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Boss: Richard J. Daley of Chicago

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"The best book ever written about an American city, by the best journalist of his time.”� Jimmy Breslin

New edition of the classic story of the late Richard J. Daley, politician and self-promoter extraordinaire, from his inauspicious youth on Chicago’s South Side through his rapid climb to the seat of power as mayor and boss of the Democratic Party machine. A bare-all account of Daley’s cardinal sins as well as his milestone achievements, this scathing work by Chicago journalist Mike Royko brings to life the most powerful political figure of his his laissez-faire policy toward corruption, his unique brand of public relations, and the widespread influence that earned him the epithet of “king maker.� The politician, the machine, the city—Royko reveals all with witty insight and unwavering honesty, in this incredible portrait of the last of the backroom Caesars.

New edition includes an Introduction in which the author reflects on Daley’s death and the future of Chicago.

216 pages, Paperback

First published January 1, 1971

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About the author

Mike Royko

36books46followers
Pulitzer prize columnist, Mike Royko was nationally known for his caustic sarcasm. Over his 30 year career he wrote for three leading Chicago newspapers, "The Daily News", "The Sun-Times", and "The Chicago Tribune", and was nationally syndicated.

The Polish-Ukranian son of a cab driver, Royko grew up on Chicago's southside and never left the city. At age 64, he died in Chicago of complications arising from a brain aneurysm in the spring of 1997. Royko was survived by his wife, Judy, a 9-year-old son, Sam, and 4-year-old daughter, Kate, as well as two grown children from his first marriage. His first wife, Carol, died in 1979.

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Displaying 1 - 30 of 316 reviews
Profile Image for Kevin.
61 reviews6 followers
April 2, 2015
Mike Royko must have had balls of steel to write this book in 1971, during the heyday of the Chicago Machine! Royko knew the city and all those running it, inside-out. The intimate political details of all who ran "The Machine" could not have been well received when this book debuted.

I still miss reading Mike Royko's columns in the Trib. He was one of the last great journalists who still did a damn good job! He certainly didn't pander to anyone, i.e. "Faux News, etc."

Unexpected takeaway: In light of today's obstructionist and corrupt Republican party fostered by Karl Rove and the Koch Brothers, I was truly taken aback by the corruption and brutality of the Chicago Democrats of the 1950s-1970s. This book made Republicans seem like "the nice guys."
Profile Image for Ebookwormy1.
1,810 reviews338 followers
May 7, 2018
I got this book out of a stack from my mom. It was only after I started reading it, and was led to do some outside research that I discovered it's a classic of city journalism.

This hard hitting account of the reign of Mayor Richard J. Daley illuminated many things about the great city of Chicago. It put into perspective some of the things going on now, and made me look at our current mayor, Mayor Richard M. Daley, a little more skeptically. It also answered some questions I'd had for a long time (why is Mr. Luther King, Jr. Drive tucked away on the South Side?). Interestingly, Royko notes that Richard J. had positioned his sons well in politics, and the references to Richard M. were especially intriguing as Royko did not know at the time that Richard M. would hold the mayoral office even longer than his father.

The tongue in cheek style, the biting sarcasm, with which this is written made for laugh out loud moments, and I couldn't resist reading certain paragraphs to my husband. An easy read, Royko doesn't spare you the details and tells it not only like it is, but how Mayor Daley wants you to see it; the disconnect is simultaneously hilarious and outlandishly horrifying.

Although Royko is clearly critical of the Chicago Democratic Machine, and probably didn't make any friends in the Daley family with this book, he is generous enough to point out their successes, which have only become more obvious with time as more cities in the Midwest rust away and face challenges that never materialized in our fair city (such as a dearth of downtown residents). He also credits them with preserving the lake shore for all Chicagoans, a magnificent feature of our city that pays increasing benefits with every passing year.

An excellent read. Highly recommended for those interested in Chicago. It's true, Royko is no saint, but in his reporting about Chicago, it seems it takes one to know one. My only regret is that Royko won't be around to write a similar account of our current mayor. Hopefully another Chicago insider (with a desire to live out their years in another country) will have the guts to write "The Boss' Son". If so, I'd love to read that too.
Profile Image for alex.
112 reviews73 followers
April 12, 2023
At the 1893 Columbia Exposition in Chicago, Henry Adams perceived a world-historical shift bubbling up in human consciousness. He famously described this with two images: The Virgin Mary and the Dynamo. For Adams, up to that point in Western history, The Virgin Mary was an image that could neatly sum up the spirit of the age since the fall of Rome. That era was passing and in its place was the Dynamo, a machine of great power, almost incomprehensible in its complexity.

