Chicago’s Elections Are Feb. 26. Here’s Your Crib Sheet

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Paula Friedrich / WBEZ
Chicago Election 2019 banner
Paula Friedrich / WBEZ

Chicago’s Elections Are Feb. 26. Here’s Your Crib Sheet

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The election is coming.

And if you can follow Game of Thrones, you can follow the race to be Chicago’s next mayor. After all, both have a byzantine web of characters, dizzying plot twists, and a scandal-a-minute pace.

Mayor Rahm Emanuel sent shockwaves through Chicago politics when he announced he wouldn’t run for re-election. Now, every warm-bodied human in the city (and at least one lion) wants to replace him. (Fine, not everyone, but there are 14 friggin’ candidates.)

In addition to the mayoral race, all city-wide officials and 50 aldermanic seats will be on the ballot Feb. 26 (even the aldermen running unopposed). In races where no one gets more than 50 percent of the vote, there will be a runoff election between the top two vote-getters on April 2.

Here’s what you need to know to get ready to vote.


What’s the deal? We’re already too tired to write all the candidates’ names and titles. Just scroll up a bit.

Why should I care? By law, the mayor hand picks who gets to run the schools your kids attend, the parks you visit, the buses and trains you take to work, and maybe even your housing. By practice, the mayor’s power over the City Council – which is supposed to check him – goes nearly unchecked. The next mayor will set the city-wide agenda on the big stuff you care about (tax and fee hikes, policing, even those damned parking meters). By tradition, they are a boss whose outsized political clout provides a power to influence lots of stuff outside the official orbit.

What do I need to know? The race is super close. If you look at polls, several candidates have consistently clustered near the top: Preckwinkle, Daley, Chico and Mendoza. Sometimes, Wilson and Enyia. But in this landscape, almost anybody could rocket into contention with, say, a big endorsement from a major newspaper or a rap superstar with a huge Twitter following.

A strong anti-establishment mood from voters seems to be influencing both the policies and the horserace of the campaign. Policy-wise, the Progressive vs. Establishment line is what separates candidates on issues like how to make Chicago more affordable while also dealing with its titanic fiscal woes. Or whether to close schools. Or how to root out corruption.

On the horse track, the burgeoning corruption scandal involving longtime Machine Ald. Ed Burke (see below) has obliquely ensnared Preckwinkle and Mendoza. (They attack each other for having ties to Burke, even though they both have ties to Burke. So does Chico.) And other candidates’ placements in the six degrees of Ed Burke has become a litmus test for how Establishment they are. Daley, meanwhile, gets attacked because his name is Daley.

Upshot: The Feb. 26 final tallies could be extremely close. Your vote matters.

Want more on the mayoral race? We asked all of the candidates 20 yes or no questions. See their answers and then answer the questions yourself and see which candidate you agree with most.


What’s the deal? Two pols and a newcomer are running for this open seat: State Rep. Melissa Conyears-Ervin (D-Chicago), outgoing Ald. Ameya Pawar (47th Ward), and accountant Peter Gariepy.

Why should I care? Your wallet and a rare opportunity to choose a city treasurer in an open race. The treasurer is the city’s financial planner: They take take your tax dollars and invest them in hopes of reaping good returns so that, later, City Hall might ask you for fewer tax dollars (in theory). Also, the treasurer sits on the boards of all four city pension funds, so they’ll be a key voice in deciding what to do about Chicago’s coming pension nightmare.

What do I need to know? All candidates agree that dealing with the looming spike in required pension payments is priority No. 1. They also see the office as a tool to spur investment in low-income neighborhoods.

Pawar wants to take a more activist approach to the office, using it to promote a progressive agenda to eliminate income inequality. While on the City Council, Pawar led efforts for paid sick leave protections and universal basic income. Conyears-Ervin wants to continue the office’s push for a more environmentally-friendly investment strategy.   

The 14th Ward

What’s the deal? Ed Burke, once the City Council’s most powerful alderman, is vulnerable thanks to a corruption scandal and changing demographics. He faces two challengers on the ballot: lawyer Jaime Guzman and civil engineer Tanya Patino.

