Above:Emanuel at the new South Loop Elementary School, which he pushed to open this fall Photo: Clayton Hauck; Grooming: Alisa Radoi / Distinct Artists

In his obituary of Chicago’s greatest mayor, Mike Royko wrote that “if a man ever reflected a city, it was Richard J. Daley and Chicago.” That was true, but Daley, who died in 1976, was mayor of a Chicago very different from the one we live in today: Daley’s Chicago was an unsophisticated blue-collar town, with a broad middle class, powerful industries, and neighborhood loyalties stretching back generations.

If any man reflects the city Chicago has become since Daley’s death, it is Rahm Emanuel. A suburban striver who grew up in Wilmette, he moved to the city in adulthood with a fancy master’s degree from Northwestern, built a lucrative career in politics and business, competed in triathlons, and settled at a tony North Side address. Emanuel’s Chicago is a global business and cultural capital whose bifurcated economic structure is a microcosm of 21st-century America — only fitting for this most American of cities.

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Since Emanuel became mayor, in 2011, Chicago has become more prosperous and more educated — achievements of which any civic leader would be proud — but those characteristics have become increasingly concentrated in the urban core. Imagine the city’s skyline as a bar graph of its demographics, the tallest buildings representing the most wealth, scaling downward to two-flats, bungalows, and vacant lots as it flatlines from its peak.

Emanuel did not create this Chicago, which has been developing since at least the 1990s, when the city began reversing a postindustrial trajectory that threatened to consign us to the same Rust Belt ash heap as Cleveland and Detroit. His mayoralty is, however, a product of it. In his first election, he ran up his biggest vote totals in the wealthy lakefront wards, which are populated by transplanted Midwestern professionals who share his conviction that the business of Chicago is business. The most significant decisions of his mayoralty have accelerated the city’s rise to global status. Emanuel is, arguably, one of the architects of the 21st century’s global economy. As an aide to President Bill Clinton, he helped sell the North American Free Trade Agreement to skeptical prolabor Democrats. Once he got his hands on the levers of power in an alpha world city, it only made sense that he would move to aggregate money and talent in its core. There are very few winners in globalization, and he wanted to make sure Chicago was one.

Like so many American cities, Chicago has been experiencing what urbanist Alan Ehrenhalt calls a “demographic inversion,” in which a once-derelict inner city attracts wealthy residents, while the poor are forced into outlying neighborhoods or suburbs. In the mid-2000s, Tom Tunney, the alderman of one of those wealthy lakefront wards, which Emanuel would carry with 74 percent of the vote in 2011, told me, “In 25 years, the entire city is going to look like this. It’s going to be Manhattanized. There’s nothing anyone can do about it. There’s too much demand for land in the city.”


“Then where will the poor people live?” I asked him.

“In the suburbs.”

Parts of Chicago have been Manhattanized. But other parts — the Second City’s second city — have turned into Cleveland and Detroit, losing their industries, their business districts, their middle class. According to demographer Alden Loury, who works as the race, class, and communities editor for WBEZ, “The city is losing more of its lower-income folks and gaining more higher-income workers.” While the African American population is expected to drop to 665,000 by 2030 — half what it was in 1980 — whites are the fastest-growing ethnic group. The Loop and its adjacent neighborhoods are gaining population, while the South and West Sides are declining. For the first time, Lake View has surpassed Austin as the city’s most populous community area.

The African American population declined under Mayor Richard M. Daley, but he “tried to manage the fallout,” says Jawanza Malone, executive director of the Kenwood-Oakland Community Organization. “He saw himself as another Chicago guy who knew what was happening in the neighborhoods. Emanuel is not a Chicagoan. He doesn’t see himself as a Chicagoan. He brought in all these people from outside Chicago who didn’t understand the Chicago Way.”

Emanuel simultaneously nurtured the rise of a global metropolis and managed the decline of a Rust Belt city, both coexisting within Chicago’s borders. The exigencies of this dual task ultimately undermined his mayoralty. Emanuel left Chicago a more prosperous place, but at the cost of his own popularity. A police shooting — the murder of 17-year-old Laquan McDonald — created the biggest crisis of his administration and may have done more than anything else to bring about his downfall, because many Chicagoans believed, rightly or wrongly, that he had covered up the video of the crime to preserve his 2015 reelection. As an urban planner, he succeeded; as a politician, he failed, because some Chicagoans came to believe he was indifferent to their struggles.