Henry Adams in Chicago saw the beauty and horror in watching the machine work. Nine years later and a few blocks away, Richard J Daley was born.

I think I came across this book once before but dismissed it because of its short length (about 200 pages) and that’s obviously my bad because this is a dang masterpiece on American urban politics. This book is right up there with Caro’s Power Broker and certain aspects, surpasses it. It strikes a good balance between a painstaking walkthrough of all the parts of a political machine, and lifting you off the ground with its lyrical sense of grandeur.

Boss shows you Chicago starting from the bottom. How the machine works. How the people ignored by power built power through clubs, churches, and gangs, block by block, lifting each other up until they’ve captured every corner of power from the protestant elite and guarded it with their lives

Daley is the last great urban Boss and both the apogee of its form and author of its destruction. It’s an incredible American tragedy masterfully told by Mike Royko
Profile Image for Jason Smith.
80 reviews1 follower
December 12, 2017
This devastating account of the first Daley regime works as a kind of history of Chicago from the fifties through the sixties. I say that because Daley had a desire to have absolute control when possible and domineering influence when the previous proved difficult. Its not hard to see why Daley wanted the book banned and his wife was going around vandalizing copies in book stores.

This is a truly damning book if ever there was one. But at the heart of all the vitriol being piled on by Royko is his the reminder of the fact that people kept on electing this authoritarian virulently racist man term after term, no matter what scandals appeared, no matter how many young black men were being murdered by cops, innocent skulls bashed in, houses razed for insider development, etc, etc, etc. You can level some of the blame on the machine's "get out the vote" patronage schemes, or Daley having all the media outlets in his back pocket (the Tribune sucked back then, too), or people's fear of the cost of having to change the name of millions upon millions of placards, signs and labels that coated the entire city. But at the heart of this story is a depressing realization that democracy is easily manipulated, and people will all to often vote for a choice that is in opposition to their well being.

Great read though.
Profile Image for Mary Baker.
49 reviews2 followers
February 13, 2019
This book hit me like a ton of bricks. My extended family hails from Canaryville and Bridgeport, and while I'm all too aware of the racism and resistance to change that persists in those neighborhoods, I have never read something that spelled out the distinct brand of prejudice that can be found there so eloquently. It all makes so much more sense now.

And Daley's Chicago makes so much more sense now! Royko paints a scathing portrait of Daley through his characteristic wit. The man comes across as a true egomaniac, and based on Daley's response to civil rights, liberals, and the free press, you really wonder if Trump counts Daley as one of his role models. It's also crazy to hear echoes of Daley and his crew in things that are happening in Chicago this very minute (Police Academy, new Sterling Bay development, and, uh, the mayoral election, to name a few).

There are no footnotes in this book, and it often shows. But it never claims to be a comprehensive history. Royko had an agenda and a perspective, and in my eyes, he nailed it.

P.S. I strongly recommend pairing this book with The Nix for a pretty astonishing view of the 1968 Democratic National Convention.
Profile Image for Johnny.
Author10 books138 followers
September 21, 2018
Mike Royko was one of Chicago’s treasures. Even when I lived on the West Coast and had never been to Chicago (in the early �70s), I would go to DeLauer’s Super Newsstand in Oakland and buy at least one Chicago Tribune per week, just to read Royko. And for years, I had been meaning to read his highly critical biography of the “first� Daley of Chicago’s prominent political machine (at the time of this writing, a THIRD Daley has thrown his hat into the ring to run for Chicago mayor). BOSS: Richard J. Daley of Chicago is both a stimulating and a depressing book. It is stimulating because of its insights and little gems of history, but it’s depressing because of its “tell-all� nature.

