Few readers will need What Next, Chicago?’s subtitle, Notes of a Pissed-Off Native Son, to grasp that journalist Matt Rosenberg is angry about conditions in the city where he grew up. During almost 30 years there he experienced Chicago as “a celebration and a calamity.” But coming home after the 2020 Black Lives Matter riots, Rosenberg encountered little worth celebrating and much that’s calamitous. Twice during that summer’s mostly peaceful mayhem, Mayor Lori Lightfoot ordered city workers to raise Chicago River drawbridges in a desperate attempt to prevent looting on the “Magnificent Mile,” North Michigan Avenue’s shopping district. But, Rosenberg observes, with police “diverted to riot duty or riot prevention, deadly violence worsened.” Chicago recorded 105 murders that July, making it the city’s most lethal month since 1992.

Chicago’s “dicey schools, violence, corruption, and sharply rising taxes have taken a toll,” Rosenberg writes. They’ve diminished not only the city’s spirit but its ability to attract and retain residents and enterprises, which are crucial to hopes for a prosperous future. In contrast to Chicago’s deficiencies, suburbs and exurbs around the country, as well as many Sun Belt cities, offer “good schools, good governance, reasonable taxes, culture, and diversity,” the book contends. Those who live in such places expect to be “prosperous and safe.” Chicago’s lakefront, universities, architecture, and cultural heritage won’t count for much if these predicates of domestic tranquility disappear. More than the fate of a great American city is on the line. “If a lasting turnaround can’t take hold in Chicago,” Rosenberg warns, “perhaps the era of big Northern cities in this nation will be over. They’ll all shrivel.” And as hard as sustaining Chicago and other cities like it will be, coping with their demise will be much worse, “an exhausting and resource-heavy endeavor.”


City, Sun Belt, Suburb

We can begin to consider Rosenberg’s diagnosis, prognosis, and prescriptions by unpacking one of the most important statistics he offers: Chicago’s population peaked in 1950, when 3,620,962 people lived there. By 2020 it had declined to 2,746,388. Though What Next, Chicago? lets this fact speak for itself, the two numbers are in some ways worse and in others better than they seem. The bad news is that while Chicago’s population was decreasing by 24%, America’s increased by 120%, from 150,697,361 in 1950 to 331,449,281 in 2020. Measured as a proportion of the U.S. population, Chicago declined by 65% over seven decades, from 2.39% of the national population to 0.83%. To put it differently, one out of every 42 Americans lived in Chicago in 1950. (Were that still the case today, the city’s population would be over 7.9 million.) By 2020, that figure had fallen to one out of 121.

City 1950 population 1950 population rank % of 1950 U.S. population 2020 population 1950 – 2020 change, % of 1950 2020 population rank % of 2020 U.S. population
New York 7,891,957 1 5.22% 8,804,190 +11.56% 1 2.66%
Chicago 3,620,962 2 2.39% 2,746,388 -24.15% 3 0.83%
Philadelphia 2,071,605 3 1.37% 1,603,797 -22.58% 6 0.48%
Los Angeles 1,970,358 4 1.30% 3,898,747 +97.87% 2 1.18%
Detroit 1,849,568 5 1.22% 639,111 -65.45% 27 0.19%
Baltimore 949,708 6 0.63% 585,708 -38.33% 30 0.18%
Cleveland 914,808 7 0.60% 372,624 -59.27% 54 0.11%
St. Louis 856,796 8 0.57% 301,578 -64.80% 69 0.09%
Washington 802,178 9 0.53% 689,545 -14.04% 20 0.21%
Boston 801,444 10 0.53% 675,647 -15.70% 24 0.20%


On the other hand, Chicago’s population decline is not especially large in historical context. As the accompanying table shows, each of the ten most populous cities in 1950 accounted for a smaller portion of the national population by 2020, and only Los Angeles and New York increased in absolute terms. Of the rest, Washington, D.C., Boston, and Philadelphia declined by somewhat smaller percentages than Chicago; while Baltimore, Cleveland, St. Louis, and Detroit experienced more severe contractions. Cleveland has a smaller population today than it did in 1900. St. Louis has fewer residents than in 1870.

Given all that, Chicago’s population loss doesn’t look so bad. Rather than standing as an indictment of the city’s quality of life and governance, it is better understood as a reflection of three nationwide trends. First, the middle of the 20th century saw urbanization crest in America. Chicago got smaller after 1950, but so did Philadelphia, Detroit, Baltimore, Cleveland, St. Louis, Washington, D.C., and Boston, all of which attained a population in 1950 that was higher than any of them recorded before or since. We’re not doing justice to the facts if we emphasize how far these cities fell without taking into account how high they had climbed.

