Forrest Claypool & A Master Class in Chicago Politics

Welcome to the Pro Politics Podcast. I'm Zach McCrary. I've been working in politics for the better part of two decades, but at heart I'm a political junkie who wants to talk to interesting people involved in politics. My guest today is Forest Clay Poole, who's been all over politics in Chicago for 40 plus years. As an operative, two stents as chief of staff to the mayor of Chicago, running the Chicago Transit Authority, running the Chicago Board of Education, running the Chicago Park District, and as a candidate himself, including serving a term on the Cook County Board and being involved in multiple high-profile, high-drama, Cook County elections. No one has a resume in and around Chicago politics, like Forest Clay Poole, and he's recently added another line to his resume that of author, writing a new book, chronicling his time, working for Chicago Mayor Richard M. Daley, the son of the original, Mayor Richard J. Daley, for us working for Daley in the 80s and 90s. This is a wide ranging discussion, both about Forest Book, the Daily Show, which I highly recommend, and the last 40 years of his own professional life, which maps very neatly onto the story of the last four decades of Chicago politics. Forest Clay Poole, tell me a bit how you grew up. I grew up in a small town of about 1,700 folks in deep southern Illinois, Rockwellian, Norman Rockwellian upbringing at a time when small towns, when there were still plenty of jobs, and you know, there was the Labor Day parades, and the Fourth of July fireworks, and on summer nights, the kids were in the lit-up swimming pool, and the old men were playing horse shoes in the park, and it was a wonderful way to grow up. That's all, of course, changed, as rural areas have been part-hit economically, and the social media has driven children indoors, and all the things that we can lament, but it was a great place to grow up. And did you come from a political family at all? Was that front and center for you, for the Clay Poole's growing up? Well, we talked politics a lot. My dad, particularly, and my mom and dad canceled each other's votes out in almost every election. My dad usually go to Republican, and my mom, Democrat, occasionally, they were together, like Jimmy Carter in '76. Yeah, so politics was certainly on the dinner table, but I wouldn't say, you know, we were novertly political family. And what about from your own perspective? What are your own early political memories? Yeah, that's a good question. My first sort of awakening to politics was when a guy named Dan Walker ran for Governor of Illinois, and he was running against the Chicago machine, and of course, ironically, when I was growing up in Southern Illinois, everybody hated this Chicago machine and hated Mayor Daly, and so here was this guy running against the bad guys up north, and he walked the whole state from the southern tip to the north as part of this insurgent campaign, and he defeated Mayor Daly's candidate. And so that's how he got involved in active and politics. And then shortly thereafter, a few years later, went to college in Jimmy Carter, caught my attention, and he was someone that I'd then joined the local Democratic Party and worked the precincts door-to-door in deep Southern Illinois in Jackson County where I went to school at Southern Illinois University. So that was sort of my beginning in politics. And say a little bit about the Illinois that you were seeing in the '70s, I guess. Was it always Chicago, Cook County versus everybody else? What were the dynamics as you were figuring out how Illinois politics works? You have kind of fascinating, because it's all changed so much. But back then, deep Southern Illinois where I was from was Democratic, and long history of being Democrat. That part of the state was sympathetic to the Confederacy during the Civil War, and was just uniquely different, much closer to Kentucky, which is almost down the road than it was to Chicago. As you went further north, it got more Republican in the farmlands. North and then of course, Chicago was very Democratic, but the suburbs were extremely Republican. So that was the dynamic at the time. Now of course today, downstate is Republican, the suburbs are Democratic. The city is a mixed bag, but still mostly Democratic. So it's a blue state, but it's funny how just the shift in demographics and voting patterns over decades. So you mentioned Dan Walker, you mentioned Jimmy Carter. What do you look back on as the how and the when that the switch flips for you that you got interested in politics? Not just as something follow, but as a potential career? Yeah, I was always sort of a little bit in the back of my mind because I was always so interested in politics and public policy, but I started out to be a lawyer, I graduated at the University of Illinois Law School, and then I made my first trek to a big city in my life, to the big city of Chicago for an interview with a firm called Jenner and Block, where I worked for a bit. But my part in passion was always a politics. So when I first got an offer to work for another in search and a guy named Pat Quinn, who had worked for Dan Walker, running against the machine for this, this, this eye glazing agency called the Board of Tax Appeals, which had been subject to a corruption probe because all the folks are passing up tax breaks to the award commitment who doubled his property tax appeal lawyers in exchange for bribes. That caught my attention. So I worked for him as a volunteer, but then he got elected and offered me a job to be his deputy. And so we spent a couple of years cleaning up that office until I again had another opportunity serendipitously. My downstate congressman, the one that I'd grown up with Paul Simon, who went on to, as you may know, obviously, I do know, went on to become, you know, US Senator later. He was running for the US Senate at that time. And because I'd known him and was admire of his from Southern Illinois, here he was running statewide. So I finagled my way in and asked off my credentials, having a journalism degree to get the press secretary's job in the primary when nobody really wanted to join before he, and he kind of came from behind and beat again, beat the establishment, beat the machine, which was very appealing to me. Back then, that was sort of my, you know, that was my, the appeal of it all was, you know, the underdog taken on the big bad machine and the establishment and winning. And of course, we did David Axelrod, who of course is now more famous for having been steered Barack Obama, both to the US Senate and the presidency, was in that campaign. I developed a relationship, became close to him, was just a lieutenant. And then he asked me to join him after the campaign to, to a political consulting firm he was founding, which of course went on to become one of the more dominant ones nationally. And it was in that role a few years later that I met a client of ours, named Richard M. Daley, who was running for his third term of state's attorney and eyeing another race for mayor. And I spent a lot of time with him got to know him. And when he got elected mayor, he offered me to come into the administration as his chief of staff. And that's sort of the journey I went through was he was combination of lock bean in the right place, the right time, some serendipity. And it was an interesting journey. And in a field of smart, hard working, ambitious people, what have you seen that has made David Axelrod successful? The ex-factors he possesses, what sets him apart from the rest of the pack? You're certainly thinking more back to his days as a working media consultant campaign strategist. Yeah, I mean, I think some of them were the things you would always associate with anyone who's extremely successful, you know, an incredible work ethic. Incredibly smart. He does have a unique creative gene that comes into the fore when he's writing ads or trying to condense a message into something that's cogent and appealing and has an edge to it. One thing he kind of like I think