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The City Is Up for Grabs: How Chicago Mayor Lori Lightfoot Led and Lost a City in Crisis
Chicago is a world-class city, but it is also a city in crisis.
Crime is up, schools have repeatedly shut down due to conflict between City Hall and the powerful teachers’ union, and COVID-19 only deepened the entrenched poverty, institutional racism, and endless tug of war between the city’s haves and have nots.
For four years, the person at the center of this storm was Lori Lightfoot. A groundbreaking figure—the first Black, gay woman to be elected mayor of a major city and only the second female mayor of Chicago—she knew the city was at a critical turning point when she took office in 2019. But the once-in-a-lifetime challenges she ended up facing were beyond anything she or anyone else saw coming.
Chicago Tribune reporter Gregory Royal Pratt offers the first comprehensive behind-the-scenes look at the tumultuous single term of Mayor Lightfoot and the chaos that roiled the city and City Hall as she fought to live up to her promises to change the city’s culture of corruption and villainy, reform its long-troubled police department, and make Chicago the safest big city in America.
Some of Chicago’s problems can be explained by forces greater than the national polarization, long-standing cultural and racial tensions, our plague years. But some are the result of Lightfoot’s poor leadership at City Hall, a story that hasn’t been told in full—until now.
Crime is up, schools have repeatedly shut down due to conflict between City Hall and the powerful teachers’ union, and COVID-19 only deepened the entrenched poverty, institutional racism, and endless tug of war between the city’s haves and have nots.
For four years, the person at the center of this storm was Lori Lightfoot. A groundbreaking figure—the first Black, gay woman to be elected mayor of a major city and only the second female mayor of Chicago—she knew the city was at a critical turning point when she took office in 2019. But the once-in-a-lifetime challenges she ended up facing were beyond anything she or anyone else saw coming.
Chicago Tribune reporter Gregory Royal Pratt offers the first comprehensive behind-the-scenes look at the tumultuous single term of Mayor Lightfoot and the chaos that roiled the city and City Hall as she fought to live up to her promises to change the city’s culture of corruption and villainy, reform its long-troubled police department, and make Chicago the safest big city in America.
Some of Chicago’s problems can be explained by forces greater than the national polarization, long-standing cultural and racial tensions, our plague years. But some are the result of Lightfoot’s poor leadership at City Hall, a story that hasn’t been told in full—until now.
264 pages, Hardcover
Published April 2, 2024
24 people are currently reading
1633 people want to read
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June 18, 2024
There may be no role more scrutinized than a city mayor. Chicago Tribune journalist Gregory R. Pratt details the rise and fall of Lori Lightfoot, Chicago's mayor from 2019 to 2023. "Hard-charging litigator with a mean-streak" (p.5), a description that seems to stick to Lightfoot's persona clings hard through the mayoral years, of which Pratt covered.
Lightfoot's story fascinates; she bridges post-Obama centrism of former mayor Rahm Emmanuel with a broader coalition of Lakeview/Northside progressives. The liberal/progressive split has become more visible after the political flash points of the past few years: post-Floyd police reforms, amnesty and border crisis,increased income inequality, and reactionary events from the larger Trump administration. Coalition building and compromise may be out of reach with national politics, but mayors and local politicians are expected to manifest the changes in their communities. Bringing an outsider energy, a challenger to the Daly machine and institutional politics, and highlighting her identity as a black queer woman, Lightfoot became a phenomenal success and eventual lighting rod of derision.
One of the beguiling things about Lightfoot is that she has the resume and experience to excel as mayor, but her personality, detailed in multiple stories, was toward high personalization of conflict and a detached arrogance.
She appears to have had an adversarial relationship with G. Pratt, or the Tribune, but that is not too surprising, considering many people who had given her support would renege on it. Belittling staff, using insults , and raging hard about her large..um...endowment (https://www.thedailybeast.com/chicago...), became the stuff of legend.
Pratt walks us through emails, conversations and turning points in the city where Lightfoot's brand of raw power met fierce resistance. In Pratt's analysis, he admired her warrior heart, but also saw her lack of adaptability as the defining Archilles heel. At her best, a defender of miniorites and civil rights; at her worst a caricature of an elitist self-serving politican.
Pratt uses a Hemingway, no nonsense style, but often acts as his own umpire; calling balls and strikes about people and their motivations. I think a more data heavy approach would be more interesting and helpful to readers given the polarized nature of politics in these times. I admired his courage in facing off with the mayor, and not holding back in compliments or criticism, when warranted.
Often though, I wished Pratt brought a deeper analysis. He could compare Lightfoot to other mayors during this uniquely stressed time; he could take a more holistic view of the unique challenges of covid and racial reckonings that impacted the electorate. Far too much time is spent on an election that many people have put behind us, and more time could have been spent discussing the chronic issues Chicago faces, such as crime, the pension crisis, the bellicose CTU, and the Chicagoian experience during Lightfoot's reign. Also, I think he could have better assessed Lightfoot's impact on the status quo of Chicago politics.
There were certainly a lot of episodes that I read and felt personally. Regarding the increased feelings of lawlessness and crime after the pandemic began, Pratt does a great job of building the story with perspectives of the mayor, alderman, police, and citizens.
I also appreciate that he includes the rare moment that Lightfoot acknowledged the fears of her constituents. Late in the mayoral race she acknowledged a crime spike - brazen robberies, increased homicides, and disprect of police; and seemed sincere in her goal to work with the police rather than abolish.
Ironically, many Chicagoans I know have felt regrets for being too hard on Lightfoot. Less a reflection on her accomplishments and more a reflection on current mayor Brandon Johnson - a puppet for the Chicago Teachers Union and widely seen as incompetent. Lightfoot's profile and legacy may strengthen over time, considering how difficult the social issues were in her tenture.
Political reporting is difficult work, and the barriers to good journalism are many. I applaud Pratt and his coverage of this difficult chapter of Chicago.
Lightfoot's story fascinates; she bridges post-Obama centrism of former mayor Rahm Emmanuel with a broader coalition of Lakeview/Northside progressives. The liberal/progressive split has become more visible after the political flash points of the past few years: post-Floyd police reforms, amnesty and border crisis,increased income inequality, and reactionary events from the larger Trump administration. Coalition building and compromise may be out of reach with national politics, but mayors and local politicians are expected to manifest the changes in their communities. Bringing an outsider energy, a challenger to the Daly machine and institutional politics, and highlighting her identity as a black queer woman, Lightfoot became a phenomenal success and eventual lighting rod of derision.
One of the beguiling things about Lightfoot is that she has the resume and experience to excel as mayor, but her personality, detailed in multiple stories, was toward high personalization of conflict and a detached arrogance.
She appears to have had an adversarial relationship with G. Pratt, or the Tribune, but that is not too surprising, considering many people who had given her support would renege on it. Belittling staff, using insults , and raging hard about her large..um...endowment (https://www.thedailybeast.com/chicago...), became the stuff of legend.
Pratt walks us through emails, conversations and turning points in the city where Lightfoot's brand of raw power met fierce resistance. In Pratt's analysis, he admired her warrior heart, but also saw her lack of adaptability as the defining Archilles heel. At her best, a defender of miniorites and civil rights; at her worst a caricature of an elitist self-serving politican.