Indeed, there’s a case to be made that the real peak of American urbanization was 1930, when the combined population of the ten biggest cities reached its highest figure ever, 15.5% of the national total, almost one out of every six Americans. Chicago, Detroit, and New York were among the cities whose populations represented their highest-ever portion of the country that year. One out of every 36 Americans was a Chicagoan in 1930, and one out of every 18 resided in New York. Chicago’s population increased from 503,185 in 1880 to 3,376,438 in 1930, a remarkable 571%, four times faster than the U.S. population, which grew by 140%. A city that had not existed in 1800 was, by 1900, the fifth largest in the world. Historians Edwin G. Burrows and Mike Wallace show in Gotham (1999), their history of New York City, that one motive for the 1898 consolidation of what became the five boroughs into the “City of Greater New York,” was civic leaders’ fear that Chicago’s dynamic growth would soon cause it to eclipse New York as America’s most populous and important city.

The second trend is the emergence of the Sun Belt, which was neither a term nor a reality in 1950. The democratization of air conditioning over the second half of the 20th century made it standard operating equipment in American homes, workplaces, stores, and automobiles, which helped transform the geographical distribution of the U.S. population. Economist Edward Glaeser pointed out in a 2019 interview with Harvard Magazine that average January temperature has become the single variable that best predicts changes in a metropolitan area’s population. In 1950, Los Angeles was the only one of the ten most populous cities located outside the country’s northeastern quadrant. In 2020, it was one of three California cities on the list, along with San Diego and San Jose. Texas also had three—Houston, San Antonio, and Dallas—as well as Austin (#11) and Fort Worth (#13). Phoenix, Arizona was the fifth most populous city in 2020, and Jacksonville, Florida ranked 12th. New York, Chicago, and Philadelphia are the only northeastern cities that made both the 1950 and 2020 top-ten list.

Technological changes have reduced the competitive advantages of older Northern cities in a second way. Prior to the 20th century, access to navigable rivers or good harbors had been indispensable for a city to flourish. Modern revolutions in transportation and communication meant that, for the first time in history, a landlocked city could thrive. The absence of a waterfront has even come to convey an important benefit: a “360 city” can add housing more easily than a geographically constrained “180 city.” This makes housing cheaper, which in turn makes a city more attractive to employees and employers. Relatively inexpensive housing has been an important factor in the growth of Dallas-Fort Worth, Phoenix, San Antonio, Las Vegas, Oklahoma City, and other inland cities.

That some neighborhoods added in these expansions are located beyond the central city’s border brings up suburbanization, the third national trend relevant to Northern cities’ declining population. It was a new phenomenon in 1950; Levittown started selling homes on Long Island in 1947. Thereafter, subsidized mortgages, expressways, shopping malls, and office parks made it one of the most important features of modern American life. In 1950 the Census Bureau examined America’s 168 “Standard Metropolitan Areas.” At the time, it found that 58% of the 83,930,000 people living in them were residents of central cities. In 16 of the 20 most populous, a majority of residents lived in the city. Seventy years later, a majority of the population lived outside the central city in all 20 of those Metropolitan Statistical Areas, to use the Census Bureau’s current term.

In 1950, for example, 66% of the population of metropolitan Chicago lived in the city of Chicago. By 2020, only 29% did. And yet, metro Chicago increased in population by 76% over these 70 years—slower than the national growth of 120%, but fast enough to mitigate both the area’s and the city’s decline relative to national trends. Chicago continues to figure more prominently in its metropolitan area—the third most populous after New York and Los Angeles—than other Rust Belt cities do in their regions. The city of Detroit, for example, accounted for 62% of its metro area population in 1950, when it was the country’s fifth largest metro area. By 2020 that proportion had fallen to 15%, and the metro area was the nation’s 14th largest, having increased its population by 48%. Other Midwestern metro areas have seen their entire population decline relative to the nation while the cities also declined relative to their suburbs. St. Louis and Cleveland were, respectively, the country’s ninth and 11th most populous metro areas in 1950. In 2020 they were 21st and 34th. The city of St. Louis used to account for 51% of its metro area population; today the figure is 11%. In Cleveland the corresponding 70-year decline has been from 62% to 18%.


Migration Logic

The best interpretation, then, of Chicago’s population decline between 1950 and 2020 is that it was the result of fundamental forces that diminished nearly every Rust Belt city, but to which Chicago was more resistant than most. As the mutual fund advertisements warn, however, past performance is no guarantee of future results. The fact that Chicago has not cratered doesn’t mean that it cannot or will not in the future…including, perhaps, the near future. Matt Rosenberg tells us that he came home to see if Chicago is “really circling the drain or not.” He doesn’t give a definitive answer, but his choice of details makes a civic demise sound like a genuine threat rather than an abstract possibility. “Ultimately the question seems, can this city be saved? And if so, how?” These are not doubts one poses regarding merely speculative dangers.

