What to read to understand Chicago
CHICAGO SUFFERS from an identity crisis. Its many nicknames are proof enough. The Windy City also claims to be The City of Big Shoulders, The City in A Garden, The City by the Lake, The City that Works and the Second City, a self-mocking title that is no longer true, at least in terms of population, since Los Angeles overtook it. In addition, it is Chi Town, Chiberia (on the coldest winter days) and occasionally still Chiraq, an out-of-date update to Beirut by the Lake, often heard during the 1980s. When you include the suburbs it becomes Chicagoland, which conjures up ideas of a theme park where none of the hotdogs has ketchup. Yet Chicago has an outsized grip on Americas imagination. It is considered to be, in the words of Barack Obama, its most famous adopted son, a quintessentially American city. Whereas New York and Los Angeles are elite, coastal and a little foreign, Chicago is in the heartland. Partly for this reason, it remains influential in national politics. The Democratic Party is holding its convention there in 2024; Fox News devotes much time to discussing its problems. Here are six books to understand what the Windy City is really about. Boss. By Mike Royko. Plume; 240 pages; $18 The Power Broker, Robert Caros biography of Robert Moses, sits on the shelves of political obsessives throughout the English-speaking world. If Chicago were as big as New York, Boss by Mike Rokyo would probably be just as famous. In the 1960s, 1970s and 1980s, Royko was a columnist for the Chicago Daily News, and later, when the News folded, the Chicago Sun-Times and the Chicago Tribune. Boss is his contemporary biography of Richard Daley, perhaps the most powerful elected mayor in American history. Just as it is impossible to understand modern New York without knowing how Moses rebuilt it, comprehending Chicago today requires you to understand the political machine that Daley built, which even today is not entirely dead. Royko explains zippily how Daley amassed power and exercised it, while giving as good a pen-portrait of Chicagos neighbourhoods as you will find of any city. Though it lacks the magisterial depth of Caros book, Roykos has two big advantages: it is much shorter and a lot funnier. Humboldts Gift. By Saul Bellow. Penguin Classics; 512 pages; $18 and 10.99 Humboldts Gift, published in 1975, won Saul Bellow a Pulitzer prize the following yearwhen he also scooped the Nobel prize in literature. It is about a washed-up writer, Charlie Citrine, who inherits a bizarre gift from his former mentor, a poet named Von Humboldt Fleisher (who is apparently named after a park near where Bellow grew up). Critics did not all love the novel: it is, in some ways, two books in one. One is a slow musing on middle age, Jewishness and success; the other is a madcap farce involving incompetent mafia men, grasping mothers-in-law and comically inept divorce lawyers. Yet it is also fundamentally a Chicago novel. Citrine is, like Bellow, from the north-west side, and having achieved success young, he returns to Chicago to muse on the fundamental nature of boredomsomething he believes a provincial, cold, Midwestern city to possess the very essence of. But try as he might, things keep happening to him. A lot of Chicagoans might recognise that. The Warmth of Other Suns. By Isabel Wilkerson. Knopf; 640 pages; $18. Penguin; 14.99 Though not strictly a book about Chicago, Isabel Wilkersons magnum opus about the great migration of African-Americans from the fields of the South to the industrial cities of the north begins in Chicago, and so it should. Whereas New York or Los Angeles grew up around ports, Chicago is a railway capital: one that connects America to itself, rather than America to the world. And so when the formerly enslaved people of the South began to seek out better opportunities than picking cotton, and an escape from the racism of Jim Crow, many drifted to Chicago. Their arrival, beginning in earnest around a century ago and continuing until the 1970s, reshaped the city. As Ms Wilkerson writes, the imprint of the great migration is still today everywhere in urban life. Even as it created for the first time a large and prosperous black middle class, able to support a thriving musical and cultural world, it also sparked a backlash, accelerating white flight, suburbanisation and the citys bifurcation. Read our full review of the book, published in 2010. Fire on the Prairie. By Gary Rivlin. Temple University Press; 312 pages; $34.95 The election of Harold Washington, Chicagos first black mayor, in 1983, was such a shock to the country that Royko wrote a column in which he told his readers not to worry: the new mayor doesnt want to marry your sister. Gary Rivlins Fire on the Prairie explains how it happened, and what ensued when Washington had to contend with a hostile city council that worked to hamper his every move. As Mr Rivlin writes, when Washington won, he toppled the most fearsome political-patronage machine still working in any American city, but what people reported on was the colour of the man who kicked it over and the hatred on the faces of those opposing him. In that election, 82% of Chicagoans turned out to votean almost unimaginably high proportion today. Washingtons victory in part inspired Mr Obama to move to Chicago to work as a community organiser. It still echoes in Chicago today. Few politicians in the city can resist invoking Washingtons legacy. Every Goddamn Day. By Neil Steinberg. University of Chicago Press; 408 pages; $25 This book is a collection of anecdotes, all connected to Chicago, with one for every day of the year. Together, they make up a veritable guide to the history of the Windy City, taking in both its momentous dayssuch as Washingtons surprise victory in the Democratic mayoral primary in 1983, or the eruption of race riots in 1919. But there are also joyously ephemeral entries too. Journalists from the Sun-Times opened their own bar, the Mirage, in order to prove that businesses were being shaken down by city officials. And a visiting Oscar Wilde offended half the city at once by denouncing its gothic water towera survivor of the great fire of 1871as a castellated monstrosity, with perforated pepperboxes stuck all over it. Chicago: City On The Make. By Nelson Algren. University of Chicago Press; 152 pages; $17 and 7 Before you earn the right to rap any sort of joint, you have to love it a little while, begins the fourth chapter of this long-form poem. Chicago, Algren went on, is a backstreet, backslum loudmouth whose challenges go ringing round the world like any green punks around any neighbourhood bar. Through a blistering 100 pages, the poet leads the reader through the foundation of the city up until 1951, when he wrote this book. Chicago, he opined, was a city founded by hustlersa frontier town, where the gouging and the cunning and the no-holds-barred spirit of the Middle Border still holds as true as rent day. Hustlertown keeps spreading itself all over the prairie grass, always wider and wider. It is, he wrote, the most native of American cities. Today, Chicagos claim to be a rough frontier town is more and more a fiction; in fact, it is a gentrifying centre of professional services. But Algrens words still help Chicagoans to define themselves otherwise, as denizens of a brokers portage, which has always been a fighters town. Long may it continue to do so. Also try Read our special report on Americas Midwest (from 2020) and the role of Chicago as the regions capital city.