The Daley Show by Forrest Claypool

Forrest Claypool was deeply involved with Chicago politics after Richard J. Daley and the rise of the Boss' son and has written a fascinating book that helps document Richie Daley's history

By Ray Hanania

FREE/Mayor Daley, Chicago Politics, City Hall/Friday, June 13, 2025

The story of Chicago politics is as fascinating as a modern-day Shakespearean drama involving local conspiracies, broken relationships, power grabs, and the impact on everyday lives.

Forrest Claypool was involved in regional politics from the day he graduated from Law School at UIUC College of Law in 1981 and rose to become one of former Mayor Richard M. Daley’s political consultants, as well as running for and winning several public offices.

Though he was the editor of his Law School Review, Claypool was more of a political insider who learned to understand the art of relationships, alliances, and the evolution of public issues.

He has brought those two talents together, writing a fascinating account of Richie Daley’s rise from the shadows under his powerful father, fighting through rivalries in his father’s Machine to become the savior of Chicago’s race relations.

I covered Chicago City Hall from 1976 through 1992, fulltime from 1978 working from a desk in the City Hall Press Room, and covered the news that Chicago politicians, aldermen, committeemen, and the lobbyists who influenced those circles. And I encountered Claypool many times, a professional who always seemed to maintain his humanity despite the ugly world we both walked.

While I know everything about Daley, his stumbles, his rise, his failures, and his successes from firsthand coverage of his political life, Claypool has put it together in a compelling chronology that helped separate the Machiavelli from the reality.

Daley struggled after his father died in December 1976, which was only months after I first met The Machine Boss in his offices with, at his side, Col. Jack Reilly, who had a Pirate’s patch over his left eye.

That struggle became the focus of much of my political writing between 1976 and 1989, when Richie Daley finally won office to follow in the steps of his powerful father.

Claypool does a precise job of detailing all that and more in his book, “The Daley Show: Inside the Transformative Reign of Chicago’s Richard M. Daley,” published by Three Fields Books, an imprint of the University of Illinois, in September 2024.

What Claypool did in his book that others have not is to present Richie Daley in the context of his different eras, which all contributed to his political successes.

Reading through the first several chapters was like reliving those early days when Richie Daley would call and ask for help, as Mayor Jane M. Byrne would target his allies and organization. Byrne wanted to undermine what she feared was his plan to eventually oust her and take over the Mayor’s 5th Floor executive offices.

Talking with Richie Daley put me on Byrne’s hit list, and she constantly attacked me, asserting that I was his “voice” because my newspaper writings and weekly Political Grapevine Columns appeared in the pages of the Southwest and Suburban Southtown Newspapers.

It also exposed me to being exploited by Ricchie Daley himself, like when he wanted to mislead Byrne and her choice for Cook County State’s Attorney, Ald. Edward M. Burke, by lying to me about his decision to run for Cook County Clerk rather than for the office of the county’s chief prosecutor.

Daley also lied to Sun-Times political editor Basil Talbot, and he also wrote that Daley planned to run for Clerk.

It all convinced Byrne and Burke to delay their announcement long enough so Richie Daley could get his announcement out first.

I knew I was screwed at that announcement press conference on Monday morning when Daley told the gathering, “First, I would like to acknowledge a reporter who I admire and who is honest and who has done so much to open theeyes of the Chicago public …” WIND Radio reporter Fran Spielman, who carried my clerk story on the airwaves, nudged me and said to me, “Well, he really fucked you.”

That entire period from his father’s death to the day Daley finally won election as mayor is the essence of Chicago politics at its finest machinations. It doesn’t get better. Claypool captures all of that atmosphere and the political machinations in the book’s first six chapters, what I call the First Era of his political career.

Daley’s persona changed dramatically in the second period, and he became more focused on bigger issues, less personality, and more entanglements that eventually convinced him to retire while he was still standing on his two feet. (Most mayors I know and covered cling to office until they are carried out on an emergency response gurney in cardiac arrest.)

That First Era in Richie Daley’s life defined him forever, and his politics that followed in his subsequent terms, which were never as exciting as the first “Richie Epoch.” That’s the Richie Daley and the Chicago politics I loved.

Yet Claypool transforms the politics of the new mayor’s power into a fascinating understanding of how politics works in a big city like Chicago.

And then there is the Third Period, the “end” of the Daley era, in which Richie Daley just stepped down, succeeded by politicians who could never even come close to what he had achieved, offered, or even experienced.

I was riveted by the first part of the book because it was so close to home, so personal for me. Claypool nailed it all so precisely.

The rest of Richie Daley’s 22 years in office I will leave to history, and Claypool’s book makes a major contribution towards helping readers understand the bigger picture that Richie Daley sought to fulfill.

Clearly, Claypool had the enthusiasm for politics, and the firsthand insight that is all reflected in his book, from someone who was there on the frontlines every day and who also paralleled in political offices.

Claypool’s bio is extensive. He served as: twice as chief of staff to Chicago Mayor Richard M. Daley (89-91, 98-99); Superintendent of the Chicago Park District (93-98); two terms as a commissioner on the Cook County Board (2002-10); the Chicago Transit Authority president (2011-15); Superintendent of the Chicago Public Schools (2015-17), as well as stints as deputy State Treasurer and deputy Commissioner on the Cook County Board of Appeals.

“The Daley Show” is available at most bookstores. Click here for Amazon.

Of all the books on Chicago politics, this one brought me back so closely to what happened, and it is the best.