Pratt uses a Hemingway, no nonsense style, but often acts as his own umpire; calling balls and strikes about people and their motivations. I think a more data heavy approach would be more interesting and helpful to readers given the polarized nature of politics in these times. I admired his courage in facing off with the mayor, and not holding back in compliments or criticism, when warranted.
Often though, I wished Pratt brought a deeper analysis. He could compare Lightfoot to other mayors during this uniquely stressed time; he could take a more holistic view of the unique challenges of covid and racial reckonings that impacted the electorate. Far too much time is spent on an election that many people have put behind us, and more time could have been spent discussing the chronic issues Chicago faces, such as crime, the pension crisis, the bellicose CTU, and the Chicagoian experience during Lightfoot's reign. Also, I think he could have better assessed Lightfoot's impact on the status quo of Chicago politics.
There were certainly a lot of episodes that I read and felt personally. Regarding the increased feelings of lawlessness and crime after the pandemic began, Pratt does a great job of building the story with perspectives of the mayor, alderman, police, and citizens.
I also appreciate that he includes the rare moment that Lightfoot acknowledged the fears of her constituents. Late in the mayoral race she acknowledged a crime spike - brazen robberies, increased homicides, and disprect of police; and seemed sincere in her goal to work with the police rather than abolish.
Ironically, many Chicagoans I know have felt regrets for being too hard on Lightfoot. Less a reflection on her accomplishments and more a reflection on current mayor Brandon Johnson - a puppet for the Chicago Teachers Union and widely seen as incompetent. Lightfoot's profile and legacy may strengthen over time, considering how difficult the social issues were in her tenture.
Political reporting is difficult work, and the barriers to good journalism are many. I applaud Pratt and his coverage of this difficult chapter of Chicago.
July 15, 2024
Very nice enjoyed a lot of these first-hand
September 5, 2024
It’s fascinating reading a biography of a time you lived through first hand - I lived under Lightfoot, and even I didn’t know the full scale of some of the insanity that Mr. Royal Pratt details here. It’s also fascinating to see a biographer be up front about “hey, I went in liking this person but I hated her by the end of her time in the office and so did she”. Definitely worth reading for when she inevitably tries to parlay her time as Chicago mayor into something
May 7, 2024
I guess it doesn’t really matter who is in charge. Same old same old.
December 19, 2025
"Politics always intrudes."
February 14, 2025
While the author is uniquely situated to tell the story of the Lightfoot administration, without direct interviews from Lightfoot or many of those around her, I think this book falls short of its intended goals, often relying on testimony from critics and Twitter over more substantive analysis of Lightfoot's successes and failures.
April 26, 2024
During LIghtfoot's term I realized I didn't know what a mayor does and couldn't assess if she was doing a decent job despite people complaining about her on Reddit, where people like to complain. This book cleared a lot of those details up for me, as well as general things about the different political forces in Chicago and the socio-economic trends. It can be a little slow at times and if you're not interested in the topic it'll be hard to get into, but it's a comprehensive read.
April 9, 2025
This was exactly what I wanted- a thrilling, juicy behind the scenes story by a local reporter who covered every day of Lightfoot's term.
If you love Chicago politics- this one's for you.
If you love Chicago politics- this one's for you.
April 15, 2025
And it was all a dream
March 13, 2025
Loved this book! It's truly journalism at its finest. The use of public records, the drama, the history — it's all so well done. I loved how it went beyond just Lightfoot and her term and examined the past and current political trends and the state of the city of Chicago itself. Pratt's journalistic integrity and commitment to the truth shine throughout this book, and it was a pleasure to read.
January 30, 2024
The City is Up for Grabs is the story of Lori Lightfoot's term as mayor of Chicago. It is less like Mike Royko's Boss and more like Peter Nolan's Campaign! in how it is a sociological slice of Chicago politics as opposed to a rise and fall narrative, at least Chicago politics as of the time it is set (the nature of politics means that there are already changed fortunes).
The book is comprehensive enough to work as a primer on Chicago politics, including much in the way of explanatory asides. But what I loved here was the intensity. Politics in Chicago is an axe fight, and while it is easy to grow inured to that, the author here keeps the text fresh and imparts an almost serialized drama urge to keep finding out what happens next, even though the ending is at the beginning of the book. It is not embellished, and instead feels like a product of an infectious curiosity and consistent sense of surprise. Keeping that up while managing to provide enough information that even someone new to the topic will not get lost is impressive.
And what a story it is. The cliche is to bring in allegories to fictional power struggles, but that really doesn't apply: political fiction doesn't contain so much texting. It is pure fracas, the narrative of the almost constant thoughtless mistakes by Lightfoot and her team, with rare references to good calls, directly called out as good (though not elaborated on). There is no rise; it is all fall.
The story is composed mostly as a series of crises. I can question the fairness of that framing but I cannot question its accuracy. Only one seems purely Lightfoot's doing (Anjanette Young, and even that happened on the prior mayor's tenure), but her decisions almost always make things worse, often in a florid sort of way that feels like a parody of Rahm's (put a pin in that).
It is unfortunate that Lightfoot refused to participate in this book. There is plenty of reporting and documentation, so much so that her absence is usually not noted (thank you FOIA). But there are a handful of events, most strikingly from her pre-mayoral career, where I felt that the absence of her mattered, or points where I wish that I had her later considerations.
The only place the book fails is in its discussion of the George Floyd protests. For being the event that gives rise to the title of the book, the section on the summer of '20 is spare. This is odd particularly because the book so often provides context to the reader in an even-handed manner, even to events (the CTU fight) that are not customarily granted that.
But situation with protests, and the story of how things went down, is a section that I repeatedly re-read, thinking that I was missing something, but instead it seems to be missing both facts and interpretation. The missteps regarding the curfew and the bathos of Lightfoot in the control center are great. But what I am left with is either that the author felt the subject too inflammatory, or that the reader is supposed to infer fault on Lightfoot, most particularly from the pointedly medieval act of raising the drawbridges. If this section needs its own book, then perhaps start with that, the write the Lightfoot book. Or at least do not make it the titular event of the story.
I am also a little weak on the author's conclusion. It feels tacked on, but this feels okay, as history is not about arbitrary stop and starting points. But I feel as though it provides some credence to some of Lightfoot's complaints. So Lightfoot could not stop being a trial lawyer in her methods and demeanor and it destroys her chances...yet this is the City that still talks about an idea of Emmanuel, legendarily profane and abusive, as aspirational?
Of course, the author notes why Emmanuel was different, and I think that one of the books highlights is the source in Emmanuel's camp who might as well be the Oracle at Fucking Delphi for their eerie soothsaying about the Lightfoot term. I do think that an opportunity was missed. Trump, Lightfoot, and Pritzker are all creatures of the same urge, a feature of American-style democracy that's become a bug. Their political trajectories are all different. I feel that the analysis there is a highly necessary thing, and Lightfoot as the multi-car wreck represents a necessary goalpost in the study. I can't fault the book for not being that, but its tepid ending highlights it, and I think does create more questions about gender, race, et cetera and their performance in politics. Which, again, is strange to the extent that the book otherwise on the account here is great in dealing with the highly racial politics of Chicago that get most cynically abused by politicians. The book puts a name to this in ways that I do not usually see in political texts. In fact, one such event of it is what puts the author in the story. So again, I hesitate to complain about the book not being all it might have been, but it is a criticism that arises out of its strength of the same element in other aspects.