Rahm Emanuel has his super-fans. To tech entrepreneur Howard Tullman, he is the best mayor of a big city in the United States — an irreplaceable civic ambassador who connected with international businesspeople and White House staffers as no mere ward politician could have done. If Richard M. Daley was a transitional figure between the industrial Chicago in which his family’s political dynasty was born and the cultural and financial capital it was destined to become, Emanuel put the final stamp on Chicago as a global city.

“I think that in these days it has a more direct impact on more people’s lives to be the mayor of one of these megacities than to be a governor or senator or member of Congress,” Tullman says. “I don’t think it ever used to be a global job. Now it’s important to attract talent. It’s important to get financing, investment, and connections.”

In 2013, Emanuel was instrumental in hiring Tullman to run 1871, the city’s new tech incubator, named for the year Chicago burned, only to rise again. It was actually the brainchild of then future governor J.B. Pritzker, but Emanuel made it his baby, seeing it as integral to transforming Chicago into a technological rival of Silicon Valley — an ambition of his that fueled even his lame-duck months, when he made a last-ditch pitch to bring Amazon’s second headquarters here after the company announced it was pulling out of New York City.

Emanuel loved bringing distinguished visitors to 1871’s offices on the 12th floor of the Merchandise Mart, where young entrepreneurs sit behind gunmetal-gray MacBook Pros in the wide-open bullpen, beavering away at Chicago’s next internet success story. On a wall of the auditorium are tiles with the 1871 logo signed by visitors such as Emanuel’s ex-boss Bill Clinton, YouTube cofounder Steve Chen, and Shark Tank investor Daymond John.

“Emanuel was there a lot,” says Tullman, who spoke with the mayor about 1871’s progress at least once a month before stepping down in 2017. (He now heads the Ed Kaplan Family Institute for Innovation and Tech Entrepreneurship at the Illinois Institute of Technology.) “He put the arm on companies to be supportive by giving, doing events, working with our startups. He was a great bully pulpit in the sense that he talked it up all the time. It was a funny thing. As it got bigger and bigger and more successful, it wasn’t clear whether he was doing us a favor or we were doing him a favor.”

Mayor Rahm Emanuel speaks at the groundbreaking ceremony for the $1.2 billion expansion of O’Hare Airport Terminal 5 on March 20, 2019
Mayor Rahm Emanuel speaks at the groundbreaking ceremony for the $1.2 billion expansion of O’Hare Airport Terminal 5 on March 20, 2019 Photo: Stacey Wescott / Chicago Tribune

SpotHero, a service that helps motorists find parking spaces, spent its early years inside 1871 and now has 165 employees in its own Loop office. Thyng, an augmented reality platform that has been used to create everything from ads for Rice Krispies to 3D medical images for physicians, found both investors and employees through 1871. Thyng’s founder, Ed LaHood, has been part of the Chicago tech scene since the early 1990s. Never in his career has the city nurtured new tech businesses the way it does now, he says: “Thirty years ago, if you wanted to start a startup in Chicago, you were on your own. 1871 really created a technology ecosystem in Chicago. Rahm has been a huge part of the tech sector’s growth. Not only in 1871, but wanting to bring tech industries to Chicago.”

During Emanuel’s tenure as mayor, the share of the city’s economy attributed to tech more than quadrupled, from 2 percent to 9 percent, according to 1871. The footprint of tech companies inside the Merchandise Mart increased from 100,000 square feet to 1.5 million. As LaHood notes, it wasn’t just 1871, even though companies founded there have now created more than 8,000 jobs. Salesforce, Facebook, Yelp, and Google all opened Chicago offices while Emanuel was mayor. When Google was planning to open a Midwestern headquarters in the Fulton Market district, Emanuel “was in almost constant communication with their executives,” says Andrea Zopp, a former deputy mayor who is now president and CEO of World Business Chicago. “I think if you talk to any CEO who’s moved here, they’ll tell you he’s relentless.”


