Cautionary Tale: What’s the Matter with Chicago?

Podcast: Blue City Blues, S1, episode 21: What’s the Matter with Chicago?

Blue cities matter. Increasingly, they are the economic engines that power the country. In the 2024 presidential election, Kamala Harris won only 14 percent of the nation’s counties – her support was concentrated in what Dan Savage 20 years ago presciently dubbed the urban archipelago – but (as a post-election Brookings analysis found) they accounted for 63 percent of US GDP.

The metropolitan bastions of blue America matter politically as well. A lot. They are home to the bulk of increasingly culturally cosmopolitan base voters of the latter day Democratic Party. They are the places where progressive governance reigns supreme, and where many of the policy ideas that animate Democrats nationally are first adopted and tested.

And blue cities loom increasingly large in the fever swamps of the MAGA Republican imagination, too. Their efforts to turn poor outcomes and mounting problems in blue cities into a political cudgel with which to beat Democrats is at least partially to blame for the election of Trump (in November 2024 big blue cities like New York and Los Angeles were the places where the percentage shift towards Trump was the greatest).

Of course, much of what the anti-urban right has to say about American cities is ludicrous hyperbole. Trump often derides blue cities as Grand Guignol hellscapes run by Marxist radicals, where everyday life supposedly resembles a Hobbesian state of nature or the grotesqueries depicted in a Hieronymus Bosch painting. In announcing the federal takeover of policing in Washington, D.C., Trump absurdly claimed “our capital city has been overtaken by violent gangs and bloodthirsty criminals and roving mobs of wild youth” and has previously called D.C. a “rat infested, graffiti-infested shithole.” Indeed, “living in hell” has become a favorite and oft-repeated Trump phrase to describe life in blue cities generally.

Which brings us to Chicago, the city Trump and other Republicans arguably most often use rhetorically as their urban punching bag. In their telling, Chicago stands out as a particularly disastrous blue city, a violence-plagued blast zone of failed and overly permissive progressive governance. During his first term, as crime and gun violence in the city was on the rise, Trump tweeted about Chicago often, claiming the city was “worse than some of the places we’re hearing about like Afghanistan” and a “total DISASTER.” He’s continued the rhetorical barrage in his second term, including suggesting that after the D.C. takeover Chicago may one of the cities he directly intervenes in next.

Unfortunately for Democrats, given that their national fortunes are increasingly linked to the state of governance in blue cities, Trump’s claims about Chicago, while exaggerated, aren’t exactly off target. Sharp criticisms of progressive governance in Chicago in recent years comes not just from Trump, but from many of the city’s own civic leaders, who say that inexperienced, hyper-ideological mayors, first Lori Lightfoot and now her successor, Brandon Johnson – who has quickly become the most unpopular big city mayor in the country, with a record low 14 percent approval rating – have driven the city in to a ditch.

One such critic is Forrest Claypool, our guest on the latest Blue City Blues episode. Claypool is a Democrat, who served on Barack Obama’s media team in 2008. He’s also the consummate Chicago power broker, who boasts a breathtaking résumé traversing the halls of municipal power: two stints as Chief of Staff for six-term Mayor Richard M. Daley (son of “Boss” Richard J. Daley), another under Rahm Emmanuel, a former business partner with Obama political consultant David Axelrod, and who at various points ran the Chicago parks department, transit authority and school system. But, as comes through in our conversation, Claypool is also a committed municipal reformer who took on the old political machine as a Cook County Commissioner, and who believes in the importance of good governance.

Claypool tells us that the Windy City is not just a great American city – the third largest in the United States – it is a world class city, recognized globally as a center of finance, trade and economic dynamism, and as a cultural and tourist mecca. But… he then offers a counter-narrative about Chicago, telling us a declension story of a great and proud urban powerhouse now fallen to its knees, beset by incompetent governance, fiscal mismanagement, declining quality of life, and unacceptable levels of crime and violence. He argues, in short, that present day Chicago is in dire trouble.

Claypool is the author of The Daley Show, a recent, fascinating account of the tenure of the younger Mayor Daley, who led the city for 22 years (a slightly longer tenure in power than his father), leaving office in 2011. Claypool wrote the book out of anger at witnessing the sharp decline in Chicago’s fortunes since Daley left office. While Daley was far from perfect and was ultimately brought down by accumulating scandals and controversies, Claypool cogently argues that the city worked, and thrived, in the Daley years, as economic vibrancy and quality of life soared, the schools improved markedly, and the city took on big challenges and projects – hosting the 1996 Democratic convention, building Millennium Park – successfully.

But those days are in Chicago’s rear view mirror. We explore with Claypool what’s gone wrong since first Lori Lightfoot and now Brandon Johnson (elected in 2023) took the reins of power. How could such a great and successful city lose its mojo so quickly? He argues it is about poor and inexperienced and overly ideological leadership, combined with the rise of new political machine in the city centered on the powerful and deeply itself-interested Chicago Teachers Union, as well as long-standing structural issues like Chicago’s massively underfunded pension obligations, which he says have rendered the city functionally “insolvent.”

When we asked Claypool what will fix Chicago and other ailing blue cities – and restore the fortunes of the Democratic Party more broadly – he points to the abundance arguments put forth by Ezra Klein and Derek Thompson in their bestselling new book as a potential pathway forward, particularly their focus on lowering costs and improving results. “Like, in Chicago right now they’re building so called affordable housing at $1.1 million a pop, because of all the goofy regulations, all the politically correct stuff that is elevating costs,” Claypool says. He adds, “who are we trying to serve here? The politicians, the activists, the ideologues? Or are we trying to serve the people?”