I will admit that I dreaded the writing of this review. I too am a person with many options on Chicago politics. Sure, I suppose that makes me like all the other people at the tavern on a Tuesday, but I was unsure of how I would end up managing my own takes, as I feel like that sort of editing exceeds the ordinary purview of a review. But even as I have some different interpretations, this is good. Danny Solis is the only one that nags at me, and that feels a bit of being honored in the breach. And different ways of telling a history are expected, as the story of a City is always up for grabs.
Thank you to Gregory Royal Pratt and Chicago Review Press for the ARC.
The book is comprehensive enough to work as a primer on Chicago politics, including much in the way of explanatory asides. But what I loved here was the intensity. Politics in Chicago is an axe fight, and while it is easy to grow inured to that, the author here keeps the text fresh and imparts an almost serialized drama urge to keep finding out what happens next, even though the ending is at the beginning of the book. It is not embellished, and instead feels like a product of an infectious curiosity and consistent sense of surprise. Keeping that up while managing to provide enough information that even someone new to the topic will not get lost is impressive.
And what a story it is. The cliche is to bring in allegories to fictional power struggles, but that really doesn't apply: political fiction doesn't contain so much texting. It is pure fracas, the narrative of the almost constant thoughtless mistakes by Lightfoot and her team, with rare references to good calls, directly called out as good (though not elaborated on). There is no rise; it is all fall.
The story is composed mostly as a series of crises. I can question the fairness of that framing but I cannot question its accuracy. Only one seems purely Lightfoot's doing (Anjanette Young, and even that happened on the prior mayor's tenure), but her decisions almost always make things worse, often in a florid sort of way that feels like a parody of Rahm's (put a pin in that).
It is unfortunate that Lightfoot refused to participate in this book. There is plenty of reporting and documentation, so much so that her absence is usually not noted (thank you FOIA). But there are a handful of events, most strikingly from her pre-mayoral career, where I felt that the absence of her mattered, or points where I wish that I had her later considerations.
The only place the book fails is in its discussion of the George Floyd protests. For being the event that gives rise to the title of the book, the section on the summer of '20 is spare. This is odd particularly because the book so often provides context to the reader in an even-handed manner, even to events (the CTU fight) that are not customarily granted that.
But situation with protests, and the story of how things went down, is a section that I repeatedly re-read, thinking that I was missing something, but instead it seems to be missing both facts and interpretation. The missteps regarding the curfew and the bathos of Lightfoot in the control center are great. But what I am left with is either that the author felt the subject too inflammatory, or that the reader is supposed to infer fault on Lightfoot, most particularly from the pointedly medieval act of raising the drawbridges. If this section needs its own book, then perhaps start with that, the write the Lightfoot book. Or at least do not make it the titular event of the story.
I am also a little weak on the author's conclusion. It feels tacked on, but this feels okay, as history is not about arbitrary stop and starting points. But I feel as though it provides some credence to some of Lightfoot's complaints. So Lightfoot could not stop being a trial lawyer in her methods and demeanor and it destroys her chances...yet this is the City that still talks about an idea of Emmanuel, legendarily profane and abusive, as aspirational?
Of course, the author notes why Emmanuel was different, and I think that one of the books highlights is the source in Emmanuel's camp who might as well be the Oracle at Fucking Delphi for their eerie soothsaying about the Lightfoot term. I do think that an opportunity was missed. Trump, Lightfoot, and Pritzker are all creatures of the same urge, a feature of American-style democracy that's become a bug. Their political trajectories are all different. I feel that the analysis there is a highly necessary thing, and Lightfoot as the multi-car wreck represents a necessary goalpost in the study. I can't fault the book for not being that, but its tepid ending highlights it, and I think does create more questions about gender, race, et cetera and their performance in politics. Which, again, is strange to the extent that the book otherwise on the account here is great in dealing with the highly racial politics of Chicago that get most cynically abused by politicians. The book puts a name to this in ways that I do not usually see in political texts. In fact, one such event of it is what puts the author in the story. So again, I hesitate to complain about the book not being all it might have been, but it is a criticism that arises out of its strength of the same element in other aspects.
I will admit that I dreaded the writing of this review. I too am a person with many options on Chicago politics. Sure, I suppose that makes me like all the other people at the tavern on a Tuesday, but I was unsure of how I would end up managing my own takes, as I feel like that sort of editing exceeds the ordinary purview of a review. But even as I have some different interpretations, this is good. Danny Solis is the only one that nags at me, and that feels a bit of being honored in the breach. And different ways of telling a history are expected, as the story of a City is always up for grabs.
Thank you to Gregory Royal Pratt and Chicago Review Press for the ARC.
May 31, 2025
The City Is Up for Grabs by Gregory Royal Pratt was an entertaining read on The Lightfoot Administration (2019-2023) and was an excellent primer on the modern political dynamics of Chicago. The book is functionally divided into two sections -- 1) Lori Lightfoot's journey to becoming Chicago's 56th Mayor and 2) the duration of her singular term.
Pratt's recurring theme within the first section was the dichotomy between Chicago's existing political machine (the Daleys, Rahm Emmanuel) and the appetite from residents for real, lasting reform. This dichotomy was best demonstrated through the Emmanuel Administration's handling of the murder of Laquan McDonald, a case in which a 17-year-old black teenager was shot 16 times in the back by a police officer. This case was covered up for over a year - both through the blue wall of silence and the fact that the Emmanuel administration tried to prevent the body cam footage from being released. With the video eventually being released, Mayor Emmanuel knew that reform (or rather the image of reform) was needed - enlisting Lori Lightfoot to serve as head of the Chicago Police Board and the Chicago Police Accountability Task Force. Lightfoot had previously worked for the Office of Professional Standards (OPS) within the CPD, where she had a track record of being hard on individuals but soft on institutions. While Lightfoot didn't have a background that screamed reform, she utilized her positions with CPB and CPATF to criticize the Emmanuel Administration on issues like crime and police reform (Pratt posits whether this is genuine or opportunistic), and eventually decided to run for mayor. Running on a progressive & reformist platform, at a time when some members of the City Council were actively under investigation from the FBI, Lightfoot was able to win election against Toni Preckwinkle - being the first and only mayoral candidate to win all 50 wards in an election.
Riding this wave of "political will" from Lightfoot's election, Pratt leads us into the beginning of Lori Lightfoot as Mayor. From the beginning, Lightfoot misunderstood what got her elected in the first place, thinking that her historic win was a product of something intrinsic to her a candidate, rather than an overwhelming desire from residents across all wards for change in city government.
One of Lightfoot's biggest public mistakes of her administration was her handling of the COVID pandemic. While her COVID policies were largely responsive to Springfield, her rhetoric around implementing changes was scattered and contradictory - being inconsistent with closing of schools, public spaces, and businesses; threatening to close businesses; focusing on preventing private gatherings rather than public gatherings. (It is important to note that Pratt praises her for her vaccine rollout for black and brown communities in the South and West sides, which likely saved hundreds or thousands of lives.) Arguably the biggest consequence of Lightfoot's COVID response was her conflict with CTU over teachers being in classrooms during pandemic surges. This led to a brief strike in 2022, and very nearly a second one. Lightfoot's struggles with CTU looked similar to Emmanuel's relationship with activist groups - in these clashes with CTU, whether it be in labor negotiations, an elected school board, or teacher COVID concerns, Lightfoot fought for the status quo, rather than reform.
