democratic Primary in March, narrowly defeated Clayton Harris III to win the Democratic nomination, and is now facing Republican nominee Robert Fioretti and Libertarian Andrew Charles Kopinski. We still think Eileen O’Neill Burke is the right choice.

We have a weird soft spot for Bob Fioretti, a former alderman with a strong independent streak who wasn’t afraid to speak truth to power under Mayors Daley and Emanuel. For his troubles, his ward was split up into seven new wards in the 2010 redistricting map, and after not running for reelection in 2015 he’s become somewhat of a perennial candidate for office³. We admire a lot of Fioretti’s time as alderman - we really do - but that kind of perennial candidacy doesn’t really seem like someone who’s particularly passionate about the State’s Attorney’s office in particular. While we don’t really love to judge attorneys by the cases they take, we have to admit we’re also a bit perturbed by his choice to represent Dolton Mayor Tiffany Henyard, who’s currently under federal investigation for corruption and other misconduct, in her 2022 fight against a recall election (he won, for what it’s worth).

O’Neill Burke’s experience as a former prosecutor, judge and defense attorney strikes us
as a much better resume for State’s Attorney. We want a candidate who we trust can hit the ground running from day one, and we think it’s clear she can do that. We still like her emphasis on rebuilding and retaining talent in the state’s attorney’s office, cracking down on felony gun charges and getting more serious about public safety. Vote for O’Neill Burke.

Chicago School Board

Now to the meaty part. We just recently covered a lot of the chaos going on at CPS and the Chicago school board. In the wake of all that, it’s time to elect half the board for the first time in CPS history.

Among their many duties, this is the body which is responsible for negotiating the collective bargaining agreement with the Chicago Teachers’ Union (CTU). Mayor Johnson, of course, was an organizer with the CTU prior to entering public office, he’s remained a strong ally of the CTU as an elected official and the CTU was one of his largest donors to his mayoral campaign. The CTU has also made endorsements and donations to candidates in all ten races for board seats this November.

Collective bargaining is an important process. We think it’s remarkably dangerous that Chicago could be left in a position where the teachers’ union is bargaining against a board of members who are primarily funded and elected by - or appointed by - the union itself. At best, that seems like a dangerous conflict of interest; at worst, it’s a dynamic ripe for the taxpaying public to get ripped off.

Eleven members of the incoming board are set to be appointed by Mayor Johnson, and we’d expect those eleven to be broadly sympathetic with whatever the CTU would like to do. Given that, for the ten elected seats we view it as an imperative to elect independent, reform-minded candidates whom taxpayers can trust to serve as a strong check on the CTU. As such, we view a CTU endorsement as absolutely disqualifying and would urge voters to choose someone else. That’s the first layer of logic which informs the recommendations below.

District 1 - Vote for Michelle Pierre

School Board District 1 is on Chicago’s Northwest side, consisting of Edison Park, Portage Park, Jefferson Park, and Norwood Park. Jennifer Custer and Michelle Pierre are the two candidates for office. Custer is a current CPS parent and former teacher (and assistant principal) in Wisconsin and the Chicago suburbs (she is currently a stay-at-home mom). Pierre is also a current CPS parent and taught in New York City before becoming a principal in Washington, D.C., the Chief Academic Officer at Cleveland Metro Schools, and the chief of schools at the LEARN Charter School Network in Chicago.

Custer is the CTU-backed candidate in this race, and while we don’t otherwise have too many issues with Custer, we particularly like Pierre’s long tenure of experience on the administration side, which we think would serve us well on the school board. We also prefer appreciate Pierre’s response to the Sun-Times question on property taxes, where she specifically advocates to only turn to property tax hikes as a last resort (instead of raising by the maximum amount allowed by law each year, as CPS has done for many years - and as Custer favors). Vote for Pierre.

District 2 - Vote for Kate Doyle

District 2 stretches from the North Lakefront to the Far North Side, covering Lincoln Square, Ravenswood, Peterson Park, Budlong Woods, Andersonville, Rogers Park and West Ridge. Four candidates are running: Ebony DeBerry, Maggie Cullerton Hooper, Bruce Leon, and Kate Doyle. DeBerry is the CTU candidate in the race. Cullerton Hooper seems to have staked out ground adjacent to DeBerry - including committing to maximal property tax hikes, and equivocating on support for selective enrollment schools. 

