The Windy City is not just a great American metropolis – 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 there is an emerging counter-narrative about Chicago, 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 shocking levels of crime and violence. There’s an argument to be made – and you’ll hear it in this episode – that present day Chicago is in dire trouble.

How could a great American city lose its mojo so quickly? For answers we turned to Forrest Claypool, a man who could credibly be dubbed (and we mean this as a compliment) the Robert Moses of Chicago, a consummate power broker. Claypool boasts a breathtaking résumé: two stints as Chief of Staff for Mayor Richard M. Daley (son of Richard J. Daley), another under Rahm Emmanuel, a former business partner with David Axelrod, and who at various points ran the Chicago parks department, transit authority and school system. But Claypool is also a committed reformer who took on the old political machine as a Cook County Commissioner and who believes in the importance of good governance.

The author of The Daley Show, a recent, fascinating account of the tenure of the younger Mayor Daley, who led the city for six terms (leaving office in 2011), Claypool tells us he wrote the book out of anger at witnessing the sharp decline in Chicago’s governance 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. 

But no longer. We explore with Forrest what’s gone wrong since first Lori Lightfoot and then in 2023 Brandon Johnson – arguably the most unpopular big city mayor in the country – took the reins of power in Chicago. And we conclude by discussing what it will take for the city to regain its tattered glory. 

Our editor is Quinn Waller. 

About Blue City Blues

Twenty years ago, Dan Savage encouraged progressives to move to blue cities to escape the reactionary politics of red places. And he got his wish. Over the last two decades, rural places have gotten redder and urban areas much bluer.  

 
America’s bluest cities developed their own distinctive culture, politics and governance. They became the leading edge of a cultural transformation that reshaped progressivism, redefined urbanism and remade the Democratic Party.

But as blue cities went their own way, as they thrived as economically and culturally vibrant trend-setters, these urban cosmopolitan islands also developed their own distinctive set of problems. Inequality soared, and affordability tanked. And the conversation about those problems stagnated, relegated to the narrowly provincial local section of regional newspapers or local NPR programming. 

The Blue City Blues podcast aims to pick up where Savage’s Urban Archipelago idea left off, with a national perspective on the present and the future of urban America. We will consider blue cities as a collective whole. What unites them? What troubles them? What defines them?