On the front of police reform, Lightfoot again more closely resembled the status quo and performative activism than actual reform. Her Police Department prioritized preventing property damage in downtown at the expense of small businesses in the South and West sides during the George Floyd protests; her administration blocked the release of police body cam footage from when police officers wrongly entered Anjanette Young's home; and her administration didn't allow for a truly independent selection of a new police superintendent during her term. Additionally, her alienation of public safety officials made the post-COVID crime spike in Chicago persistent, with crime being the number one issue for voters heading into the 2023 election, which Lightfoot ultimately losing City Hall to Brandon Johnson, who had the backing of CTU.
Ultimately, Lightfoot's time as mayor was mostly more of the same entrenched machine politics of Chicago. To answer Pratt's earlier question, Lightfoot, in my view, had largely framed herself as progressive as a way to obtain power, rather than because she had any interest in systemic change. She also had an inability, unwillingness, or lack of knowledge to do the most important thing in politics - build relationships. In the words of a former aldermanic ally of hers: "I have never met anybody who has managed to piss off every single person they came in contact with." Lightfoot didn't own her mistakes, or ask for forgiveness from her constituency. Adaptability is important in leadership, but Lightfoot maintained the mindset of a prosector, even if it didn't work for the many problems the city faced during her term.
A Lightfoot aid said the following after her loss in 2023: "You can't run against the status quo, and then fill your administration with the status quo. And you can't be mean to everyone who tried to help you." And perhaps this demonstrates in the simplest terms what Lightfoot got wrong, and how she missed the moment.
Pratt's recurring theme within the first section was the dichotomy between Chicago's existing political machine (the Daleys, Rahm Emmanuel) and the appetite from residents for real, lasting reform. This dichotomy was best demonstrated through the Emmanuel Administration's handling of the murder of Laquan McDonald, a case in which a 17-year-old black teenager was shot 16 times in the back by a police officer. This case was covered up for over a year - both through the blue wall of silence and the fact that the Emmanuel administration tried to prevent the body cam footage from being released. With the video eventually being released, Mayor Emmanuel knew that reform (or rather the image of reform) was needed - enlisting Lori Lightfoot to serve as head of the Chicago Police Board and the Chicago Police Accountability Task Force. Lightfoot had previously worked for the Office of Professional Standards (OPS) within the CPD, where she had a track record of being hard on individuals but soft on institutions. While Lightfoot didn't have a background that screamed reform, she utilized her positions with CPB and CPATF to criticize the Emmanuel Administration on issues like crime and police reform (Pratt posits whether this is genuine or opportunistic), and eventually decided to run for mayor. Running on a progressive & reformist platform, at a time when some members of the City Council were actively under investigation from the FBI, Lightfoot was able to win election against Toni Preckwinkle - being the first and only mayoral candidate to win all 50 wards in an election.
Riding this wave of "political will" from Lightfoot's election, Pratt leads us into the beginning of Lori Lightfoot as Mayor. From the beginning, Lightfoot misunderstood what got her elected in the first place, thinking that her historic win was a product of something intrinsic to her a candidate, rather than an overwhelming desire from residents across all wards for change in city government.
One of Lightfoot's biggest public mistakes of her administration was her handling of the COVID pandemic. While her COVID policies were largely responsive to Springfield, her rhetoric around implementing changes was scattered and contradictory - being inconsistent with closing of schools, public spaces, and businesses; threatening to close businesses; focusing on preventing private gatherings rather than public gatherings. (It is important to note that Pratt praises her for her vaccine rollout for black and brown communities in the South and West sides, which likely saved hundreds or thousands of lives.) Arguably the biggest consequence of Lightfoot's COVID response was her conflict with CTU over teachers being in classrooms during pandemic surges. This led to a brief strike in 2022, and very nearly a second one. Lightfoot's struggles with CTU looked similar to Emmanuel's relationship with activist groups - in these clashes with CTU, whether it be in labor negotiations, an elected school board, or teacher COVID concerns, Lightfoot fought for the status quo, rather than reform.
On the front of police reform, Lightfoot again more closely resembled the status quo and performative activism than actual reform. Her Police Department prioritized preventing property damage in downtown at the expense of small businesses in the South and West sides during the George Floyd protests; her administration blocked the release of police body cam footage from when police officers wrongly entered Anjanette Young's home; and her administration didn't allow for a truly independent selection of a new police superintendent during her term. Additionally, her alienation of public safety officials made the post-COVID crime spike in Chicago persistent, with crime being the number one issue for voters heading into the 2023 election, which Lightfoot ultimately losing City Hall to Brandon Johnson, who had the backing of CTU.
Ultimately, Lightfoot's time as mayor was mostly more of the same entrenched machine politics of Chicago. To answer Pratt's earlier question, Lightfoot, in my view, had largely framed herself as progressive as a way to obtain power, rather than because she had any interest in systemic change. She also had an inability, unwillingness, or lack of knowledge to do the most important thing in politics - build relationships. In the words of a former aldermanic ally of hers: "I have never met anybody who has managed to piss off every single person they came in contact with." Lightfoot didn't own her mistakes, or ask for forgiveness from her constituency. Adaptability is important in leadership, but Lightfoot maintained the mindset of a prosector, even if it didn't work for the many problems the city faced during her term.
A Lightfoot aid said the following after her loss in 2023: "You can't run against the status quo, and then fill your administration with the status quo. And you can't be mean to everyone who tried to help you." And perhaps this demonstrates in the simplest terms what Lightfoot got wrong, and how she missed the moment.
This entire review has been hidden because of spoilers.
April 13, 2024
When people ask me where I get my local political news, I say the Chicago Tribune's Gregory Pratt. He delivers the goods.
I have followed this author's articles for YEARS and can say that if Abe Froman is the Sausage King of Chicago, then Chicago Trib reporter Gregory Royal Pratt is the FOIA King of Chicago. He's got the 411.
Based on his years of writing and seemingly tenacious ways, I figured this book would be great, and let me tell you... it was worth the wait!
Dove into it that night! I was up until 1am! Dang it!
It is a political junkie's dream! I have followed my city's politics forever, but getting this rare, behind-the-scenes tell-all about our failed ex-mayor's term sure does fill in the pieces. I do like the author's fairness & impartiality, which is just like how he approaches the topics in his Trib articles.
He came out swinging on page one!! He told the story about how the mayor ignored one of her youngest (and probably only) fans. It's sad. She's clearly been rude to people in her years, but I did not expect that kind of behavior towards a kid—not even from her.
I am still laughing in the book's first part when the author suggests she watch a certain horror movie. Then they were someplace (where I don't recall), and she leaned to him and said that the movie "scared the S*&^ out of me." I truly laughed out loud at that section. It, indeed, showed that she does have a human side. And the author does a great job of reminding us that there really is a person in that oversized suit.
He also spoke of her life, intelligence, and successful law career. Again, it's not just a book to rip her apart but to tell a story thru the author's lens about Chicago's first elected female black gay mayor who could have truly left a great legacy, but sadly, she could not get out of her own way.
The mayor always put up this tougher-than-nails façade, and even made a stupid (and well-known) "I've got the biggest (male part) in the city" comment. Yet, she had no command of anyone and had lost the respect of so many.
