Five Reasons Chicago’s Coming Election Will Indicate America’s Future

Chicago mayoral candidates Lori Lightfoot and Toni Preckwinkle. Credit: Mike Fourcher and WBEZ

Unless you’re a local, American mayoral elections can seem provincial and quaint. “How could a contest for chief garbage collector and town booster be important to the rest of America?” we ask.

But Chicago, preparing for a groundbreaking city election on Tuesday, is a true bellwether city for urban America, and much more conservative than decades of Democratic Party control lets on. Tuesday’s runoff election for mayor and city treasurer, and final contest for many City Council seats, will reveal a great deal of insight on what urban residents, now 80% of America, will be prioritizing in the coming years. While city dwellers set the pace for American politics, Chicago’s Midwestern values hew more to the middle than coastal Los Angeles and New York City, providing a better prediction of what’s to come on the national stage.

Since the start of Chicago’s runoff campaign five weeks ago, polling has pointed to a mayoral victory by rookie politician Lori Lightfoot. Yet, the mayoral runoff has been mostly about style, rather than policy substance, since Lightfoot and her opponent, Cook County Board President Toni Preckwinkle, have very similar liberal outlooks on policing, housing, taxation–and just about everything.

Meanwhile, polling for many for City Council runoffs has been favoring lefty, progressive candidates seeking to sweep out old guard pols, making it unlikely that the last few “machine” aldermen will be able to keep the reins of power away from a new, progressive mayor. On top of that, Chicago is about to elect for the first time a city treasurer who was not pulled into office by mayoral coattails, resulting in a new city-wide office held by someone with their own, independent electorate.

Once the ballots are counted, Chicago will see a whole lot of change Wednesday morning. There are five major reasons why all of America should pay attention.

1. Race and minority status have been election issues in brand new ways. Both Toni Preckwinkle and Lori Lightfoot are African-American women, a first for Chicago in the mayor’s office, no matter which is elected. And Lightfoot is married and openly gay with a daughter, another big first for Chicago, if she is elected. Yet, because both candidates are black women, minority status has not been a divisive campaign issue, but instead repeatedly affirmed as a gain for Chicago.

This is a remarkable development for a city that has lost 181,000 African-Americans in the last eight years, and one that has struggled with “a tale of two cities” with crime and economic underdevelopment raging in minority communities, while white Chicago has been booming in every way imaginable. A black, woman mayor with working-class roots (Preckwinkle’s father was a letter carrier in Minneapolis and Lightfoot’s was a steelworker in Ohio) will be a radical change from the white, professional class mayors Chicago has had since 1989.

Under Lightfoot or Preckwinkle, perhaps the project of racial reconciliation and equitable neighborhood development begun by Chicago’s first African American mayor, Harold Washington, and halted by his untimely death in office in 1987, can be restarted. All signs seem to suggest that Chicago voters are ready for it.

Unlike Chicago’s other recently famous black politician, Barack Obama, both Preckwinkle and Lightfoot have a history of speaking plainly about race and the role it plays in policymaking. Also, both candidates have demonstrated an awareness of how white, Latino, black and Asian perspectives differ, and how personal racial transgressions can feel. With its new leadership, Chicago will be positioned to be a model for post-Donald Trump racial reconciliation.

2. Chicago’s coming crime and policing policies will worth watching. As I mentioned before, Chicago is much more conservative than its Democratic voting record suggests. One leading “moderate” candidate for mayor eliminated in the general election, Illinois Comptroller Susana Mendoza, was nicknamed “Electric Suzy” when she was a state legislator, because of her strong support for the death penalty. As a 2019 mayoral candidate, Mendoza attracted campaign staff from outgoing Mayor Rahm Emanuel’s team, and made “get tough on crime” policies a major plank of her campaign.

In contrast, both Lightfoot and Preckwinkle are strong proponents of police reform, and each of them played a role in pushing Chicago towards the consent decree it is now under that will make major changes in how the police department operates. This is a big departure from Mayor Emanuel (and his predecessor Richard M. Daley) and from many other leading mayor candidates eliminated in the first round of voting. Long before Laquan McDonald was killed by a Chicago police officer in 2014, views on policing had been a dividing line between white and minority communities, with Emanuel and Daley resisting major policy changes.

