When Cook County Democratic brass met 65 years ago to pick a new leader, a cadre of almost exclusively white, ethnic, suit-clad men assembled inside their old, smoke-filled hotel headquarters at Clark and Madison to crown then-County Clerk Richard J. Daley as chairman of an organization fueled by patronage.
The optics were quite different in April, as party officials again gathered to elect a leader. A diverse lot of men and women, some casually dressed, milled about an open, contemporary conference room in a high-rise at LaSalle and Lake. Smoking, of course, was banned.
Yet some of the sights would have been familiar, perhaps comforting, to the Daley-era power brokers. There were close handshakes, back slapping and hushed conversations off to the side. And when they got down to business, it was a Daley — John, the son who looked the most like his father — who seconded the nomination.
“The November election, we can’t take this for granted, and Toni never takes anything for granted,” said Daley, committeeman of the family’s ancestral 11th Ward, in the clipped, straightforward style his father favored.
Within 15 seconds, County Board President Toni Preckwinkle was elected by acclamation, the outcome decided beforehand, as it was when Richard J. Daley took the ring in 1953.
Preckwinkle was now running the political party that — if not the Chicago machine of yore — still controls the significant levers of government power in the city and county. Afterward, Preckwinkle rebuffed the suggestion that her decadeslong political career had taken her from machine critic to the boss of that very same operation.
“I’m a leader of the Democratic Party. I wouldn’t say that I’m a leader of the machine,” said Preckwinkle, the first African-American and first woman to lead the party. “With all due respect to the former mayor, I think we are quite different people. And that’s reflected both in the arc of our service, and in gender and race.”
Just as Daley did in the first city election after he became party chairman, Preckwinkle announced her candidacy for mayor in late September, declaring that she’s running “because I can.” If elected next year, she’ll be the first person since Richard J. Daley to be both mayor and party chief.
So how did Preckwinkle rise from high school history teacher who got trounced for alderman to the cusp of Daley-like boss status?
Like the legendary Daley, Preckwinkle had a great deal of political fortune as opponents stumbled from self-inflicted mistakes, and she took advantage of those opportunities. She also paired her advocacy of progressive causes with alliances she built with old-school Democrats and organized labor. And along the way, she honed a sharp-elbowed political style that saw her dispatch County Board foes and part ways with key staff who became liabilities.
In the mayor’s race, though, Preckwinkle is campaigning as a progressive reformer. Opponents trying to run in that same lane are crying foul, quick to point out where Preckewinkle’s pragmatism and loyalty to the party have gotten in the way of her progressivism. They’re calling her the “boss of the party bosses” and “the establishment.”
Preckwinkle makes no apologies, noting she didn’t get into politics to tilt at windmills.
“Your job always, if you’re in office, is to try to move your agenda forward and get things done,” she told the Tribune in a recent interview. “You know, I’m not into being Don Quixote.”
Slow rise
Raised in St. Paul, Minn., Preckwinkle got her introduction to politics in 1964, when a high school history teacher got her involved in a losing City Council campaign of local civil rights icon Katie McWatt. Preckwinkle stuffed envelopes and licked stamps as a 16-year-old volunteer.
She headed south to attend the University of Chicago and got involved in the progressive politics of Hyde Park, long known as a home base for the city’s independent, anti-machine Democrats.
It took three tries, but Preckwinkle eventually became 4th Ward alderman. In 1983, she was teaching high school history as she forced veteran Ald. Timothy Evans into a runoff before losing by 12 percentage points.
Evans went on to become Mayor Harold Washington’s floor leader during Council Wars, while Preckwinkle worked on economic development in the Washington administration. She lost a 1987 rematch to Evans in a rout.
Two years later, though, Evans ran as an independent in a special election for mayor following Washington’s death. Many people in the black community felt Evans’ candidacy ate into the support for interim Mayor Eugene Sawyer, who was defeated by Richard M. Daley in the Democratic primary.
The resulting perception that Evans helped restore City Hall’s fifth-floor offices to the Daley clan weakened him — and provided Preckwinkle with an opportunity to finally shift the power paradigm in the 4th Ward. She eked out a 109-vote victory in the runoff, ousting Evans, who eventually landed as the county’s chief judge.