carried out throughout his career, though, that he understood innately. And sometimes a lot of consultants never figured it out was that a candidate's biography and how it related to his message was critical. So all of his candidates, he tried to find what's the pearl, what's the part of their biography that reinforces the message we're delivering and getting those to, you know, reinforce themselves. And of course, I could give you a lot of examples over the years. But of course, the most famous was in the US Senate race when Barack Obama was way behind three other better funded candidates with a month to go before the primary election, David got him on the air and his ads perfectly blended his biography with his message. And here's this charismatic guy, African American, you know, who had overcome all these sort of challenges, including racial discrimination and being fatherless and so forth. And yet he had succeeded. And here he was talking about an America in which anyone can succeed, anyone can get ahead that this is the country we believe and we love. And so there was this optimism and power that contrasted so sharply with the normal negativity and drudgery of political campaigns. And he just he just exploded once he was on the air. And an axe rod had blended his biography and his message so powerfully that he went on to win 53 percent of the vote in a seven person field and just became a national phenomenon. And so this was several years working with with Axel Rod at the early days of I guess eventually would become AK PD media consulting in your time there. Is there a client in your days as a working operative, you know, media consultant? Is there a candidate you especially became emotionally invested in or felt like you learned a lot in an early phase of your career? Is there a specific race or two that comes to mind? You know, there was a guy in Kentucky in 1987 named Fred Cowan who was running for attorney general and he was not very well known. He was not he was not very well-funded. He had a he was a terrific super high integrity guy though. And then extremely competent lawyer. Just a wonderful guy with a wonderful family. And we had to it was interesting because I was very emotionally invested in him. And I know David admired him very much as well. And we had to make a judgment. His family wanted to basically put him on the air and you know what a great guy is and that wonderful record he has. And we had the tough position to tell him the family look, you know, he only have a little bit of money. And the guy you're running against is very well known. And he's got some pretty he's got some real skeletons in his closet. And the only chance of winning is to run a hundred percent negative campaign. And the family didn't like that. Fred overruled them reluctantly went with us on election night. We went into the to the with the family to watch the returns and David sort of said to me privately. We're either going to be heroes or we're going to have where we're going to be the biggest villains this entire family. And so we watched with trepidation. But Fred pulled out the victory went on to be a great attorney general. And he was the strategy was right. David had the guts to take that despite the family's objections. And I think Fred obviously was a very satisfied client. And I'm not bouncing around on the timeline here. But and you you mentioned it, but under the header header of political campaigns. If I have it right, you had a role in the debate process within Senator Obama in 2004 playing the role of his opponent that year conservative bomb thrower Alan Keyes. Do I have that right? Can you tell that? Yeah, it's funny because I was I was selected as the debate partner because it because the guy that won the Republican nomination was this young charismatic guy named Jack Ryan who was a conservative you know conservative white guy. So that I'm like a player conservative white guy. So I read this all record. I was prepped. I was ready to go. And then and then suddenly he had to withdraw from the race because his divorce file was unsealed. And then people learned that his ex-wife had accused him of of the forcing her to go to sex clubs with him. So the Republicans couldn't quite figure out what to do. And they sort of a combination of sort of, I don't know, desperation and parity. They went out to Maryland recruited this guy Alan Keyes who was an evangelical radio talk show host whose main claim to fame was opposing abortion and gay rights. And so I suddenly I was I was not playing a conservative white guy. I was playing him a colorful African American, you know, homophobic. And and I enjoyed it actually. And and in the course of that, you know, he really got under Obama's skin. He would say Obama has a slaveholder mentality when he's talking about abortion and he's condescending to black churchgoers who don't share his tolerance of gay relationships. And so I'm in these debates, even though they were just practice debates, I oftentimes really got under Obama's skin. And he would react with anger and frustration because he really he took his religious faith seriously and trying to reconcile his support for abortion rights and other things. And keys, even though he was crushing keys and did crush keys, keys did manage to at least get under his skin and annoy him. And speaking of Obama, this is 2004, but I imagine he must have crossed paths with him. What a decade earlier years and years earlier, what made an impression on you when you saw whether a state senator Obama, maybe pre-state senator Obama in his early days, starting to make arounds in Chicago politics? Yeah, he was, I mean, obviously, his innate intelligence immediately struck you, but also the fact that he was just so normal, just a normal downed earth guy in every conceivable way. And his judgment was really exceptional. And I always used to say, after years of working in the business, I would I would always tell David and others, I said, you know, most of the people we work with are either crooks or crazies. I mean, you that they, they're sort of, you know, I don't mean we work with the people in politics and generally, they're crooks or crazies. They were either normal people who were there to kind of make some money or they were kind of whack-a-doodle ideologues or people who were so narcissistic, they had to have politics in their life in order to sustain themselves and their sense of themselves. So when you ran into somebody who was both normal and super intelligent and capable and a good politician and that you sit up and go, wow, let's, let's, we all want to be part of this. And while we're talking about this early era going back to your days in the 84 Paul Simon campaign getting your foot in the door politically, I believe I have the timeline right, right? What about the Rahm Emanuel you first encountered in the mid 80s? Yeah, he was, he was a guy who was extremely aggressive, hyperactive. He would, he was super ambitious, as you can imagine. And he had hooked up as I had, independently, with this guy named David Robinson, who was running a long shot campaign against congressman, a veteran congressman named Paul Finley, who, who oddly was the principal champion in the United States Congress for the Palestine Liberation Organization at the height of its enmity with Israel. When Yassar Arifat, for those of you who remember Yassar Arifat was the, was in charge and and there we had, you know, he would dine with Yassar Arifat. And I think he felt like I'm from deep southern, you know, I'm from deep central Illinois and rural, there's not a Jewish person down here, but what he didn't take into account was something like Rob coming along saying, you know, we can raise a whole bunch of money nationally from supporters of Israel in the Jewish community and, and he did and turned that into a, that's very sleepy rural race, which Finley was used to custom to winning by 50 point margins, you know, against any Democrat and, and turned it into a relatively close race. And so that was the first time I'd met, met Rahm. And it was funny