Despite President Donald Trump’s promotion of 1980’s-era police tactics, urban America is calling for change. Preckwinkle’ leadership on eliminating cash bail, and Lightfoot’s recognition as principal author of the 2016 Chicago Police Accountability Report stating that the Chicago police department struggles with racism, suggests that Chicago is preparing to address crime and race in ways America’s federal government has been avoiding.

3. Chicago policymaking is about to get much more progressive. There was an incredible moment in one of the many televised debates between Lightfoot and Preckwinkle, where they argued over which one would be a more aggressive proponent of affordable housing and moving resources to underdeveloped communities. After eight years of Emanuel’s New Democrat, pro-business policies, where the Chicago Housing Authority sat on hundreds of millions of dollars while the city endured a low-income housing crisis, it was revolutionary to hear an argument about who would build houses faster. Both mayor candidates have promised liberal-friendly changes to city school governance, policing, neighborhood development and cannabis law, all areas where Emanuel has exhibited feet of clay.

While nationally, urban America is having a left-wing moment, Chicago’s incoming leadership will be liberal enough to make big changes but yet challenged to move a big city bureaucracy that naturally resists lefty impulses. Like much of America, Chicago will resist quick fixes and illustrate how hard it will be to implement a progressive agenda.

4. Downtown big business won’t be the first priority. Elected in 1989, Mayor Richard M. Daley put a top priority on building up Chicago’s downtown and pushing it to diversify into more finance and national corporate headquarters, as many other Rust Belt cities’ downtowns withered throughout the 1990’s. Emanuel, Daley’s successor in 2007, put the downtown-first policy on steroids, pouring resources on while doing everything he could to draw corporate headquarters to the Loop. Emanuel’s downtown focus has been hugely successful, as Crain’s Chicago Business recently reported that since 2010, the Loop added 130,000 new jobs.

But this boom has been mostly to the benefit of professionals, who are mostly white, as high wage industrial jobs working class blacks and Latinos relied on dried up. During the same time black neighborhoods have emptied out, and large parts of the South and West Sides have been locked into a cycle of disinvestment and high-unemployment since the 1960’s. Preckwinkle and Lightfoot have both made neighborhood investment top planks of their campaigns. While it’s possible for neighborhood investment to not be anti-business, many of Chicago’s business leaders are concerned about what they hear from the mayor candidates, expecting rent control, higher commercial property taxes, and less support for big downtown projects.

Like the rest of America, Chicago’s neighborhoods need infrastructure and private investment to spur growth. The 21st Century manufacturing and knowledge economies still need to take hold in Chicago and the city’s next mayor will have to write a playbook most of America has yet to discover.

5. The end of mayoral autocracy and a more activist City Council is coming. Chicago’s fifty alderman have long quailed under the gaze of their mayor, but come Wednesday, more independent-minded aldermen will hold office than ever before, with the vast majority of alderman elected to office without significant help from the mayoral candidates – a big change from past elections. Past mayors have held power by allying with aldermen who ignored city-wide issues in return for dominance over their home wards and help from the mayor around election time. But this year’s Council will bring a majority of aldermen with a history of asking unpleasant questions, and too few of “old machine” pols to keep the levers of power away from activist Council members.

We should expect a bumpy ride for the new Chicago mayor, as City Council pushes back in ways it hasn’t done since the early 1980’s. But unlike those days’ Council Wars between a progressive African-American mayor and reactionary white aldermen, Chicago’s next Council session is likely to be pulled between independent-minded aldermen that are more left than the mayor, and reactionary whites and minorities who are more conservative on policing and/or taxation than the mayor. As it stands today, it is unclear what kind of legislative coalition a new mayor will be able to assemble, and that suggests conflict is on the horizon.

America’s Democratic Party wrestling match between lefty populists and centrist establishment-types is about to be played out in Chicago. What happens here could be a good indicator of how hard it will be to establish a coalition if a Democratic president ascends to the White House in 2020.