He takes us thru her years of inability to manage Chicago and those in it- leading to its total unraveling before her very eyes (and ours). She continued to lose control over her 4 years in office, slamming beautiful Chicago further into the ground. It felt like we hit rock bottom at the end of her term, but then Brandon Johnson said, "Hold my beer." (I can't wait for THAT read.)
Throughout the book, he covers subjects we already knew about BUT with details that only HIS front-row seat allowed him to see. So many things were done for the public, but we want to know what was said and done behind the scenes, and the author does not fail to deliver.
From racial riots to the removal of the Christopher Columbus statue to the COVID situation, Anajanette Young, the renaming of the famous Lake Shore Drive, her reverse racism against white reporters, there is so much revealed that I am shocked he got it all in just over 200 pages. Phew! After listing these and knowing there are many more topics in this book that she screwed up, he could have named the book "Mishandled."
It's one of the best political books I have read in a very long while. His ability to keep things concise & not get lost in the details makes this book that much more enjoyable. I HIGHLY recommend!!
Thanks, Gregory Pratt!! This book rocks!! I am sending one to my son! He's gonna LOVE it, too!
I have followed this author's articles for YEARS and can say that if Abe Froman is the Sausage King of Chicago, then Chicago Trib reporter Gregory Royal Pratt is the FOIA King of Chicago. He's got the 411.
Based on his years of writing and seemingly tenacious ways, I figured this book would be great, and let me tell you... it was worth the wait!
Dove into it that night! I was up until 1am! Dang it!
It is a political junkie's dream! I have followed my city's politics forever, but getting this rare, behind-the-scenes tell-all about our failed ex-mayor's term sure does fill in the pieces. I do like the author's fairness & impartiality, which is just like how he approaches the topics in his Trib articles.
He came out swinging on page one!! He told the story about how the mayor ignored one of her youngest (and probably only) fans. It's sad. She's clearly been rude to people in her years, but I did not expect that kind of behavior towards a kid—not even from her.
I am still laughing in the book's first part when the author suggests she watch a certain horror movie. Then they were someplace (where I don't recall), and she leaned to him and said that the movie "scared the S*&^ out of me." I truly laughed out loud at that section. It, indeed, showed that she does have a human side. And the author does a great job of reminding us that there really is a person in that oversized suit.
He also spoke of her life, intelligence, and successful law career. Again, it's not just a book to rip her apart but to tell a story thru the author's lens about Chicago's first elected female black gay mayor who could have truly left a great legacy, but sadly, she could not get out of her own way.
The mayor always put up this tougher-than-nails façade, and even made a stupid (and well-known) "I've got the biggest (male part) in the city" comment. Yet, she had no command of anyone and had lost the respect of so many.
He takes us thru her years of inability to manage Chicago and those in it- leading to its total unraveling before her very eyes (and ours). She continued to lose control over her 4 years in office, slamming beautiful Chicago further into the ground. It felt like we hit rock bottom at the end of her term, but then Brandon Johnson said, "Hold my beer." (I can't wait for THAT read.)
Throughout the book, he covers subjects we already knew about BUT with details that only HIS front-row seat allowed him to see. So many things were done for the public, but we want to know what was said and done behind the scenes, and the author does not fail to deliver.
From racial riots to the removal of the Christopher Columbus statue to the COVID situation, Anajanette Young, the renaming of the famous Lake Shore Drive, her reverse racism against white reporters, there is so much revealed that I am shocked he got it all in just over 200 pages. Phew! After listing these and knowing there are many more topics in this book that she screwed up, he could have named the book "Mishandled."
It's one of the best political books I have read in a very long while. His ability to keep things concise & not get lost in the details makes this book that much more enjoyable. I HIGHLY recommend!!
Thanks, Gregory Pratt!! This book rocks!! I am sending one to my son! He's gonna LOVE it, too!
January 7, 2025
4.5 stars, but I'm willing to round up.
I pay some attention to Chicago politics, but not super-close attention. I wondered: how is it that Lori Lightfoot won election in a landslide in 2019 (a 3:1 edge over Toni Preckwinkle) to not even making the run-off in a crowded field in 2023?
The answers? Well, first her personality was all wrong for office. She took everything personally and lashed back accordingly. A former prosecutor, she treated everyone as if they were all hostile witnesses for her to break down. She won over no new allies and alienated seemingly all of her election-time allies. Second, her huge margin of victory in 2019 papered over her weak political core. Rahm Emmanuel noted that her support was an inch deep but a mile wide. Many supported her, but no one was really that gung ho for her. Basically, every thing broke her way in the 2018-19 election cycle (and yes, she also ran a very good campaign then, too). She got in the campaign before Emmanuel bowed out, the indictment of Eddie Burke worked well for a non-office holder like her, allowing her to run as an outsider more effectively, and Preckwinkle ran an absolutely atrocious campaign. Beyond that, Lightfoot misjudged how much support she really had, assuming her huge win was a sign she was that widely popular.
In fact, her campaign was different from who Lightfoot was. She ran as a progressive and an outsider, but she really wasn't that progressive. She'd once been part of a civilian watchdog crowd looking at the police, and generally turning a blind eye to its problems. She campaigned for school reform (creating an elected board to run the schools) then immediately dismissing that idea upon election. It reminds me more than a little bit of Jane Byrne campaigning in 1979 opposing Eddies Burke and Vrdolyck and then immediately becoming key allies with each other.
There's an overall theme with Lightfoot: she manifested a real "girl boss" energy. I mean that as an insult, to be clear. She was a black female lesbian, and therefore any successes she personally had was a success for women and for black people and for the LGBTQ+ community. Anyone who opposes her, opposes them. And those groups must supprot her, even if she isn't really doing much for them. It's all about her.
The book is not without flaws. There isn't too strong a narrative flow. It's a bunch of small chapters that don't always add up. Despite being barely 200 pages long, she isn't elected mayor until around page 80, and starts her reelection campaign 100 pages later.
But Pratt knows his stuff. He's a reporter on the beat and he knows the players and intervies tons of them, off and on the record. It's an enlightening book. I'd like to see what he has to say about Brandon Johnson's mayorship, which right now seems destined to land in similar one-term ignominy.
I pay some attention to Chicago politics, but not super-close attention. I wondered: how is it that Lori Lightfoot won election in a landslide in 2019 (a 3:1 edge over Toni Preckwinkle) to not even making the run-off in a crowded field in 2023?
The answers? Well, first her personality was all wrong for office. She took everything personally and lashed back accordingly. A former prosecutor, she treated everyone as if they were all hostile witnesses for her to break down. She won over no new allies and alienated seemingly all of her election-time allies. Second, her huge margin of victory in 2019 papered over her weak political core. Rahm Emmanuel noted that her support was an inch deep but a mile wide. Many supported her, but no one was really that gung ho for her. Basically, every thing broke her way in the 2018-19 election cycle (and yes, she also ran a very good campaign then, too). She got in the campaign before Emmanuel bowed out, the indictment of Eddie Burke worked well for a non-office holder like her, allowing her to run as an outsider more effectively, and Preckwinkle ran an absolutely atrocious campaign. Beyond that, Lightfoot misjudged how much support she really had, assuming her huge win was a sign she was that widely popular.