because he, he just, you know, his name is Rahm, Israel Emanuel, and here he is in rural down state. So in order to kind of, you know, get along and not raise eyebrows, he went by the alias Ron Madison during, during that time. And your past, you know, certainly continued across with all these, all these folks for, for years and years, you mentioned how you move from the operative world to the world of working in city politics. You had a lot of jobs in and around city government, multiple stances, mayoral chief of staff on the county board, running the Chicago Transit Authority, running the Chicago Board of Education, running the Chicago Park District, among others, of all you did, what were you most excited every morning, which job were you most excited to get to every morning? Well, I think the, the Park District job was unique and that it was a vast system and it was so dysfunctional and there were just so many opportunities to do great things for kids and families every day. You just, there just so much you could do. And that was, that was, and it was early in my career. So it was a wonderful opportunity. The mayor gave me to prove my managerial chops and to, and, and also my, you know, there was obviously a political acumen was important in a job like that as well. And we turned around that system with help of some wonderful people that I was able to recruit and it, and it became a, a business school case study, University of Virginia wrote because the nature of how we restored this, this, this gym that had fallen into disrepair under the old patronage system that had dominated before daily got there. So that was fun. From a, from a business, from a standpoint of just sort of managerial pride, I think, taking over a, a, a, a distress, Chicago Transit Authority and turning that around was something that meant a lot to me and especially because it's so critical to the, and so critical as a lifeblood of the city in both its economy and, and, and how people move around to exercise a quality of life. So I'd say those two, for sure. And not many people turned down a pretty close to a sure thing, seat, and Congress. But can you tell that story of, seemed like you kicked the tires a little bit perhaps, but then decided the federal path wasn't right for you, the aforementioned around manual playing a role in that story as well. But why didn't you run for Congress and what made you then eventually throw your hat in the ring for, for local office, for county office, not too long after? Sure. Mayor Daley had approached me. I was in the private sector of the time after, sure, having served us as chief of staff. Rod Blagojevich, who was the congressman, Blagojevich is sort of famous or infamous for later as governor attempting to sell Barack Obama's vacant Senate seat and he went to prison for a number of years, like many Illinois governors. But at that time he was resigning his congressional seat to run for governor. So the seat was open. And Daley was at the peak of his popularity and power and intended to fill it with whoever he wanted. So his two candidates were me and Rahm Emanuel. And I had a better mayoral relationship and had lived on the northwest side with the district was for 15 years. So he gave me first, first dibs. And yeah, I did kick the tires. You know, when I grew up, this would be a dream, right? Going to Congress and all that. But by this time, I had young kids and the notion of spending four nights a week in Washington. It was not terribly learning. But more important, I'd become less in tune with the sort of orthodoxy liberalism of the Democratic Party. And as a friend of mine, Richard Dennis told me, you might as well just hand him your voting card and you walk in the door because you have to fall in line with leadership. You can't break ranks. You can't, you can't be independent. And that, and that, you know, so that was a big part of it. And then finally, Daley had spoiled me. I'd give him the opportunity to run a, you know, the Chicago Park District to be a chief of staff and to turn around a great city. When you can touch and feel the things you do every day and that are real to people and really elevate the quality of life and the neighborhood in a great city. You know, that, that pales in comparison to being one of four hundred and thirty five members of Congress. So that's, that's kind of how I made that call. And, and of course, he was the right move too, because Ram, because of his Clinton White House experience and fundraising skills, he quickly bonded to leadership. And once you're in leadership, you can do a lot of great things. He brought home the bacon for Chicago for years to come. So I think it worked out for both of us. And you ran multiple races, won some races, lost some races. We're not a political novice by any means. Very savvy who'd been around politics a lot. But once you started running for office, you're running for the county board, cook county board, you'd been around politics at a high level. But what part of it weren't you ready for when it was actually your name on the ballot? What surprised you when it was actually you putting yourself in the fraying? Yeah, I don't know that it surprised me, but clearly the loneliness of being on the ballot when everyone is against you. And I must say everyone, what I really mean is the entire establishment. That's what I did. I ran both my first race for the county board and then for the county board presidency against the entire combined forces of the Democratic machine. I managed to win the first one, but not the second. And it was it's a difficult it's a difficult to do to be an insurgent. Of course, that was part of the appeal to me and part of the motivation and part of what drove me and the people that supported me. But you know, it is daunting, you know, I think for most folks to be successful, you need some establishment support, you know, wherever that's going to come from. In my case, it came from the business community at which which funded me very well because they understood what I was trying to do. And they were the ones that were obviously suffering under the high taxes and they were also sympathetic because of the failures of the government for people that depended on the government. In this case of Cook County, it was people who needed health care and juveniles who were who were being educated while they're waiting, processing in criminal cases. There were huge scandals in both areas that gave me some fodder during during during that race for Cook County board president. And this may not be a fair question, but an elected official like a member of the Cook County board or not that this would describe Rahm Immanuel, but if you'd become sort of just a back bench member of Congress, an elected position like that versus an appointed position like mayoral chief of staff or heading up the CTA, how do you think about who's who's getting more done, who's having more of an impact, a bit more ability to help people who have more ability to move the needle? Yeah, I think heading a major agency in a great city like the transit authority of the parks or whatever is much more impactful than being just a simple member of Congress. Now, of course, if you can do what Rahm Immanuel did and become a member of leadership and then it's a different story because you can really have an enormous impact both in Chicago and nationally, which he which he did. But I think, you know, and from a political standpoint, obviously being a congressman was a big advantage when when Rahm ran for mayor then gave him a lot of support financially and otherwise. There's also people like, for example, Paul Vales, Rangel Kaga Public School successfully for years and then ran a race for mayor and he was he was a good manager and a passionate education advocate, but not a skilled politician. And so he ran a terrible campaign and he didn't have nearly as much money as the winner, Rod Blagojevic, but he came within 2% of winning. And I think that's because of the impact he had made in this very high profile agency. So I think a path to politics for