Upon hearing the first official candidacies for the post of mayor, Rahm Emanuel responded, at a news conference: “There will be a campaign season. We’re in the governing season. And the best way to get ready for the campaign season is to do your job during the governing season.” Was this the relaxed, unhurried talk of a lifelong fundraiser who knows that the $6.2 million that currently sit in his campaign war chest can easily be increased if it becomes necessary? Or was it the slightly worried exhortation of a mildly unpopular mayor who knows that he needs more time to enact policies that will aid him in his reelection? Either way, his advice did little to deter either Amara Enyia or Robert Shaw—the former a burgeoning community organizer and activist, the latter a former city councilman who has (sometimes unwillingly) been on the sidelines of Chicago politics for the last decade—from announcing their campaigns to unseat Mayor Emanuel in the election on February 25, 2015, though concerns about their viability as challengers remain.

In an appearance at Give Me Some Sugah, a South Shore bakery, Amara Enyia looked every bit as intelligently formidable in real life as she does online, where she blogs and tweets under the name Municipal Maven. Enyia’s whip-smart posts are filled with the type of data-driven analysis that one might expect from a graduate department rather than a mayoral campaign. Unsurprisingly, Enyia holds a PhD in education policy, as well as a law degree, both from the University of Illinois. Yet her interest in community organizing took her out of the political arena after a couple of years in Mayor Daley’s office. She chose instead to found ACE Municipal Partners, a consulting firm specializing in local government. Enyia has also worked with a couple of non-profits aimed at crime prevention and rehabilitation.

At the event, she opened by lightly referring to herself as “the crazy black woman who wants to challenge Rahm Emanuel.” Quickly, though, she launched into a smooth series of talking points, including the inspiring story of her parents, Nigerian immigrants who fought against dictatorship in their home country before moving to Chicago, where they still faced harassment from Nigerian government supporters. She had clearly rehearsed her lines well, recycling several of them from a brief interview she gave before the talk.

As for the issues, she opposes a “dual education system,” and calls instead for an elected school board and well-funded public neighborhood schools as a means of fighting both crime and poverty. Additionally, she wants to close corporate tax loopholes and create a financial transaction tax. More broadly, Enyia sees her candidacy as an attempt to create a voice for the thousands of perennially underrepresented people on the city’s South and West Sides, many of whom feel betrayed by Emanuel’s stances on some of the most controversial issues of his tenure, including charter schools and health clinic closings.

Enyia, who can hardly outspend the mayor on advertising, outlined a general plan for creating an effective grassroots campaign to listen to and connect with potential voters within every single neighborhood, though it sounded more optimistic than tangible. Fundamentally, this may prove to be Enyia’s main problem: despite her qualifications and passion, she is banking on the activist inclinations of an electorate she herself describes as filled with “cynicism and apathy,” an attitude that may be easy to adopt when giving a talk to an audience composed mostly of sympathetic community organizations (over half the people there seemed to be eagerly distributing business cards to anyone available). But in the long run that probably doesn’t translate into a feasible campaign strategy. Nevertheless, her pointed criticism and thoroughly professional, policy-driven platform should do much to win her support among informed voters.

Perhaps the most immediately notable aspect of Robert Shaw, the other significant candidate who has declared for mayor, is his almost complete lack of an Internet presence, especially when compared to Enyia. He claims that he has both a Facebook page and personal website, but they are impossible to find for all but the most dedicated sleuths (though, for anyone interested, there is a Robert Shaw running for mayor of Porirua City, “the greatest middle-sized city in New Zealand!”). He maintains, though, that he will be ramping up his online persona within the next couple of months, noting, “You have to move with the times.” In person, however, he is talkative, willing to take time away from his weekly Saturday lunch with a group of local ministers to outline his plan for governance, which appears to be mostly based on a principle of “fairness.”

Shaw, at age seventy-seven, has been in politics since he was seventeen, when he started out as a local ward captain on the West Side. For the last ten years, though, he has been on the outside looking in, as he lost a bid for mayor of South Holland in 2005 after two terms on the Cook County Board. Prior to that, he was the 9th Ward alderman, though he briefly lost his seat after supporting Jane Byrne for mayor instead of Harold Washington, in what he calls his “one mistake.” (Though he doesn’t mention if it was a mistake of politics or principles, as he quickly aligned himself with Washington, and just as quickly won reelection.) Much like Enyia, he is undaunted by Emanuel’s money, replying that he’s “yet to see a dollar bill in the voting booth,” and citing his eighty percent name recognition among African Americans as proof that he doesn’t really need money for publicity, because most people already know who he is.

Much of Shaw’s platform is similar to Enyia’s. He cites Emanuel’s opposition to unions as a particularly egregious example of an attitude foreign to Chicago and he, too, would like to see an elected school board, as well as an overhaul of the parking meter contracts. His policies seem designed to generate broad goodwill. For example, one of his proposed crime-reduction programs would involve informal gatherings of people from every section of the city, such as mothers and fathers who have reared their children successfully, to simply interact. While the sentiment is admirable, it doesn’t really inspire much confidence in Shaw’s ability to seriously analyze crime in the city; as he vaguely insists, he’ll “have to take a look” at the Chicago Police Department. Nevertheless, Shaw exudes a certain calm—or perhaps apathy—and speaks in a slow, deliberate voice that shows he still knows how to put on a proper political persona, even if he does give the impression, at times, of a political machine whose gears are slowly grinding to a halt.

In the end, however, the winner of these early campaigns could be Emanuel, who will sit back and let these two candidates split an African-American vote that, in all likelihood, will not plump for Rahm nearly as enthusiastically as they did in 2011. At the same time, there is speculation that Shaw’s support will last only until a more serious African-American candidate, like Cook County Board President Tony Preckwinkle, enters the race. Ultimately, neither Enyia nor Shaw seem to have much of a chance at winning this mayoral election, but their campaigns could still prove very telling as a sort of referendum on their diverging political stocks—Enyia’s seemingly rising, Shaw’s seemingly falling—as well as an indicator of exactly how tired Chicagoans are of old-school city politics.

Correction May 10, 2014: Due to an editing error, this article originally misquoted Amara Enyia; she is against a dual education system, not a dual-enrollment education system.

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