If you thought the primary season was madness in March, be warned: That brief reprieve you enjoyed from election ads and campaign mailers will soon come to an end.
First up are the Nov. 3 school board elections, followed by a short break before the Feb. 23, 2027, mayoral contest.
Together, they will help determine the direction of Chicago for years to come.
Comptroller Susana Mendoza told us all she’d have a “big announcement” on Wednesday, and indeed she did: She’s running for mayor.
“We’re tired of paying for big promises that are never kept,” she said in a punchy announcement ad. “Chicago deserves more than promises. It deserves progress.”
Mendoza joins Cook County Treasurer Maria Pappas, who has said she’s running for mayor, as well as small business owner Liam Stanton and entrepreneur and former teacher Joe Holberg, with whom we met earlier this week. The field could grow further still, likely including Secretary of State Alexi Giannoulias, as well as the potential for some other familiar faces such as U.S. Rep. Mike Quigley. The breadth of interest reflects widespread recognition that Chicago is approaching a pivotal moment.
Chicago’s financial woes are no secret. Year after year, city leaders balance budgets without meaningfully addressing the underlying debt and pension challenges. It’s a math problem with an unappetizing answer, which will include cuts and rightsizing the current administration has no interest in touching.
Little wonder, then, that so many candidates see an opening.
Mayor Brandon Johnson has not confirmed whether he’ll run for a second term, but the mayor’s popularity is waning, as polling regularly shows more Chicagoans view the mayor unfavorably than have a positive view of him.
The city’s financial situation remains precarious, its crime problems still felt acutely, and its public schools are still struggling to produce acceptable student outcomes.
Which leads us to the other major race — all 21 seats are on the ballot for the city’s first fully elected school board. For the first time in history, every seat is up for grabs. These races will rival the mayoral election in 2027 in importance to the future of Chicago.
An astonishing 51 candidates have thrown their hats in the ring. We’ll be kept busy with our endorsement duties.
These are the men and women who will steer the fate of Chicago Public Schools, helping to make decisions that affect whether CPS can get kids reading and writing proficiently and whether the district can stabilize its finances.
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And they’ll have a tough job to do in a district facing a $732.5 million deficit, which has prompted plans to cut teaching staff. This is a moment for difficult conversations and serious action.
When the first round of seats were up for election in 2024, backers poured in over $13 million. A big spender was the Chicago Teachers Union; this time around, President Stacy Davis Gates already has warned businessman and Democratic donor Michael Sacks against getting involved, an early sign of how contentious these races will be.
Regardless of any such warnings, expect enormous spending from unions, charter advocates, business interests and wealthy donors.
Chicago voters won’t lack for choices. The challenge will be sorting through the noise and deciding what kind of city they want Chicago to become.
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