someone who's interested in that can be done both through elected office and through appointed office. And you ran campaigns for other people for yourself, big city departments when you're on the Cook County Board, you run your own office. How did you tackle running a big organization or small organization? These are very different roles, very different types of jobs, but were there consistent things that you did best practices that you adopted or that you figured out by the time you had had some this under your belt? What was your approach to get your arms around a new role, a new organization since you were in this startup turnaround space in multiple different times and places? Yeah, but my advice to people was always and I would tell this to my managers when they when we're starting out or when they were taking over a department recruit recruit recruit half of good management is hiring talented people who are committed to your mission. And part of that is also inspiring them to want to do that to give up in my you know people I recruited gave up lucrative jobs in the private sector or came from other places where they they had opportunity because they believed in the mission and they believed that I could be the force to turn it around. And because I had Mayor Daley support that was that was there and that that's really key. If you can just give a sense of people if they're going to be part of something big and achieve great things and they can carry the football you know down the field you know without you know if they're making success and not be micromanaged you can get some incredible people and believe me they will make you look good every day and that's certainly what happened to me. You saw city politics as close as almost anybody could talk a little bit about your own whether it's ideological or just political evolution in that time. One point you were you know foot soldier arm and arm in the in the daily machine you were part of it not that long after it you're throwing rocks at it taking on the machine at times being using a moniker like independent Democrat and at other times just being a by God independent give a little sense of how that happened what you saw what you tribute your your evolution. Yeah I was taken by the irony was that you know I had as I mentioned earlier my earlier early fast nation of politics came from supporting anti establishment candidates and people that were running against the machine so it was ironic that at my first big job was with Richard M. Daley so the son of the king of the machine and someone who had you know eventually built his own his own version of the machine but you know he was ironically a reformer you know he had been kicked out of the machine by Jane Byrne the mayor who who saw him as a threat and so he had to reinvent himself as a liberal reformer down in Springfield as a state senator and as a state's attorney with liberal allies and taking on their organization and and cleaning up government and what you know taking on the you know all the all the vestiges of that machine so that was the irony and that's what attracted me to him and I was part of the early years when when he was incredibly successful in doing that and he continued to be very successful in doing that but you know I left the government at some point you feel like oh I need I want to do something else and you do something else and and being an elected official in the county government wasn't appealing to me but to get there I had to you know there's the old saying that you know nobody gives you power you have to you have to knock down the door and that's sort of what I had to do against the machine candidate for county board and and the mayor's you know was supported that person so it made it much more hard harder for me but but it was in that process because we're here's the mayor for a very practical reason supporting really a guy who was a the worst of the machine a guy who basically was in politics for himself to to basically pat his pensions and make money and and really didn't care about the people he was serving but he did that for very practical power politics reasons and so obviously it sort of sourd our relationship and it made me more of a of a committed to reform within the county structured daily didn't run the county so he wasn't responsible for what went on there per se but that's where I let my focus just to try to take on this this this this terrible organ at this county government that was dominated by the machine it was a patronage dumping ground and the people that suffered were the were people who couldn't get health insurance people who couldn't get their medications kids who were beaten abuse sexually assaulted at the juvenile center just a cesspool and it obviously was a very angering and motivating part of you know what I did what I did and what I did let me turn to your book the daily show and certainly we'll continue to weave in your own perspective on all of this but your book about your time around mayor Richard M. daily and more than that the impact his impact on the city and beyond for more than 20 plus years in the mayor's office what made you want to write this book I wrote the book because in the years since daily is left office Chicago has declined significantly and so much of his legacy has been undone and I would just angry and so many of my friends and other people you know share that anger and I felt like people need to be reminded of of what the city of Chicago was like in 1989 when mayor daily took office with crime and Demick public schools and terminal jobs leaving in droves homelessness graffiti you know horrible quality of life a city in deep decline that the Chicago Tribune called an economic invalid a city on the brink and that by the time he left office in 2010 foreign policy magazine ranked Chicago sixth as the most important global cities in the world it was an incredible urban renaissance and yet here we are today with violent crime and Demick again with businesses and people leaving again with the public schools and terminal again and yeah seem to me that the lessons of his mayoralty need to be told so people are reminded of what type of governance and leadership makes great cities because cities have historically been the engines of human progress people want people who are ambitious and talented want to be in cities because they get to collaborate intimately with peers who then you know can can use leverage in the scale of cities to have breakthroughs in art arts and architecture and law and finance and medicine and technology so all of us should care about the health and vitality of cities and what type of leadership and what type of policies make healthy cities that that was really what motivated me to write the book on the book about Richard M. Daily but let me start probably not as surprised by asking about Richard J. Daily the also long-term mayor the father of Richard M. Daily famously not a great orator not personally charismatic yet really has an iron grip on Chicago for a couple decades and not just any 20 years but from the mid 50s to the mid 70s until he dies in office everything else in America changes dramatically everything else in politics changes dramatically in that period from the mid 50s to the mid 70s except for mayor Richard J. Daily of Chicago how did he dominate the city's political scene so thoroughly well he was the big city boss by the time he you know died in 1976 he had ruled with iron-handed bravado for two decades having built this massive pattern machine in which nobody could get a city job you know and there were tens and tens and tens of thousands of city jobs and related agencies without working in the precincts for the machine you basically it was a it was an entry ticket until years later court struck down you know the use of patronage as a violation of the Constitution's First Amendment but so that's he used that leverage in power to be daily the builder to you know turn Chicago from the sleepy provincial midwestern town into an international city you know that's that's how he used that