Chicago voters face historic choice for mayor in city divided by tensions | TheHill - The Hill

CHICAGO -- After years of escalating political corruption, gang violence and racial tensions, voters in Chicago appear likely to elect an outsider promising wholesale change to a city where the gaps between those with means and those without are growing dramatically.

Chicago voters face a historic choice in Tuesday's runoff between Toni Preckwinkle, the president of the Cook County Board of Commissioners, and Lori Lightfoot, a former federal prosecutor who has held several positions in the last two mayors' administrations.

Whoever wins will become the city's first black woman mayor -- and only the second black person and the second woman to lead the nation's third-largest city.

Some in this city's African American communities see the choice as momentous, an opportunity to refocus attention from the prosperous Loop and the growing South Side to the impoverished West Side, where in some wards unemployment rates look more like the depths of the Great Depression than the results of a decade of economic expansion.

"It's about history, and it's about hope. History from the standpoint of the first black woman who will lead our city," said Richard Boykin, a former Cook County commissioner who backs Lightfoot.

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Others are less optimistic, conscious of the work left to do.

In Austin, the West Side neighborhood where gang violence has soared to record levels, residents are still waiting for economic development projects that would attract a business as basic as a grocery store.

"There are some things that will get better, I believe. If history is any guide, it's going to be a high hurdle," said Malcolm Crawford, who runs the Austin African American Business Networking Association. "A lot of the West Side still looks like the day after King was killed."

The two African American women who finished first and second in the initial round of voting in February attracted support from very different parts of the city.

Lightfoot won support in many North Side and Lakefront wards, where white liberals dominate the political scene. Preckwinkle finished well in many of the city's African American wards on the South Side.

Together, they beat out other big-spending and well-known candidates, including former White House chief of staff Bill Daley, state Comptroller Susana Mendoza, the former president of the Chicago Public School board, a former superintendent of the Chicago Police Department and the prominent philanthropist Willie Wilson.

In Tuesday's runoff, the insider now faces the outsider. They share a race and gender, and not much else. 

Preckwinkle, 72, has served in elected office since 1991, when she won a seat on the city council.

She is the chair of the Cook County Democratic Party, a once-powerful machine that could generate tens of thousands of votes for its favored candidates.

Preckwinkle is closely tied to the most powerful Democrats in the city, including several who are facing indictments and other scandal.

Lightfoot, 56, has never served in elected office.

She has cast herself as an outsider crusading against the city's long history of corruption, as head of two police oversight boards under Mayors Richard M. Daley and Rahm Emanuel, and then, as the number two at the Chicago Department of Procurement Services, where she investigated Democratic fundraiser Tony Rezko.

That contrast -- between a candidate with deep ties to Chicago's historically powerful political machine and a candidate who has never been a part of that machine -- defines the contest in a city where a new generation of voters seem hungry for change.

"It's basically the old guard versus the new," said Gregory Seal Livingston, a civil rights activist who is the interim pastor at the New Hope Baptist Church. "If Toni wins, we can then declare the machine is alive and well. If Lori wins, then the machine is dead."

Polls both public and private show the patient on virtual life support.

Lightfoot led the February 26 round of voting with 17.5 percent of the vote, just ahead of Preckwinkle's 16 percent. In the month since the first round of voting, virtually every voter who has decided on a candidate has broken for Lightfoot.

The most recent public survey, conducted by the Democratic firm Normington Petts & Associates, showed Lightfoot with 53 percent of the vote, compared to just 17 percent who said they backed Preckwinkle. Every other public survey has showed Lightfoot up by double digits.

"We've had too much corruption in the city. I think [Lightfoot] is truly an independent Democrat," Boykin said.

If Lightfoot wins, "it's going to be a break with the past, with the Chicago machine and the Chicago way of doing business."

After a century or more in which Chicago's powerful machine hand picked candidates, even those who promised reform, Lightfoot chose perhaps the perfect year in which to run as an outsider change agent. 

She was virtually unknown when she launched her bid against Mayor Rahm Emanuel last year. After Emanuel said he would not run for a third term, Lightfoot was vastly outspent by wealthier candidates. 

But two months before voters went to the polls, federal authorities charged the city's longest-serving alderman, Ed Burke, with shaking down businesses seeking help from the city.

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Among the top candidates running for mayor, almost all had ties to Burke.

Preckwinkle had hired Burke's son, and Burke held a major fundraiser for her at his home. Another candidate had been Burke's aide; a third got married at his home. Daley is the son and brother of machine mayors whose family had received thousands in campaign contributions from Burke.

Lightfoot was the only one with no ties to Burke.

"Toni comes with some baggage, just simply because she's been in elected office for a long time," Crawford said.

The next mayor faces a massive set of challenges, from the violence that has claimed thousands of lives to rising property taxes that fall disproportionately on the least wealthy Chicagoans.

But perhaps the most challenging will be the rising racial tensions that plague what has historically been one of the most segregated cities in America.

The election comes five years after a Chicago police officer shot the black teenager Laquan McDonald, and five months after that officer was convicted of second degree murder, racial tensions are near an apex.

"We are a city of diversity, but many times we are siloed," Lightfoot said at a forum focusing on African American and Latino issues here Thursday. "The world is multicultural. The city is multicultural. And we have to be respectful of that diversity."

Both candidates have pledged a renewed focus on impoverished neighborhoods far from the prosperous Loop and the booming North and South Sides.

They have pledged to offer city contracts to minority-owned businesses, and to bolster economic development and quality of life in neighborhoods where the average life expectancy can be 20 years lower than it is in the Loop.

"The downtown area glitters and sparkles, and it is filled with cranes," Preckwinkle said at a February forum at Malcolm X College. "But in many of our neighborhoods, there are empty lots."

In the final days before voters head to the polls, the race has turned decidedly negative.

Running far behind, Preckwinkle has castigated Lightfoot for her actions on the police board and when she served in the Office of Emergency Management and Communication.

Preckwinkle's last advertisement, citing a 2004 fire in which four children died, has drawn criticism from the surviving family members.

Lightfoot supporters say Preckwinkle's attacks are exacerbating the tensions that plague the city.

"Things are not good, and we've got to figure out how do we reduce tensions," Boykin said. "The people really want change in this election."

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