In fact, her campaign was different from who Lightfoot was. She ran as a progressive and an outsider, but she really wasn't that progressive. She'd once been part of a civilian watchdog crowd looking at the police, and generally turning a blind eye to its problems. She campaigned for school reform (creating an elected board to run the schools) then immediately dismissing that idea upon election. It reminds me more than a little bit of Jane Byrne campaigning in 1979 opposing Eddies Burke and Vrdolyck and then immediately becoming key allies with each other.
There's an overall theme with Lightfoot: she manifested a real "girl boss" energy. I mean that as an insult, to be clear. She was a black female lesbian, and therefore any successes she personally had was a success for women and for black people and for the LGBTQ+ community. Anyone who opposes her, opposes them. And those groups must supprot her, even if she isn't really doing much for them. It's all about her.
The book is not without flaws. There isn't too strong a narrative flow. It's a bunch of small chapters that don't always add up. Despite being barely 200 pages long, she isn't elected mayor until around page 80, and starts her reelection campaign 100 pages later.
But Pratt knows his stuff. He's a reporter on the beat and he knows the players and intervies tons of them, off and on the record. It's an enlightening book. I'd like to see what he has to say about Brandon Johnson's mayorship, which right now seems destined to land in similar one-term ignominy.
March 23, 2024
An old political axiom often quoted at City Hall notes there are no permanent friends or permanent enemies, just permanent interests" (viii).
"Consider Chicago's first congressional district, which stretches from Streeterville and Navy Pier downtown to the impoverished neighborhood of West Englewood. It has a life-expectancy gap of 30 years--people live on average to ninety in Streeterville, but just to 60 on the South Side. The median income is $100,000 in Streeterville, but only about a quarter of that in West Englewood" (xiv).
"The statement by Lightfoot best encapsulates a theory journalist Jamie Kalvin once shared with me about 'cover up by investigation.' The idea is that agencies say they're looking into a matter, then sit on it indefinitely, creating a veneer of respectability but really covering it up" (17).
"A rumor spread midweek that LIghtfoot had been beaten up by her wife, who had allegedly found out the mayor was having threesomes. It morphed into a variety of different outlandish scenarios, including one allegation that Lightfoot had trysts at a city-owned apartment in Elmhurst, Illinois
Where it started is unclear, but it probably has some roots within the police department, as cops are some of the gnarliest gossips" (161).
"Weeks later, as Lightfoot's two-year mayoral anniversary approached, she implemented a policy saying she would only talk with reporters of color to mark the occasion. As a Latino, I qualified, but I canceled my interview because we didn't believe she gets to dictate to media outlets whom they send to cover her. It was a controversial move, largely praised by my fellow journalists, though some thought my position was wrong. I just didn't want to be a pawn in her game--I believe the move had more to do with avoiding Crain's, Fran Spielman, and Mary Ann Ahern than a good-faith belief in diverse media. It back-fired on Lightfoot, too, when she gave an interview to The TRiiBE, a site focused on Black Chicago, but couldn't name a single Black restaurant on the West side" (162).
"Politicians try to avoid getting on the debate stage with their rivals when they're in the lead (or are facing clowns, as Richard M. Daley did in 1995 when he was challenged by Spanky the Clown)." (197).
"Consider Chicago's first congressional district, which stretches from Streeterville and Navy Pier downtown to the impoverished neighborhood of West Englewood. It has a life-expectancy gap of 30 years--people live on average to ninety in Streeterville, but just to 60 on the South Side. The median income is $100,000 in Streeterville, but only about a quarter of that in West Englewood" (xiv).
"The statement by Lightfoot best encapsulates a theory journalist Jamie Kalvin once shared with me about 'cover up by investigation.' The idea is that agencies say they're looking into a matter, then sit on it indefinitely, creating a veneer of respectability but really covering it up" (17).
"A rumor spread midweek that LIghtfoot had been beaten up by her wife, who had allegedly found out the mayor was having threesomes. It morphed into a variety of different outlandish scenarios, including one allegation that Lightfoot had trysts at a city-owned apartment in Elmhurst, Illinois
Where it started is unclear, but it probably has some roots within the police department, as cops are some of the gnarliest gossips" (161).
"Weeks later, as Lightfoot's two-year mayoral anniversary approached, she implemented a policy saying she would only talk with reporters of color to mark the occasion. As a Latino, I qualified, but I canceled my interview because we didn't believe she gets to dictate to media outlets whom they send to cover her. It was a controversial move, largely praised by my fellow journalists, though some thought my position was wrong. I just didn't want to be a pawn in her game--I believe the move had more to do with avoiding Crain's, Fran Spielman, and Mary Ann Ahern than a good-faith belief in diverse media. It back-fired on Lightfoot, too, when she gave an interview to The TRiiBE, a site focused on Black Chicago, but couldn't name a single Black restaurant on the West side" (162).
"Politicians try to avoid getting on the debate stage with their rivals when they're in the lead (or are facing clowns, as Richard M. Daley did in 1995 when he was challenged by Spanky the Clown)." (197).
June 16, 2025
A pretty fascinating book for all its closely observed stories about Lori Lightfoot's election and tenure as mayor of Chicago, but a pretty frustrating one at the same time, because closely observed stories is all it is. There's a real lack of narrative to this book overall, apart from a little big-picture framing at the outset, about how Lightfoot alienated everyone around her.
By halfway through, I was a little lost amid dozens of stories that amount to a list of names and "He said this, then she said this, then he said this," etc., without much sense of context. I came away with a long list of times Lightfoot said or did something that pissed someone off (including her allies, or in some cases people on both sides of the issue), but no real sense for her as a person, for what she actually believes or wants, or why she treats people the way she does. Maybe the author doesn't either -- I have to think it'd be hard to get that out of a politician. But this book really could have used some analysis, some theorizing or top-level observations or historical context about Chicago history, for a sense of how Lightfoot's strategies compared to others.
Maybe the best illustration of the problem here is that this book treats the COVID pandemic exactly like, say, a threatened teacher's strike, as just a series of anecdotes involving individual decisions and face-offs about them, rather than like a huge, unprecedented challenge that would have challenged any mayor, and was a particularly significant chance to get a sense for who Lori Lightfoot is. There's no sense that any of the things she faced was more important, difficult, or telling than any other. Put another way, this reads like a recap of six years of newspaper stories, rather than like an after-the-fact consideration of what Lightfoot's term as mayor meant to anyone: to the city, to the crises it was facing during this era, or to Lightfoot herself.
By halfway through, I was a little lost amid dozens of stories that amount to a list of names and "He said this, then she said this, then he said this," etc., without much sense of context. I came away with a long list of times Lightfoot said or did something that pissed someone off (including her allies, or in some cases people on both sides of the issue), but no real sense for her as a person, for what she actually believes or wants, or why she treats people the way she does. Maybe the author doesn't either -- I have to think it'd be hard to get that out of a politician. But this book really could have used some analysis, some theorizing or top-level observations or historical context about Chicago history, for a sense of how Lightfoot's strategies compared to others.
Maybe the best illustration of the problem here is that this book treats the COVID pandemic exactly like, say, a threatened teacher's strike, as just a series of anecdotes involving individual decisions and face-offs about them, rather than like a huge, unprecedented challenge that would have challenged any mayor, and was a particularly significant chance to get a sense for who Lori Lightfoot is. There's no sense that any of the things she faced was more important, difficult, or telling than any other. Put another way, this reads like a recap of six years of newspaper stories, rather than like an after-the-fact consideration of what Lightfoot's term as mayor meant to anyone: to the city, to the crises it was facing during this era, or to Lightfoot herself.