Royko takes us on a hypothetical limousine ride with Daley toward the end of his reign where one sees monuments to Daley’s efforts to both revitalize (certain sections with certain demographics) of the city while simultaneously enriching his friends. For years, I’ve identified the twin eggshell towers of Marina City with Chicago, but I didn’t realize Charlie Swibel, the one-time slumlord and friend of Daley, had constructed these towers with funding from the Janitor’s Union (p. 14). I suppose it is to be expected in a city that has its own Director of Patronage (p. 22) such that Daley “…let civil service jobs slip back into patronage by giving tests infrequently or making them so difficult that few can pass, thus making it necessary to hire ‘temporary� employees, who stay ‘temporary� for the rest of their lives.� (p. 69). I knew about some of the scandals during the Daley administration, but I nodded my head when I read a creed alleged to Daley, “Scandals aren’t public scandals if you get there before your enemies do.� (p. 25)

The book is full of astonishing revelations, but one could have knocked me sideways. Did you know that Richard J. Daley was first elected to statewide office as a Republican? It was precipitated by the death of a state legislator named Shanahan. Shanahan was a Republican running unopposed and the ballots were already printed. So, the machine came up with a write-in vote for Daley in the only space provided, under the Republican (p. 46). Daley’s fans will be glad to know that he didn’t even last out the first hour in Springfield as a Republican, moving to the Democratic side on the first day.

When Daley was running for re-election after fulfilling none of his promises with regard to the neighborhoods, national magazines and local newspapers focused on his revitalizing of the Loop. As Royko put it, “The propaganda was being poured as thickly as the overpriced highway concrete.� (p. 104) Royko also recounted the story of the incompetent fire commissioner who celebrated the 1959 Chicago White Sox World Series victory by turning on the city’s entire civil defense siren system. Since no one knew this was merely happening to celebrate the victory, widespread panic ensued (p. 116).

But what I remember most clearly about Chicago during the Daley administration was seeing video of the events surrounding the 1968 Democratic Convention. The video was bad enough, but the material that was suppressed was sickening. Royko recounts the near police riot prior to the convention (p. 124). Indeed, the police brutality associated with the convention was nearly as severe as the violence perpetrated on civil rights demonstrators. As Royko noted, “If the Negro was equal in the eyes of the law, the men wearing badges needed glasses.� (p. 138) And to all these atrocities, Daley gave denials until the news footage shined the light on his face. At that point, Daley insisted that he had special information (which, strangely, the FBI didn’t have) that the demonstrators were planning to assassinate the three main Democratic contenders for the nomination, as well as many leaders—including himself (p. 191). Even though this was as bogus as the rumored plan to lace the Chicago water supply with LSD, Daley told this lie on television.

Despite some of the heavy police baton swinging, Royko listed some lighter moments when he quoted Daley’s former press secretary, Earl Bush, who contended, “’It was damn bad reporting,� he said, ‘They should have printed what he meant, not what he said.’� (p. 169) But Royko says that printing what he meant would have been difficult with statements like, “Today the real problem is the future.� Or he said, “I don’t see any more serious division in our country than we had in the Civil War and at other times.� (both on p. 169) Or maybe one could consider the almost Freudian attitude to a poor neighborhood, “We want to make Austin in the future what it has always been in the past.� (p. 170)

Late in the book, though, Royko lays out a horrendous injustice---the raid on the Black Panthers apartment in 1969. The police claimed that they shot up the apartment because the Panthers had been firing out at them. Even in California, I remember hearing this story. What I didn’t hear was the results of an FBI investigation which found all of the bullet holes going IN rather than OUT (p. 211).

