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The Daley Show: Inside the Transformative Reign of Chicago's Richard M. Daley
American cities once had mayors who actually governed.
For twenty-two years, Richard M. Daley ran Chicago with the type of authority that is unthinkable today. He reshaped downtown, triggered a jobs boom, delivered the iconic Millennium Park, and slashed violent crime to 40-year lows. He outfoxed Republican legislators to retain control of O’Hare Airport and expand it into the nation’s premier international aviation hub. Leveraging carefully built national political ties, he sidelined a powerful nemesis to tear down Chicago’s infamous public housing projects.
Rebuilding parts of his father’s legendary political machine through brazen (and illegal) patronage deals, he centralized power to a remarkable degree, cut deals behind closed doors, racked up piles of debt, and made long-term bets whose consequences are still unfolding.
This is not simply a biography. It is a challenge to contemporary urban
Do cities thrive because of strong, decisive leaders—or despite them?
Through vivid storytelling, this book exposes how Daley consolidated power, aligned business and labor, navigated crises, survived damaging scandals, and imposed discipline on a sprawling city. It dares readers to reconsider what kind of leadership modern American cities truly need.
For twenty-two years, Richard M. Daley ran Chicago with the type of authority that is unthinkable today. He reshaped downtown, triggered a jobs boom, delivered the iconic Millennium Park, and slashed violent crime to 40-year lows. He outfoxed Republican legislators to retain control of O’Hare Airport and expand it into the nation’s premier international aviation hub. Leveraging carefully built national political ties, he sidelined a powerful nemesis to tear down Chicago’s infamous public housing projects.
Rebuilding parts of his father’s legendary political machine through brazen (and illegal) patronage deals, he centralized power to a remarkable degree, cut deals behind closed doors, racked up piles of debt, and made long-term bets whose consequences are still unfolding.
This is not simply a biography. It is a challenge to contemporary urban
Do cities thrive because of strong, decisive leaders—or despite them?
Through vivid storytelling, this book exposes how Daley consolidated power, aligned business and labor, navigated crises, survived damaging scandals, and imposed discipline on a sprawling city. It dares readers to reconsider what kind of leadership modern American cities truly need.
- GenresNonfictionHistory
352 pages, Kindle Edition
Published September 10, 2024
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Displaying 1 - 9 of 9 reviews
June 12, 2025
The Daley Show is a fascinating account of Mayor Richard M. Daley’s time in office, and it made me realize how much I tend to look back on his tenure with rose-colored glasses. The book dives into one of the classic political science insights: that public officials can “build up a reservoir of goodwill” with constituents through big, visible infrastructure projects—Millennium Park, Navy Pier, O’Hare expansion, downtown revitalization, investments in public parks, & even very basic things, like city cleanliness—and later cash in that goodwill to push through less popular policies (privatizing city assets, Chicago’s failed 2016 Olympics bid).
It’s also packed with intriguing tidbits (like the backstory behind the CTA Orange Line—who knew Reagan played a role?). I really enjoyed learning about the political shenanigans behind control of O’Hare airport & the perennial discussion on adding a 3rd major airport. That said, the author doesn’t shy away from the valid criticisms, especially around the parking meter debacle, truck patronage scandals, Jon Burge & police brutality, and chronic underinvestment in neighborhoods outside the city core, particularly on the South and West Sides.
Still, I genuinely believe Daley was a solid mayor who deeply cared about Chicago and Chicagoans. When a public library opened up in my Southwest Side neighborhood growing up, he showed up & gave a great speech. That was a pretty cool experience as a 10-year old, who practically lived in the local library at the time.
It’s also packed with intriguing tidbits (like the backstory behind the CTA Orange Line—who knew Reagan played a role?). I really enjoyed learning about the political shenanigans behind control of O’Hare airport & the perennial discussion on adding a 3rd major airport. That said, the author doesn’t shy away from the valid criticisms, especially around the parking meter debacle, truck patronage scandals, Jon Burge & police brutality, and chronic underinvestment in neighborhoods outside the city core, particularly on the South and West Sides.
Still, I genuinely believe Daley was a solid mayor who deeply cared about Chicago and Chicagoans. When a public library opened up in my Southwest Side neighborhood growing up, he showed up & gave a great speech. That was a pretty cool experience as a 10-year old, who practically lived in the local library at the time.
January 10, 2025
An OK look at Mayor Daley's run as mayor. It might be useful for some folks in City Hall to read this just to remember what things were like when he started. There are some excellent insights in his rare criticisms. I would have loved to read more about Degnan and Bedore and the guys that started at the beginning.
May 6, 2025
This is a very thorough book about Daley that is largely pro-Daley, a fact that shouldn't be surprising given that the author is Daley's one-time chief of staff (and at another time the guy Daley pegged to run the Chicago Park District).
Sometimes the pro-Daley-ish of the book can be a bit much, as when he offers a partial defense of the parking meters deal. (Hey, with the rise of uber, the 75-year deal may not be the complete catastrophe it first appeared to be!). That said, there is a lot of things Daley did that were positive, especially in those boring details that often get overlooked.