During nearly two decades as alderman, she successfully pushed for Chicago’s first affordable housing set-asides, changes to a ward remap after judges determined the original version diluted black voting rights and criminal justice reforms including the release of police misconduct records.
A sign of Preckwinkle’s melding of a progressive agenda with a pragmatic approach is seen in how she and 22nd Ward Ald. Ricardo Munoz won approval in 1998 for a living wage ordinance, which required that workers for city contractors get paid a higher wage.
The proposal had languished for more than two years and was presumed dead after the powerful Finance Committee led by 14th Ward Ald. Edward Burke rejected it. But Preckwinkle and Munoz saw an opportunity to resurrect the idea when allies of then-Mayor Richard M. Daley were looking for cover as they prepared to give themselves and the mayor big pay boosts.
With protesters outside council chambers vowing “Payback Time in ’99” at the ballot box for aldermen who padded their own pockets but ignored the working poor, a deal was struck. First, the council approved the living wage. Then, aldermen passed their own pay hikes, which Munoz rejected but Preckwinkle voted for.
Reminded of that day, Preckwinkle chuckled and described her philosophy: “Politics is always the art of the possible.”
Asked if she casts herself in the same mold as the late Mario Cuomo, a three-term New York governor who styled himself a “progressive pragmatist,” Preckwinkle drew a distinction.
“I tried to put myself in a place where I could both serve and move an agenda forward,” said Preckwinkle, who noted she was one of three original council Progressive Caucus members, a co-chair of the Women’s Caucus and vice chair of the Black Caucus. “Cuomo may have described himself as a progressive pragmatist. I usually just describe myself as a progressive.”
There were times when Peckwinkle decided it best not to go along with the mayor. In 1999, she voted against Daley’s choice for fire chief. In 2006, she was the lone vote against his budget — a protest against what she called the city’s “pattern of insensitivity” to African-Americans, particularly in city contracting. And in 2008, she was one of five aldermen who bucked Daley and voted against the controversial 75-year lease of the city’s parking meters for $1.15 billion.
The following year, however, Preckwinkle eyed a promotion to County Board president, and Daley’s opposition could have diminished her chances. At first, she balked at his doomed bid for the 2016 Summer Olympics. Later, she voted for it after securing guarantees about how related development in her ward would be done.
Preckwinkle wasn’t the favorite in the 2010 Democratic primary. She wasn’t widely known and didn’t have a lot of campaign money. But then-Board Chairman Todd Stroger was unpopular because he’d raised the sales tax by 1 percentage point and had numerous patronage scandals.
She was the first to announce she would challenge Stroger, giving her a chance to line up early support. And Preckwinkle was fortunate as the other top Democratic candidate had her own controversies. Circuit Court Clerk Dorothy Brown had taken thousands of dollars in campaign contributions and gifts from employees and required employees to pay for the privilege of wearing jeans on Friday.
The unions got behind Preckwinkle, who aired much-lauded TV ads featuring an actor portraying famous penny pincher Benjamin Franklin as she promised to eliminate what remained of Stroger’s partially repealed tax increase. Preckwinkle handily won.
Governing’s harder
It’s Preckwinkle’s eight years as County Board president that has provided the most fodder for her mayoral opponents. Leading as a chief executive is different than being one of 50 aldermen, and Preckwinkle raised the very same sales tax she had earlier cut and muscled through a politically disastrous pop tax. Mayoral foes say those tax increases were regressive, tending to hit low-income people harder than the wealthy.
Preckwinkle maintains the sales tax increase was the only option available to bail out the underfunded county worker pension system after the state failed to act on her plan to fix the system at a lower cost. “I did what I thought I had to do in order to ensure the financial stability of the county and to keep from burdening future generations with our unpaid bills,” Preckwinkle said.
She still defends the pop tax, even after a citizen backlash fueled by a multimillion-dollar campaign funded by the beverage industry led the County Board to quickly repeal it.
Preckwinkle had hoped the pop tax would allow the county to cover costs for years to come without other tax hikes and produce health benefits from reduced sugar consumption.
“I say sometimes good public policy is neither possible nor popular,” said Preckwinkle, who noted she balanced the budget for now by laying off hundreds of employees.
