Daley vs. Daley

For much of the past half century, a mayor named Daley has towered over Chicago. We compare the reigns of father and son, assessing their triumphs and failures, their impact on the city—and what their enduring dominance at the polls says about us

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Like father? Richard M. Daley shares more than a hint of his dad’s features. Richard J. Daley (left) in 1964



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On a blustery morning early in March, Mayor Richard M. Daley was running late for a constituent’s birthday party. A very important constituent, practically family: the City of Chicago. One hundred seventy-one years old this year, Chicago was being feted at the History Museum in Lincoln Park, and the second-floor banquet hall was decked out for the occasion—there were hot dogs, balloons, and a cake decorated with the stars and stripes of the city flag. By the time the mayor walked in, 20 minutes behind schedule, the Marist High School Jazz Band was playing an impromptu recital of the school fight song to fill the dead air for the few hundred guests.

Waiting to be introduced, the mayor fixed his windswept comb-over and straightened his blue pinstripes. When it came his turn to speak, he read his prepared remarks in a robotic monotone. Rattling on about the founding father Jean Baptiste Pointe du Sable, the city charter, and world’s fairs past, the mayor seemed bored—like a man who has spent six long terms schlepping to untold thousands of such ceremonial events.

About halfway through, the mayor paused. Perhaps he sensed his lackluster performance, because he looked up at the audience and started speaking off the cuff. He riffed about the visit he’d made earlier that morning to an eighth-grade class in the tough Back of the Yards neighborhood on the city’s South Side—at a school named for his late father, Mayor Richard J. Daley. With passion in his voice, he mused about how many of these young, mainly Hispanic and black students were succeeding in the classroom despite the daily scourge of gangs, guns, and drugs they faced. Then, in one of his characteristic non sequiturs, he segued into a story about the meeting he’d had the day before with the former British prime minister Tony Blair and how the city must meet the vast and varied challenges of the global economy. His face flushed as he stressed the need for safer neighborhoods, better schools, new libraries, and vibrant cultural attractions. His boyish enthusiasm spoke better than words of his love for the city and for a job he gives no indication of ever leaving.

Like father, like son.

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Walking in his father’s footsteps: Richard M. and Richard J. in 1972

Richard Michael Daley, who turned 66 in April, is the country’s longest-serving big-city mayor—at presstime, 7,059 days as “The Man on Five” in City Hall. If he serves out the rest of this term ending in 2011, he will have surpassed by four months the 21 years and 8 months his father, Richard Joseph Daley, spent in office before suffering a fatal heart attack. Together, the Boss and Son of Boss have ruled the city for 40 out of the last 53 years and nearly a quarter of Chicago’s history. The marks of their tenures are everywhere—from the big stuff like the mass of highways and towering skyscrapers, O’Hare International Airport and Millennium Park, to the smaller things, such as bicycle lanes, wrought-iron fences, and well-illuminated streets.

Over the years, they have inspired many Chicagoans with a feeling that the city works, even when it sometimes doesn’t. In the process, their overwhelming popularity with voters has brought stability to a city government that, by tradition, has been politically unruly. (Consider: Chicago went through five mayors in the 13 years between the reigns of Daley I and Daley II.)

But there are other, deeply troubling marks, too: the numerous scars of corruption and scandal; the perpetuation of one-party rule—make that one-man rule; and the ugly results of racism and segregation, which are still felt in the city’s downtrodden neighborhoods.

Daley I’s legacy is by now more or less a closed book—or a shelf full of books. To many Chicagoans, he was a city savior who kept Chicago from plunging into the downward spiral of urban failure that ravaged other Midwestern industrial cities. To others, he was an intolerant despot who saved only half of the city, the white half. He built lasting monuments, but could not handle the political and social upheaval of his times. The jury is still out on Daley II’s legacy. His career, in some respects, has surpassed his father’s, and over the years he has both atoned for some of his father’s past sins and repeated others. Granted, the two men confronted different generations, different cultures, and different political eras. “It’s like comparing A-Rod to Babe Ruth,” says the Cook County state’s attorney, Dick Devine, who worked as an administrative assistant to Daley I and served as first assistant under the son when the latter was state’s attorney.

Our goal here is not to determine who was a “better” or “worse” mayor, but to examine the two administrations across a range of issues to see what the similarities and differences tell us about the men, the city, and ourselves. We tried to focus on areas where there are strong and illuminating contrasts or similarities without delving into the Oedipal complexities between father and son.

In compiling this report I interviewed more than 30 people—from Daley allies and critics (several of whom bridge the father-son generational gap) to former staffers, journalists, and academics. Some of the sources were reluctant to criticize the Daleys too harshly for fear of jeopardizing their relationship with the mayor or with other members of his clout-heavy family.

Daley II himself is fiercely loyal to his father. In March, I met with the mayor in his fifth-floor conference room. He was genial, yet slightly on edge. “I don’t compare myself,” he said tersely, when asked to line up his mayoral legacy against his father’s. As the mayor’s youngest brother, Bill Daley, explains it: “You’re not going to get a lot of self-psychoanalysis by Rich Daley—neither [would you] with my dad.”

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Photography: (Daley I) © Hulton-Deutsch Collection/Corbis; (Daley II) Kevin Banna; (Father and son) Chicago Tribune photograph by James Quinn




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