There’s another aspect of globalization that Emanuel turned to Chicago’s advantage: In the aftermath of late-20th-century deindustrialization, there could be only one Midwestern metropolis. Chicago was the winner, and it’s been sucking the economic vitality out of surrounding states — and the rest of Illinois — ever since. At first, this took the form of brain drain, as college graduates from Indiana, Michigan, and Wisconsin flocked to the city. Now, under Emanuel, Chicago has been the No. 1 American city for corporate relocations for five years running. Headquarters that were once synonymous with their small Midwestern hometowns are following the talent here. Archer Daniels Midland moved its global HQ from Decatur to an office on West Wacker Drive. ConAgra moved from Omaha to the Merchandise Mart. And corporations that built office campuses in Chicago suburbs during the urban flight of the 1960s and 1970s are following the white-collar class back into the city: McDonald’s from Oak Brook, Motorola from Schaumburg. So powerful is the global city’s lure that Emanuel rarely granted tax breaks.


“The mayor’s philosophy about it is, ‘If I have to buy your way here, don’t come,’ ” says Zopp. “We have so many great assets. They’re coming because their people want to be here. It’s the trend toward urban growth.” Still, Emanuel’s approach was hands-on: He lured Ferrara Candy from Oakbrook Terrace to Chicago after striking up a conversation with a company employee on a flight. She told him many of her coworkers wanted to work downtown, and suggested he call the CEO. Emanuel did, and Ferrara’s 400-employee headquarters are now in the Old Post Office.

The thousands of employees working at relocated companies didn’t just want to live in the city; they wanted to live right by their jobs. Though neighborhood life is the essence of the Chicago experience, the Loop was designed as a place of business. Emanuel set out to change that, with a special emphasis on the desires of millennials, who are “uniquely city-dwelling compared to previous generations,” according to demographer Ed Zotti. Emanuel hired a hotshot transportation planner from D.C., Gabe Klein, who laid down bike lanes and established the bike-sharing service Divvy. “Increasingly, young people were looking for that — tech companies in particular,” says Ron Burke, executive director of the Active Transportation Alliance. “Rahm saw this eight years ago.”

Emanuel cleaned up the Chicago River and built kayak liveries along its branches. The $100 million Chicago Riverwalk expansion, with its restaurants and bars, brought the public down to the level of a body of water that became known as the city’s second shoreline. “[The Riverwalk] has helped define the Loop,” says Michael Edwards, president and CEO of Chicago Loop Alliance, and it is among the reasons Chicago has one of the fastest-growing downtowns of any big city in the United States, adding 5,000 residents to the Loop between 2010 and 2016. Those newcomers are moving into buildings such as Marquee at Block 37, which opened in 2016 and rents one-bedroom apartments for $2,400 a month. (That’s affordable housing in the Loop, where 82 percent of residents have college degrees and the median household income is $98,000.) So intense is the demand for downtown housing that Magellan Development is building on the river the 101-story, 396-unit Vista Tower, which will be the city’s second-tallest residential structure.

Five miles south of the Loop, at the corner of 49th Street and Indiana Avenue, Irene Robinson stands alone on the playground of Anthony Overton Elementary School. The playground has been empty since 2013, when Overton was one of 49 “underutilized” or “underperforming” schools closed by Emanuel’s handpicked school board. A map of Chicago stenciled on the asphalt pinpoints their locations: almost all in African American neighborhoods on the South and West Sides.

“This was my second home,” Robinson says. “All my kids went to this school. My grandkids. I raised so many children here. Now it’s like a graveyard.”

When Robinson learned that Overton was closing, she thought her family’s world was coming to an end. She confronted the mayor at public meetings. She was arrested for protesting outside his City Hall office. The school was shuttered and sold to developers who plan to repurpose it as a business incubator. But six years on, Overton remains empty, boards covering its windows, graffiti climbing its walls, the words “Anthony Overton” visible only as ghost lettering above the front door. Robinson’s grandchildren were scattered to elementary schools throughout the South Side. Robinson, who for 15 years lived cater-cornered from the school, moved out of the neighborhood. One of Robinson’s daughters took her children to Iowa partly for a more stable educational environment.

Emanuel believes political capital is worthless unless spent on difficult decisions. In his first term, he spent a lot of capital on the school closings, and he never recovered it. Some of that was a result of the policies themselves, and some was a result of a perception that the prickly Emanuel was an autocrat and a bully who did not truly understand the city he governed.