that power now of course there were abuses of that power and and and of course when the 1960s rolled around Martin Luther King came to town and and was noting that Chicago's most segregated city in America and calling for an open housing ordinance and Daily responded vitriolically against King and then two years later at the convention his police club the heads of anti-vietnam protesters and he he became a symbol of sort of racial repression and segregation and intolerance as opposed to his original images daily the builder so that was sort of the backdrop of the Richard J daily years which were followed by sort of twelve years of chaos after his death before his son coming into a different environment entirely with it with it kind of a different world view was elected yeah let me ask about that one thing that may surprise some people who don't go back to the 70s and 80s haven't looked deep into it is it Richard M daily the son did not have a glide path into the mayor's office he wants some close races early lost some close races early before becoming mayor what can you say about that time a decade or so after his father died Richard M daily in the wilderness for a while and how he overcame that to take the mayor's office what 10 12 years after the death of his father yeah he was this is great irony there the mayor Richard J daily played the inside game and played it brilliantly started out as a county clerk a bureaucrat estate legislator states state senator county clerk and then became chairman of the democratic party which he leveraged to remove Martin Cannelli the the mayor when the machine when he fell out of favor with the machine so he played the the inside game brilliantly and ironically his son who at one point was a prince in waiting in Springfield is in his old his father's old legislative seat assumed to be the heir apparent this this sort of immature and petulant prince and waiting his world got knocked upside down when his father died and then his and then when daily's hand pick predecessor Michael Blanic was defeated by Jane burn who viewed Richard M as a threat suddenly he was cast into the wilderness burned began firing all of his allies and and all of his patronage workers and began isolating all of his previous allies and friends from him so that he was literally alone and it was at the same time he was struggling with the death of his three-year-old son who had was born was fine a bifida and he would fly home from Springfield every night to sit by his bedside and I think the combination of that experience his son's death deep into empathy and matured him in a way that was truly remarkable but politically he also had to transform himself and to win and to get back into power to as I say in the book to lead in assault on the castle that his father built he had to build alliances with liberals he passed landmark liberal legislation springfield on nursing home reform mental health care reform repealing the sales tax on food and medicine he he signed the patronage decree a state's attorney saying no political hiring in the in the state's attorney's office he became you know remarkably sort of the antithesis antithesis of what his father had represented and it repositioned him in a way to take on the the very machine his father built to run for state's attorney and that was that was a you know a difficult race that he did manage mid did manage to win and you touched on it one difference is that Richard J. Daley the father was a master at the inside game Richard M. Daley had to become good at the outside game what does that mean what is an example what are you what are you thinking of when you're talking about that difference sure well inside game I mean you've got the whole establishment supporting you you've got precinct where in Chicago it means armies of thousands of precinct workers going door to door for you carrying your message asking their neighbors and their friends to support you shaking down all the businesses and contractors to do business with the city for money to support you that's that's the insight and doing what and doing the bidding of those who are backing you the outside game obviously is when you're an insurgent you don't have the backing of those those precinct captains you have less money you've got you you are taking on the the entire our structure of the of the political apparatus and so in in Daley's case back in in the day he when he announced to run for state's attorney none of the precinct ward offices and bosses could be for him because Jane Byrne had his had her thumb on them he was running against that very machine his father had built that Jane Byrne had now solidified under her control and he ran a campaign that elevated sort of the message above that taking on you know calling out the you know the corruption in the machine calling out the ties to the mob you know the various things that the average citizen could understand is is nefarious and he overcame some of those structural disadvantages by doing so I mean clearly his name helped but he had there he really really did have to run a sophisticated message oriented campaign in order to beat that powerful machine mentioned it just now and it's in the book as well this detail that the mob controlled was it first word yeah right into the 80s maybe into the 90s give me some more on that we're not talking about the era of al Capone and alien s uh what does it look like for the mob to control a part of Chicago into the 80s and 90s and what does it mean for a mayor what does it mean for a mayoral chief of staff trying to run the city when portions of it are again your term mob controlled yeah I mean the mob for many decades the mob which is sort of a part of Chicago is sort of you know in the background but there they controlled Chinatown they controlled the river wards where they had their illegal gambling dens and other vice brackets um and Jane burn was in bed with the with the guy who controlled most of that John de Arca who was the ward committeeman in the first ward was a big supporter of Jane Burns and it was just part of a sort of part and parcel and so it was it you could sometimes had to understand if that was always sort of there in the background there was a councilman named Fred Rody who was on the city council to represent the mob's interest on the city council and there was never a direct sort of like deal making your interaction with the mob but but their presence was always sort of felt and and manifested itself in in different ways and you have a riff in your book the daily show about becoming aware of the importance of abandoned cars what does that mean yeah I was kind of surprising to think that the number one civic concern in 1989 was abandoned automobiles and tens of thousands of abandoned automobiles scattered throughout the city of Chicago not surprisingly in some of the more distressed and impoverished neighborhoods but it was a symbol of the disorder and decay at that time it included weed strewn lots graffiti homelessness um some of the things that returned today but abandoned automobiles was the number one issue and so it was the first thing the daily asked me to clean up which we did through a private partnership but it was sort of the first step towards him sending a signal to these these distressed communities that you know people we do care and we are going to reestablish a sense of order and cleanliness we're going to tow the cars away we're going to kill the rats we're going to fence the lots we're going to we're going to move homeless off the streets to shelters we're going to eradicate graffiti he did all those things and was and created a sense of of order and cleanliness that then allowed for a sense that this area is safe that the quality of life is improving that we can invest here we can live here it was a critical sort of first step in those first two years that I call housekeeping issues that allowed him to lay the foundation for the more complex things that came later like turning around the troubled public school system tearing down the cancer of the ubiquitous