For Chicago: Preckwinkle For Mayor, Conyears-Ervin For Treasurer

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There’s truism about politics: campaigning and governing are totally different skills, and just because you’re good at one, doesn’t mean you’re good at the other. Campaigning is packed with artificially black and white comparisons, inflated statements, and poorly declared ideas. Messaging and advertising is the messy and imprecise business of elections. But in a democratic system, we citizens have agreed that campaigning is what politicians need do to get elected, and when the votes are counted we hope the winners are just as good, or better at governing.

This is the root of my lament about Toni Preckwinkle, my preferred candidate for Chicago mayor. She’s run an abysmal campaign, wasting opportunities, allowing herself to be defined by opponents, and generally seeming leadfooted. While I have no real complaints about her runoff opponent, Lori Lightfoot, Toni’s thirty-year record of progressive accomplishment in government is tremendous, and something I’d like to see continued in the mayor’s office.

Her work as Cook County Board President, the job she currently occupies, has been a study in the hard work of governing. After decades of mismanagement before her tenure, Preckwinkle steered county government into solvency, moved the massive county hospitals and health system into the black, enrolled 320,000 people onto a new CountyCare managed health insurance program, rebuilt the state’s second-largest public housing agency and helped to push back the judicial travesty of cash bail.

These are boring, unsexy accomplishments that none-the-less affect hundreds of thousands of people in very real ways. And while Preckwinkle has earned a reputation of grinding through staff, and her demeanor is gruff and unforgiving, few statues have been erected in honor of a leader’s sense of humor. We demand concrete results from our leaders, and Preckwinkle has delivered it time and again.

Yet, Preckwinkle has run a terrible campaign. She was largely invisible during the first round of elections, nursing her resources for the second round and expecting that her base of support would give her a first place finish in the first round. But because she didn’t spend time and money defining herself to voters for the February election, other candidates did, setting the tone and defining what they had to offer.

Then, nine days before the February election, a hubris-filled Preckwinkle supporter crashed a Lightfoot press conference, attempting to belittle her. Instead, in an unprompted, televised argument that will go down in Chicago political history, Lightfoot directly engaged the man and earned her bonafides as the change candidate.

It was a terrible “own goal” by Team Preckwinkle, and Team Lightfoot has been matching “change” and “machine” with “Preckwinkle” at every opportunity since then. We’ve heard very little from Lightfoot about how her turn at the mayor’s office would be substantially different from Preckwinkle’s (in fact, it seems both candidates would make many of the same policy choices), but Chicagoans seem to be hungering for a break from the past. And since Preckwinkle has a 40 year history as a Chicago and Cook County elected official – no matter that almost that entire past was opposing the old machine and reforming the dreck they left behind – the zeitgeist has shifted to Lightfoot’s candidacy of new, rather than Preckwinkle’s history of reform.

I’ll be voting for Toni Preckwinkle for mayor, but I don’t have anything bad to say about Lori Lightfoot. I spent a great deal of time talking to her about police reform when I was running and reporting for The Daily Line. She is a deep, thoughtful person, genuinely interested in service – and she has a sense of humor. She can be a bit imperious at times, but so has every other person I’ve met that has achieved her level of success. While it doesn’t serve her well, I suspect it’s a habit born of being in command – I’ve never sensed her to foster self-doubt.

Me and State Rep. Melissa Conyears-Ervin, candidate for Chicago Treasurer.

And while so much attention has gone to the mayoral campaign, I’ve been spending most of my energy on the city treasurer race, volunteering for Melissa Conyears-Ervin. I’ve worked and volunteered for dozens of candidates over the years, and Melissa is one of the few I’ve known to be the “whole package”. She’s got a Horatio Alger story, having risen from a West Side family, raised by a single mother working a union job to become the first in her family to go to college, and then get a job working for Allstate, a Fortune 500 company. While there, she earned an MBA in finance and managed a office of hundreds. Then, sensing there was more to life than the corporate ladder, she left her corporate job to work at a West Side non-profit focusing on housing. Only after all this life experience, did she run for State Representative. And, except for when she went to college, she lived the whole time on Chicago’s West Side, never leaving her roots.

Volunteering for and working with Melissa, I’ve found her interest in people to be genuine, her grasp of financial issues to be real (I have an M.B.A. myself) and that she reads and studies in depth to get up to speed on issues. She understands and is committed to protecting Chicago’s $8 billion of cash and short-term investments. She has some genuine ideas on how to help our pensions perform better, and she is energized by the idea of forcing Chicago banks, who benefit from holding our massive cash deposits, to create programs to serve significant Chicago’s unbanked population.

