Stephanie Skora and Ellen Mayer, the authors of “Girl, I Guess: Progressive Voter Guide for Chicago, 2019,” are having trouble trying to decide whether to vote with their hearts or their heads.

Their hearts are telling them to vote for Amara Enyia, whom they deem to be “genuinely the most progressive person in the race.

“She has a genuinely transformative vision for Chicago,” they write, "and substantive plans for how to bring about that transformation through a fundamental redistribution of resources in Chicago and an emphasis on cooperative models for businesses and housing.”

But, Skora and Mayer have a few concerns. Enyia has run a disorganized campaign, and they want a strong progressive challenger to Bill Daley, whose well-funded campaign looks likely to make the runoff. So their heads are telling them to consider casting a “strategic vote” for Toni Preckwinkle.

“Typically, we’d say ‘fuck strategic voting,’ ” Skora and Mayer write. But, they concede, “[t]he fact is, the stakes are incredibly high in this race. The chances that we end up with another Daley mayor are looking pretty good. And that would be, well, disastrous. There are radical organizers that we trust who feel pretty strongly that progressives should vote for Toni — not because she’s the most progressive but because she is the least bad candidate who also has a shot at beating Daley.”

Of all the candidates running for mayor, Preckwinkle is most likely to benefit from strategic voting. She’s the best-funded, highest-polling, and most viable of the progressive black women in the race (a lane she tried to clear by knocking Enyia and Lori Lightfoot off the ballot, but that’s another story).

Chicago progressives who actually prefer Enyia and Lightfoot may suck it up and vote for Preckwinkle. They’re willing to overlook Preckwinkle’s alliances with Ed Burke and Joe Berrios, because the prospect of a third Mayor Daley is even worse — especially a Mayor Daley beloved by the same business establishment that supports Rahm Emanuel. Daley took $2 million from billionaire hedge fund manager Ken Griffin, who also contributed generously to ex-Gov. Bruce Rauner. Daley has also been endorsed by the establishment Chicago Tribune and Crain’s Chicago Business.

But there’s a way to avoid compromising yourself inside the voting booth — and Chicago might want to look at adopting it, especially if we continue to face mayoral fields the size of the Kentucky Derby.

The system is called ranked choice voting.

In this mayoral election, instead of choosing a single candidate, voters would rank each candidate, from 1 to 14. The candidate with the fewest first place votes would be eliminated. Then, each of that candidate’s first-place votes goes to the candidate ranked second on that given ballot.

Suppose your first choice is Neal Sales-Griffin, and your second is Preckwinkle. If Sales-Griffin is eliminated, your vote goes to Preckwinkle. The process would continue, eliminating a candidate in each round until someone gets a majority. (Ranked choice voting eliminates the need for a runoff, which is why it’s also called “instant runoff voting.”) This video from Minnesota Public Radio provides a good visual representation of the process.

According to Fair Vote, a non-partisan electoral reform organization, ranked choice voting helps people avoid casting a strategic ballot: “[I]n elections without ranked choice voting, voters may feel that they need to vote for the ‘lesser of two evils,’ because their favorite candidate is less likely to win. With ranked choice voting, you can honestly rank candidates in order of choice without having to worry about how others will vote and who is more or less likely to win.”

In this election, ranked choice voting would be a boon to Preckwinkle, and a disaster for Daley, Garry McCarthy, and Willie Wilson.

Preckwinkle would be second or third on the ballots of Enyia and Lightfoot voters, and possibly those of Gery Chico and Paul Vallas as well. Most voters who don’t rank Daley, McCarthy, or Wilson first would rank them near the bottom — Daley because he’s another Daley, McCarthy because he’s a carpetbagger who was police chief during the Laquan McDonald shooting, and Wilson because Republicans love him almost as much as he loves himself.

A candidate loathed by most of the public would not be able to slip through to the runoff with a hardcore bloc of support. They’d be eliminated in an early round.

Maine recently adopted a ranked choice system after a raving loony named Paul LePage was twice elected governor without a majority of the vote. Ranked choice is also used in progressive cities such as Berkeley, Cambridge, Minneapolis, Oakland, San Francisco, Santa Fe, and St. Paul.

That’s not the system we’re working with in Chicago, though. On Election Day, instead of voting for the candidate of your choice, you may end up feeling obligated to vote for the least of 14 evils.

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