public housing notorious high rises that ironically his father had built to contain the black community for expanding oh hair airport building millennium park the things that were we think of today is great parts of his legacy and in your estimation is there a single accomplishment of the biggest accomplishment that you keep coming back to from the Richard M daily era that you put at the top of the list probably the most amazing one really if you think about it both politically and managerial was the fact that he was able to knock down these horrific notorious public housing high rises that had trapped generations of primarily African-American families or families into dependency and not just on the welfare state but on gangs that controlled the high rises and controlled their lives in the violence and the drug dealing and the and the sexual assaults and just the horrific nature of that he was it was it was a credible thing he had to overcome to finance that and to overcome federal objections and to get the regulatory approvals and I tell talk about that a lot in the book how that all happened and how Andrew Cuomo who at the time was the head secretary you know tried to block it it didn't want daily to be able to do that and almost succeeded in blocking it so that was a miracle to me and I would probably say that certainly high up there obviously Millennium Park was a miracle to and it's a fascinating story which I talk about in the book how it came to be and just an amazing story and an example of how one person can make a difference and how how the land was acquired but also how daily in the community built this remarkable asset and of course the I think if you asked daily he would say his turn around of the troubled Chicago public school system which was considered the worst in the nation by Ronald Reagan's education secretary famously called them the worst in the nation and he turned them around to a place where the majority of students were meeting national standards that Chicago was a leader middle-class families returned to the city that had abandoned them to send their kids to public schools he would certainly put that I think number one on this list no shortage of accomplishments but what do you think was maybe the biggest missed opportunity many problems are intractable of course but is there something that was in his grasp that just didn't get done because of lack of will or for whatever reason yeah I I uh I mentioned one in the book uh you know may not seem big but but the Diaz for school reformers he Chicago had the shortest shortest school year and the shortest school day of any system in the country and most education reformers understood that instructional time was was critical and he did not just 10 minutes it's like five and a half hours or something yeah five and a half hours versus the typical seven seven and a half and most reformers understood that that instructional time is a key part of of a school reform and whether children are learning and advancing the daily was so focused on labor piece so absolutely I don't know if he was fearful of strikes because because Chicago had suffered through nine teacher strikes in 18 years before he became mayor or whether he just bought that in this was important to his legacy not to have any disruption but as a result of that he never addressed that issue and he also he also in the last seven years of his administration he he increased teacher salaries 50 percent which all of us contributed to some of the problems we have today with pensions and the CPS near bankruptcy and so forth so there were some warts on that education success story because of I think he just didn't quite have the political will to do some of the things he could have done and should have done I would that would circle that one is certainly as one somebody could be very involved in politics and a lot of the many many parts of the country many many important races and not understand never have to grapple with the complexities that involve airport politics but you reference one story about mayor daily I think you some language like that he utilized the most brilliant ploy you saw him use as mayor in reference to the always controversial issue of whether or not to build the new airport some part of the Chicago land area can you give a little background on that brilliant ploy you saw him exercise yeah this is a great for those who love politics who love you know the law constant the constitution all that stuff this is a wonderful story because it underscores both both power politics but also how you know the U.S. Constitution works and some other things but in the in 1994 we all remember Newt Newt Gingrich in his contract with America the republicans swept to power and in Illinois they swept all three branches of government the house centered in the governor's mansion under unfettered GOP rule and that they were dominated by suburban a downstate interest so that immediately they made a power play a Machiavillian power play the republicans to take over O'Hare and midway airports from daily in the city and put them under a suburban authority they wanted the jobs they wanted the contracts and there was also some suburban protests about how much noise there was an O'Hare because of all the growth so they also wanted a third airport because of that growth and they wanted in the suburbs and they thought if we control the airports we'll also be able to fund that with revenue from from the revenue so it was a huge power play and it was a huge threat to Chicago because there is no greater economic propellant for the city and the region than O'Hare Airport midway airport they drive so much job growth and creation so the stakes were huge and it looked like it was futile because you know the municipalities are creatures of the state the Springfield this passes out authority to the cities based on their discretion so it seemed hopeless but there was this young lawyer in the city's corporation council's office former professional prosecutor named Larry Rosenthal who came up with this idea that if the city of Chicago could find a partner in another state and create a compact regional airport authority daily his own regional airport authority he would reempt the state of Illinois because under the U.S. Constitution a two state act trumps any entity created by a single state legislature and so the candidate was obvious it was right across the road 45 minutes down the road Gary Indiana which had this little tiny airport in the outskirts of town so his idea was let's create the Gary Chicago International Airport Authority it'll be a two state compact and they'll trump them and it was brilliant daily loved it but it had to be kept super secret because if if it word got out you know the Republicans would immediately move the takeover build a passing so there was this whole cloaking dagger secret process it went on for weeks where they put this all together with Gary and it all came down at the end to this the city councils in both cities had to pass it but you have this problem you know both you have this open meetings access you have to put out in the gen to 48 hours before the meeting and tell people what you're going to be voting on so a little bit of a problem there so they say well let's have Gary go first because the press isn't going to pay much attention to Gary we'll have them go on a Thursday night we'll go on a Saturday morning and we'll have it on Easter weekend with the overlapping Passover celebration so we'll put out the agenda and we'll say yeah it's an airport agreement but we'll have the lawyers make it as vague as possible so they did that but throw reporters off the scent they said no we they'll pick it up so we got to have something to throw them off the scent so they put on the agenda a 36% pay raise for the alderman and the mayor that work because the reporter said well of course the odd timing of the city council meeting makes sense they're holding it on Easter and Passover so that the news of their pocket lining will be buried on the Saturday night news and everybody