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Does Rahm Emanuel have a challenger who can win?

What Toni Preckwinkle, Karen Lewis, and Robert Fioretti need to do

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If you were busy watching flops in the World Cup, or preparing your float for the Pride parade, you might have missed the unofficial start of the 2015 mayoral race last Thursday.

That's when Cook County board president Toni Preckwinkle had an exchange with reporters at the City Club in which she absolutely, positively refused to rule out running against Mayor Rahm Emanuel. For the ever-cautious Preckwinkle that's as good as saying: Hey, you know I don't like the guy—and somebody needs to take him on!

Later that same day, Karen Lewis, president of the Chicago Teachers Union, told the Sun-Times that she's "seriously thinking about running" against Emanuel because she doesn't care for the dude either.

As she put it: "I'm a little sick of the mayor."

The consensus among many elected officials, political operatives, activists, and pollsters is that Mayor Emanuel can be defeated, but no one wants to say so too loudly, for the simple reason that he's still the safest bet to win in February. He has the name, the money, the connections, and the proven ability to get elected, and there's no doubt that he's running. You can't say that about anyone else.

But a lot can change in a few months. Here's what the potential matchups would look like and how the challengers might change the equation:

Toni v. Rahm:

Anticipation about a possible mayoral run was building in the days before Preckwinkle addressed a packed house at the City Club last week—and then she gave a speech that entirely avoided the subject of her political future. In an unusually spirited exchange with reporters afterward, Preckwinkle repeatedly insisted "I'm running for the job I have." But she refused to rule out a challenge to Emanuel after her reelection in November. In fact, a reporter suggested that if she's staying put she should just say so—to which Preckwinkle shot back "Thank you for the advice." And who said she was humorless?

Preckwinkle is Emanuel's most formidable potential opponent. The mayor is unpopular in black and Latino areas hit by school closings, city budget cuts, and stubbornly high violent-crime rates. Preckwinkle, who's African-American, has strong support in those same neighborhoods. But in winning the county job in 2010, she also collected votes from thousands of whites who continue to embrace her no-nonsense style and sales-tax cuts. For better and for worse, she's also a political operator who's not above muscling aside foes or forging alliances with old-school pols.

Like everyone else, she'd have less money than Emanuel, who already has more than $7 million on hand. But she has a lot of friends in the City Council and ward organizations around Chicago.

Can she win? Not if she doesn't run. "She would wallop Rahm in my ward," says an alderman of an affluent white part of the city—which is supposed to be the mayor's base.

Karen v. Rahm:

There's a very good chance that Lewis's Sun-Times announcement was an attempt to force Preckwinkle's hand. But if Lewis runs, it would be a fascinating showdown between two powerful personalities who openly dislike one another, leaving reporters hyperventilating with excitement.

Could Lewis do it? Well, it's hard to see if you never stray from the predominantly white north lakefront. Her shoot-from-the-hip style may win over a Reader columnist, but it has many north-side liberal types knocking their knees. They'll tell you she's too much of a loose cannon. Or she's too aggressive. Or that they don't have anything against teachers—but can't we all just get along?

It's the sort of thing you used to hear north-lakefront liberals say about another outspoken black candidate: Harold Washington.

This is why it's important to remember that most of Chicago is outside the north lakefront.

Lewis might be able to win if she forges a coalition like Washington's: almost all the black voters, half the Hispanics, and 20 percent of the whites, nervous Nellies or not.

If she runs, look for her to surround herself with lots of teachers and rabbis. Don't forget—Karen Lewis is Jewish. In fact, she probably speaks better Hebrew than Rahm.

Here's an idea: have one debate in Yiddish. We're happy to moderate.

Bob v. Rahm:

Robert Fioretti, the alderman of the Second Ward, is one of the City Council's great characters: the prosperous lawyer who became a council progressive, then kept moving to the left after mayoral allies mapped his home out of his ward. As the old adage says, at least they didn't stab him in the back—it was right in the chest.

Fioretti is still weighing whether he'll run for alderman or say screw it and go for the big job. In 2010 he gathered 40,000 signatures to get on the ballot to run against Mayor Richard M. Daley. But that campaign was halted by a bout of cancer, which he subsequently beat.

He's now on year four of what he describes as a "listening tour," hitting churches on Sunday mornings and driving through wards far from his own. And as a white guy representing a mostly black area, he's shown, at least on a modest scale, that he can build a wide base.

Fioretti's best bet would be if Preckwinkle and Lewis bowed out, leaving him as the only elected official still willing to go after Emanuel. Then he could hope for an outpouring of anti-Rahm sentiment—sort of the way Jane Byrne beat the machine in 1979, though Fioretti won't want to remind anyone of how she then joined the machine upon taking office.

Karen v. Toni v. Bob v. Rahm:

This is as good a time as ever to remember that Chicago has a runoff system. That means that if no single candidate gets more than 50 percent of the vote in February's election, the top two finishers will face off in April for all the marbles. In other words, it's possible that, by ego or by design, all the major candidates could decide to run against each other. At which point a certain Reader columnist will get so excited he'll start doing cartwheels down State Street, which is dangerous at his age, especially given all the potholes this year.

Imagine the wild scenarios that, in a democracy, shouldn't be all that wild: What if Preckwinkle, with an assist from Fioretti, forces Emanuel to campaign on the north side? What if the presence of one or even two strong African-American candidates inspires historic turnout on the south side? What if the mayor has to bust his butt to avoid a third-place finish? Quick, call your guy in Vegas—there may be a line on this action right now.

The other candidates:

For the record, there are at least three other candidates who've formally declared: former alderman Robert Shaw, west-side community activist Amara Enyia, and west-side police officer Frederick Collins. Neither Enyia nor Collins has won an election for public office before.

If Lewis, Preckwinkle, and Fioretti don't run, we will have essentially returned to the later years of the Daley regime. That's when horribly underfunded unknowns like William "Dock" Walls and the Reverend Paul Jakes ran kamikaze campaigns against the powerful incumbent.

We know how those elections went. It's now been 25 years since an incumbent mayor had to face the possibility of defeat at the polls.

The central question is whether Daley, Emanuel, or whoever comes next would rule differently if reelection weren't a given.

We're still waiting to find out.

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