Also coming under fire is Preckwinkle’s leadership style. Mayoral candidate Lori Lightfoot said Preckwinkle governs from the top down — a trait she said Preckwinkle shares with Mayor Rahm Emanuel. Lightfoot also said the way Preckwinkle handled the recent firing of her former chief of staff amid allegations of sexual misconduct and her security chief after a probe into use of a county vehicle for political purposes shows a lack of commitment to reform.
Toni Preckwinkle’s former security chief alleges she fired him to save her mayoral campaign »
“There are shades of the way in which he operates and what we’ve seen in the way in which she operates, and people in this city have said loud and clear — which is why Rahm is not on the ballot — they want change,” Lightfoot said. “They don’t want four more years of somebody who is tone-deaf, who doesn’t listen, who doesn’t engage, who doesn’t feel like the people whose lives are most affected by government, that they don’t have a role to play. That’s not progressive.”
But the area where mayoral foes target Preckwinkle for the most criticism is her frequent backing of establishment and sometimes machine-schooled politicians over ideological progressives.
Preckwinkle backed Hillary Clinton over progressive darling Bernie Sanders in 2016, an endorsement that got her a nationally televised cameo appearance sitting next to former President Bill Clinton when then-first lady Michelle Obama delivered her speech at the Democratic National Convention.
Preckwinkle also did not back then-County Commissioner Jesus “Chuy” Garcia against Emanuel in 2015, even as he took the mayor to a runoff. And Preckwinkle chose J.B. Pritzker over progressive state Sen. Daniel Biss in the March Democratic governor primary.
Preckwinkle said she “couldn’t come to agreements” with Garcia, who at the time was her County Board floor leader. As for Biss, she “didn’t see that he had a path to victory” in a contest where Pritzker had so much money.
That didn’t stop Preckwinkle from praising Biss as she runs for mayor. Democratic midterm victories were “the direct result of years of organizing, of advocating for progressive ideals, and for standing up for working families. You led that charge. Bold candidates like Daniel did as well — even when analysts and pundits doubted him, he kept fighting for everyday people,” she said in a campaign email.
In addition, Preckwinkle has been ripped for her steadfast backing of former county Assessor Joseph Berrios, an unabashed defender of the old-school patronage politics that the Daleys perfected. That support continued even after “The Tax Divide,” a series published by the Tribune and ProPublica Illinois that showed he ran a system that unfairly shifted the property tax burden from wealthier homeowners to the less-affluent.
Many other longtime progressives, including several Preckwinkle allies, lined up behind reformer Fritz Kaegi, who defeated Berrios. Lightfoot called Berrios “the poster child for anti-progressive, machine, establishment, maintaining-incumbency politics at its worst.”
“It’s hard for me to reconcile Toni Preckwinkle calling herself a progressive and consistently embracing a guy like Joe Berrios,” Lightfoot said.
Preckwinkle credits Berrios, in his role as county Democratic chairman, for backing more minorities and women for office, restoring the party’s finances and helping make it more relevant as the power of patronage waned under the so-called Shakman decree that dramatically reduced the power of politicians to hand out jobs to campaign workers.
Even so, it was Berrios’ defeat for assessor that made possible Preckwinkle’s ascension to county Democratic chair. Berrios agreed to step aside as chairman after his loss in the March primary to Kaegi. As the party’s second in command who could do business with both establishment and progressive Democrats, Preckwinkle quickly secured the votes needed to claim the spot in April.
She sought to project an aura of party reform, first by installing Committeeman Michael Rodriguez as executive vice chairman. He’s an ally of Garcia, who has become the city’s best-known progressive standard bearer. Preckwinkle also set up a new campaign fund that successfully fought the retention of Circuit Court Judge Matthew Coughlan, who as a former prosecutor had been accused of being involved in a wrongful prosecution.
But even as Preckwinkle portrays herself as progressive, she’s received help from some decidedly establishment quarters. Ald. Burke, who’s been on the council for nearly 50 years, held a January fundraiser for Preckwinkle in his Gage Park home.
With Burke now under federal investigation, Preckwinkle said he should step down from his long-held post as chairman of the City Council Finance Committee. And she said she will take steps to remove Burke as the head of the powerful party judicial slating committee. On Tuesday, she said she was donating $12,800 in campaign contributions from Burke to two Latino organizations.