Claypool goes term-by-term for Daley's six terms, with a series of short chapters. A ten-pager qualifies as a long one here. Some stuff from the book . .. ..
Daley used a I&I hotline (Inquiry and Information) to let citizens give the city info on small-time problems in their area, and then the city did a good job responding. The rat population went down by 90%. The homeless were removed from O'Hare. Area Two and its torture of suspects occurred for a long time, with so many turning a willfully blind eye. Daley was the first mayor to serve as Grand Marshall in a Gay Pride Parade. TIFs were used to help rebuild blighted areas, even as the definition of blight was stretched to the breaking point. Cows on Parade and Gallery 37 were sucessess and casino efforts failed. The River Flood and '95 heat waves were disasters (Daley comes off terrible in the heat wave). Airport wars with downstate was one with a Gary two-step creating a multi-state aviation area, putting it outside Springfield's control (letting Chicago keep the O'Hare proceeds from Pate Phillip). The park district's den of patronage and incompetence was clened up and revenue went up. Crack cocaine and the crime with it peaked in the early 1990s. Daley used the broken windows philosohpy (Claypool doesn't even acknowledge criticism that late came with this approach). City authorities met regularly with civic neighborhood groups in CAPS (Community Alternative Policing Strategies).
Claypool says the Bulls helped revitalize the West Side. The 1996 DNC also helped. Daley was able to keep IIT in chiago and put a new police station nearby it. The Robert Taylor Homes went down. The GOP controlled Springfield from 1994-6 and gave Daley full control of the schools to hurt him. But he embraced it and schools improved under Chico and Vallas. The Meigs Field fight happened. LSD was shifted to create the Museum Campus. THey found out the Illinois Central didn't own the Millennium Park grounds after all. Daley used tech to help policing (which sounded a little Orwellian, frankly). There were two seprate shooting of black men killed by cops on June 4, 1999, neither of whom were criminals.
Daley fired Vallas, who was getting too full of himself. Arne Duncan began a less confrontational style. O'Hare was renovated into six parallel runways which increased traffic flow considerably. Millenium Park went up. Public housing went down.
21 died at the EZ Club after a stampede caused by pepper spray. 13 died in a deck collapse in June 2003. This is the problem of silo'ed city bureacuracies. The Tomczak scanal around hired trucks happened. Daley increasingly demanded full city council obediance, becoming more high and mighty. There's Sorch and the patronage scandal. Daley: the micromanger who doesn't know? Reinassane 2010 replaced the worst Chicago schools and you can point to some big successes but overall it didn't move he needle too much. To promote safety, schools were turned into communisty centers, allowing for more afterschool programs. County government under Stroger was a shitshow, especially at the hospital. His budget failed to pass in 2004. More of the cops were used dynamically in the "cops on dots" program. Area Two came to light. Some off-duty cops beat up some bartendrs. The chief wasn't defending them leading to more "blue flu." A new education reofrm included teacher residencies in Renaissance 2010. They finally get a longer school day under Rahm.
The Skyway was privitized in 2005. Grant Park's underground parking was as well. Then came the parking meters. It was poorly done, poorly implimentned, affected residents more than suburbanites, and didn't bring in enough money. The Olympic bid failed. Daley stepped down.
Claypool doesn't think much of Pritzker or Brandon Johnson, aruging lots of good reforms are being undone.
Sometimes the pro-Daley-ish of the book can be a bit much, as when he offers a partial defense of the parking meters deal. (Hey, with the rise of uber, the 75-year deal may not be the complete catastrophe it first appeared to be!). That said, there is a lot of things Daley did that were positive, especially in those boring details that often get overlooked.
Claypool goes term-by-term for Daley's six terms, with a series of short chapters. A ten-pager qualifies as a long one here. Some stuff from the book . .. ..
Daley used a I&I hotline (Inquiry and Information) to let citizens give the city info on small-time problems in their area, and then the city did a good job responding. The rat population went down by 90%. The homeless were removed from O'Hare. Area Two and its torture of suspects occurred for a long time, with so many turning a willfully blind eye. Daley was the first mayor to serve as Grand Marshall in a Gay Pride Parade. TIFs were used to help rebuild blighted areas, even as the definition of blight was stretched to the breaking point. Cows on Parade and Gallery 37 were sucessess and casino efforts failed. The River Flood and '95 heat waves were disasters (Daley comes off terrible in the heat wave). Airport wars with downstate was one with a Gary two-step creating a multi-state aviation area, putting it outside Springfield's control (letting Chicago keep the O'Hare proceeds from Pate Phillip). The park district's den of patronage and incompetence was clened up and revenue went up. Crack cocaine and the crime with it peaked in the early 1990s. Daley used the broken windows philosohpy (Claypool doesn't even acknowledge criticism that late came with this approach). City authorities met regularly with civic neighborhood groups in CAPS (Community Alternative Policing Strategies).
