Carol Felsenthal, author of Power, Privilege & the Post: The Katharine Graham Story, is a contributing writer to Chicago and the magazine’s political blogger.

It ought to be a coronation, Rahm Emanuel must figure. But as he nears what might or might not be the end of his exhausting race for a second term as Chicago’s mayor, the former White House chief of staff and tough-guy insider on Tuesday faces a possibly humiliating setback—particularly ego-crushing because he is running against an extremely weak field of four, has vastly more money than any of them, has television ads airing 24/7 and has run the table on endorsements. He ought to be resting easy—well, Rahm seems never to rest, but at least he should be confident of a win.

That’s never been the case in this contest, though, and every day that the uncertainly lingers is a day that exposes Emanuel’s weaknesses, especially in minority neighborhoods that seem sometimes to double as shooting galleries, where schools are hopelessly bad and jobs are near impossible to find. During his first run, against more seasoned competitors, it was clear early on that Emanuel would win; four years later, after Chicagoans have gotten to know the guy who spent most of his career in Washington—he was a congressman for four terms before heading to the White House—it’s not clear whether he wins outright tomorrow (he needs 50 percent plus one vote) or, according to the rules, faces a time- and money-consuming runoff on April 7 against the second-place candidate.


That will almost certainly be fellow Democrat Jesus “Chuy” Garcia, a Cook County Board member, former alderman, state senator and protégé of the beloved (by minorities and progressives) late Mayor Harold Washington. While I regularly tell friends and colleagues that I think Rahm will win outright, I’m too chicken to make that prediction here. A Tribune poll last week had Rahm at 45 percent to Chuy’s 20. Rahm’s trend is inching up slowly, but so is Chuy’s. An autodial poll of 737 people conducted Saturday by Chicago-based Ogden & Fry found Rahm at the tantalizingly close 48.3 percent; Chuy had 26.5.

I am brave enough to predict, however, that while there’s a chance Rahm might have to roam the frigid, windy wards of Chicago eating many slices of humble pie during the six weeks between Tuesday, February 24, and Tuesday, April 7, he will win in April. And when he does, I’ll also predict that Rahm, not known for introspection or self criticism, will become an even more arrogant and impatient version of the mayor who appears to think he is smarter, more energetic and more disciplined than any of the Chicagoans he governs—or certainly than any of his opponents and their supporters.

But here’s hoping that tomorrow’s election at least brings a wakeup call for the mayor and the city he is struggling to serve. The race might still be a crapshoot, but Emanuel has so many advantages, he should never have had to break a sweat.

To begin with, his opponents, all Democrats, except perhaps for Willie Wilson, who supported Republican Governor Bruce Rauner last November, are small names. Not even I, an avid follower of Chicago politics, knew who Chuy Garcia was when he announced his candidacy a few months ago. Bob Fioretti, one of 50 city aldermen—and, to his credit, one of the very few on the City Council who dares to vote against Emanuel—has little to show voters except his council dissent and an endorsement by former Bears coach Mike Ditka. (Rahm has Magic Johnson in his corner.) Fioretti and Dikta might appeal to the city’s white ethnics, but so does Emanuel’s predecessor, Richard Daley, who has endorsed Emanuel. Wilson, a multi-millionaire businessman—hospital supplies and gospel music—has a 7th-grade education. (On Sunday, speaking at a west side Baptist church, he urged young people to remain in school but also noted that, although he could afford to return to school himself, he chose not to “because our young men need to know that if they drop out of school, they can look at me and say, ‘I still can make it like he made it.’”) Finally, William “Dock” Walls might as well have the word “perennial” as his first name, because he runs regularly for mayor and loses always, usually with low single-digit totals.

Karen Lewis, the one opponent who would certainly have given Emanuel a runoff, emerged the victor in their faceoff during the 2012 teachers strike. Vibrant, hyper-articulate, funny (she’s a former standup comic), the president of the Chicago Teachers Union was on the verge of announcing her candidacy last October, when she was diagnosed with a malignant brain tumor. After her initial surgery, she called Chuy, one of her key backers, to her house and pleaded with him to run. (She is undergoing chemotherapy and radiation, and the fact that she has not cut an ad for Chuy, or made a robo-call, likely indicates she’s too sick to do so.)

With Emanuel’s name recognition has come much more spending and fundraising. Since leaving the White House as President Obama’s chief of staff in 2010 to run for mayor the first time around, Emanuel has raised about $30 million, $15 million alone for this election—an eye-popping four times as much as the total of his four challengers combined.

Chuy Garcia (who is backed by MoveOn.org, the progressive group begging Senator Elizabeth Warren to run for president) has raised about $1 million, mostly in teachers’ union money. Emanuel’s other opponents—and opponents seems way too serious a word—are fundraising paupers. Fioretti has raised next to nothing, as has Walls. Wilson has raised about $2 million—almost all out of his own wallet. (Wilson and Walls, both African American, are polling in the single digits, as is Fioretti, who is of Italian and Polish descent.)

And Emanuel is spending freely, nearly $7 million to monopolize the airwaves with ads—4,600 of them since November. By comparison, his opponents are nearly invisible. Fioretti and Walls have each run zero television ads, while Wilson has kept his ads limited to cheaper air times.

Chuy now has ads up, but their impact is diminished by Chicago Forward, a pro-Emanuel PAC that is running another $450,000 worth of ads specifically attacking Chuy. According to the Tribune, Emanuel “has aired twice as many ads on Spanish-language TV stations as Garcia,” who moved from Mexico to the United States at age 9 and whose wife is Puerto Rican.