The title What Next, Chicago? takes in what happens to the city but also what it does: officials’, civic leaders’, and residents’ choices and actions. In a 2007 City Journal article, “Can Buffalo Ever Come Back?” Edward Glaeser made a point so basic that it is regularly forgotten: “Urban migrations aren’t random.” A city gains population if it proves conducive to securing a high quality of life and running a successful business, and loses population if it becomes inimical to these fundamental pursuits. Many determinants of growth or decline are beyond the control of any mayor or city council. The Erie Canal wasn’t built for Buffalo’s benefit, Glaeser explains, but the city grew rapidly after people began to realize and exploit the advantages of a location that connected the Great Lakes to the Atlantic Coast. Similarly, by the end of the 19th century, Niagara Falls was not just a tourist attraction but a source of hydroelectric power, giving Buffalo, “City of Light,” an enormous competitive advantage against other locations. Over the 20th century, however, technological changes negated these advantages while the disadvantage of long, fierce winters remained. Like so many other Rust Belt cities, Buffalo saw its population peak in 1950, at 580,000, and then decline: it stood at 278,000 in 2020, a 52% reduction.

The urban migrations that made Chicago grow dynamically until 1930, then contract at a measured pace in the years since 1950, were also not random. The city occupies the southwestern edge of the Great Lakes. After constructing some canals, none of them especially long or challenging, to link the Des Plaines River and Lake Michigan, Chicago also sat at a northeastern corner of the Mississippi River basin, which made it the key transit point between the Eastern seaboard and North American interior. Donald L. Miller’s history of Chicago, City of the Century (1999), stated, “New York, the busiest ocean harbor in the world, and Chicago, the busiest inland harbor in the world, became linked by nature and man,” the growth of each accelerating the growth of the other.

Chicago used the vast wealth created during its ascent to build infrastructure so formidable and institutions so admirable that they moderated its decline. But Buffalo, St. Louis, Cleveland, and Detroit, cities that fell apart gradually, then suddenly, once made similar investments. To avoid their fate, Chicago needs to take the steps necessary for its collapse to be an increasingly remote possibility rather than an increasingly imminent disaster.


Schools and Streets

To this end, What Next, Chicago? devotes a chapter to each of three reforms, two substantive—improving public education and fighting crime—and one procedural—making government in Chicago reasonably honest and efficient. Rosenberg provides sound policy recommendations, some borrowed from The New Chicago Way (2019) by Ed Bachrach and Austin Berg, a pension expert and an Illinois Policy Institute researcher, respectively. Others come from the Civic Federation, Chicago’s venerable, quixotic good-government advocacy organization. None of them is a surprise, something no one ever suggested before.

The surprise is that ideas of such obvious merit were not implemented long ago. Rosenberg wants both the school system and the police department to be rigorous, accountable, and obsessed with simple but crucial goals: educated students and safe streets. He calls for more charter schools, more ways for public school students to attend private schools, the intelligent use of testing to determine what works and what doesn’t, and policymaking that is more responsive to children’s needs than to Chicago Teachers Union demands. He also wants community policing—more proactive foot patrols and fewer reactive squad cars racing to the scene of a crime that has already taken place—along with violence prevention programs and bail reforms that astutely balance suspects’ rights with public safety.

Effective schools and safe streets are good in themselves, and good for their effects. Both are imperative if a city hopes to come out ahead as cities gain and lose population. One way modern cities prosper is by attracting young professionals. They propel the economy with high levels of discretionary spending, but also avail themselves of few public services while paying a disproportionately large portion of local taxes. The only hope that some significant portion of them will eschew suburbia after they begin forming families, however, is for the city to provide good educational options. If a decent percentage of these well-educated children later choose the city where they grew up as the venue for their adult lives, so much the better for the city’s population growth.

The rule that people are drawn to advantageous places and avoid disadvantageous ones applies even more strongly to crime than to education. Rosenberg spoke to Arne Duncan, President Obama’s secretary of education and a native Chicagoan, who calculates that the direct cost to Chicago of each homicide is $1.5 million: the taxes not paid, the multiplier effect of purchases not made by families and businesses moving out of the city or deciding not to move in, as well as tourists and conventions choosing other destinations. What Duncan calls “the reputational hit that Chicago has taken nationally and internationally” is over and above this seven-figure penalty.

Duncan’s contention aligns with research by economists Julie Cullen and Steven Levitt showing that every reported crime corresponds to a net loss of one resident from a city, and every murder corresponds to a net loss of 70. Earlier this year the Citadel hedge fund announced that it was relocating its headquarters from Chicago to Miami. “If people aren’t safe here, they’re not going to live here,” founder Ken Griffin told the Wall Street Journal. “I’ve had multiple colleagues mugged at gunpoint. I’ve had a colleague stabbed on the way to work. Countless issues of burglary.” This social and public-sector failure, he concludes, makes it “really difficult…to draw talent to your city.”

