raincitygirl

Are you thinking of Royko's "Boss" which focuses on Richard Daley? That's the classic on the Chicago machine. My mom was from Chicago so I know it well. In the nineties, a more nuanced but dryly academic biography came out from Biles: "Richard J. Daley: Politics, Race and the Governing of Chicago."

There's another one that is less Daley centred, called "Grafters and Goo Goos" which goes back to the nineteenth century, showing the endemic levels of corruption in American urban politics.