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Ten years of Chicago mayors

Take a look back at the three administrations that shaped Chicago’s City Hall in the 2010s.

For a city that spent 43 years run by a father and son named Daley, the last decade has been a comparative revolving door at City Hall.

Chicago said goodbye to Richard M. Daley, transitioned to Rahm Emanuel’s hyper-kinetic, two-term tenure and elected its first openly gay, African American female mayor after Lori Lightfoot was catapulted into office by the biggest corruption scandal Chicago has seen in decades.

The beginning of the end for Daley, Chicago’s longest-serving mayor, can be traced to the day Chicago lost its $100 million bid to host the 2016 Summer Olympic Games.

On Oct. 2, 2009, thousands jammed Daley Center Plaza for what they thought would be a celebration. Instead, Chicago suffered a humiliating defeat.


Fans at Daley Plaza in Chicago react in disappoint seconds after Chicago’s bid for the 2016 Olympics was rejected, Friday, Oct. 2, 2009.


The 2016 Olympics would be held in Rio de Janeiro. Chicago was knocked out in the first round of International Olympic Committee voting, despite personal appeals from Oprah Winfrey and then-President Barack Obama.

After exhausting $100 million and all his political capital on the Olympics while ignoring higher priorities, Daley had virtually nothing to show for it.

Returning from the IOC meeting in Copenhagen, Daley faced a $520 million budget gap, a $300 million CTA shortfall and the continuing fallout from the horrific videotaped beating death of a Fenger High School student.

Already distracted by corruption scandals and his wife’s terminal cancer, Daley clearly lacked the political will to dive back into Chicago’s intransigent problems without the bonanza of federal funding, jobs and contracts that an Olympics would have provided.

“You have my obituary already set. You’ve been writing that for years,” he said.

Less than a year later, Daley announced he would not seek a seventh term after surpassing his father as Chicago’s longest-serving mayor.


Mayor Richard M. Daley announces he will not run for a seventh term during a news conference in Chicago on Sept. 7, 2010 as his wife Maggie and son Patrick look on.


“Simply put, it’s time. Time for me. And time for Chicago to move on,” the then-68-year-old mayor said, his announcement hitting Chicago like a political earthquake.

“I’ve given it my all. I’ve done my best. Now, I’m ready with my family to begin the next phase of our lives. … Many of you will search to find what’s behind my decision. It’s simple. I have always believed that every person, especially public officials, must understand when it is time to move on. For me, that time is now. … It just feels right.”

As stunning as it seemed, Daley’s decision was no real surprise.

His approval rating had fallen to a low of 35 percent after a year marred by the parking meter fiasco, political fallout from his nephew’s pension fund deals and a budget crisis that forced him to deplete the city’s long-term reserves and demand furlough days and other cost-cutting concessions from city employees.

Chicago was facing more of the same. The city’s bond rating had been lowered. Its homicide rate was on the rise, including the recent murders of three Chicago Police officers.

Emanuel resigned as White House chief of staff to run for mayor; he was replaced at the White House by Bill Daley, the retiring mayor’s brother. It looked like the classic back-room Chicago deal — even if Emanuel had to endure a residency battle that nearly knocked him off the ballot.


Mayor Rahm Emanuel shakes hands with former Mayor Richard M. Daley as Sen. Dick Durbin smiles after the completion of the inauguration ceremony for his second term as mayor at the Chicago Theatre on May 18, 2015 in Chicago.


Emanuel’s eight-year tenure began with Chicago’s first teachers strike in 25 years.

He famously used profanity in an early confrontation with then-Chicago Teachers Union President Karen Lewis. He infuriated her members by canceling a previously-negotiated 4% teacher pay raise and forcing immediate implementation of his signature longer school day, then added insult to injury by persuading the Illinois General Assembly to raise the strike-vote threshold to 75%.

Incensed teachers blew past that benchmark; 90% voted to strike. They remained on the picket lines for seven days and got the better of the mayor when the strike was settled.

Emanuel’s record as Chicago’s “education mayor” also was marred by his decision to close 50 public schools all at once; nearly all of them were on Chicago’s South and West Sides.