Griffin is not trafficking in “anecdata.” According to the University of Chicago Crime Lab, the number of shooting incidents in Chicago rose by half from 2019 to 2020. Then, instead of receding after the George Floyd unrest ended, the number of people wounded and killed by gunfire in Chicago rose again in 2021. The number of shootings in the Loop, Chicago’s central business district, rose from two in 2019 to 27 in 2021.

Crime is particularly threatening to Chicago’s future. Like most big cities, it saw crime recede in the 1990s after 30 years of increasing lawlessness. But because crime did not fall as far in Chicago as it did elsewhere, the more recent rise began from a higher plateau. Bachrach and Berg’s book notes that Chicago had 762 homicides in 2016, the same year there were 335 in New York and 294 in Los Angeles. In other words, the two biggest U.S. cities, with a total population in the 2010 census of 11,967,754, had 629 homicides between them. The third-largest city, with a 2010 population of 2,695,598, had 21% more than those two combined. The resulting homicide rates: 4.1 (per 100,000) in New York, 7.8 in Los Angeles, and 28.3 in Chicago.

By 1993 crime had become such a severe problem that both New York and Los Angeles resorted to the drastic step of electing Republican mayors, something New York had last done in 1965 and Los Angeles in 1957. (Chicago’s most recent Republican mayor left office in 1931.) The question of partisanship is relevant because most of the reforms that Rosenberg as well as Bachrach and Berg recommend have an unmistakable GOP vibe: market-based solutions, holding municipal agencies to rigorous standards, putting city finances on a sound basis through spending discipline, being solicitous of private business but disposed to resist public employee unions. And yet, none of America’s ten most populous cities (the only ones, as it happens, with a population of at least one million in the 2020 census) has a Republican mayor. And of the 26 cities with a population between 500,000 and 1,000,000, only five do: Jacksonville; Fort Worth; Oklahoma City; Fresno, California; and Mesa, Arizona.


Out of Sorts

So, even if we stipulate that there’s a strong case for Rosenberg’s reforms, that doesn’t guarantee that they will find a political constituency big enough to guarantee their enactment. Municipal democracies are shaped by forces that don’t ordinarily affect national politics. Despite celebrities’ tweets, few people follow through after threatening to emigrate because their party loses an election, or even a series of elections. At the state and local level, however, people vote not only with their ballots. They also vote with moving vans, by either hiring one or declining to. People who move out of a city because of bad schools and high crime have a lower tolerance for these civic dislocations than people who elect to stay despite them. As a result, the raw material for an electoral coalition that will demand, support, or even tolerate reforms like Rosenberg’s is heavily skewed toward people who live outside Chicago.

Why would anyone choose to remain in a city with dysfunctional schools and dangerous streets? In 2019, even before the post-George Floyd spike in crime across the country, St. Louis had the highest murder rate of any American city, 65 murders per 100,000 residents. Detroit ranked fourth, with 41 per 100,000 residents. As we have seen, both cities have lost most of their population since 1950. But neither city has lost all its residents.

In “Two Chicagos, Defined,” a 2014 post on his blog, The Corner Side Yard, urban planner Pete Saunders described Chicago as two parts Detroit and one part San Francisco. (Eight years ago San Francisco was increasingly affluent and dynamic, and not yet beset by the pathologies that Seth Barron describes elsewhere in these pages.) In the Detroit part, Rust Belt Chicago, urban decline is self-mitigating, though not in a healthy way. Depopulation reduces the demand for houses and apartments, lowering their price. As Glaeser wrote in his Buffalo essay, “declining areas…become magnets for poor people, attracted by cheap housing.”

In the San Francisco part, or “Super Global” Chicago, highly educated, well-paid people calculate that city living’s attractions outweigh its drawbacks. (Chicago’s murder rate in 2019 was 18 per 100,000, the 28th highest in the country.) The term “yuppie”—young urban professional—came into use in 1982, when crime rates were high and there was no good reason to expect that they would ever descend. To cope with Manhattan life, one yuppie advises another in Tom Wolfe’s Bonfire of the Vanities, “you’ve got to insulate, insulate, insulate.” (The bestselling novel was published in 1987, three years after Rolling Stone magazine started serializing Wolfe’s first draft.)

When urban crime, unexpectedly, began to decline in the early 1990s, and then continued to abate for another 20 years, the amount of insulating city life required also fell. Greater safety attracted more professionals to cities, a process that came to be described as “gentrification.” Some of the new gentry went so far as to complain that city streets had become a little too safe. Sociologist Derek S. Hyra’s Race, Class, and Politics in the Cappuccino City (2017) describes “living the wire,” a reference to The Wire, HBO’s hit series about the Baltimore drug trade. The cachet of some Washington, D.C., neighborhoods, Hyra found, corresponded to their association with “danger, excitement, poverty and blackness.” It seemed, he observed, that “neighborhood violence gave newcomers…something interesting to talk about at parties.”