Running through Election Day is Emanuel’s closer ad, shot last Thursday, when his former boss, Barack Obama, traveled to Chicago to bestow national monument status on the Pullman district on Chicago’s far South Side. In the ad, Obama hugs Emanuel and tells voters, “He’s making sure every Chicagoan in every neighborhood gets the fair shot at success that they deserve.”

The message is perhaps Emanuel’s most direct attempt yet to blunt criticism from Chuy, who has 48 percent of the Hispanic vote to Rahm’s 33. Calling himself “the neighborhood guy”—Chuy has lived in the same West Side neighborhood, Little Village, almost since arriving in Chicago, and he has raised his children and foster children there—he regularly chastises Rahm for his focus on downtown and big business, and his inattentiveness to the city’s poorer neighborhoods.

If endorsements still matter, Emanuel should be residing in endorsement heaven, after winning nods not only from the Tribune, the Sun-Times and Crain’s, but also from the city’s historic African American paper, the Chicago Defender. He has also been backed by Representatives Bobby Rush and Luis Gutierrez, City Clerk Susana Mendoza and Gery Chico—an attorney with deep experience in city government who lost to Emanuel for mayor four years ago.

Yet the circles around the hyper-competitive mayor’s eyes keep getting darker and deeper, now well into raccoon territory. Rahm knows he has a festering problem with African Americans, who make up one-third of the city’s population. His decision to close 50 Chicago public schools, mostly in the African-American and Latino South and West sides, remains deeply unpopular; many of those schools were failing, but many also served as social centers and provided jobs in those neighborhoods. And it is not lost on voters that Rahm’s own three children attend the private, prestigious University of Chicago Lab School, where Malia and Sasha Obama went before moving to Washington, D.C.

Four years ago, when Rahm won outright with 55 percent of the vote, he carried every majority black ward in the city, capturing 59 percent of the black vote in total. No one expects him to do that well this time. Experts say he needs at least 40 percent of the black vote to avoid a runoff.

On top of some tangible advantages, Rahm continues to enjoy another advantage that no pollster has yet figured out how to measure: That’s luck, and throughout his career, from his time in the Clinton and Obama White Houses to Congress to his office on the fifth floor of City Hall, Emanuel has had an abundance of it.

It’s not just that the gods of snow and artic temperatures have been kind to Rahm this election season, leaving residents with relatively little reason to gripe about unplowed streets. (A blizzard gave Chicago’s only female mayor, Jane Byrne, the win in 1979.) While it sounds counterintuitive, Rahm has also managed to reap some luck from the city’s alarming woes: huge pension liabilities, unaffordable union contracts, a teachers’ contract negotiation looming and, with it, the threat of another strike, failing schools, foreclosed houses and empty storefronts, shootings every night, deaths many nights, a proposed budget by the rookie Republican governor that would cut $135 million in income tax revenue to Chicago, crumbling roads and bridges.

Would anyone really want to put Chuy or Bob or Willie or Dock at the helm of a city that is now occasionally, if incorrectly, compared to bankrupt Detroit? By sheer energy or will or intimidation, Rahm, for all his faults, gets stuff done. He may, as Chuy charges, be getting more done for business and for the downtown interests, than for the parts of the city that tourists never see and would fear to visit. Chuy and the others like to call Rahm “Mayor 1 Percent,” but none of them, Rahm doesn’t mind pointing out, has proposed a coherent plan to revive the city’s neighborhoods.

Finally, there’s turnout, which is expected to be low. (In February 2011, it was 42 percent, though it is expected to be lower this time around.) That could end up being a boon for Emanuel who has the money to create a better-oiled and tended turnout machine. The Tribune today reported higher than usual early voting numbers and one particularly interesting statistic: Ballot numbers for early voting, which ended Saturday, were up 84 percent in the ward of Illinois House Speaker Mike Madigan, a big Rahm supporter and political powerhouse. Madigan’s army of volunteers will be out on Tuesday rounding up voters for Rahm, likely including in their canvassing low-turnout Hispanic precincts —which one would otherwise expect to go to Chuy.

Carol Marin and John Kass, influential columnists for the Sun Times and the Tribune, respectively, have written that they are rooting for a runoff as a lesson to Rahm: Lose the imperiousness, and listen to Chicago voters. Neither argues for Emanuel’s opponents, but they have advocated a debate between Rahm and Chuy as a means of forcing them to discuss the issues. As Kass wrote, “It would make [Emanuel] a better, perhaps more humble mayor, rather than that Mayor Antoinette that erupts on occasion.”

Marin wrote that a runoff would remind Emanuel that “he is a mere mortal representing a public that needs answers from him, not press releases.”

Assuming that Rahm wins his second term tomorrow or, come April, I doubt that, like Rich Daley or his father, he will aspire to be mayor for life. Unless he is asked to be vice president on Hillary Clinton’s ticket in 2016—highly doubtful—Rahm, I predict, will be a two-term mayor with eyes on D.C. and, eventually, the White House. He certainly can’t return to Congress, where he’s no longer on track to be the first Jewish Speaker of the House, and the Senate is too slow. In Illinois, the mayor of Chicago is a way cooler job than governor.

Rahm’s reputation will be damaged short term, but maybe the struggle will benefit the city and, by extension, its mayor, giving him the motivation he needs to get back to serving all his constituents. Here’s hoping for a humbling.