I suppose I went into the book with a sense that there was corruption in the Daley administration, but some of the evidence cited by Royko completely unnerved me. Chicago history fascinates me, but much of this history disgusted me. I know Royko had an anti-Daley bias, but I have seen evidence of some of what he ascribes to this era in other volumes of history related to Chicago. Lose one star for bias, and BOSS: Richard J. Daley of Chicago is still a fascinating book.
Profile Image for Carol Storm.
Author28 books219 followers
December 16, 2021
How on earth could this book be so dull? A colorful maverick like Mike Royko writes about a charismatic big city boss like Richard Daley and makes him seem unbelievably lifeless and dull. His bigotry and cruelty are legendary, but he just doesn't jump off the page the way Archie Bunker jumps off the TV screen. We're told a lot, but we don't ever see him in action. Boring as hell, Mike!
Profile Image for James Murtha.
9 reviews1 follower
August 2, 2017
Nearly fifty years since Mike Royko published this scathing, methodical documentary of the rise and rule of Chicago’s Machine and its iron-fisted monarch, Richard J. Daley, the book reads like a cautionary tale at the six month anniversary of Donald J. Trump’s reign in the White House.
Daley, born of working class Irish immigrants who escaped the potato famine, grew up quiet and hard-working, eschewed alcohol, married another devout catholic and remained faithful to her until his death. He spent two decades quietly rising to the head of the city’s Democratic Party before running for mayor.
I approached this 80,000-word narrative with trepidation, having been accustomed to Royko’s 1000-word newspaper columns I read religiously during my graduate school years in Madison, a stone’s throw from Mike’s beloved Chicago, which I visited often to see my best friend.
Daley ruled his city with an iron fist, demanding loyalty and quick to exact revenge from anyone who crossed him. Royko’s journalistic style drives the story forward. Punctuated by scenes of police brutality, hypocrisy, and widespread corruption, the theme is complete dominance from the top. Daley’s ultimate Theory X management style culminated in the confrontation between 10,000 protestors and 23,000 police and guardsmen at the1968 Democratic convention.
I recall those few days in August watching Walter Cronkite and Dan Rather on TV and examining dozens of photographs of bloodied people taken by my friend as he roamed about dodging clubs, rocks and mace. Those were turbulent times, not only in Chicago, but throughout the US. While others have written about the violence in other cities, no one showed us better than Royko how the perfect storm came about in one place at one time because of one man, Richard J. Daley.
There are no dull moments in Boss. I’m surprised it was never adapted to film.
Profile Image for Emma.
129 reviews19 followers
October 10, 2011
Royko's writing style wears a bit thin at times (he was a columnist for the Sun-Times, and most of the book is written in that sort of punchy, jump-to-conclusions, one-sentence-paragraph style) but overall this is an excellent and accessible introduction to some of the ugly political legacies and relationships that continue to define Chicago's governance.

The book also provided me with some provocative questions about the relationships between political power, organized labor, and equity. Obviously the Machine was (and is, in its current form today) racist, corrupt, and brutal, and for those outside of its embrace it was a force for state neglect and violence. But it was also the only way for white working-class folks to make it to the top of the political power structure, and Daley poured so much into the Machine that upheld that structure in part because, without it, a guy like himself would never have become mayor. Instead, he said, political power would be consolidated in the hands of the hated elite, who could finance their own campaigns and work their connections with the other super-rich. Which, as it turns out, was actually a pretty prescient prediction.
Profile Image for Keith Koeneman.
Author1 book5 followers
September 4, 2012
What are the strengths and weaknesses of Boss as book? On the positive side, Royko knows how to write a beautiful sentence. He also knows Chicago, and captures Daley and the city at a key juncture in American urban history. Moreover, Rokyo is an honest writer, which gives his words an emotional power, a resonance that lingers somewhere deep in the reader. On the flip side, Rokyo may have been too close to his subject -- too deeply and emotionally engaged -- to place Daley in a broader historical perspective. He sometimes fails to pull back his lens and give the reader a wide-angle shot of the man's talents and the challenges he faced as mayor of a large city during a very difficult time in history.

But the bottom line is that Boss is a classic, one of the great books of American literature. If you have never read it, I recommend it to you. If years have passed since you immersed yourself in Rokyo's Chicago, it would be well worth your time to once again read the slim volume. Chicago is a much changed city since Boss was written, but Rokyo's words still carry insights into our city and politics.
Profile Image for Jim.
1,359 reviews89 followers
June 22, 2017
One of the great classics of American urban politics written in the unique journalistic style of Mike Royko. I first read it when it came out in the early 70s when "da Mare" Hisself was still alive. Living in Chicago, the book had an immediacy for me that was important. Being a fan of Mike since the 60s, I was happy to read a complete book by him, slim as it is. Now, reading it more than 40 years later, it seems like ancient history, almost like reading about the Punic Wars or the Civil War. However, I finished the book feeling deeply disheartened, as the problems of race and poverty remain, with violence actually increasing in the city while the population decreases. A big part of the Daley legacy is that he did not deal adequately with the major problems of the city. I feel now that we certainly lack the will--and we certainly lack the greatness of spirit--to address the problems of race and poverty in our society. It seems to me that the Romans could not resolve the problems of their failing republic as it became a corrupt empire and the Southerners could not resolve the problem of slavery without abolition being forced on them in a bloody civil war. Will we do any better?
Profile Image for Tom Stamper.
642 reviews36 followers
August 16, 2020
How Mayor Richard Daley became Boss Daley is a practical example of Bruce Bueno de Mesquita classic book, . Chicago’s power structure divided into wards was giant pyramid where the ward bosses brought in the vote and Daley rewarded them with patronage jobs where the graft could be more lucrative than the salary. Now Daley never got rich doing this job. His greed was for power and as long as he could keep those greedy for money in the chips, he could retain the power and he did. Even though Mike Roylo was the most read newspaper columnist in Chicago and this book is damning in most everything that happens, Daley still won re-election and eventually died in office.

