Forrest Claypool, author of The Daley Show: Inside the Transformative Reign of Chicago’s Richard M. Daley, answers questions on his new book.
Q: Why did you decide to write this book?
I was motivated by Chicago’s seemingly inexorable slide downward, with the return of endemic, violent crime; a flight from public schools; and an outmigration of companies and jobs. I wanted to remind people of what Chicago was like not that many years ago and could be again. I felt that despite many mistakes and failures, the 22-year mayoralty of Mayor Richard M. Daley held innumerable lessons about successful municipal governance–lessons that are neither understood nor appreciated in today’s political climate and culture. Those lessons are important for Chicago, but also for many other struggling American cities.
Q: What is the most interesting discovery you made while researching and writing your book?
That so much of what Mayor Daley accomplished—things that lifted the city from a historical morass to international status—almost didn’t happen. The book contains behind-the-scenes stories that show the fine line between success and failure–how one key mayoral decision, one resourceful act by a staffer, one political alliance or one unexpected election outcome, made great things possible. The history could have been much different. Chicago’s airports might be a shadow of themselves and under suburban control; the razing of the public housing high rises might have been blocked; the mayor may never have been given state authority for his turnaround of the public schools; Millennium Park could never have come into being. So many big things came down to little things. But their ultimate success depended on Daley’s unique skills as a politician, planner, recruiter, and manager.
Q: What myths do you hope your book will dispel or what do you hope your book will help readers unlearn?
One myth is the mantra from today’s political class that there has been “disinvestment” in Chicago’s poor or working-class neighborhoods in the preceding decades. That’s simply not true. Nobody invested more in Chicago’s neighborhoods than Rich Daley. People need to remember what the city was like in 1989. His prodigious investments and thoughtful policies turned many poor neighborhoods into middle-class ones; and he elevated the quality of life for citizens in other struggling neighborhoods and gave them hope for a better future. We’ve seen regression since, because of the Great Recession and poor management and policies, but it’s not from “disinvestment.” A second myth is that Mayor Daley broke the city’s finances. He certainly was a big spender, and left too much debt, but the biggest cause of Chicago’s fiscal woes today are the unrealistic, unfunded pension mandates foisted on the city by state politicians in Springfield.
Q: Which part of the publishing process did you find the most interesting?
The re-organizing, editing, and proofreading. I find that process of “polishing,” or adding hundreds of incremental improvements, more enjoyable than the main manuscript writing. I include in this “polishing” the footnotes, which are great places to add information or share anecdotes that don’t fit in the flow of the text. I came to appreciate footnotes when I was a writer and later editor-in-chief of the University of Illinois Law Review. Law reviews are infamous for sprawling footnotes that dwarf the main text. A University of Pennsylvania law student wrote a wonderful parody for his law review entitled, “The Common Law Origins of the Infield Fly Rule.” The first sentence is “In the beginning,” and is footnoted to Genesis, with a description of how God created heaven and earth.
Q: What is your advice to scholars/authors who want to take on a similar project?
Make sure you’re passionate about the subject matter. Without it, the discipline to write is hard to come by. I wrote The Daley Show while holding down a full-time job. It took years, but without my passion for the subject, I could not have managed to do both.
Q: What do you like to read/watch/or listen to for fun?
Like millions of others, I am anxiously awaiting Robert Caro’s final installment of The Life and Times of Lyndon Johnson. But I’m less a book reader than a daily consumer of a cross section of publications, from the New York Times and Wall Street Journal to the National Review, Politico, Barron’s, the Economist, and The Free Press. I even read Popular Mechanics, despite being a functional illiterate. I watch CNN and enjoy Margaret Hoover’s Firing Line and the Bill Maher Show, as well as the Comedy Channel’s The Daily Show, which is more insightful than most real news outlets. I watch a lot of Netflix (recent winners: One Day and The Gentleman) and my wife and I recently discovered a long-running, dryly hysterical British comedy, Doc Martin. I like listening to the two Chicago sports radio stations during football season, and of course every Bears game. But my real passion is Illinois basketball. I live and die with the orange and blue.

Forrest Claypool has served as the Chief Executive Officer of the Chicago Park District (1993–1998), the Chicago Transit Authority (2011–2015), and the Chicago Public Schools (2015–2017). He was the chief of staff to Mayor Richard M. Daley in his first and third terms.