As frivolous as living the wire may sound, it reflects an important sociopolitical reality. In The Big Sort: Why the Clustering of Like-Minded America Is Tearing Us Apart (2008), journalist Bill Bishop showed that, more and more, politics follows the logic of fraternity rush week. People reside near other people with whom they feel comfortable and avoid living around people with whom they feel uncomfortable. It is no longer just states that are red or blue—and getting either redder or bluer—but counties, cities, neighborhoods, career paths, religious denominations, and most other forms of social connection.

In the 1976 presidential election, 26% of voters resided in a “landslide county,” one that gave at least three fifths of its major party vote to one presidential candidate. (That is, the more popular nominee had a victory margin in that county of at least 20 percentage points.) The share of the electorate living in such counties has grown steadily: 38% in 1992, 48% in 2004, 51% in 2012, and 62% in 2016, falling back slightly to 58% in 2020. The share of voters casting ballots in a county where the winning presidential candidate received at least 70% of the major party vote—yielding a victory margin of at least 40 percentage points—grew from 7% in 1992 to 16% in 2004, 30% in 2016, and 29% in 2020. A 2019 GQ article on dating app users’ growing focus on a prospective match’s political preferences said that, since 2016, “partisan identification has inched even closer in alignment to social identity.” As a result, someone’s political preferences are an increasingly reliable proxy for that person’s “entire worldview.”

So, Jussie Smollett to the contrary, Chicago is not MAGA country: Joe Biden won 83% of the vote there in the most recent presidential election. More generally, the strengthening connection between urban living and Democratic voting is one of the Big Sort’s most consequential features. According to one researcher, Donald Trump lost 90 of the 100 largest cities in the 2020 election…including seven of the ten cities judged the country’s most conservative by two political scientists who had examined municipal politics. The biggest city Trump carried against Biden—but only by a margin of 49% to 48%—was Oklahoma City, the nation’s 20th-largest.

Today’s Democratic Party has a simple, obvious way to appeal to every segment of the urban electorate. For the Detroit parts of a modern city, there’s the promise of more and bigger social welfare programs, along with the commitment to fight systemic racism. For the dwindling urban middle class, dominated by municipal workers who are often required to reside inside city limits as a condition of employment, the Democratic Party and public employee unions are symbiotic in their defense of government workers’ pay, benefits, pensions, and honor. And for the city’s gentrified, San Francisco parts, being a Democrat affirms a worldview and offers identification with the like-minded, fortified by a shared disdain for those who really do live in MAGA country. Trading stories about urban violence for these Democrats is not just a way to enliven parties. It also affirms that they would rather be exposed to, and make excuses for, physical danger than share a neighborhood with narrow-minded, barely educated yahoos in small towns or exurbia.


The Chicago Way

Rosenberg’s education and crime agenda, then, will be hard to enact in almost any modern American city. Chicago, however, will be singularly resistant to his earnest, sensible ideas about reforming government.

He recommends, for example, that the city council be reduced from 50 to 25 aldermen, as its members are called. New York, with a population more than three times Chicago’s, has a city council of 51 members. Los Angeles, with 42% more residents than Chicago, gets by with a council of 15. This profusion of politicians is connected to another problem Rosenberg wants to fix: the “aldermanic prerogative,” as he calls it, which gives each alderman veto power over any zoning decisions required by a building project in his ward. This privilege guarantees that the insurance brokerages and law practices maintained by many aldermen will serve as toll booths that extract fares from builders and developers. Aldermen are as fiercely opposed to relinquishing their ability to collect such tolls as they are to eliminating half the booths.

Since Chicago has more real estate developers than city council members, one might suppose that the correlation of democratic forces would curtail aldermen’s ranks and power. In many cities it might. In Chicago, however, corruption has long been not merely pervasive but broadly participatory. It is not seen as the governing class exploiting a resentful citizenry but as how everyone, high and low, goes along to get along. As a result, good-government reformers are usually received as interlopers and pests, not the people’s defenders.

“Chicago: Pride of the Rustbelt,” a 1985 New Republic essay by labor attorney Thomas Geoghegan, recounts a federal prosecutor’s crusade against local judges who took bribes.

After the indictments came, the conventional wisdom was that Chicago voters would throw out all the sitting judges running for retention. Instead, the voters reelected every one of them. The real public outrage was of a different kind. “Hell,” one man complained to my brother, “now the average guy won’t be able to get a ticket fixed.”

In Chicago, Rosenberg says, corruption is “embedded in the DNA.” No one can recall a time when scrupulous government was the default assumption. An 1894 bestseller about the nexus between corrupt government and the underground economy was titled If Christ Came to Chicago. (Spoiler alert: He’d be displeased.)