Claypool says the Bulls helped revitalize the West Side. The 1996 DNC also helped. Daley was able to keep IIT in chiago and put a new police station nearby it. The Robert Taylor Homes went down. The GOP controlled Springfield from 1994-6 and gave Daley full control of the schools to hurt him. But he embraced it and schools improved under Chico and Vallas. The Meigs Field fight happened. LSD was shifted to create the Museum Campus. THey found out the Illinois Central didn't own the Millennium Park grounds after all. Daley used tech to help policing (which sounded a little Orwellian, frankly). There were two seprate shooting of black men killed by cops on June 4, 1999, neither of whom were criminals.
Daley fired Vallas, who was getting too full of himself. Arne Duncan began a less confrontational style. O'Hare was renovated into six parallel runways which increased traffic flow considerably. Millenium Park went up. Public housing went down.
21 died at the EZ Club after a stampede caused by pepper spray. 13 died in a deck collapse in June 2003. This is the problem of silo'ed city bureacuracies. The Tomczak scanal around hired trucks happened. Daley increasingly demanded full city council obediance, becoming more high and mighty. There's Sorch and the patronage scandal. Daley: the micromanger who doesn't know? Reinassane 2010 replaced the worst Chicago schools and you can point to some big successes but overall it didn't move he needle too much. To promote safety, schools were turned into communisty centers, allowing for more afterschool programs. County government under Stroger was a shitshow, especially at the hospital. His budget failed to pass in 2004. More of the cops were used dynamically in the "cops on dots" program. Area Two came to light. Some off-duty cops beat up some bartendrs. The chief wasn't defending them leading to more "blue flu." A new education reofrm included teacher residencies in Renaissance 2010. They finally get a longer school day under Rahm.
The Skyway was privitized in 2005. Grant Park's underground parking was as well. Then came the parking meters. It was poorly done, poorly implimentned, affected residents more than suburbanites, and didn't bring in enough money. The Olympic bid failed. Daley stepped down.
Claypool doesn't think much of Pritzker or Brandon Johnson, aruging lots of good reforms are being undone.
January 1, 2026
In-Depth View of Chicago’s Landscape
This was a great book by Mr. Claypool and went in-depth regarding a lot of the transformative actions that has influenced Chicago over the last 4 decades. It’s amazing how good leadership can change the trajectory of a city. I feel he was unbiased and caught the good and bad of Major Daley’s tenure. A great read for people who love cities and politics.
This was a great book by Mr. Claypool and went in-depth regarding a lot of the transformative actions that has influenced Chicago over the last 4 decades. It’s amazing how good leadership can change the trajectory of a city. I feel he was unbiased and caught the good and bad of Major Daley’s tenure. A great read for people who love cities and politics.
January 11, 2025
Being the mayor of Chicago is not easy and really requires understanding many perspectives. Chicago's finances today are pretty bad but the author presents a series of chapters around key moments/big things that Chicago has done. Very focused on bread and butter government issues
July 3, 2025
There is a great story to be told about the R M Daley administration but this isn’t it.
The book does contain many segments and matters of his time in office which as a professional working in the City at the time I enjoyed.
I thought it was just not woven together with a clear conclusion.
The book does contain many segments and matters of his time in office which as a professional working in the City at the time I enjoyed.
I thought it was just not woven together with a clear conclusion.
February 1, 2025
Really interesting take on the Daley reign in Chicago. Towards the end author talks about personal political aspirations too much. Seemed to now follow the theme of the book.
March 25, 2025
A ton of good facts, but not a lot of storytelling. Felt like the chapter Betrayal was the only one written with perspective
June 4, 2025
This insider account of the Daley years unfortunately comes out feeling primarily like a vanity project for the author. By focusing on showcasing Daley’s successes, it allows him to burnish his own credentials.
He glosses over the “white mayor” controversy, which almost cost son of Boss the election. He claims that Daley was the first mayor to see the need to develop Chicago as a cultural magnet, completely overlooking the efforts of his Predecessor Jane Byrne to showcase the city by attracting films and starting events like Taste of Chicago.
He claims Daley solved problems of crime, reformed the schools, straightened out city finances. Yet, all these problems persist today. Of more importance, Daley borrowed heavily and overspent, leaving Chicago with horrendous debt that complicates financial decisions today.
So if you want to know about all the roles Claypool held and the efforts he undertook over 3 decades of public service, this book is for you.
He glosses over the “white mayor” controversy, which almost cost son of Boss the election. He claims that Daley was the first mayor to see the need to develop Chicago as a cultural magnet, completely overlooking the efforts of his Predecessor Jane Byrne to showcase the city by attracting films and starting events like Taste of Chicago.
He claims Daley solved problems of crime, reformed the schools, straightened out city finances. Yet, all these problems persist today. Of more importance, Daley borrowed heavily and overspent, leaving Chicago with horrendous debt that complicates financial decisions today.
So if you want to know about all the roles Claypool held and the efforts he undertook over 3 decades of public service, this book is for you.
Displaying 1 - 9 of 9 reviews