With three non-CTU backed candidates in this race, we’re a bit worried about a vote split between multiple candidates resulting in DeBerry getting elected. While Leon would bring some needed financial experience and is endorsed by the Tribune, he was a late entry to the race, doesn’t have a campaign website, and hasn’t raised any external money. That makes us a bit worried about how broad support is for his campaign. 

Doyle, on the other hand, seems like a candidate well-suited to win votes from these progressive neighborhoods and is working hard for your vote. She has a policy platform that’s strong on the basics and includes items like safer streets for kids biking and walking near schools, while still emphasizing independence from the CTU. She’s been endorsed by a number of local representatives including Ald. Andre Vasquez (40th) and has come out against efforts by the Mayor to force out current CPS CEO Pedro Martinez. Vote for Doyle.

District 3 - vote for Carlos Rivas 

District 3 is a mostly Hispanic district on the northwest side covering Humboldt Park, Logan Square, Hermosa, Avondale, and Belmont Cragin. This is a head-to-head race between Jason Dónes and Carlos Rivas, both lifelong residents of Humboldt Park. Dónes is a former teacher and current executive at an en education startup. He’s the CTU-backed candidate (per CBS this week, 98% of his campaign’s funds have come from the CTU), and has stated his support for the current board’s decision to deprioritize selective enrollment, magnet, and charter schools in the CPS system. 

Rivas is also a former CPS teacher and currently works for the city’s Civilian Office of Police Accountability (COPA). His platform is more supportive of CPS’s selective enrollment schools, he’s opposed the CTU’s efforts to get CPS CEO Pedro Martinez fired, and he’s also talked about the importance of board independence from the CTU. He’s the right choice. Vote for Rivas. 

District 4 - vote for Ellen Rosenfeld

District 4 covers much of the North Side, including Old Town, Lincoln Park, Lake View, and part of Uptown. It’s also home to the most crowded field, with six candidates running for the seat. Retired CPS teacher Karen Zaccor is the CTU-endorsed candidate and her platform seems largely lockstep with the union’s views. 

Of the other five, Ellen Rosenfeld is the clear choice. She’s a former CPS teacher and current CPS staffer. She has a clear, strong platform around fiscal responsibility and improving CPS schools. Her campaign has has the best financial resources of any candidate, and she has a really strong endorsement list, including the Tribune and five different northside aldermen (Lawson, Knudsen, Martin, Hopkins, and Silverstein), among many others. That sort of institutional support seems really important in what’s likely the most expensive and competitive of any of these ten races. Vote for Rosenfeld. 

District 5 - write in Jousef Shkoukani 

This district covers most of the West Side, including Austin, Garfield Park, the West Loop, and parts of West Town. The only candidate on the ballot is CTU-backed Aaron “Jitu” Brown. 

Attorney Jousef Shkoukani filed as a write-in candidate - his name won’t appear on the ballot, but he’s eligible to receive votes if you write in his name. He supports Pedro Martinez and his candidacy highlights independence from the CTU and better fiscal management. While we don’t expect a write-in to win, we still think it’s worth writing in Jousef Shkoukani. 

District 6 - vote for Jessica Biggs 

This District runs from Wicker Park over into River North/downtown and then south to Englewood, Grand Boulevard, Washington Park and part of Woodlawn. Anusha Thotakura is the CTU candidate. Andre Smith is a perennial candidate. 

Biggs is the real deal - she’s a former CPS principal with a detailed platform, and has come out hard against the proposed $300M high-interest loan floated by the mayor. It’s not surprising that she’s been endorsed by everyone from Ald. Jeanette Taylor (20th) to Cook County Board Chair Toni Preckwinkle to the Tribune Editorial Board. Biggs deserves your vote. 