Melissa is deeply committed to the boring, uninteresting parts of government that create real long-term results. And for this guy with twenty-five years in and around government, her commitment to the boring, is the most exciting thing ever. If you live in Chicago, please give Melissa Conyears-Ervin your vote.

Monica’s Poise

John Oliver’s recent show about public shaming has kicked off a discussion on whether or not the habit is socially useful. But don’t overlook the incredible interview of Monica Lewinsky starting at the 15:00 mark of his show. Her poise, thoughtfulness and overall strength is amazing. If you’re going through a tough time, watch this. Because she survived the worst kind of hell and has managed to be a good, decent person that doesn’t hate everyone, which would be a perfectly understandable response.

Chatham House

I’ve recently read about a couple different conferences that invoke Chatham House rules, where ideas and speeches can be quoted, but none of the quotes can be directly attributed. This is a fantastic concept. More conferences and meetings should employ this.

Four Non-Americans’ Views of America

University of Wisconsin-Madison’s Bascom Hall. You can study here and get smart, but you can’t stay. (Credit: Richard Hurd/Flickr)

Listening to non-American friends living overseas, the United States seems like a lumbering giant with little idea of how it impacts the world. Its democracy and merit culture remains a draw for people in developing nations who desire to do better, but President Donald Trump’s immigration policies are confusing everyone.

Two weeks ago I told you about my conversations with four American friends living overseas and how they view the United States as expatriots. This week I spoke with four more friends, all non-Americans that once lived in the United States at some point, live in other countries now, and occasionally travel here on business or on vacation.

Everyone I spoke to is highly educated: We all went to business school together at University of Wisconsin-Madison. Sebastien Rexhausen is an energy sector business consultant living in Bonn, Germany. Faisal Siddiqui, whom I wrote about last week, has been a hospital CEO in numerous Indian cities. Leonel Preza is an El Salvadoran now working as a factory manager in Vancouver, British Columbia. Qasim Munir is a chemical engineer working for a fertilizer manufacturer in Islamabad, Pakistan.

Geography it seemed, was everything, as I spoke to my old friends. My German buddy, Sebastien, who flies into Houston for work on a regular basis, finds America to be pretty much the same as he’s always experienced it. He applied for and obtained a five-year work visa with no problem. But as a European, he’s acutely aware of America’s sharp divide between rich and poor.

“The big divide between the affluent and poor is a topic that’s big in the news back home – coupled with drugs,” particularly the United States opioid epidemic, says Sebastien.

My El Salvadoran friend living in Canada, Leonel, now views everything through a Canadian lens (more on that later). Looking over the U.S. border just a few minutes away from his home in Vancouver, he sees the U.S. as divisive and centered on capitalism, that forgets to provide residents with the basics.

“[Canada is] like the U.S. thirty years ago. They are not as competitive, aggressive as in the States. In general people are nice, everything is organized, orderly. Here in Canada, you get health care and schooling for free. The university is less expensive than in the States. For me, experiencing the States is the sheer volume of the economy,” Leonel says.

Leonel and his family drives to visit Seattle every few weeks, and he has family he visits in Las Vegas and Boise, Idaho. So he manages to check in regularly on the U.S.

“The States have changed. You see more immigrants, but you see more poverty. Divisions from the rich to the poor, you see those big gaps. But you don’t see that as much in Canada.”

But my friend in Islamabad, Qasim, sees less of the rich-poor divide and more of the opportunity.

“[America] is an ideal place to immigrate, because the systems and processes are fair, there’s very little corruption, and you can excel and go fairly. My time there I found it to be the same. It’s a dream place for lots of people.”

Qasim expressed a bit of concern about prejudice against immigrants, but not too much. “It’s a country which 95% of the time makes you feel welcome. Every now and then you run into a person who makes a remark and it ruins your next hour or so, but that happens very little.”

But when discussion turns to American foreign policy, everyone had big criticisms for the U.S.

“Who would think people in Wisconsin would vote for Donald Trump?” asked my friend from India, Faisal. “What we hear about America is that it is not what it used to be. As a free country, as a place accepting of people of different backgrounds. From our perspective the bubble has burst.”