Why should I care? Burke sits at the center of the scandal that is roiling City Hall politics. What’s more, his race is emblematic of the changing demographics and political power shifts in Chicago as the Latino population grows.

What do I need to know? As the city’s longest-serving alderman, Burke epitomizes Chicago’s once-mighty Irish Machine. But now, he’s been charged with attempted extortion for allegedly abusing his power to shake down the owners of a Burger King to try and win their lucrative business for his private law firm.

Scandal aside, Burke already faced an uphill re-election fight due to his ward’s fast-growing Latino population. Both his challengers are Latino, with ties to political king/queenmaker U.S. Rep. Jesus “Chuy” Garcia. Guzman is a former Garcia aide, and Patino won the congressman’s influential endorsement. Burke, for his part, has learned to speak – and Instagram – in Spanish. Still, the head of the City Council’s Latino Caucus is hoping to fill this seat with a new Latino alderman.

Where else are similar issues/dynamics playing out? The 20th, 25th, and 30th wards.

The 25th Ward

What’s the deal? The surprise retirement of longtime Ald. Danny Solis leaves this race wide open. Five young Latinos from Pilsen are vying to represent the diverse 25th Ward: Alex Acevedo, Hilario Dominguez, Aida Flores, Troy Antonio Hernandez, Byron Sigcho-Lopez.

Why should I care?  The race to replace Solis has gotten a lot of media attention ever since he was outed as a government mole in the FBI investigation against his colleague, Ald. Ed Burke (the Viagra and massage parlor visits didn’t hurt, either). Gentrification and neighborhood development, which affects many parts of the city, are front-and-center in this ward, which covers parts of the South Loop, West Loop, Pilsen, and Chinatown.

What do I need to know? All five candidates have tried to distance themselves from Solis and the federal corruption scandal rocking City Hall, with varying success. Whoever wins will continue to face development pressures and changing demographics, as a wealthier, whiter population moves near downtown. The ward is also home to a controversial proposed mega development – The 78 – that’s in line for big money from City Hall. As the city contemplates other such gargantuan projects, look for the next 25th Ward alderman to to be a voice in how Chicago handles them.

Where else are these issues/dynamics playing out? 1st, 2nd, 35th, and 43rd wards, among others.

The 20th Ward

What’s the deal? This wide-open race on the city’s South Side is one of the most crowded aldermanic races in the city, with nine candidates on the ballot. The local interest is bolstered by neighborhood concerns over the long-term impact the Obama Presidential Center will have on the Woodlawn neighborhood.

Why should I care? This race could impact the development of the high-profile Obama project being built in Jackson Park, in the neighboring 5th Ward. The curse of the 20th Ward also casts a shadow over this race: The last three aldermen who’ve held this seat, including the outgoing incumbent, have attracted the attention of federal corruption investigators.

What do I need to know? Thanks to the unwritten rule of “aldermanic prerogative,” which gives aldermen unfettered control over development their wards, candidates in the race could force concessions like a community benefits agreement to address concerns over displacement. Jeanette Taylor, known for leading the 34-day hunger strike at Dyett High School, is advocating for a CBA, as is Nicole Johnson, a self-described “community development  consultant.”

The newly elected Democratic Committeeman Kevin Bailey has a natural advantage in race, as it’s his job to staff the polls on election day. Other candidates: CPD veteran Jennifer Maddox; local business owner Andre Smith, 25-year-old Anthony Driver; lawyer Dernard Newell; lawyer Quandra Speights; and activist Maya Hodari.

Where else are these issues/dynamics playing out? 5th Ward.

The 30th Ward

What’s the deal? Ald. Ariel Reboyras has been on the Council since 2003, and is one of Chicago’s longest serving Latino alderman. He is facing two young challengers: 31-year-old Jessica Washington Gutierrez, the daughter of former Congressman Luis Gutierrez, and 23-year-old college student Edgar ‘Edek’ Esparza.