It would be a mistake, however, to reduce the city’s corruption and the citizens’ acceptance and even defense of it to inertia and perversity. The Chicago Way, as those who live there understand it, is not just time-honored but time-tested. It reached its apotheosis under Richard J. Daley, Chicago’s Democratic mayor from 1955 until he died of a heart attack in 1976. In Don’t Make No Waves…Don’t Back No Losers (1975), political scientist Milton Rakove distilled the Chicago Way: “there is no such thing as the public interest insofar as the electorate is concerned.” Politics is, instead, about “the private, self-interests of the various groups that compose the electorate.” It is to their narrow and prosaic concerns, rather than to solving “broad social problems,” that the politician should attend. In that delimited moral universe, Daley’s favorite maxim is infallible: “Good government is good politics and good politics is good government.”

To borrow terminology Helen Andrews uses in her book, Boomers (2021), practitioners of “transactional” politics categorically reject the idea that governance can or should be “transformational.” (She calls Daley “America’s transactional leader par excellence.”) The transactional politics objection to the transformational is that when idealistic reformers campaign on the proud claim that they don’t owe anything to anyone, they sometimes get elected…whereupon their hapless tenure in office makes clear that nobody owes them anything, either. John Lindsay vindicated this warning as mayor of New York from 1966 to 1973, shortly before Jimmy Carter demonstrated its accuracy during his one-term presidency.

Transactional politics is not inherently corrupt. While climbing the political ladder, Daley spent eight years in the Illinois state senate, during which one of his colleagues marveled, “You couldn’t give that guy a nickel.” But transactional politics does lend itself to corruption: reduce politics to quid pro quo, emphasize that the purpose is to address narrow interests and concerns, and it is inevitable that some of the quids and quos will directly benefit politicians.

Whether those benefits harm the public or break the law is sometimes clear and sometimes not. In 2016, after Virginia’s former governor Robert McDonnell had been tried and found guilty in federal court of doing favors for a campaign donor, the U.S. Supreme Court overturned McDonnell’s conviction, faulting the prosecutor and trial court for an excessively broad interpretation of “official acts.” In an opinion for the unanimous Court, Chief Justice John Roberts wrote, “The basic compact underlying representative government assumes that public officials will hear from their constituents and act appropriately on their concerns.” Mayor Daley could not have said it better.


Plunder and Lightfoot

In Chicago’s latitudinarian court of public opinion, “act appropriately” has usually meant that a politician may collect some tolls, provided that nobody gets seriously hurt and that the government goes on to perform its essential functions competently and reliably. Chicago’s semi-official motto during the Daley years was “The City That Works.” Once in a while, though, evidence that Chicago doesn’t work becomes so strong that voters make the uncharacteristic decision to vote for transformation and against transaction. This is how Jane Byrne was elected mayor in 1979, weeks after the city government had been overwhelmed by one of the worst snowstorms in Chicago history.

Byrne ran as an outsider, tried to govern as an insider, and proved inept at both. In 1983 she lost to Harold Washington who, like Daley, died in office of a heart attack. After a decade of tumult, order was restored when Richard M. Daley, oldest son of the former mayor, was elected mayor in 1989, and went on to hold the office 22 years, longer even than his father.

By 2019, the city was again restive. Richard M. Daley’s successor, Rahm Emanuel, announced that he would run for a third term, then decided not to. Amidst the city’s rising crime and declining prospects, the news that the longest-serving alderman in Chicago history, Edward M. Burke, was being indicted for extorting business for his law firm, which specialized in property tax appeals, was met with anger instead of shrugs. Voters were disposed to believe that the city, rather than working through the medium of corruption, had stopped working because of it. The aligned planets allowed a long-shot outsider, attorney Lori Lightfoot, to win the mayoral election against better-known insiders, including William Daley, another of Richard J. Daley’s sons. She took office as Chicago’s first gay, second female, and third black mayor.

Rosenberg says that even though Lightfoot’s election “marked a hoped-for fresh start,” it was clear by her second year in office that she was a failure. “Although many of Chicago’s greatest policy problems were well established before Lightfoot took office,” he writes, “she has made things incalculably worse” by, above all, resorting to a “Unified Theory of Systemic Racism” to excuse every social pathology and government blunder.

Lightfoot is not uniquely responsible for Chicago’s decline and peril, however. The, well, systemic failing she personifies is the worst-of-both-worlds synthesis of the transformational and the transactional. Chicago politics has caught up to its demographics: Rosenberg highlights that 32 of the 50 current aldermen are black or Hispanic. But as Chicagoan Joseph Epstein anticipated 51 years ago in an essay for Commentary magazine, the demise of the Daley machine has yielded nothing better than its replacement by “a new set of thieves.” Chicago’s ascendant rainbow coalition of chiselers, in Rosenberg’s words, speaks “oleaginously about ‘social justice,’ equity, and equality. In practice, they follow the long-established script: you play along, or you get played.” The resulting predicament, described by Helen Andrews, is especially acute in Chicago: “we have all of the old machine politicians’ vices and none of their virtues.”