be celebrating the holidays so this makes perfect sense and no one noticed the the airport agreements and Thursday night the Gary passes it and the next day word breaks and everybody realizes this happening but it's too late for the Republicans to respond in fact the governor's over in Israel at the time and he's in the holy land without a prayer to stop it and the thing goes through and the the city council adopts it and they daily standing there at the podium with a sardonic smile enjoying the hot shots all the alderman are taking it the Republicans and this wonderful glorious moment this coup in which he in a matter of weeks turned the tables on the on the capture Republicans who would you know so arrogantly and blightly said we're going to take over the crown jewels of the city and there's nothing you can do about it yeah no a great story and do I have it right that that maybe never happens if you don't have a cameo appearance from Evan by Indiana governor Evan by yeah Evan by the republican state legislature in india and the legislature in indiana was republican so there was a little bit of a fear that if we do this well maybe there were you know partisanship will overcome local economic development and they'll reverse the deal and concert with the Illinois Republicans but Evan by fortunately was a Democrat so that that that that that that obviated that concern and he was part of the conspiracy he provided the lawyers for Gary to make sure that they had the perfectly written agreement that would pass muster and also get through the scrutiny of the open meetings act so yeah by was was part of the part of the action and he was there on the day they signed the agreement with the mayor daily in the in the mayor of uh Gary uh mr. Barnes and you mentioned your own forays in the politics your first race taking on a machine backed candidate but somebody who not necessarily a favorite of the machine but somebody they felt obligated to try to protect any if I if I read it correctly even when you got into that race it wasn't even necessarily sure that the machine was going to support him and turn out they did and you overcame that but the next race you run for what president of the county board you know he's really one one for the book your book is um the word surprise admission may be just for that story you i'm a campaign guy great campaign story a race where uh you get in you challenge in a democratic primary the sitting board president ramen manual endorses you richer daily and what endorses your opponent Barack Obama says he's going to vote for you bill Clinton endorses your opponent so as as divisive as driven a race as as possible uh and you mentioned that that was uh an example of you budding heads with the daily machine and mayor daily as well did you and mayor daily that race you lose very narrowly under some very strange circumstances people can can read uh the book to find the details and you did you and mayor mayor daily bury the hatchet at some point does it ever back like it was i never felt like we had to bury the hatchet i mean i understood why he did what he needed to do and why he did it john stroger who was the incumbent president of the board was was the leading african-american figure in the state and a long time daily ally so you know both racial politics and old-fashioned power politics and loyalty sort of dictated that he's stand by his long time ally so i i didn't begrudge him that even though the county was horribly managed and there were tragic consequences to it it's it's difficult to say he should basically break with all of that to support a former aide so i i never felt animosity to him as a result of that i think it's sad for the for the citizens who had to continue to suffer under conditions of that particular management at the county but i certainly understand where mayor daily was coming from actually the first ratio ran you tell the story this running for county commission your opponent an old school blue collar culturally conservative ethnic paul uh who used to representing those areas hadn't quite realized that his district had started to gentrify you take advantage of that but one of his tactics actually tried to imply to voters that you force clay pool were a black candidate uh and that's his theory of the case of how he was gonna snuff out your your primary challenge can you tell a little bit of that story sure and this and this is the product of down ballot races i mean this was a down ballot race in fact it was the very last race on the ballot at the county commissioner and those races people are that you know they don't get a lot of attention and when someone who's not known is running against a well known incumbent i think this i think the idea so well no one knows who this guy is we can make him whatever we think he's going to be and my name forest clay pool always for some reason sounds african-american i've had so many people over the years i've been some place and i've been place one place once this african-american guy met me and he said you're a clay pool i always thought you were a brother so you know so i think you know so they played into that um and the fact that i wasn't known and so they they basically said i was from down south which means south side of Chicago but technically true since i was in southern Illinois and then that vendor darkened my picture to make me look african-american in the mail thing so they ran with that for a while uh it and of course it backfired in when i began raising money and and putting out picture-filled mail mailers and planning yard signs all over the district friend of mine had wisely counseled me he'd been in Las Vegas and done some campaigns and he's he's offered the first time he saw people with their pictures on their yard signs we used to seeing yard signs that just say you know parrhist or trump or whatever and so i put my picture on my yard sign which turned out to be efficient because it undercut almost immediately they're sort of the racist narrative of me being a black interloper from the south side trying to win and and conservative Polish uh uh when north west side Chicago it's a great a great story the and maybe this would have been a more appropriate question when we were talking through some of the details of the the machine but how far do you have to go back in your mind not to pair it republican talking points but how far do you have to go back to find elections run by the city of Chicago that were something less than what we would consider free and fair yeah great question one of the things i note in the book is that when Harold Washington and his nemesis edvardolia could run as his opponent for three years running during what we called council wars in Chicago in which a group of white alderman had seized power controlling the city council to try to obstruct the city's first black mayor herald washington the final fight for control the city council came down to one race and uh because so much was at stake and everyone give me a year here what what sure sure we're talking um we're talking about 1986 herald washington had been mayor three years he'd been thwarted by this this racial coalition the council led by edvardoliac a court ordered new aldermanic elections and latino dominated awards because because they were not sufficiently represented based on census changes and demographic shifts so there was this opportunity and there was multiple multiple races but it came down to one one and a run off that would control city government control the city council at that point that the chances of shenanigans were so certain from the old machine and perhaps even from the emerging new one under washington that that u_s_ attorney and ton voluca and states attorney daily sent in hundreds and hundreds of prosecutors to sit in polling stations and watch for fraud because the chances were so certain of shenanigans so i i think that those the presence of those prosecutors probably seems to have blocked fraud there particularly they remember that was just one word out of fifty but so they're certainly the