Perhaps it made demographic and financial sense to close Overton. Since the school was built, in 1963, the surrounding Grand Boulevard community area has lost 75 percent of its residents, falling from a population of roughly 80,000 to 22,000. Public housing has been demolished (most of the Robert Taylor Homes were in Grand Boulevard). The blue-collar jobs that supported the black middle class have left Chicago. Families are trying to escape gangs and crime. Changing racial attitudes mean that blacks can now live in suburbs that once discouraged them from moving in, and Chicago’s Manhattanization means housing is often less expensive outside its borders. When Overton was slated for closing, its enrollment of 431 pupils was only half its capacity.

“We’ve lost thousands of kids,” says Chicago Public Schools CEO Janice Jackson, pointing out that enrollment has dropped to 361,000 from its all-time high of 500,000. “What people don’t understand is that when a school is underenrolled, it’s harder to attract teachers. We should not be making decisions on schools based on one factor, or politics, or optics.” Jackson believes CPS students are learning more than they were when Emanuel took over. Emanuel lengthened the school day and instituted full-day kindergarten. The district’s graduation rate increased from 57 percent to 78 percent during his tenure.

“The question of whether 50 school closings are ‘necessary’ is, in my view, a little bit beside the point,” says University of Chicago sociology professor Eve Ewing, author of Ghosts in the Schoolyard, a 2018 book about the school closings. “It was one possible policy solution in an array of many possible solutions, but the point is that the people most harmed had no meaningful opportunity to shape that policy decision.”

Chicago was the birthplace of community organizing, and Emanuel was seen as stiffing the neighborhoods where that tradition was born. Emanuel’s decisions to close schools and six mental health clinics were blamed for accelerating the decline and disarray of already struggling communities. In a poor neighborhood, a school is one of the few stable institutions.

“What Emanuel did goes beyond just ignoring parts of the city; it actively worked to destabilize those communities,” says Jawanza Malone. Even more people wanted to leave. And between 2014 and 2016, shootings increased among those who stayed, as young people from rival gangs were thrown together in new classrooms.

“It wasn’t about what was right for the children; it was about what was right for Rahm and his friends: the rich and elite people,” Robinson says.

“Neoliberal” is the term most often employed by Emanuel’s detractors to describe his outlook on governing. As used by left-wing critics of moderate Democrats, “neoliberal” refers to a post–New Deal philosophy of government that emphasizes free-market capitalism, deregulation of the financial sector, privatization of public services, and cuts in government spending.

Emanuel was, according to Ewing, “the precise archetype of a neoliberal mayor.” Fiscally, it might have made sense to put resources into the growing areas of town and withdraw them from the shrinking neighborhoods. And Emanuel was always a fiscally responsible mayor, unafraid to raise property taxes, hike water rates, or impose unpopular fees such as speed camera tickets to balance the city’s budget. Joe Moore was a critic of Daley’s shortsighted use of funds from the Skyway and parking meter leases in order to close budget gaps, but the alderman became an ally and admirer of Emanuel (which helps explain how Moore lost his reelection bid in February in independent-minded Rogers Park). “Rahm confronted the challenges,” Moore says. “He convinced the City Council to vote for significant property tax increases. He exhibited a willingness that Daley never exhibited to spend political capital.”

Emanuel was elected mayor in 2011 with strong support in the black community. By 2015, that support was eroding. Between 2011 and the first round of voting in 2015, his share of the vote dropped from 63 percent to 49 percent in the 27th Ward, which includes East Garfield Park, and from 60 percent to 45 percent in the 4th Ward, which covers part of Douglas. (Emanuel saw little or no drop-off in the downtown wards in which he had so assiduously invested.) That loss of support from black voters was the difference between an outright win and a humiliating runoff against no-name Jesús “Chuy” Garcia, which he may have won because African Americans were reluctant to vote for a Latino mayor.

“Why did such a loyal support group get the short end of the stick?” asks political consultant Don Rose. “I think his biggest failure was to deal with the Other Chicago.”

Michigan Avenue protest
A December 2015 protest on Michigan Avenue, weeks after the Chicago Police Department released video of the Laquan McDonald shooting Photo: Brian Cassella/Chicago Tribune

If a Taser had arrived at the corner of 41st Street and Pulaski Road one minute earlier, Rahm Emanuel might still be mayor.

“Someone with a Taser?” an officer is heard asking a police dispatcher on a recording of radio traffic on the night of October 20, 2014. “This guy’s walking away with a knife in his hand.”