Why should I care? This race will help shape the future of Chicago political power. There’s a movement of young Latinos running for elected office in Chicago, and these dynamics –a young progressive versus an establishment Democrat – are at center stage in the 30th Ward. The number of Latinos in City Council will be significant when aldermen redraw the political map after the 2020 census.

What do I need to know? While Reboyras has a strong record of delivering services to his constituents, he’s also criticized for being a “rubber stamp” for Emanuel. He chaired the City Council Public Safety Committee during the release of the dashcam video of the Laquan McDonald murder, which put him at the fore of the city’s police reform efforts. Meanwhile, Gutierrez sees her base as younger millennials, white progressives, and Mexicans in the area who have long supported her father. She supports increasing the minimum wage to $15 an hour, legalizing marijuana, and an elected school board. Esparza’s message to voters is that he’s the only true independent in the race and will focus mostly on constituent services and reducing crime and corruption.

While the 30th Ward is mostly Latino, there’s a strong Polish immigrant population, and a growing number of younger, whiter residents that have moved north along the gentrifying Milwaukee Avenue corridor. The voting dynamics of this ward could make this race a close one and a top contender for a runoff.

Where else are these issues/dynamics playing out? 12th, 14th, 15th, 22nd, 25th, and 31st wards.

The 40th Ward

What’s the deal? Incumbent Ald. Pat O’Connor, Mayor Rahm Emanuel’s City Council floor leader, has represented this North Side ward since 1983, making him the city’s second-longest-serving alderman. He faces four challengers, all young and politically active.

Why should I care? Because how this race turns out could tell you whether Chicago voters are (or aren’t) ready for reform. O’Connor could be vulnerable, and the defeat of such a powerful politician, absent an active public scandal or investigation, could signal broader changes in city government.

What do I need to know? This is one of those races where a long-term incumbent is having an uphill battle holding onto his seat. Being a loyal ally to Emanuel could end up hurting O’Connor in a ward where homeowners have been hit hard by a record property tax hike and increased water bills. His longevity could also hurt him if voters adopt a throw-the-bums out mentality amidst the swirling City Hall corruption scandal (see above). 

The challengers going up against O’Connor are very politically active. Maggie O’Keefe helped newly elected Cook County Assessor Fritz Kaegi topple Joe Berrios, the former chair of the Cook County Democratic Party. Community activist Ugo Okere has worked in the City Clerk’s office and for Congressman Mike Quigley. Other candidates: Andre Vasquez is a senior manager for a “major utility company,” and Dianne Daleiden, a Chicago Public School teacher, is taking another run at the seat after garnering nealy 42% of the vote in 2015.

Where else are these issues/dynamics playing out? 49th Ward.

The 43rd Ward

What’s the deal? Two-term Ald. Michele Smith of Lincoln Park faces a crowded field of candidates in this rapidly growing lakefront in ward: public relations executive Leslie Fox, former city lobbyist Jacob Ringer, former senior aide in Emanuel’s administration Derek Lindblom, former Preckwinkle aide Rebecca Janowitz, and local school council member Steven McClellan.

Why should I care? Two words: Lincoln Yards. The fight over this controversial mega-development, which neighbors the 43rd Ward, has become a proxy for the larger debate in Chicago over development and affordability.

What do I need to know? This lakefront ward is one of the wealthiest and most politically active in the city (ever heard of the term “lakefront liberal”?). Smith made waves when she voted against a plan to overhaul the zoning of the North Branch of the Chicago River because she didn’t think it had enough guarantees for public recreational space. The looming Lincoln Yards development will have a significant impact on her ward. The ward also has the highest concentration of Airbnb rentals, and Smith fought hard to impose stricter rules on hosts, like ensuring the city create a so-called “banned list” of buildings where no rentals are allowed.

Where else are these issues/dynamics playing out? 44th and 46th wards.

Images via campaign websites.

Correction: A previous version of this story mistakenly left Chicago mayoral candidate Neal Sales-Griffin off the graphic listing candidates and misspelled the name of Peter Gariepy. The graphics have been updated.