He was re-elected despite fallout from those school closings — and good thing he was, at least for the finances of the city and the Chicago Public Schools, as Emanuel found dedicated revenue sources for all four city employee pension funds.

He more than doubled the property tax levy for police, fire and teacher pensions; pushed through two telephone tax hikes for the Laborers pension fund; and phased in a 29.5% surcharge on water and sewer bills to bankroll the Municipal Employees pension fund, the largest of the four.

He persuaded the Illinois General Assembly to give CPS a $450 million cash infusion and bankroll teacher pensions going forward.

But all of that — and hundreds of millions more in tax, fine and fee hikes and budget cuts — still just chipped away at the rock that is Chicago’s $28 billion pension crisis.

For all the once-formidable political capital Emanuel risked and spent, he did not stick around long enough to finish the job.

Still, there were other achievements.

Emanuel moved heaven and earth to nail down $1.1 billion in federal grants to modernize the CTA’s Red Line before then-President Barack Obama left the White House. His efforts included persuading the City Council to authorize a transit tax-increment-financing district to provide the local matching funds; he signed the ordinance on the final day by which the city needed to demonstrate its commitment to qualify for those federal grants.

After years of political stalemate, Emanuel also brokered the deal paving the way to renovate Wrigley Field and develop the land around it. It included an avalanche of advertising signs — but no taxpayer subsidy.

He negotiated several rounds of union concessions that made McCormick Place a more attractive convention center.

He also built Wintrust Arena, a project whose $55 million TIF subsidy became such a symbol of his misplaced priorities, the financing had to be rearranged: instead of going toward stadium costs, the subsidy was used to acquire land for that project and also surrounding hotels.

Riding an economic wave, Emanuel also benefited from a steady march of employers — many from the suburbs — moving downtown. Hardly a week passed without Chicago’s hard-charging salesman-in-chief speaking at a new office or cutting a ribbon on something that promised jobs.

He opened 760 acres of previously-protected North Side industrial land for residential and commercial use that now includes the massiveLincoln Yards development, made possible by $1.3 billion worth of infrastructure improvements bankrolled by the largest TIF subsidy in Chicago history.

Emanuel also tried desperately to overcome his reputation as “Mayor 1 percent” whose downtown-centric development left neighborhoods behind.

He moved city buildings to inner-city neighborhoods, hoping they would serve as catalysts for development. And he created a share-the-wealth fund: developers pay user fees to be allowed to build bigger and taller buildings in a broader swath of downtown; the money goes to support small businesses in disadvantaged areas.

Despite all that, Emanuel’s second term will forever be defined by his handling of the Laquan McDonald shooting video.

It showed a white police officer, Jason Van Dyke, firing 16 shots into McDonald, a black teenager, on Oct. 20, 2014. The video wasn’t released until Nov. 24, 2015 — and even then, only after a judge ordered the city to do so.

That same day the video was released, Van Dyke was charged with the first-degree murder. He was convicted of second-degree murder and 16 counts of aggravated battery, one for each shot he fired.

For weeks, protesters demanded Emanuel’s resignation for keeping the shooting video under wraps for more than a year and waiting until one week after the April 7, 2015, mayoral runoff election to authorize a $5 million settlement to the McDonald family — before the family even filed a lawsuit.


Demonstrators led by Rev. Jesse Jackson march down State Street to protest the death of Laquan McDonald and the alleged cover-up that followed on Dec. 6, 2015 in Chicago.


Emanuel emphatically denied keeping the video under wraps to get past the election.

But he acknowledged adding “to the suspicion and distrust” of everyday Chicagoans by blindly following the city’s long-standing practice of withholding shooting videos to avoid compromising ongoing criminal investigations.

In the political furor that followed, Emanuel fired Police Superintendent Garry McCarthy and replaced him with Eddie Johnson, chief of patrol, who hadn’t even applied. Emanuel then asked Police Board President Lori Lightfoot co-chair a Task Force on Police Accountability.

After an exhaustive investigation that included cathartic public hearings, the task force released a scathing indictment of the Chicago Police Department that laid the groundwork for the U.S. Justice Department to do the same. That set the stage for the consent decree now in place outlining the terms of federal court oversight over CPD.