Like Richard J. Daley, Preckwinkle is closely tied to organized labor, particularly the Service Employees International Union. SEIU played a key role in backing her first race for board president and recently contributed $1 million to her mayoral campaign. It also backed Preckwinkle’s tax increases, which helped cover union raises and for a time avoided layoffs.
Some of those who’ve crossed Preckwinkle on issues of criminal justice reform and taxation lost re-election efforts. In 2016, Preckwinkle helped protege Kim Foxx defeat Anita Alvarez for state’s attorney. In March, Richard Boykin and John Fritchey, two of the most outspoken Democratic critics of her pop tax, were defeated in their County Board primaries by opponents backed by Preckwinkle and her union allies.
‘Progressive’ debate
As she campaigns for mayor, Preckwinkle’s early platform has some progressive planks, including calls for an elected school board, criminal justice system reform and a remake of the city’s tax increment finance district program. She also backs lifting the state ban on rent control and supports a higher transfer tax on sales of homes that sell for more than $1 million.
Running as a progressive is a way to corral a large block of votes, given the recent electoral trends here and across the nation, but other mayoral hopefuls say it’s unfair for Preckwinkle to claim the tag.
“I think we can get caught up in the label, because everyone wants to bear the mantle, because it’s just easy,” said mayoral candidate Amara Enyia, a West Side activist. “Everyone wants to bear the mantle because it’s popular. What we really should be looking at are what are the substantive things that people have done to ensure progress.”
Preckwinkle has yet to convince progressive standard bearers like Garcia, a onetime ally who’s on his way to Congress. He was asked on a recent TV appearance whether Preckwinkle is a progressive.
“The details will be in what vision she offers,” Garcia said on WTTW’s “Chicago Tonight.” “She enjoys a reputation, but now seeking the most important office in Illinois, the mayorship of the city of Chicago, will give her an opportunity to show how she will be transformative and not simply status-quo politics in Chicago. The city cannot afford it any longer.”
Longtime Democratic U.S. Rep. Jan Schakowsky of Evanston endorsed Preckwinkle, citing a litany of progressive issues she has pushed at the county, including a successful early implementation of the Affordable Care Act that expanded health care coverage for the poor.
Preckwinkle is “the progressive in the race who has all the other advantages too — the kind of experience of being the head of a very large governmental body and has all the preparation and skills,” she said.
Supporters note that Preckwinkle has led the way on criminal justice in recent years. She first backed decriminalization of possession of small amounts of marijuana in 2011, before other politicians were making such proclamations; corralled other county officials to reduce the number of people held at the jail; and won changes in state laws to treat juvenile offenders less harshly.
Investigative journalist Jamie Kalven said Preckwinkle helped him learn how many bullets hit Laquan McDonald, the teenager whose shooting by police brought U.S. Department of Justice scrutiny to the Chicago Police Department and the second-degree murder conviction of Officer Jason Van Dyke.
Kalven had sought Preckwinkle’s help to find out more about what happened to McDonald because her authority extends to the Cook County medical examiner’s office. That led to a chance encounter in Hyde Park. “Sixteen shots, front and back,” Kalven said Preckwinkle told him.
“It’s one of the reasons we titled the piece ‘Sixteen Shots,’ ” said Kalven, who broke the story open. “That really reverberated with me, just the way she said it. … Toni reporting the number shots was the moment at which I knew this was huge … that it was a big story, an atrocity.”
In addition, Preckwinkle was a leading voice on the City Council to push for hearings on notorious former police Commander Jon Burge. Last year, she fired the county homeland security chief after media reports noted his role as a commander of now-convicted Chicago cops who committed crimes while working in public housing.
And Preckwinkle recently said that if elected mayor, she would fire police Superintendent Eddie Johnson, who was in the room as a deputy chief when top brass watched a video and agreed the McDonald shooting was justified, a lieutenant who was there said in sworn testimony.
Munoz, the 22nd Ward alderman and a longtime ally, said Preckwinkle has done what it took to move forward her progressive agenda.
“You gotta get stuff done,” said Munoz, an original Progressive Caucus member with Preckwinkle. “And to get stuff done in Chicago, sometimes you gotta make deals with the devil, whoever that devil is.”
Twitter @ReporterHal
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