District 7 - vote for Eva Villalobos

Three candidates are running in District 7, a predominantly Hispanic district on the Southwest Side encompassing Pilsen, Little Village, Brighton Park, Archer Heights, and parts of Bridgeport and Chinatown. Yesenia Lopez, currently an executive assistant in the Illinois Secretary of State’s office, is the CTU-backed candidate, and doesn’t strike us as particularly impressive, with no background in education or public management. Of the two alternatives, Eva Villalobos’s candidacy seems more solid, with broad enough support to win. She’s a former accountant and has advocated for a full audit of the CPS budget as a first step towards better financial management. Vote for Villalobos. 

District 8 - vote for Angel Gutierrez

This predominantly Hispanic district runs all the way from the western half of the Loop down through Bridgeport and Back of the Yards, then over around Midway Airport and down around Chicago Lawn/Ashburn. 30 year old music teacher Felix Ponce is the CTU-backed candidate. He’s running against Angel Gutierrez, a nonprofit consultant with over 25 years of nonprofit management whose platform emphasizes better board transparency and responsible financial management. Gutierrez’s experience strikes us as a much better fit for the board. Vote for Gutierrez. 

District 9 - vote for Miquel Lewis

This is a majority black district on the South side, running south from Englewood all the way down to Beverly and Mount Greenwood. Four candidates are running, which again makes us concerned about a vote split between the non-CTU options. 

Lanetta Thomas is the CTU candidate. Of the other three, Miquel Lewis seems the most legitimate and electable candidate. He’s a current Beverly resident who grew up in Englewood and actually has previous board experience, having served on the Chicago Board of Education under Mayor Lightfoot. He’s also chairman of the board of directors for the NOBLE Network of Charter Schools, which are consistently some of the best performing charters schools in the CPS system. That background seems pretty ideal! 

The two other candidates are La’Mont Raymond Williams and Therese Boyle. Williams is currently the chief of staff to County Commissioner Bill Lowry, and we don’t see much about his candidacy that stands out. Boyle has a more compelling background - she was a CPS teacher on the South Side for 35 years -  and she was endorsed by the Tribune, but we’re a bit concerned about how viable her campaign is (she’s largely self-funded her campaign and has very little cash on hand compared to the other candidates). That, coupled with Lewis’s compelling resume, is enough to tip the scales for us. Vote for Miquel Lewis.

District 10 - vote for Karin Norington-Reaves

This district covers a large portion of the South Side, running from Bronzeville to the city limits. Four candidates are running. Pastor Robert Jones is the CTU candidate. Adam Parrott-Sheffer is a former principal and education expert with strong credentials, but not a lot of political support. Che “Rhymefest” Smith is a recording artist and community activist. 

Karin Norington-Reaves is by far the right choice. She began her career as a bilingual teacher with Teach For America. Since then, she’s spent 30 years in public service. Most recently she served as the founding CEO of the Chicago Cook Workforce Partnership, a truly impressive non-profit that has helped more than 100,000 Chicagoland residents find permanent employment. Now she’s running for school board, and has taken a firm stance against high-interest loans and cuts to selective enrollment schools. For her trouble, the CTU is smearing her with guilt-by-association mailers that accuse her of being connected to Project 2025:

Please ignore their nonsense, and vote for Norington-Reaves. 

Judicial Retention

This is consistently one of the weirdest and most annoying parts of the ballot. If you’re a judge in Cook County, once elected to office you no longer face challengers. Instead, every six⁴ or ten⁵ years you face a simple yes/no vote from the public on whether you should get to keep your job. Judges need 60% yes votes to keep their seat.

There are a lot of judges up for retention, so I’ll try to keep this brief, with a recommendation for each but commentary only where needed. Note that the below order should match the order in which they’ll appear on your ballot (I’ve included the relevant ‘punch numbers’ as well).

201 - Appellate Court - Thomas E. Hoffman - YES

203 - Appellate Court - David W. Ellis - YES

206- Circuit Court - Kathy M. Flanagan - NO

• Flanagan is one of five judges not recommended for retention by the Illinois State Bar Association. Earlier this year, misconduct accusations against Flanagan were referred to the Judicial Inquiry Board after she had an attorney in her courtroom handcuffed to a chair (and had yelled to a courtroom deputy to “take him”). Call us old-fashioned, but that strikes us as the sort of behavior we should discourage from our judges.

