Prologue: January 6, 2011
Rich Daley, the mayor of Chicago, stood in front of a podium at Saint Mark International Christian Church in the Austin neighborhood on the far west side of Chicago. African-American community leaders and educators surrounded the mayor as he started a news conference. In a few months, Daley would turn sixty-nine years old and time had dusted his once dark hair with a white layer of color. The mayor announced that the city and its partners would expand its Safe Haven activities program so that more than a thousand grade school students could participate during after school hours. “We all want our young people to stay safe from violence, stay away from a life of violence and achieve their full potential in life. And among the most important things we can do to help are to give them the best education possible and give them plenty of positive activities after school,” said Daley.
The serious tone of the news conference took a sudden, more lighthearted turn, however, when the mayor fielded a question about his brother Bill Daley. He smiled. His eyes brightened. His body relaxed. The president of the United States had held a press conference and named his brother as White House chief of staff. Rich Daley was clearly proud of his younger brother. The mayor fielded questions from news reporters, one of whom inquired whether his sibling’s appointment confirmed that the “Chicago [political] mafia” controlled Washington, DC, and national politics. Daley rejected the suggestion, noting that most presidents had brought advisers to Washington that they trusted and respected. The mayor and the black leaders on the stage laughed lightheartedly as Daley used his familiar style of public speaking— clumsy but heartfelt—to compare the current president’s decision to those of Kennedy, Nixon, Reagan, Bush, and Clinton.
When Daley spoke of US presidents and their exercise of the powers of office, he spoke of a subject that he knew well. The Daley family had exerted political power on the local and national stage for nearly sixty years. His father, Dick Daley was one of the most dominant American politicians of the twentieth century—a kingmaker, a president picker. A political talent so influential that Rich Daley and his brothers grew up visiting presidents, sleeping at the White House, and having private, intimate conversations with the highest elected officials in the United States of America.
Yet for all his talents, Daley’s father had been a flawed leader. Dick Daley started his political career in 1919—the same year as Chicago’s infamous race riots—and as he aged and increased in power he grew more reactionary, especially on the issue of race.
Rich Daley also knew how to exercise power. He served as mayor for nearly twenty-two years, and his legacy included transforming Chicago from an ethnic Midwestern urban center to one of the world’s truly global cities. As mayor, he also tried to repair the mistakes of his father: to improve race relations, fix the public schools, and resuscitate public housing. Rich Daley plugged away for more than two decades, trying to finish the unfinished business of the Daley family.
There were certain paradoxes, however, in the two winter press conferences that day that discussed the appointment of a Daley to high political office—one in Washington, DC, and one in Chicago. In the nation’s capital, President Obama announced the selection of a fellow Chicagoan as his chief of staff and admiringly described Bill Daley’s deep knowledge of politics as a “genetic trait.” Obama—the nation’s first black president—had brought in a pragmatic Daley to try to shape up his administration and win greater approval from the American public. Moreover, four of the other most senior advisers to the liberal black president—Rahm Emanuel, David Axelrod, Valerie Jarrett, and Arne Duncan—had grown up politically in Chicago as advisers to Bill Daley’s brother, the no-nonsense mayor. On the west side of Chicago, Rich Daley stood surrounded by black leaders and educators as he once again tried to improve public education and reduce crime. Daley appeared completely at ease in the company of these African-Americans, a group with whom he had spent much of the last two decades.
Three months prior, the mayor had announced that he would not run for reelection and would retire at the end of his sixth term. This decision made Daley the first Chicago mayor in over eighty-five years to voluntarily retire from office. He would not die in office like his father had done.
Yet the Daley clan would continue to exercise political power even as Rich Daley prepared to retire. Bill Daley and the president’s other senior advisers from Chicago would continue to perform on the world’s stage. In Chicago, Rahm Emanuel—a person who the normally closed-mouth mayor had once described as the most focused and effective person he had ever worked with in public life—prepared to replace Daley and ascend to the city’s mayoralty. Chicagoans abhorred a political vacuum, and it was likely that the smart and pugnacious Emanuel would govern with a strong hand. A new era called for a new leader. The Daleys and their protégées, however, would continue to exercise power at the highest levels of American government, in ways both visible and unseen by the public. A nearly century-old political dynasty would continue to influence the lives of many.