Royko is thorough in the details of the corruption and how it spread through the entire state. He gives you names and dates and incidents so numerous he could be spelling out a grand jury indictment. But that seems a prelude to his real goal of shaming Daley for his actions during the 1968 Democrat Convention when the city became a brawl between police and anti-war protesters. Royko paints the protesters as all peaceful and the police under orders to make people bleed, especially reporters. Royko seems nonplussed that this incident made Daley more popular in Chicago and in turn popular in the entire country that was tired of the unrest. But then again it makes sense when you read Mesquita.

From a historical view Daley’s Chicago is what happens when power is centralized into fewer hands. When you remove the checks and balances and any one office or branch is the final word, you’re on the road to dictatorship no matter how benevolent the speeches may appear. Without term limits you’ll often need death to end the grips of the corruption.
Profile Image for Ben Gartland.
8 reviews1 follower
August 12, 2018
When I study historical figures, I try and see them less in a black and white manner where they were either a genius or a POS. I couldn't do that with Mayor Daley.

I do concede that Mike Royko is a journalist, not a historian and that further research is probably needed to gain a more complete picture of Daley but it is clear to see that Daley's legacy is that of a maliciously inept mayor whose two decades in office have led to many of the problems Chicago sees today. Daley is not the first nor the last leader of the Machine, but his misdeeds ranged from looking the other way in the face of police brutality and racial discrimination to actively building up the patronage system, using the expressways as a natural barrier between white and black neighborhoods, and bulldozing low-income housing to replace it with mid-to-high income housing. It pains me to read that he was a Daily Mass goer, DePaul law alum, and, at least in rhetoric, a fervent Catholic who hated when his machine members cheated on their wives when his policies and responses to outcry from people of color were frankly despicable.

I didn't realize at the beginning of reading this book that it was written during the administration, which was incredibly ballsy during the height of the Machine. However, that does mean the last five years of Daley's administration are not in the book, nor is his death in office and immediate aftermath. Leading up to the mayoral elections in early 2019, I'm hoping to read more recent Chicago history so I'll need to find something that covers his last five years, Harold Washington, and the second Mayor Daley.

For all people interested in Chicago politics and history, I recommend this book. It's quick, witty, and does not hold back on Daley, the Machine, and, hilariously, the Chicago Tribune.
Profile Image for Cynthia.
702 reviews51 followers
November 5, 2008
Royko is so amazing, every sentence is funny, informative and loaded with hidden meaning. I read this book maybe 20 years ago while I was still living in Chicago, when Royko was still alive, when Daley Sr. was still fresh in my memory; it was great then, but is even more interesting to me now that I live far outside the city limits, Royko is gone and Richie Jr. is in charge of the city.
Back then, reading Boss was a little like reading the newspaper; now it feels different, more like reading history � but history that I lived through and didn't really understand while I was living through it, and about people that I knew or who were still alive, but who I didn't really appreciate.
****
Well, having finished it... the book starts out GREAT but devolves after the first few chapters into a pure rant by Royko against Daley. The rest ofthe book lacks the subtlety and finesse of the first few chapters; it turns into a long listing of reasons why Daley is the American answer to Stalin. But it's like, ok, we get it.
Still, very much worth reading if you've ever wondered what everyone's talking about when they talk about the 1968 democratic convention...
Profile Image for Patrick Peterson.
503 reviews280 followers
February 12, 2019
11 Feb. 2019 - I just saw this book on a ŷ friend's list "To Read" and remembered that I had read it when I was in high school or Jr. High in the early 70s.