Goodbye, Columbus

So, again: What next, Chicago? It’s easy to describe what utter failure would look like: Detroit. That city has one of the nation’s worst crime rates, was forced into American history’s biggest municipal bankruptcy nine years ago, and has fewer than half as many residents today as it did when the last Model T rolled off an assembly line in 1927. Detroit is now in the midst of its most encouraging decade since the epic 1967 riot. Nothing else having worked, in 2013 America’s most predominantly black major city (77% by the Census Bureau’s 2021 estimate) elected a white mayor, Mike Duggan, the first to hold that office in 40 years. Reelected by landslides in 2017 and 2021, he drew praise from the national press along the way for improving a situation the world had assumed was hopeless. Despite these encouraging signs, however, Detroit’s population fell by another 11% between 2010 and 2020.

The reassuring way for a Chicagoan to think about Detroit is to emphasize that its dramatic decline had a great deal to do with uniquely unfavorable causes. Many cities had race riots in the late 1960s. None had one as bad as Detroit, a riot that “never stopped,” one local television journalist said in 1990. No city was as dependent on one industry as Detroit was on automobiles, which meant that the travails of Chrysler, Ford, and General Motors had a devastating impact on Detroit. Finally, no city had a more antagonistic relationship with its own suburbs than Detroit, where a growing metropolitan area sought to flourish by divorcing its future from the shrinking, dysfunctional city at its center.

Chicago’s problems are not these problems, which supports the hope that it won’t suffer Detroit’s fate. Unfortunately, other Midwestern industrial cities without Detroit’s problems have also lost population: Cleveland and St. Louis, as we have seen, but also Cincinnati (which declined by 39% from its peak in 1950 to 2020), and Milwaukee (whose population peaked in 1960 and was 22% smaller by 2020). Even Minneapolis-Saint Paul, widely touted for effective governance and a high quality of life, had a combined population in 2020 that was 11% lower than it had been in 1950. That so many cities in the same part of the country have diminished over the same period of time argues that their problems are more regional than local.

The possibility that Chicago’s fate may be largely out of its own hands provides equivocal comfort. In 2012, urban policy expert Aaron Renn argued in City Journal (Second-Rate City?”) that Chicago should disabuse itself of hopes to recapture the global preeminence it enjoyed over 100 years ago. Rather, its best attainable future is to perform capably the role it has played throughout the 20th century, the “unofficial capital of the Midwest,” in Renn’s words. He quotes an economist who says, more specifically, that Chicago’s path forward is to be the “business service center of the Midwest, serving regional markets and industries.”

The problem is that the Midwest has been declining for over a century, with no end in sight. By the Census Bureau definition, the Midwest comprises 12 states: Illinois, Indiana, Iowa, Kansas, Michigan, Minnesota, Missouri, Nebraska, North Dakota, Ohio, South Dakota, and Wisconsin. In 1900—when twice as many people lived in Missouri, America’s fifth most populous state, as in California, ranked 21st—the Midwest accounted for 35% of the U.S. population. By 1950 its share had fallen to 29%. In 2020, it stood at 21%. Each of the Midwest’s 12 states now has a smaller proportion of the U.S. population than it had 72 years ago, and ranks lower in the list of states by population than it did in 1950.

A few Midwestern cities have outperformed the region. Columbus, in particular, has grown by 141% since 1950, faster than the nation overall. In its history, Columbus has never had a decade where its population declined from one census to the next. Most recently, it increased 27% between 2000 and 2020. This is a Sun Belt rather than a Rust Belt pattern, abetted by the Sun Belt practice of annexing new developments just beyond existing city borders. Columbus is now the largest city in Ohio (with more residents than Cleveland and Cincinnati combined), second largest in the Midwest, and ranked 14th in the country.

Could Chicago, or even Detroit, reverse its fortunes by figuring out what Columbus is doing, and then imitating it shamelessly? Such a course tracks closely with Rosenberg’s advice to stick to the basics. Columbus had nine murders per 100,000 residents in 2019, a rate half of Chicago’s. Intel recently announced a decision to invest $20 billion in new manufacturing facilities outside Columbus. Its CEO said that key considerations were the favorable tax and regulatory environment, affordable housing, and “a strong commitment to industrial education,” in the words of urban affairs scholar Joel Kotkin.