May 7, 2024
A slightly dry, relatively breezy encapsulation of the rise and fall of Lori Lightfoot. Pratt has covered Lightfoot for years, so his construction and occasional analysis of her mayoralty is definitely an informed perspective. That said, the book kind of lacks the heft that other political books usually do. Pratt almost keeps too much of a journalist's perspective; just the facts, ma'am, when some deeper connectivity could do.
That said, getting an inside look at how Lightfoot saw her job and the behaviors she felt were acceptable in conducting her work does go a long way to helping explain why it was that she squandered so much goodwill from the people of Chicago. It also provides a little bit of a balm for those of us who live here - Lightfoot overwhelmingly won her election in 2018. It was hard not to feel a little hoodwinked when candidate Lightfoot ended up being in such a different place than Mayor Lightfoot. Pratt gets the scoops here on the extent to which her private conversations differed from her public statements.
The truth is we love political figures that can be described as "Shakespearean" and Lightfoot more than qualifies. She's a textbook example of a leader being done in by their own worst impulses. In that sense, it's a good addition to the long line of "what happened" political books seeking to cover a candidate or leader, particularly in the case of Chicago, a city that has a long history of titanic mayors.
That said, getting an inside look at how Lightfoot saw her job and the behaviors she felt were acceptable in conducting her work does go a long way to helping explain why it was that she squandered so much goodwill from the people of Chicago. It also provides a little bit of a balm for those of us who live here - Lightfoot overwhelmingly won her election in 2018. It was hard not to feel a little hoodwinked when candidate Lightfoot ended up being in such a different place than Mayor Lightfoot. Pratt gets the scoops here on the extent to which her private conversations differed from her public statements.
The truth is we love political figures that can be described as "Shakespearean" and Lightfoot more than qualifies. She's a textbook example of a leader being done in by their own worst impulses. In that sense, it's a good addition to the long line of "what happened" political books seeking to cover a candidate or leader, particularly in the case of Chicago, a city that has a long history of titanic mayors.
April 2, 2024
Greg Pratt is the essential Chicago politics journalist. He was on Lori Lightfoot like a tick during her whole time in office (and before). There is no one better to tell this story — and in this book, that shows.
This book is absolutely in the pantheon of great books on Chicago's mayors (our city is blessed with a few classics) because Greg knew so damn much about what the people around the mayor and in the City Council are thinking. His absurdly strong reporting offers pretty unprecedented persepctive and allows him to get above political cliches to offer a more real (and engaging) look into the challenges Lightfoot faced. What emerges is a clear sense of how she rose to power and slowly lost her foothold to burn out and lose.
Her fall and ascent is a GREAT story for any reader interested in not just Chicago politics, but American politics. Lori Lightfoot clung close to identity politics (and was sometimes unfairly abused with them), had ties to reformist progressivism and management-style neoliberalism, and dealt with all the swirling forces of our day. The story of her time at City Hall reflects deeply on how our politics are changing.
Also, Greg has some pretty damn funny anecdotes, in large part because he's the best records-requestor around. For what it's worth, I'm going to reread -- that's the best praise I can give.
READ READ READ READ READ READ READ READ
This book is absolutely in the pantheon of great books on Chicago's mayors (our city is blessed with a few classics) because Greg knew so damn much about what the people around the mayor and in the City Council are thinking. His absurdly strong reporting offers pretty unprecedented persepctive and allows him to get above political cliches to offer a more real (and engaging) look into the challenges Lightfoot faced. What emerges is a clear sense of how she rose to power and slowly lost her foothold to burn out and lose.
Her fall and ascent is a GREAT story for any reader interested in not just Chicago politics, but American politics. Lori Lightfoot clung close to identity politics (and was sometimes unfairly abused with them), had ties to reformist progressivism and management-style neoliberalism, and dealt with all the swirling forces of our day. The story of her time at City Hall reflects deeply on how our politics are changing.
Also, Greg has some pretty damn funny anecdotes, in large part because he's the best records-requestor around. For what it's worth, I'm going to reread -- that's the best praise I can give.
READ READ READ READ READ READ READ READ
April 7, 2024
This book incisively analyzes the Lightfoot administration, but it provides insights into so much more. It illustrates the complicated dynamics at play in Chicago during a critical period of transition after the death of the renowned Chicago political machine. As the book shows, everything in Chicago—power, influence, and alliances—is suddenly up for grabs in the resulting power vacuum.
Chicago’s future seems to be at a pivotal turning point. Will it continue to be a world class city of influence or will its problems force it to recede from prominence? And can the disparate forces of government come together to make things better or will infighting hasten the downfall? Lori’s downfall in her reelection campaign to opponents from both her far left and far right show that the story is still being written. But, as Pratt shows, what Chicago went through under the Lightfoot administration provides critical lessons for both local and national governments alike: fighting each other only makes it harder to fight our problems.
Every concerned citizen and elected representative, both in Chicago and beyond, needs to learn the lessons that Pratt imparts in this wonderful work of political analysis. As another reviewer said, read read read this book.
Chicago’s future seems to be at a pivotal turning point. Will it continue to be a world class city of influence or will its problems force it to recede from prominence? And can the disparate forces of government come together to make things better or will infighting hasten the downfall? Lori’s downfall in her reelection campaign to opponents from both her far left and far right show that the story is still being written. But, as Pratt shows, what Chicago went through under the Lightfoot administration provides critical lessons for both local and national governments alike: fighting each other only makes it harder to fight our problems.
Every concerned citizen and elected representative, both in Chicago and beyond, needs to learn the lessons that Pratt imparts in this wonderful work of political analysis. As another reviewer said, read read read this book.
September 29, 2024
I read this book a bit slower than I thought I would but sped it up towards the end. My friend gave it to me and I was like with all the news of an election nationally coming up, let me see how one was more at the local level for the third largest U.S. city of Chicago. The reporter did an excellent job even though Lori Lightfoot wasn’t interviewed. Unfortunately for her she could not tell her part, but that is on her. I think the author did an excellent job going in a chronological order but he didn’t really put much into her time as mayor during the pandemic as I imagined. The battles between her and the other alderman were highly impactful how the city was run. It’s almost like every alderman is the mayor of their ward then the mayor has his or her own powers plus being the head of the city council.
For any Chicagoan or those who are familiar with Mayor Lightfoot’s time in office I highly recommend it. Plus learning about local politics instead of just focusing on more national races this is an excellent book. You can’t think of running the mayors office like a law firm, even if voters want change it doesn’t always mean that is the best reform. I definitely learned a lot from this book and am glad I read it.
For any Chicagoan or those who are familiar with Mayor Lightfoot’s time in office I highly recommend it. Plus learning about local politics instead of just focusing on more national races this is an excellent book. You can’t think of running the mayors office like a law firm, even if voters want change it doesn’t always mean that is the best reform. I definitely learned a lot from this book and am glad I read it.
May 28, 2024
I've been closely following Greg Pratt's City Hall reporting for years now, and I was very patiently waiting for this book to come out. Overall, it was an enjoyable and quick read that quite intimately and directly tells the story of the two big crisis moments of Lori Lightfoot's tenure: the COVID-19 pandemic and the 2020 uprisings, and gives us interesting insight into her world and the way she struggled with the massive political issues that face the Windy City.