Qasim, whose country, Pakistan, just finished a series of deadly border battles with India, says many Pakistanis blamed the United States for the fighting since India’s fighter jets, bombs and artillery mostly comes from American arms manufacturers.

“We all know who was backing it up. There was someone that supporting it – the U.S. That’s who was pushing it,” he said.

Pakistanis, wedged between Afghanistan where the U.S. is fighting a hot war, and India, which the U.S. is warming up to in an effort to hem in China, are predictably sensitive to American actions.

“People here are almost convinced that whatever India was doing was with the backing of the U.S. That does not leave a good feeling at all. The more literate people say it’s more about business, there’s no such thing as ethics. It is all about give and take so the United States can leverage China. The U.S. needs a check on them.”

Pakistan is still a largely illiterate country, Qasim laments, and because of that, few people are able to read newspapers and form their own opinions about the world. So if the government says the United States is to blame, they’ll go along with that idea.

“The bottom line for a commoner, is they lack the capacity of interest to go into the depth and details. They just want a one liner from the government. Whatever they hear becomes their belief,” Qasim says.

Leonel, the El Salvadoran in Canada, thinks the U.S. is often totally unaware of its impact, and just bigfoots its way through the world. For instance, he thinks the twelve-year long El Salvadoran civil war from 1979 to 1992 was probably unintentionally lengthened by American largesse.

“The civil war in El Salvador lasted for 10 years, but the U.S. gave [the government] intelligence on where the guerilla commanders were. If they wanted, they could have ended the war in a year. But the U.S. kept sending money to maintain the war. That money [went to] the government, ‘Hey, we’re receiving free money for a war, why stop it?’ That’s why the war lasted 10 years,” Leonel claims.

I think Leonel’s analysis is oversimplified, but it does illustrate something very real, which is that America, the largest economy in the world, can quickly swamp a tiny country of 6.5 million people, and not even notice. What is certainly true, is that the United States was sending around $500 million in aid a year to El Salvador during the 1980’s, and American military officers were helping run the war for the government. We were in deep, with big consequences for El Salvadorans, and barely any for Americans back home.

This is felt by Sebastien, from Germany too. It’s big news in Germany that the U.S. has withdrawn from the Paris Climate Accords, that Trump is pressuring Germany to stop building natural gas pipelines to Russia, and that the U.S. is demanding Germany not use Chinese telecommunications technology in favor of American tech. Most of those things aren’t really talked about in the United States.

“[Trump is] trying to go away from being the institution of the world to ensuring everything benefits the U.S. [He is trying] to take a different stance of the United States’ role in the world, which in the past was balancing. But now it’s U.S. first,” Sebastien said. “The U.S. was an institution for global policy making. I’m not sure if that is not lost to a certain degree. He is enabling other bloks or parties to win in that global race for positioning.”

Finally, because that seems to be the biggest concern between the United States and the rest of the world, Leonel’s immigration story is another great illustration of how the rest of the world works.

Born in San Salvador, Leonel came to earn an M.B.A. at the University of Wisconsin after he was awarded a Fulbright Scholarship. Graduating in 2003, he headed back to El Salvador to manage a massive Maidenform factory with 10,000 workers. He gradually climbed up the ladder, and by 2008 he was managing nine factories for Hanes Brands across Central America.

By then gang violence was getting worse in San Salvador, and concerned for their two young children Leonel and his wife decided they needed to emigrate. But he told me, “To get the States, it’s very hard. You need a family sponsorship or a company visa,” neither of which this Fulbright Scholar who managed nine factories for a major global company could conjure up.

But Canada offered an opportunity, he said. “In Canada they have a point system based on education, level of English and your skills.” The system is straightforward – meet certain requirements, you get points. Get 67 points or more, and you can become a permanent resident. (Try an example test for yourself here.)

Leonel had enough points, and he and his family obtained residency in Canada in 2014. Then, just four years later, they applied for Canadian citizenship in October 2018 and became Canucks. Just like that. You only need to be a Canadian resident for one year.

“Now we have Canadian passports!” Leonel said.

These are the El Salvadorans we’re keeping out of the U.S.