awareness of that kind of fraud taking place and prior to that of course Chicago is famous for voting graveyards on behalf of the machine candidates and the like and going back but they won by so much in those years and nobody really bothered to go back through and try to prove otherwise some of this goes into how you describe your your motivation for writing the book here rama manual was mayor for multiple terms but left office relatively unpopular at a time when my sense is he would have preferred to run for another term yeah lori lightfoot comes out of nowhere becomes unpopular pretty quickly loses doesn't even make the runoff we see that the new mayor current mayor brand in johnson comes out of nowhere seems to get unpopular pretty darn quickly chicago which not that long ago the the moniker you use chicago was a city that works what has changed why isn't chicago now a city that works i think for a couple reasons one is after the great recession we saw gradual lurch to the left maybe not so gradual but a lurch to the left in city politics and which ideological left wing propaganda prevails and radicalized union environment such as chicago teachers union which elected our current mayor which which is a very left wing union that pushes not just bargaining for wages and benefits but but all kinds of social policies that they try to tie into bargaining and they've kind of created their own machine of precinct workers and money to try to support others who support their their left wing agenda and that's clearly hurt the city the other piece is that for whatever reason the voters in their wisdom in the last two elections have chose chose rank amateurs you know people who had no political no serious political experience and no managerial experience of any kind and you're talking about taking over you know a multi billion dollar vast complex metropolis with all of its complexities and putting it in the hands of people with almost no experience it's it's no different than if you turned over you know major giant international corporation to someone with zero managerial or or business experience and so we see the results of that as well and it allows for a certain amount of chaos that that hurts the city I think one example I talked about in the book is new mayor Lori Lightfoot a rookie politician not understanding how power works not understanding that she has to build alliances and and have carrots and sticks to keep people in line and have the city representative supporter went down to Supremefield the unions you know took advantage of her by pushing through two bills one to take take take the schools away from the mayor put them under elected school board despite 25 years of remarkable progress under two mayors and then another tip to large four billion new pension liabilities on Chicago taxpayers even though those funds were insolvent normally you would think how outrageous and yet not a single Chicago representative stood with the mayor they all abandoned in her because the unions that had the money the unions had the troops the unions that were they're pushing it could give them something and also they feared them they didn't fear the mayor and she and she certainly had nothing to offer them so that that was a good example of where sort of naive-tay and inexperience really hurt the city in two fundamental ways and just one of many let me end on a couple of questions just minding some Chicago political lore from you you have a favorite story maybe it's your own interaction maybe it's just Chicago lore but a favorite story about the legendary Chicago columnist Michael Rocco well you know my favorite is because it's personal was and although we we we were in a that was in a battle with Chicago Bears and Michael McCasky the president of Chicago Bears they were fighting for a new stadium they had to probably the smallest stadium in the league and they wanted the city of Chicago to build them a brand new and a taxpayer expense and mayor daily was reluctant to do that so they were trying to find ways to pressure him so I was running the parks and I was bringing in concerts rolling stones grateful dead football games college football games and it was tearing up the field and we'd have to fix the field and put in new sod or replace the sod before bears games and they said oh we can take advantage of this as a PR opportunity so they started trotting out to the sports reporters how horrible this was and how players were getting injured because the turf was so terrible and we became the greedy bureaucrats risking the safety of the beloved bear warriors in the city and so at one point this got so bad that that Michael you know that it became this huge civic issue and at the time Mike Rocco was the biggest news source in town by far the most credible and had a wonderful sense of humor and he came to our rescue with this wonderful column in which he he in mock sympathy he worried about the working conditions of the millionaire members of the monsters of the midway because the turf was in some places a little bit too moist and lack sufficient grass in other places the players were not as nimble and quick and got blocked on their uniforms Paul the sports commentators and came out and said oh this is horrible if this continues a player could get hurt and Rocco said which is really shocking because there's never we were not aware of any football players ever been injured before so it was his wonderful humorous mock sympathy and of course it just undercut the whole narrative and kind of put it to bed and that's the power that Mike Rocco had at that time which is hard to fathom now in this world today that a single journalist and columnist could be so respected and so dominant that he could have that kind of authority particularly with his humor which of course was the greatest weapon of all let me end with this a recommendation from you in terms of things that would have a historical significance political significance when people have a couple days from downtime a trip to Chicago what should be on the must see list for people interested in the history and the politics of Chicago history politics is more complicated there's they can you know it depends on how big a political junky they are they can certainly go to to the site where this only unfortunately just a plaque today where the wig wand was that nominated Abraham Lincoln for president and then the like they can those sorts of things but I think from just from a tourist standpoint but also to understand an emblem of an extraordinary urban leadership and what great urban leadership can do is millennium park which you know was a 25 acre whole dirt pit in the middle of downtown when when daily that turned it into this remarkable mecca of of unique historical modernist architecture and art and you know it was a huge tourist draw that you know it was the number one tourist draw for years and years after it was created still is a huge one as spurred all kinds of development but it is it is an example of what great cities can be should be how they contribute to the arts and economic development and architecture that's not happened by accident happened because of his political skills his urban planning vision it is a wonderful example of people to see why it matters that we have great leaders and why good policies that make healthy cities are something we support rather than some of the things that we see today that are that are governing our cities and I'd recommend anyone interested in politics at any level to get ahold the forest book the daily show of masterclass in how Chicago works how big city politics works and nobody has a resume has a story has insights like forest clay pool thanks for your time today thanks I appreciate you have me thanks for listening to the pro politics podcast please subscribe you can access each episode first thing every Tuesday morning and if you're so inclined leave a rating and a shorter view on your podcast app to help more people find this podcast and follow us on twitter and facebook for updates on upcoming guests. Thanks for listening.