Chicago voters will head to the polls tomorrow to begin the process of choosing the next mayor and City Council. But given the 14-candidate mayoral field and over 200 candidates for alderman, including replacing five who are not running and a referendum on one under federal indictment (Ed Burke - 14th), the mayoral race is just the most prominent one for a city in political chaos.

What the city is facing in this election is not the same choice as in 2015, when Mayor Rahm Emanuel failed to win outright and squared off with Jesus “Chuy” Garcia in the April runoff election. The runoff itself was a startling rebuke to a mayor who won handily four years previously, but alienated core supporters through his handling of the 2012 strike by the Chicago Teachers Union and other issues of prominence to the city’s large contingent of progressive voters.

In Rahm and Chuy, Chicago had to decide whether it wanted an outward-facing mayor with a heavy pro-business agenda willing to engage with the rest of the Midwest, or one who would put city residents first, perhaps even at the detriment of outside relations. Even in 2011, the most recent open election, only six candidates appeared on the ballot, and Emanuel avoided a runoff by winning 55 percent of the vote in the initial election.  

But when Emanuel announced his decision not to seek reelection in September of 2018 city politicos were stunned, although perhaps not completely surprised. The catalyzing event — what really set in motion the political anarchy the city currently finds itself embroiled in — was the 2014 murder of Laquan McDonald by police officer Jason Van Dyke. The fact that Emanuel buried the dashcam footage of the video, fired police superintendent Garry McCarthy (now a mayoral candidate himself), and approved a $5 million settlement with the McDonald family in an effort to prevent a lawsuit, poisoned the well for a third term even if he won.

Five months after Emanuel’s announcement the city is poised to move on from his tenure. But doing so will require confronting Chicago’s numerous divisions, aptly represented by a massive candidate field for the mayoral and aldermanic races. A candidate can be found for almost every issue imaginable in the city: crime (McCarthy), revenue (Toni Preckwinkle), progressive issues (Lori Lightfoot), banning the boot for ticket infractions (Amara Enyia), and an answer to every question (Paul Vallas).

There are also the Machine candidates: Bill Daley, son and brother to two mayors, Preckwinkle (again), Gery Chico, and Susana Mendoza. All four have ties either to the Machine, Ald. Burke, City Hall, or other questionable Chicago political practices. These relationships undoubtedly helped them get ahead, but whether this will matter to the voters will be decided tomorrow.

The candidates on the ballot tomorrow present a number of ideas and directions for the city. Everything from police reform to taxes to parking boots are on the table, as is Chicago’s status as a globally influential city. This is not just the most important election in the last eight years, but perhaps the most important since Richard J. Daley won his first term in 1955.

So in this wide open race — one without a clear front runner and as many existential questions as practical ones — what will Chicago voters decide to do?

This post has been updated.