Rich Daley had grown up as the firstborn son of Dick Daley, the Irish-Catholic political boss who fine-tuned the Chicago political machine and ruled over a city of three million people. Dick Daley was a political genius but was power hungry and a flawed leader. His son Rich inherited his great love of Chicago and a belief in the Democratic machine. But growing up in his father’s shadow, the younger Daley seemed insecure and lacking of his father’s talent or charisma.
Early in his professional career, the younger Daley was part of the Chicago Democratic machine and completely dependent on his father for his positions and accomplishments. He was also emotionally immature, intellectually unexceptional, and a bit of a bully. After his father’s death, however, Rich Daley began a dramatic personal evolution. He matured emotionally and intellectually, becoming more open to new people and new ideas. He also became a public policy aficionado and gradually gave up his belief that the Democratic political machine was essential to advancing his own career goals.
One key event in Rich Daley’s life greatly contributed to his disillusionment with the machine: the Cook County state’s attorney race of 1980. During this election, Daley fought successfully for his political survival by winning a classic political battle—against a lifelong rival, the machine politician Ed Burke—that essentially became a civil war within Chicago’s Democratic Party. After he won, Daley continued to mature in his new office, developing fresh credibility as a public servant and effective executive.
But Rich Daley then made a big mistake: he decided to run for mayor in the Chicago election of 1983. Impatience—a lifelong trait of his—provides a partial explanation for his choice. But the key to Daley’s bad decision was something deeper: the hubris of a still emotionally immature man who grew up as the privileged son of Chicago’s most powerful politician. Daley lost his campaign for mayor in 1983, and the City of Chicago anointed Harold Washington its first black mayor. Six years in the political wilderness followed for Daley.
Yet a crucial aspect of Rich Daley’s personality and long-term success was his ability to persist. Daley had started his early life with people having low expectations for him—he was not a great student, talented athlete, or charismatic leader of his classmates. Because of this, Daley became a “plugger,” developing the fortitude to persist even after suffering repeated disappointments. In 1989, Rich Daley took back Chicago’s mayoral seat for the Daley family.
As mayor, Daley retained his great political skills but also took big risks and evolved into a highly effective chief executive of the city. His legacy would not only include finishing the unfi nished business of the Daley family—improving race relations, public schools, and public housing—but also the transformation of Chicago into a global city. During his years in office, Daley physically resurrected the downtown area and Chicago’s lakefront. Out went the gritty, worn-down postindustrial Midwestern capital. In came a beautiful, sophisticated city: Millennium Park, refurbished neighborhoods, a lakefront Museum Campus, wrought-iron fences and landscaped gardens, attractive downtown colleges, and a renewed Navy Pier. Daley’s revitalized, beautified, high quality-of-life Chicago became the model for many cities in America and throughout much of the world.
But Daley was not a perfect mayor. Rather, the arc of his career was consistent with what a study of human nature would predict: a steep learning curve; a decade of disciplined work leading to mastery; the accumulation of power; and, finally, hubris and mistakes. Daley’s legacy would unfortunately also include a pension crisis, the midnight destruction of Meigs Field, persistent corruption within city government, high levels of crime, and financial mismanagement during his last years in office.
Despite his imperfections, over a thirty-year period Daley evolved tremendously as a person and as a professional. This evolution, however, did not prevent him from governing Chicago as the ultimate pragmatist, a leader who used “brass knuckle” tactics to improve the city he loved or to protect his own power. At times this meant falling back on tried-and-true Chicago politicking: rewarding loyalty with favors, using city government resources to overwhelm opponents, and tolerating political corruption. Sometimes his Machiavellian “the end justifies the means” operating style left hurt feelings, especially among colleagues and friends who had spent years serving him and the people of Chicago. “It’s not his nature. He’s just a mean, cold-hearted little prick,” said one of Daley’s long-time political allies in describing the mayor’s modus operandi. Yet Daley’s family, his friends, and many, many long-time associates believed that he was a man of humor and perspective, a somewhat sensitive man, a leader who had loved his city in a way that was truly exceptional.
Even though the mature Daley had largely resolved the conflicts between his Bridgeport roots—conservative, parochial, machine-dominated—and his own evolving belief system, the conflicts were never completed resolved. Daley—the man of history—remains a complex man and a man of occasional contradictions. Sensitive and tough, impatient yet persistent, a street-smart, cutthroat policy wonk who completely self-identifies with Chicago, the city by the lake. Despite his imperfections, Rich Daley surpassed his father’s accomplishments in office and became one of the most influential mayors in the last hundred years of Chicago, now one of the world’s truly global cities.