My biggest critique of this book is that it simply felt too short and rushed. I wish Pratt had taken more time and added more details to this book, including talking more about Invest South/West, the battle over the Chicago casino, and the efforts to remove lead pipes. These issues show examples of Lightfoot's desires to do something memorable and impactful run up against her neoliberal bones, and I think the book would have been stronger for it.
This is still a great and fast read, and I do recommend it, but I think Pratt had a really awesome opportunity to flesh out the story more, and unfortunately didn't do that.
My biggest critique of this book is that it simply felt too short and rushed. I wish Pratt had taken more time and added more details to this book, including talking more about Invest South/West, the battle over the Chicago casino, and the efforts to remove lead pipes. These issues show examples of Lightfoot's desires to do something memorable and impactful run up against her neoliberal bones, and I think the book would have been stronger for it.
This is still a great and fast read, and I do recommend it, but I think Pratt had a really awesome opportunity to flesh out the story more, and unfortunately didn't do that.
June 9, 2025
Not a bad book, but it is weakened by its lack of cohesion. It goes mostly chronologically with each chapter focusing on a big event/argument/scandal that took place during that time period.
However, there is no central message about Lightfoot's career that is being argued for in the book. As a result, it can feel somewhat disjointed hopping from one topic to the next, without a unifying message that shows how the topics of each chapter tie together.
The book is written by a reporter for a Chicago newspaper, and as a result the book can feel like reading a series of news reports about arguments Lightfoot got into rather than a political biography that teaches more about how political power works in Chicago.
The book is still valuable for detailing the major events of Lori Lightfoot's time as mayor.
However, there is no central message about Lightfoot's career that is being argued for in the book. As a result, it can feel somewhat disjointed hopping from one topic to the next, without a unifying message that shows how the topics of each chapter tie together.
The book is written by a reporter for a Chicago newspaper, and as a result the book can feel like reading a series of news reports about arguments Lightfoot got into rather than a political biography that teaches more about how political power works in Chicago.
The book is still valuable for detailing the major events of Lori Lightfoot's time as mayor.
November 28, 2024
In 2019, Lori Lightfoot, a big law firm partner, came out of nowhere to beat a more experienced candidate by a 3-1 margin. Four years later, she finished in third place.
How did she rise so fast and fall so far? Pratt explains that she rose because she was a liberal reformer at a time when Chicago's moderate elite was enmeshed in scandals; in addition, she rode the same left-wing wave that caused other left-leaning governors, mayors and prosecutors to win nationwide. She fell because of the nationwide crime wave of the early 2020s, but also because of her own personal flaws: she simply did not play well with the press or other politicians, and as a result had few allies when she ran for reelection.
How did she rise so fast and fall so far? Pratt explains that she rose because she was a liberal reformer at a time when Chicago's moderate elite was enmeshed in scandals; in addition, she rode the same left-wing wave that caused other left-leaning governors, mayors and prosecutors to win nationwide. She fell because of the nationwide crime wave of the early 2020s, but also because of her own personal flaws: she simply did not play well with the press or other politicians, and as a result had few allies when she ran for reelection.
December 28, 2024
As a resident of Cook County, I thoroughly loved this book. Gregory Royal Pratt gives his readers a front-row seat to City Hall before, during and after the tumultuous Lori Lightfoot mayoral tenure. No matter where you call home, you will enjoy the book. The City is Up for Grabs reads like a novel-- except it is all true! I was here and saw it as it played out.
Pratt documents what happens in big-city backroom politics and I guarantee you will find the book to be a great read. Funny, shocking, credible and a lot of fun, especially if you are a political junkie, like me. There are national political figures in the book so you don't have to be an Illinois resident to find it relevant.
Highly recommended!
Pratt documents what happens in big-city backroom politics and I guarantee you will find the book to be a great read. Funny, shocking, credible and a lot of fun, especially if you are a political junkie, like me. There are national political figures in the book so you don't have to be an Illinois resident to find it relevant.
Highly recommended!
March 16, 2024
This makes for an interesting sequel to City So Real, the documentary that had so much hope about it in regards to the Lori Lightfoot administration in Chicago. Her winning the 2019 election was surprising. The fact that she couldn't govern maybe shouldn't have been. She was constantly on the attack and never seemed to build solid relationships on which a functional bureaucracy is based. Lightfoot also seemed quite profane, although probably most politicians are behind closed doors. Running for office and being in office are two distinct skills sets (like interviewing and working).
April 20, 2024
Heading back into the Lori-verse was a real trip.
Pratt does yeoman's work detailing the (what feels like) thousands of forced and unforced errors of the Lightfoot administration but the book is oddly narrow. There is no real setting for what Chicago is, was, or is going, just the Lightfoot administration blundering and swearing for 4 years. As always read Fire on the Praire, the GOAT chicago politics book.
INCREDIBLE that a book about the Chicago mayor only mentions the CTA ONCE which is perhaps why things are the way they are.
Pratt does yeoman's work detailing the (what feels like) thousands of forced and unforced errors of the Lightfoot administration but the book is oddly narrow. There is no real setting for what Chicago is, was, or is going, just the Lightfoot administration blundering and swearing for 4 years. As always read Fire on the Praire, the GOAT chicago politics book.
INCREDIBLE that a book about the Chicago mayor only mentions the CTA ONCE which is perhaps why things are the way they are.
April 28, 2024
Pratt is one of the best reporters in the city and he had a courtside seat to the Lightfoot circus. He confirmed many of the stories that I had learned about with this great book. He was also at times on the receiving end of some of Lightfoot's epic and unprofessional rants. This book is an inside look of what happens when you give an individual with many low self-esteem issues the power of a positon like Mayor of Chicago. It should be a warning to voters in other big cities to not ignore red flags in candidates.
May 5, 2024
Really had no idea what a mayor has to do. You only know so much from the media; and how much of that is bogus info? I have a more concise understanding after reading Gregory's book. He is more than objective in his recounting of his history with Lightfoot through the years, and after getting the truth, the whole truth, & nothing but the truth- I can see how the promise of a new day for my favorite city went into the bathwater with the baby. Definitely would recommend reading it, especially if a native Chicagoan who lived through her time as mayor.
August 21, 2024
I'm not from Chicago and I don't know much about its politics, but this was still a really enjoyable and fascinating exploration of Lightfoot's brief stint in the mayoralty. Chicago has such a specific local political culture, and learning more about it -- and the ways in which it trips up leaders -- was engaging. Pratt is a real critics of Lightfoot, and it's not hard to see why -- her innate combativeness and irascibility made her really ill-suited to the role. A great profile, and a breeze to read.
January 3, 2025
I moved to Chicago in 23 so it was nice to get a short and sweet recent history of the city's issues and a profile of the major political players. Somewhat surprisingly, the woman at the narrative's center turned out to be a fascinating, almost Shakespearean tragic figure, in contrast to my preconception of her as somewhat of a clown.
Notably missing from the book was the issues with the Chicago Transit Authority, which were exacerbated as ridership fell during COVID and are still today one of the city's major woes.
Notably missing from the book was the issues with the Chicago Transit Authority, which were exacerbated as ridership fell during COVID and are still today one of the city's major woes.
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