A Taser was on its way, but Officer Jason Van Dyke beat it there and fired 16 shots into the guy with the knife in his hand, Laquan McDonald. A video of the shooting was released more than a year later and was at odds with the official police report, which stated that McDonald had lunged with his knife at officers. African Americans had already begun to sour on Emanuel’s policing because of the aggressive stop-and-frisk tactics of Garry McCarthy, the superintendent he recruited from Newark. Now many viewed the mayor with suspicion and mistrust.


After the McDonald video came out, Emanuel “lost the support of the majority of the black community,” says police reform activist William Calloway, who encouraged journalist Brandon Smith to sue the city for the video’s release. Although Emanuel says he did not see the video until it became public in November 2015, some suspected that he rushed a confidential settlement with the family through the City Council in order to preserve his reelection. By May 2016, his disapproval rating in the black community had risen to 70 percent.

Only then did Emanuel begin seriously directing resources to the South and West Sides. The city announced plans to build a police and fire academy in West Garfield Park; the Department of Fleet and Facility Management’s garage moved from the North Branch of the Chicago River (on the site that will become Lincoln Yards) to Englewood. The Neighborhood Opportunity Fund and Retail Thrive Zones program, established in 2016 and 2017, respectively, distributed rehab grants to small businesses in under-developed neighborhoods.

It was too little, too late; both Emanuel’s friends and enemies agree that the fallout from the Laquan McDonald shooting, including the perception that he covered it up, was likely his primary reason for not seeking a third term. “He was unelectable,” says Calloway, adding, “The police are the only public servants who are not seen as members of the community. You need a mayor who can erase that division.”

The pertinent question is whether Emanuel could have recovered from the McDonald scandal if he had retained more political capital in the black community. That community may be shrinking, but it’s still big enough to swing an election, and Emanuel may have found it impossible to contemplate another run without its support. None of his potential successors want to repeat that mistake: Nearly everyone who ran for mayor this time promised to invest in neighborhoods beyond downtown.


When Emanuel talked to Howard Tullman about 1871, “he always said he didn’t want a kid in the South Side or the West Side of the city looking at the skyscrapers downtown and not understanding in every way, shape, and form they could aspire to being part of that opportunity as well,” Tullman recalls. “The dream was that this enthusiasm, encouraging entrepreneurial activities, would eventually spread, and the benefit of technology and entrepreneurship would be distributed across the whole city.”

Tullman, at least, can see the beginnings of a more broadly shared prosperity as the Chicago that Emanuel’s administration has been building pushes out from downtown in every direction. On the Near West Side, Google is in Fulton Market. On the Near South Side, Related Midwest is building the 78, a $7 billion residential and commercial development that will fill the gap between downtown and Chinatown, near an area already booming with hotels and the addition of Wintrust Arena, the new home of DePaul basketball. Farpoint is redeveloping Bronzeville’s Michael Reese Hospital into housing and tech space. On the North Side, the industrial corridor along the North Branch of the Chicago River is set to become Lincoln Yards, a $6 billion housing and entertainment development.

“I think his latest legacy will be getting those deals financed or getting some support for those deals,” Tullman says. “Then the next real challenge is how do you do these other areas? Englewood. Bronzeville is getting healthy already. The city is as well positioned as any major city.”

Rahm Emanuel didn’t become mayor to be everybody’s best friend. He became mayor, as he puts it, to leave the city “better prepared for the future than the day I walked into the office.” Political consultant Don Rose acknowledges that Chicago “is probably in better financial condition” as a result of Emanuel’s tenure. Demographer Alden Loury believes that a lot of things that happened when he was mayor “are certainly positive for the city overall.” But Emanuel will not be fondly recalled as a civic father figure, like Old Man Daley, or even a civic little brother figure, like Richie.

“I don’t think the city ever loved him,” Rose says. “I don’t think even his supporters loved him. Even Richie, with his bumbling, and the Old Man had people who loved them. I don’t think the people who supported [Emanuel] warmed to his personality.”

Love Rahm Emanuel or not, the forces that produced him, and that he encouraged during his administration, will continue to transform Chicago. The next mayor will no doubt do more to redistribute the city’s resources to neighborhoods outside the borders of the global city on the lakefront, but she won’t be able to arrest their ultimate fates. We’ll still be living in Rahm’s Chicago.