207 - Circuit Court - Stuart F. Lubin - YES

209 - Circuit Court - Martin S. Agran - YES

211 - Circuit Court - Ronald F. Bartkowicz - YES

214 - Circuit Court - E. Kenneth Wright - NO

• Wright is one of five judges not recommended for retention by the Illinois State Bar Association. Illinois law requires judges to live in the jurisdictions they serve (in this instance, Cook County). Wright, however, has claimed a homestead exemption on the home he owns in Will County since 1978, which would make him ineligible (homestead exemptions are reserved for a property owner’s primary dwelling place). He hasn’t offered any explanation for this discrepancy.

215 - Circuit Court - James M. Varga - YES

217 - Circuit Court - Mary Margaret Brosnahan - YES

220 - Circuit Court - Maura Slattery Boyle - NO

• In 2018, Boyle was one of three judges that the Tribune recommended a vote against for retention. Earlier this year, the Sun-Times reported that the IRS filed a lien against Boyle and her husband for over $114,000 in back taxes. The Sun-Times also noted that the Boyles have been named in four lawsuits regarding properties they own (three by the City of Chicago regarding code violations, plus one by a bank regarding mortgage delinquency).

221 - Circuit Court - Carl Anthony Walker - YES

223 - Circuit Court - Daniel Patrick Brennan - YES

225 - Circuit Court - Ellen L. Flannigan - YES

227 - Circuit Court - Carol M. Howard - YES

229 - Circuit Court - Jill C. Marisie - YES

231 - Circuit Court - Mike McHale - YES

233 - Circuit Court - James Patrick Murphy - YES

235 - Circuit Court - Ramon Ocasio III - YES

237 - Circuit Court - Mary Colleen Roberts - YES

239 - Circuit Court - Celia Louise Gamrath - YES

241 - Circuit Court - Tommy Brewer - YES

243 - Circuit Court - Erica L. Reddick - YES

245 - Circuit Court - Lionel Jean-Baptiste - YES

247 - Circuit Court - Michael R. Clancy - YES

249 - Circuit Court - Regina Ann Scannicchio - YES

251 - Circuit Court - Diann Karen Marsalek - YES

254 - Circuit Court - Carl B. Boyd - NO

• In 2022, Boyd was charged with domestic battery after a woman suffered a large cut to her face after an incident in which he threw a bottle at a glass door window. The woman later decided not to pursue the case and charges were dropped.

255 - Circuit Court - Daniel R. Degnan - YES

257 - Circuit Court - John H. Ehrlich - YES

259 - Circuit Court - Terry Gallagher - YES

261 - Circuit Court - William G. Gamboney - YES

263 - Circuit Court - Elizabeth Mary Hayes - YES

265 - Circuit Court - Martin C. Kelley - YES

267 - Circuit Court - Kimberly D. Lewis - YES

269 - Circuit Court - Aicha Marie MacCarthy - YES

272 - Circuit Court - Lisa Ann Marino - NO

• Marino is one of five judges not recommended for retention by the Illinois State Bar Association, noting that “A majority [of attorneys surveyed] did raise concerns over her courtroom management skills and with the extent of her legal knowledge and ability.”

273 - Circuit Court - Michael Tully Mullen - YES

275 - Circuit Court - Karen Lynn O’Malley - YES

277 - Circuit Court - Paul S. Pavlus - YES

279 - Circuit Court - Cynthia Ramirez - YES

282 - Circuit Court - Beatriz Santiago - NO

• Santiago received a censure from the Illinois Courts Commission this year when they found her to have knowingly deceived her mortgage lender about where she lives. When running for office in 2012, she testified that she lived with her parents within the boundaries of the 6th subcircuit; when she refinanced on a home outside of the 6th subcircuit a few months after the election, she reported that home as her primary residence.