In September 2018, Emanuel stunned the city, deciding against the uphill battle for a third term — just as Van Dyke’s trial was about to start.

Political heavyweights Bill Daley, Toni Preckwinkle, Susana Mendoza and Gery Chico all jumped into the mayor’s race after Emanuel’s announcement.

But, it was the Nov. 29 raid by federal investigators on the ward and City Hall offices of then-Finance Committee Chairman Edward Burke (14th) that would ultimately determine the next mayor of Chicago.

Lightfoot — who declared her candidacy before Emanuel decided not to run — had been stuck in single-digits in the polls before the feds showed up in force.

After that, and the filing of federal charges against Burke on Jan. 3, Lightfoot became the designated change agent in a change election.

Burke was charged with attempted extortion; he’s accused of shaking down a Burger King franchise owner for legal business and for a $10,000 campaign contribution to Preckwinkle, the County Board president.

In May, Burke was hit with a 14-count racketeering and extortion indictment accusing him of using his governmental role to muscle business for his law firm.

It included the alleged Burger King shakedown. But it also alleged three similar schemes chronicled by former Zoning Committee Chairman Danny Solis (25th), who spent two years wearing a wire on Burke.

Among them: that Burke tried to extort legal business from 601W Companies, developers of the Old Post Office, in exchange for his help with a variety of matters, including an $18 million tax increment finance subsidy, a $100 million tax break and help resolving issues with Amtrak and the city’s Department of Water Management.

Lightfoot’s repeated demands for Burke’s resignation were ignored. But her hand was strengthened and she played it to the hilt.

During her inaugural address, Lightfoot turned her back to the Wintrust Arena crowd to face the aldermen she had just portrayed as corrupt and insisted they join the cheering masses in a standing ovation for council reform.

Hours later, she signed an executive order stripping aldermen of their unbridled control over licensing and permitting in their wards and promised to do the same for aldermanic prerogative over zoning.

She later put off that showdown until after a vote on her 2020 budget.

She dumped Burke as Finance Chairman, installed reform Ald. Scott Waguespack (32nd) as his replacement and humiliated Burke on the City Council floor after delivering her handpicked leadership team. And that $100 million-a-year worker’s compensation program Burke once controlled? She turned it over to a private contractor.

Lightfoot has since endured a teachers strike even longer than Emanuel’s. It ended after she agreed to a five-year contract with a $1.5 billion price tag that will be difficult for CPS to meet.

She convinced aldermen to approve her $11.6 billion budget with 11 dissenting votes. But the massive property tax increase she managed to avoid with one-time revenues may yet be necessary if she strikes out again in Springfield.


Mayor Lori Lightfoot makes her inaugural address during the city of Chicago’s inauguration ceremony at Wintrust Arena, Monday morning, May 20, 2019.

Ashlee Rezin/Sun-Times

Most recently, she fired the retiring police superintendent she had celebrated one month earlier after accusing Eddie Johnson “lying” to her and to the public about the circumstances surrounding an embarrassing drinking-and-driving incident in mid-October.

From a practical standpoint, Lightfoot’s decision simply means Johnson is gone a month earlier than the Dec. 31 retirement date he announced in October.

But, from a political standpoint, it’s a sea change.

Lightfoot said Johnson’s firing “needs to be a turning point” for CPD and the “way things are done” at a department that has struggled to meet the rigid deadlines demanded by the federal consent decree.

“That must start at the top. That hard, but important work is impossible without strong leadership focused on integrity, honesty, legitimacy and accountability.

“Time and again, line police officers are held accountable for their actions, but their supervisors get a pass — even when their supervisors were aware of or directed the conduct at issue. … Doing so today in these circumstances would have been inconsistent with who I am and with the kind of principled leadership I want to bring to the city.”

As always, there is never a dull moment at Chicago’s City Hall. And to think, the Lightfoot administration has nearly three-and-a-half years to go.

This story is a part of a larger series called Decade in Review. For more features that reminisce on the 2010s, click here.

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