I remember liking it, since the author, one of the most interesting newspaper columnists around, who wrote for the local Chicago Tribune, had a really fun time describing Chicago's longtime mayor, Richard Daley I.

I can't remember specific examples, after all this time, but I do remember enjoying the classic descriptions of how political patronage system specifics worked in the city. It was a far cry from how the basic history/civics classes taught that the system was designed and supposed to work.

I bet I would enjoy seeing how Royko anticipated some of the economic "public choice" analyses of how government actually works, if I had time to read it again. But then again, perhaps he did not, otherwise he would have become more libertarian, and less cynical.
Profile Image for J..
86 reviews6 followers
September 5, 2011
A fascinating look at the politics of Chicago and it's Boss from 1955 to 1976--Mayor Richard J Daley (as opposed to his son Richard M, who just finished 20 years as Chicago mayor). You get to see the inner workings of "The Machine" that was city politics, and how Daley controlled the Democratic party and the city. It is at times endearing, and at times scathing. It is worth the read for the insight it lends into voting/election practices and the civil rights movement alone. Written by a journalist--and it kind of reads like a newspaper article. Short, factual. An excellent read for anyone interested in politics!
Profile Image for Nelson Rosario.
149 reviews22 followers
January 8, 2018
Not being a native Chicagoan a lot of this book was a surprise to me. I knew a little about Mayor Daley once I moved here, and I am familiar with the city's history generally, but this book adds so much color to that sparse framework.

The book is written by a journalist and it many ways it reads like a juicy extended daily column. That makes sense given that Mike Royko, the author, was a daily columnist for thirty years. The story is larger than life just like the city it takes place in, and the man the book portrays.

I definitely recommend this book for a nice story behind the story of Richard J. Daley, and the city of Chicago that he made.
Profile Image for Erik Graff.
5,124 reviews1,347 followers
January 24, 2013
I found this among Dad's books when I got home from college during the Christmas break and read it in a sitting. Neither definitive nor scholarly, it's still a mildly amusing tale of Daley, Chicago politics and his rise to power within it.

I only saw Richard J. Daley in the flesh once, at the annual downtown St. Patrick's Day parade sometime during high school when my friends and I had managed to obtain positions across the street from his reviewing stand. It was a cold, grey day. The parade was boring.
Profile Image for Tom.
84 reviews2 followers
January 28, 2014
This book made me quite nostalgic, not for the Daley administration, but for reading Mike Royko's daily columns in the Chicago newspapers. There is no figure on the Chicago journalism scene (such as it is) who comes close to his knowledge of the city and its political machinations. This book provides a quick primer on Chicago politics. There really is no way to understand the current political landscape in the city without understanding its antecedents.
Profile Image for Jeff Neuwirth.
71 reviews4 followers
May 12, 2019
Solid 3.5. As someone born in the 90s, raised, and currently living in Chicago this was an interesting read. I always knew of Daley, but didn't know the story behind him & the machine. This was a dense read and took me nearly 5 months of casual reading to finish (though that can be blamed on me as I'm not super into politics). Would recommend to anyone interested in the story behind the Chicago Machine. Would like to hear how things went after - anyone have recos for the next Daley era?
Profile Image for Nick Black.
Author2 books859 followers
February 3, 2018
one of the finest political books I've ever read -- an incisive takedown of Democrat Machine local politics, yet done in eight-hundred fewer pages than .
Profile Image for Linda.
100 reviews10 followers
April 2, 2009
i finally finished this rowdy book that could be read in a single sitting at a noisy bar. what can i say? so little has changed. i am fascinated by what the current mayor thinks of his father and how he believes his regime differs. and I will never look the same way at "Venetian Night" again.
Profile Image for Richard.
705 reviews29 followers
August 31, 2012
fine fine book- a testament to the shit hole racsism and crooked cops and political machine of daley's chicago. facts no one brings up- lester maddox and bull conner were both at the '68 chicago convention.
11 reviews
May 27, 2018
A detailed look at the Machine Daley operated while in office and a nice primer on some mid 1900’s Chicago history. I also now know which streets were named after white male politicians.
Profile Image for David.
39 reviews4 followers
December 18, 2021
Among the best books ever written about Chicago or its politics
123 reviews77 followers
March 31, 2014
I can't imagine a much better reading experience on the subject of American politics.

