This article is from the archive of our partner National Journal

Chicago Mayor Rahm Emanuel is about as partisan a Democrat as there is in this country. But to win a second term and avoid a humiliating defeat, he'll need to win over and turn out the small number of Republicans in the city.

Emanuel isn't openly telegraphing his runoff strategy, but signs of his reliance on the party he has worked to oppose his whole career are everywhere. Gov. Bruce Rauner, a longtime acquaintance of the mayor's, has been working behind the scenes to help his friend, while GOP Sen. Mark Kirk warned this month that Chicago could become like Detroit if Emanuel isn't reelected. Rahm's most recent ad comes straight out of the Mitt Romney playbook, accusing his outspokenly liberal opponent, Jesus "Chuy" Garcia, of wanting to hike Chicagoans' taxes by supporting $1.9 billion in spending programs. Several of the top donors to Emanuel's Chicago Forward super PAC are conservative Republicans, including hedge-fund manager Ken Griffin, a top Romney supporter and a Crossroads contributor, and investor Muneer Satter, who spent more than $1 million over the past few years on behalf of top Republican candidates and is backing Jeb Bush's campaign for president.

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"The circles that Rahm travels in have always been pretty diverse because he has a strong connection to the financial industry," said Tom Bowen, Emanuel's former political director. "Rahm gets a diverse mix of donors—he does get money from Ken Griffin, a big Rauner supporter, but he also gets money from Michael Sacks, a big supporter of President Obama's."

The race is shaping up to be one of the Democrats' first internal battles between the party's moderate Wall Street wing and its populist liberal grassroots. Emanuel's support for educational reform, efforts to overhaul the city's pension system, and ties to wealthy donors in the financial-services sector make him an easy target for the Left. While progressives failed to recruit a top challenger, Garcia has emerged as a stronger-than-expected opponent in the runoff, while also attempting to make history as the first Hispanic mayor of Chicago.

The fact that Garcia has a realistic shot of becoming the city's next mayor would have been unthinkable months ago. He wasn't considered a particularly credible candidate by progressives, who wanted the outspoken Emanuel rival, Chicago Teachers' Union President Karen Lewis, to run. Before making a decision, she was diagnosed with brain cancer. Alderman Bob Fioretti then looked like the most serious opponent, but he had little appeal in the minority communities where anti-Emanuel sentiment is strongest. Garcia, a little-known Cook County commissioner, emerged as the default challenger. After Emanuel underwhelmed in the first round of balloting with just 46 percent of the vote, the liberal opposition rallied behind Garcia, sending a golden opportunity to oust the mayor from office.

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Now that the race is in a runoff, Chicago's unique electoral system empowers Republicans. Unlike in other big cities, Chicago's mayoral election is officially nonpartisan, even as its two combatants are proud Democrats. It's akin to the recently changed electoral system in California, which works to mobilize the middle by eliminating partisan primaries. In several of the state's House elections, two Democrats running against each other in heavily Democratic districts have found themselves wooing conservative supporters to win a majority. Likewise in Chicago, Emanuel's opponent is so liberal that the mayor has the opportunity to secure overwhelming margins among Republicans—enough to make the difference in a close race.

To be sure, Emanuel needs to improve his standing on multiple fronts, most significantly among African-American voters, who were irritated by the mayor's closing of underperforming public schools and have criticized him for his handling of the persistent violence on the South Side. Despite receiving a high-profile visit from President Obama before the primary, Emanuel won only 43 percent of the vote in majority-black wards while Garcia tallied 26 percent. Since then, prominent black leaders, including third-place finisher Willie Wilson and Rev. Jesse Jackson, have rallied behind Garcia. (Emanuel is betting on Obama's support to win over the undecideds, and hoping that black and Hispanic voters have enough disparate motivations that they won't ally to form an anti-Emanuel voting bloc.)

But in such a heavily Democratic city, Republicans are often a forgotten constituency, even though they can play a make-or-break role in a close race. While black voters make up about one-third of the city electorate, Republicans are about one-fifth. Rauner won 21 percent of the Chicago vote in 2014, and that largely affluent constituency loathes Garcia's background as a community organizer, an ally of the teacher's unions, and a supporter of higher public spending. Turnout in the wealthier, more-Republican wards was relatively low in the first round of the primary, but those voters are more likely to rally to Emanuel's side, given that the stakes are clearer in the runoff.

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The difficult task for Emanuel is to win their support while not alienating the more-progressive elements of the electorate. So the mayor is raising big money from wealthy conservative donors while sending a subtle message in his campaign ads that is designed to scare the more-affluent constituencies in the city—without trumpeting support from the Right. He has welcomed Rauner's quiet outreach for his campaign while also blasting the governor for his proposed budget cuts.

Several new public polls show the mayor pulling ahead—51 percent to 37 percent in last week's Chicago Tribune poll; Ogden and Fry's latest weekly survey showed Emanuel up 47 percent to 37 percent—but his actions belie the numbers. For such a well-known figure to be polling at or under 50 percent weeks before the April 7 election is not an encouraging sign. In Tuesday's debate, Emanuel aggressively cast Garcia as a novice for not having a plan to deal with the city's economic challenges. The mayor's main path to victory is to outspend Garcia with millions in attack ads that raise enough questions about his challenger's qualifications.

"They're trying to play up the broader message that Chuy Garcia is not really up to the job," said one Illinois-based Democratic strategist unaffiliated in the mayoral race. "The people on Rahm's campaign are really worried. I don't feel like they think they have a good handle on how they take him down and win this thing. Rahm's mystique was the inevitability of success, and once you strip that away, more voters think this thing isn't a lock."

This article is from the archive of our partner National Journal.

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