Richard M. Daley's 21-year run as mayor will end next spring with the city broadly reshaped by his vision and unprecedented grip on power, but with his image as Chicago's sure-handed leader increasingly challenged.
He stepped off the political stage in stunning fashion Tuesday, with the city in a time of great transition, years of recession taking its toll on his reputation as a shrewd manager, and money running out to keep Chicago moving forward.
His rule was defined by bold strokes and secretiveness, traits that brought him his greatest successes but gradually undermined his effectiveness.
Daley leaves a legacy of broad accomplishments, such as Millennium Park and neighborhood revitalization. Other initiatives remain incomplete, such as the ongoing efforts to improve Chicago public schools and expand O'Hare International Airport.
Daley often spoke of how his passion for leading the city remained strong, so his decision to pull the plug led to questions about his underlying motivation.
Was it the fragile health of his wife, Maggie, who has been battling cancer for years? Was it the looming $600 million city budget deficit that could make running the city in the short term about as enjoyable as a root canal? Or was it the increasing un-restiveness of a once docile City Council emboldened by public outrage over the parking meter deal and other administration missteps?
Or, perhaps, it was the realization that his city may be suffering from Daley fatigue. He was elected to his sixth term in 2007 with 70 percent of the vote, yet a Tribune/WGN-TV poll in July found that just 31 percent of city voters said they wanted him elected to a seventh term while 53 percent said they did not.
For his part, Daley on Tuesday said the answer was none of the above, though he revealed very little about his thought process as he insisted he has been thinking about retiring for the last six months. He said he became increasingly comfortable with the idea in the last couple of weeks.
"It's time, everybody is replaceable in life, no one is here forever," Daley told reporters at a reception at the Chicago Cultural Center. "I knew it was my time. I was not afraid of any election … I don't work on an election, I work on what to accomplish as an incumbent and I've done that for years.
"You know like anything else, it's time, it's personal, there wasn't one reason at all and it's hard for people to understand that and this was the best kept secret in Chicago."
For all his longevity, the younger Daley remains a sometimes baffling study in contrasts — different in so many ways from his powerful father, Richard J. Daley, yet a chip off the old block in others.
To many, he has been the model of a progressive big city mayor, straddling the need for economic development with community inclusiveness in a diverse city. Yet others see him as a well-intentioned but sometimes inflexible autocrat who for most of his time in office ruled almost by fiat rather than consensus.
When he leaves office next spring, Daley's tenure will surpass by several months that of his father, whose legacy as the last of the old-fashioned, iron-willed political bosses still hovers over the city.
That is hardly the only way that Richard M. has managed to do Richard J. one better. He has spearheaded campaigns to not just beautify downtown but the neighborhoods as well, while launching community policing efforts and attempting massive but politically perilous overhauls of the city's long-neglected schools and public housing.
Over his 21 years as mayor, the younger Daley has muscled through a multibillion-dollar expansion of one Chicago airport while deliberately sabotaging another under cover of darkness.
In the name of reform and at considerable political risk, he tightened city control over schools and public housing even while shedding direct involvement in an array of services through privatization and controversial lease deals for assets like the Chicago Skyway and parking meters.
A Democrat who often sounds like a Republican, Daley has earned a national reputation as an innovative and dynamic municipal leader. Yet the city's finances are bleak, corruption has grazed the upper reaches of his administration and the mayor can seem socially awkward, a sometimes walking, talking malapropism.
Daley, a former Illinois state senator and Cook County state's attorney, was first elected mayor in 1989. But it wasn't the first time he ran. He is even the answer to a trivia question about who was the third Democrat in the bitter 1983 primary between incumbent Mayor Jane Byrne and challenger Harold Washington, Chicago's first African-American mayor.
Two years after Washington's 1987 death in office, Daley benefited from a rift between Washington's former political allies to defeat two African-American opponents, interim Mayor Eugene Sawyer and then-Ald. Timothy Evans.
For all his accomplishments, Daley's father became a symbol of racial division with his opposition to the marches of Martin Luther King Jr. and an order to shoot to kill rioters during racial strife.
The mayoral son, on the other hand, gradually neutralized the sharp racial and ethnic divisions that had come to characterize city politics during the Washington years.
He wooed Latinos and blacks by sharing some of his power, in the form of city jobs and investments. Along the way, his operatives created a new political army that relied not on the strength of the Democratic Party but on neighborhood groups loyal to Daley.
But, like his father, Daley also knew how to steer city largesse to his friends, rewarding some with lucrative contracts. Several years into Daley's tenure, the Tribune revealed what appeared to be sweetheart fencing and janitorial contracts worth millions of dollars granted under questionable circumstances to companies with ties to the mayor or member of his family.
By the time Daley took office, federal courts had imposed strict limits on the traditional forms of political patronage that enabled his father to command intense loyalty among city workers and wield immense power. Daley adapted, cementing ironclad control over the city through the muscle of government contracts and grants and low-interest loans that were doled out to not just his friends but also used to gain the loyalty of ethnic and racial minorities.
Even so, federally imposed hiring rules continued to be bent, leading to perhaps the biggest scandal of his tenure. Senior mayoral aide Robert Sorich and three other top city officials were convicted in 2006 on federal charges of rigging the hiring process to reward those who worked for supposedly independent political organizations close to the mayor.
Daley loved to praise "thinking outside the box" when it came to governing and would frequently return from trips abroad brimming with ideas for municipal improvements that he had seen on display in Europe, Asia and elsewhere.
In his early years as mayor, he pushed grand plans for a new metropolitan airport near Lake Calumet, a Disney-like amusement park and casino complex, and a downtown trolley system. When those failed to pan out, he redirected his attention to more modest projects in the Loop and neighborhoods, incorporating wrought iron fencing and flower boxes wherever he could.
He oversaw creation of scores of special economic zones to jump-start development across the city and ripped up the State Street mall installed by Byrne years earlier, a project widely credited with bringing new vitality to the heart of the city.
Daley can also take credit, or blame depending on your aesthetic point of view, for rebuilding decrepit Soldier Field into a modern stadium that resembles a flying saucer resting on classic colonnades. He also served as the driving force behind Millennium Park as well as the Museum Campus, the latter of which served as the backdrop for an incident that came to symbolize Daley's willingness to get his way at all costs.
He waged a long battle with state officials to close Meigs Field, finally taking matters into his own hands by sending in heavy equipment without notice one night in 2003 to rip up the concrete. He claimed he acted to prevent a terrorist attack.
Tribune reporter Serena Maria Daniels contributed to this report.