I wanted to learn more about the original Mayor Daley. The extent of my knowledge about the old man came from the shaded nostalgia of my lifelong-Chicagoan parents and the title of the book American Pharaoh, mixed with my own assumptions of the mythic power of the man who preceded and paved the way for my own Mayor Daley's iron-fisted reign. As an ancillary, I looked forward to finally reading something by Mike Royko. I don't remember much about that old man except that he died when I was fairly young and was beloved by most of the older Chicagoans I knew.

What a revelation this book, then, a slim volume that goes down like popcorn. It is not a scholarly or comprehensive work, or even proper journalism. The criteria of any of those domains would have caused Royko's cynical raillery to sag. And anyway, that's not what we're here for. Boss is a devilishly keen rendering of the story of Daley's Chicago, delivered in a voice that is pitch-perfect: nostalgia stripped of wistfulness, unrelenting muckraking devoid of unctuosity, and most of all, a bird's eye view of the Chicago culture that lives in Royko's marrow. It is a superbly knowing voice and it therefore rings true, so much so that citations would be mere clutter. There are plenty of interviews, quotations, facts, and figures, but there's no bibliography and no question about the veracity of the tale Royko tells.

And anyway, one could spend an entire volume just proving the truth one way or the other about any of Daley's claims. Indeed, a key tactic of his reign seemed to be to force his opponents in the courts and the press to abide by a standard of proof and logic that he never considered; keep them back with enough shotgun blasts of bullshit and they're bound to slow down. In that way, this "non-scholarly" work is actually the exact journalistic counterpart to the Machine's lies and corruptions. An academic tone would have lost the crucial flavor of life under King Richard, and a courtroom-caliber indictment would have proved nothing we didn't already know.

He never criticizes Daley outright, but each page drips with resigned disgust. The story here is not of the vaunted "pharaoh" of lore but of a consummately ordinary, boring man who was merely the wiliest spur to emerge from Chicago's longstanding Democratic Machine. He was the third Bridgeport mayor in a row, Royko points out, and when he finally arrived at a level of real power as Chairman of the Cook County Democratic Central Committee - after two decades of working his way up the ranks; this was no Alexander the Great or Barack Obama - his accomplishment was that "he finally had his own machine." What I associate with Daley-style management is actually simply Machine politics; Daley was merely able to wield the Machine better than anyone else to that point.

Which is to say nothing of how good a mayor he was, only that the Machine's goal was power and patronage and it sustained both of those things. As an autocrat, Daley kept his troops serried and fed. As the executive of a prosperous American city, he was awful. Because he was an apparatchik instead of a visionary, he lacked the creativity or magnanimity it would have required to see beyond his own heuristics and identify, say, the need for a legitimate public health administrator, not his family doctor. (An outbreak of TB almost happened.) An actual police commissioner. (He reluctantly got a certified expert to run the CPD for a little while, and while the man was very successful in running his department, he didn't take orders from Daley and so was promptly replaced by a yes man, who brought the police back into thuggish and haphazard form.) Daley's policies somehow managed to neglect, utterly, the needs of both his white and black constituents, the former who moved to the suburbs and the latter who were segregated, South-like, into ghettos, without hope or adequate plumbing. Actually, not somehow: deliberately, the Machine only cared about furthering its existence by being a parasite on the blood that was the average Chicagoan. If the citizens shrugged and accepted it because they knew no other way, and if the system of corruption worked predictably enough that one could either leverage it if he was cunning or be squashed by it if he was out of line, that said nothing of the system's failure to cater to the city.

It's mostly frustrating to read of Daley's obduracy and monolithic view of the world. Everything was framed in terms of his power. If advocacy groups came in to ask for something, his inclination to give it to them depended entirely on how much fealty he perceived was being shown to him. If he was a legitimate leader, someone who rose to power without a vast and unstoppable Machine, he would have necessarily picked up some Napoleonic cunning along the way. He would have seen that his power was only heightened by the happiness and welfare of his people. As it was, he was none of those things and had none of those percipiences.