283 - Circuit Court - Clare Joyce Quish - YES

285 - Circuit Court - Stephanie Saltouros - YES

287 - Circuit Court - Kent Delgado - YES

289 - Circuit Court - Cecilia Anne Horan - YES

291 - Circuit Court - Joanne F. Rosado - YES

293 - Circuit Court - Toya T. Harvey - YES

295 - Circuit Court - Adrienne Elaine Davis - YES

297 - Circuit Court - H. Yvonne Coleman - YES

299 - Circuit Court - Debra A. Seaton - YES

301 - Circuit Court - David R. Navarro - YES

303 - Circuit Court - Marian Emily Perkins - YES

305 - Circuit Court - Robert Harris - YES

307 -Circuit Court - Preston Jones - YES

309 - Circuit Court - Peter Michael Gonzalez - YES

311 - Circuit Court - Jeanne Marie Wrenn - YES

313 - Circuit Court - Michael B. Barrett - YES

315 - Circuit Court - Tiana Ellis Blakely - YES

317 - Circuit Court - Joel Chupack - YES

319 - Circuit Court - Elizabeth Ciaccia-Lezza - YES

321 - Circuit Court - Kevin Patrick Cunningham - YES

323 - Circuit Court - Colleen Reardon Daly - YES

325 - Circuit Court - Beatriz A. Frausto-Sandoval - YES

328 - Circuit Court - Ieshia Gray - NO

• Gray is one of five judges not recommended for retention by the Illinois State Bar Association, and is currently under investigation by the Illinois Judicial Inquiry Board regarding an attorney’s accusation of bias and unfair treatment.

329 - Circuit Court - Jack Hagerty - YES

331 - Circuit Court - Lindsay Huge - YES

333 - Circuit Court - Kathaleen Theresa Lanahan - YES

335 - Circuit Court - Thomas F. McGuire - YES

337 - Circuit Court - Scott McKenna - YES

340 - Circuit Court - Shannon O'Malley - NO

• O’Malley is one of five judges not recommended for retention by the Illinois State Bar Association. O’Malley and his wife currently claim a homestead exemption on their home in Will County, which would make him ineligible to serve as a judge in Cook County. He has stated that he has lived in Cook County apart from his wife since 2017. In another odd note, O’Malley was previously named Phillip Spiwak prior to legally changing his name in 2012 (potentially because Irish names have typically performed better in Chicago elections). While we’re recommending a No vote, we do respect the hustle.

341 - Circuit Court - Erika Orr - YES

343 - Circuit Court - Linda Perez - YES

346 - Circuit Court - James "Jamie" Shapiro - NO

• In 2021, Shapiro was involved in controversy over his decision to remove a mother’s child custody rights because she wasn’t vaccinated against COVID-19. Per the Sun-Times, in 2018 he was also alleged to have boosted a ‘sham candidate’ to split the women vote in the race for the open judicial seat he won.

347 - Circuit Court - Tom Sam Sianis - YES

349 - Circuit Court - Rosa Maria Silva - YES

351 - Circuit Court - Kathryn Maloney Vahey - YES

353 - Circuit Court - Andrea Michelle Webber - YES

355 - Circuit Court - Arthur Wesley Willis - YES

Referenda and Local Options

For this election, all referenda and local options on your ballot are strictly advisory and don’t have any actual bearing on policy. They gauge public support for various things, but none of them concretely matter at all.

These questions cover topics including taxpayer subsidies for a new Bears stadium, a CBA to help local residents near the Obama center, opening mental health clinics on the southwest side, and requiring CPS schools in the 16th ward (largely Englewood) to have extracurriculars including “baseball, softball, flag football, track, band, and choir.” With the exception of taxpayer funding for stadiums - which remains a terrible idea - because they’re only advisory, we haven’t studied any of these issues in any sort of depth. We generally think mental health clinics seem like a good idea, the CBA seems too anti-development, and think that school administrators are probably better suited than voters to decide what programs best fit into their schools’ budgets.

1. As was the case for the primaries, a genuine offer again: if you aren’t sure if you’re registered, or don’t know how to vote, please feel free to reach out at citythatworksnewsletter@gmail.com and Conor will personally help you figure out how to do it. No excuses.

2. In 2023, about $168 million (or just under 10% of the city’s police budget) came from federal grants.

3. A brief electoral history: Fioretti ran for mayor in 2015, County Board President in 2018 (as a Democrat), Mayor in 2019, and State’s Attorney in 2020 (again as a Democrat). After going 0-for-4, he then changed his party registration in 2022 to run again for County Board President as a Republican, and is following it up with this campaign for State’s Attorney.

4. For Circuit Court judges

5. For Appellate Court judges