By contrast, Boeing and Caterpillar have announced this year that, like the Citadel hedge fund, they are moving their headquarters from metro Chicago to other states. To be fair, Google and Kellogg both committed this year to increasing their Chicago workforce and office space. Still, only three states had smaller populations in 2020 than they did in 2010: West Virginia and Mississippi, two of the nation’s poorest, and Illinois. Ohio increased by 2.4%—less than the national figure of 7.4%, but, Renn points out, the Columbus metro area accounted for 84% of the state’s growth during that decade.

It’s not clear, in any case, that governing itself more like Columbus or a Sun Belt city is an option Chicago is capable of choosing, even if the advantages of doing so are clear. As previously discussed, the fact that a reform is sensible or even imperative does not guarantee that it is politically feasible. The Chicago Way has outlived its usefulness in many respects, but that does not mean it has outlived its appeal to Chicagoans. Enlightened statesmen will not always be at the helm, nor will enlightened citizens always prevail at the polling places.

Second, embracing the Columbus Way is necessary to bending Chicago’s trajectory up, but not sufficient. Policymakers do not get to write on a blank page. Columbus never created many of its advantages vis-à-vis Chicago, which cannot now summon such circumstances at will. For the century prior to the 1970s it was to Chicago’s benefit and Columbus’s detriment that the former city had a huge manufacturing base that the latter did not. But over the past half-century, when smokestack industries have been beleaguered, this disparity meant that Columbus “had less of a hangover from deindustrialization,” in Renn’s words, giving it more latitude to shape its destiny.

To the extent that Chicago can choose its future, muddling through is the best of its realistic paths. It retains distinct advantages. For those who prize city living—“dense, walkable, mixed-use neighborhoods and extensive transit,” to quote Renn once more—Chicago is more affordable than any coastal city, and more urban than any interior one.

These benefits won’t count for much, however, if Chicagoans fear leaving their homes. (But also staying in them.) There are ways people can work around bad schools—charters, private and parochial schools, homeschooling—but none that exempts you from dangerous streets. The nationwide reduction in crime that began 30 years ago was a great achievement, and the cavalier decision to squander it due to cant about “mass incarceration” is a great outrage. The livability of heavily Democratic cities will depend, above all, on the evolving intra-Democratic consensus about criminal justice policy. San Francisco voters’ recent decision to recall prosecutor/social worker Chesa Boudin is encouraging, but hardly dispositive. His counterpart, Kim Foxx, was elected Cook County state’s attorney in 2016 on the promise to get tough on prosecutors and police officers who get tough on crime. She won reelection four years later despite higher crime and despite becoming a national laughingstock in 2019, when she secured lenient treatment for hate-crime hoaxer Jussie Smollett. In suburban Cook County, which cast 1.19 million votes in the 2020 state’s attorney election, Foxx ran behind her Republican challenger, 48% to 45%. But in Chicago, where crime is more prevalent and the Democratic Party much stronger, Foxx won 64% of the 1.08 million votes, giving her an overall victory of 54% to 39%.

To the extent that Chicago’s future chooses itself, large trends and facts that mere politicians and voters cannot control or understand will assert their power. Perhaps climate change will, to Chicago’s advantage, make July temperatures rather than January ones a good predictor of where people and businesses choose to locate. If drought in the western half of the continent is also a long-term change, then cities near the Great Lakes, where 90% of the nation’s and 20% of the world’s fresh water is located, will reap the benefits.

An exogenous variable that threatens Chicago’s future is the same one that makes cities’ prospects in general uncertain: half-empty office buildings and business districts around the country may prove the most durable of COVID’s lingering effects. In Chicago’s Loop, for example, office occupancy rates were 46% in June 2022, compared to virtually 100% at the beginning of 2020. If migrations from one city to another are not random, then the migration from the conference room to the Zoom call also reflects changing opinions about optimal arrangements. Humans, Edward Glaeser said in 2019, “are a social species that gets smart by being around other smart people.” He predicted a long, promising future for urban living because communications technologies cannot transmit the many “wonderful cues” people have for “communicating comprehension or confusion to people who are next to us.”

Three years and one pandemic later, we know that technology can change and improve, and that a surprisingly large number of people prefer to tolerate its remaining deficiencies than to devote ten hours every week, the equivalent of 21 entire days out of every 365, to a soul-crushing commute. Technological advances frequently reveal that what had been regarded as virtues really consisted of making a virtue of necessity. Many people who had considered themselves avid movie-goers, for example, have turned out to be movie-stayers, watching streaming services at home on a flatscreen the size of an SUV. We may be in the process of discovering that, given the opportunity, we are an asocial species, eager to limit and curate the list of people with whom we spend time in the same room. In the early days of the internet, its enthusiasts talked about “the obsolescence of place,” a future where one could do just about anything from just about anywhere. If that future is no longer distant, then among Chicago’s challenges will be one confronting most cities: the unplanned obsolescence of urban living.