I will say that Royko, in his unerring disregard for Daley, his administrative style, and what he did to Chicago, never seems to acknowledge what exactly kept Chicago from going the way of other industrial Midwestern cities like Cleveland or Detroit. Something must have happened at some point, because Chicago has made the transition to modern American destination city very well. Others have not. Maybe that was Daley the younger. And speaking of which, it's funny throughout this book to think of Royko's reaction must have been when it became clear that Richard M. was going to be the next mayor for life. I'm going to try to dig up what he thought of that. I have an idea.

In total, this was among the most enjoyable and informative and real books I have ever read. It's sort of a working man's Sandburg-on-Lincoln, wherein a titanic IL writer takes on a mythic IL politician. The other comparison that kept striking me, stretch that it is, was of Homer writing about the gods. The Royko of Boss is no historian; he is a witness, interpreter, cohort, and conscience. It's an understatement to say, as other reviews have, that his "intimate knowledge of Chicago" is on display here. This was Chicago who wrote the book, as channeled through Mike Royko. Thank gods for that.
Profile Image for Hasan.
246 reviews11 followers
December 27, 2024
This engaging biography paints a vivid portrait of Richard J. Daley, the legendary mayor of Chicago. Royko masterfully captures Daley's personality, showcasing how his Irish heritage and deep Catholic faith shaped his political worldview. The book delves into the intricacies of Chicago machine politics, illustrating how Daley rose to power and maintained his grip on the city for decades.

Royko doesn't shy away from exploring the darker side of Daley's reign, including the influence of nepotism and the corruption that often accompanied the political machine. Despite these flaws, the book acknowledges Daley's achievements, such as his efforts to revitalize the city and improve the lives of its residents.
Profile Image for Charlotte Piwowar.
133 reviews1 follower
March 25, 2024
Must-read for any Chicagoan. I liked the second half better (once he was in office as mayor). Really interesting to gain new perspective on the political legacy in Chicago and other historical events. Great writing from Royko as well.
1 review
May 11, 2015
“Boss: Richard J. Daley of Chicago� is a book written by Mike Royko following the story of a politician who ruled Chicago. The author who wrote this was a newspaper columnist who followed Daley closely and was capable of displaying his knowledge in the paper. This book follows Richard J. Daley’s rise up the political ladder as he took control and made bold decisions to win over the people of Chicago. Daley was born in 1902 and lived in a Roman Catholic home. He lived in Bridgeport Chicago and was an average boy with no special talent. He soon found his best qualities and began to work on them. His leadership and easy to get along with personality pushed him into college as he desired. After college he landed himself a job working in the city where his climb started. That first job was only the beginning of his forty eight year tenure. For twenty of those forty eight years Richard was able to work as the mayor for Chicago. One of Daley’s best qualities was being able to connect with the whole city. He shared qualities of a man in the office to a man doing construction. That was why people loved him so. He controlled every group even the silent majority. Throughout the book Royko followed specific times where Daley showed his leadership qualities and wonderful characteristics. He was a man who you could sit down and have a conversation without even knowing who he is. He was a confident man who walked into rooms already knowing where he was going. This book always spoke about how good of a man he was but failed to show some of his poor choices. Readers notice how strong of a presence he had in Chicago, but don't realize how that is the extent of who he can reach. His twenty years as mayor before and during the Vietnam era is where he made a name for himself by connecting with the people of Chicago and making them his own. Through the book you see the progression of Richard as a politician and as a person. You see him gain confidence and maintain composure during tough times.
In my opinion this book was a slow read but eventually it covered things that I found interesting. The way that the author wrote impressed me because of the amount of detail he was able to go into. I felt as if that I was there next to Richard J. Daley making his executive decisions and going through his tough times. I constantly desired being there in that time period because I can connect with Daley’s attitude. Also with my current knowledge with that time period from taking classes in school like Vietnam Era, I am not far away from when Richard J. Daley was working. Throughout reading this book I was able to enjoy what was going on and would read it again. This book was really well done and stands the test of time. Although this is a few decades old, it is still a strong well written book that deserves a read by anyone interested in politics. If you don't understand politics clearly, it will be hard to follow what is going on from time to time. Also, the author begins to write about areas as if you also know where it is, which makes it hard to figure out where everything is taking place. With everything considered I would give this book a solid four out of five stars. This was a quick and interesting read that portrayed Richard J. Daley in such a wonderful way.
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