The rabid attention to the little things was paired with thinking that some thought "too big." Many in the city wondered why Daley pressed the ultimately unsuccessful bid for the 2016 Olympics at a time when the city could not afford to hire more cops or improve schools.
But a walk along the Chicago River shows how the big-thinking Daley helped transition the city from its industrial past into booming hub of international commerce. There are the headquarters of Boeing Co. and United Continental, corporations he lured with millions in financial incentives. There is Donald Trump's 98-story tower, slipped neatly into the city's world-famous skyline. There is Groupon, a billion-dollar web sensation that leads a pack of dozens of start-ups sprouting across the city.
It's also in the city's neighborhoods, many of which evolved during his time in office as Daley helped a city with blue-collar sensibility become a magnet for young professionals. When Christopher Kennedy — the son of Robert F. Kennedy, head of Chicago's giant Merchandise Mart and chairman of the University of Illinois Board of Trustees — arrived in the city in 1986, "there were only two or three neighborhoods your parents would want you to live in."
"Now there are 25 or 30," Kennedy said. "I don't know that any city in America is like that."
But as the city's Loop and surrounding neighborhoods prospered in the past decade, areas on the city's South and West Sides lost population. Roughly 200,000 residents, many African Americans, left neighborhoods that didn't share in downtown's success.
Those slices of the city continue to struggle "with many of the same forces that were bearing down on them 15 to 20 years ago — poor schools, the shortage of affordable housing," said Alex Kotlowitz, a Chicago journalist and writer whose book 1992 book "There Are No Children Here" exposed the horrors of a child's life in the city's public housing.
Daley tore down those housing projects, ironically erected by his father, and aimed to improve the city's public schools by seizing control of the system in 1995. While he succeeded in balancing the district's nearly $3 billion budget, getting students to schools safely is a lingering problem left for his replacement to solve.
"If we don't get education right, then I think we continue to relegate our children to futures that are hopeless and that only further increases the burden on the rest of society," said Tim King, head of Urban Prep Academies, a private network of all-boys schools that for the second year in a row sent every senior — students from some of Chicago's poorest neighborhoods — into a four-year college or university.
The next mayor won't start from a position of financial strength. The combination of the nation's economic downturn made for an ugly combination with what critics say is a municipal government that under Daley lived beyond its means. One of Daley's solutions backfired when the city burned through all but a fraction of the $1.15 billion it received in 2008 in return for a 75-year lease of the city's parking meters — money that was supposed to last the city nearly a century.
"The person is walking into a city that is broke and they're going to have to make some tough financial decisions," said the Rev. Michael Pfleger, pastor of St. Sabina Church in Chicago. "They have to be careful those decisions are not made on the back of social programs and poor people that are already desperate."
Daley also leaves a city government that's still known as a place where it pays off to be the mayor's buddy, where people land plum jobs for no other reason than they "know a guy who knows a guy." While the prosecutors have reined in the political machine built by his father, the outgoing mayor has seen top aides end up behind bars, including one convicted for handing out patronage jobs years after federal decrees outlawed the practice.
Many say they're watching closely who the next mayor brings in to run the schools, police force and other key departments. And in contrast with Daley — who Tigerman called "a benign dictator" — the new mayor may actually have to work with a newly recast 50-member City Council, instead of simply telling them what to do.
The election is expected to bring in a big cast of new aldermen, who won't be as beholden to whoever is elected mayor. In the years before Daley was first elected in 1989, a council ensnared by racial division earned the city another nickname: "Beirut on the Lake."
That ability to lead a city as diverse as Chicago might just come down to the new mayor finding a way to become as likable as the old mayor.
Carlos Tortelero, president of the National Museum of Mexican Art in the city's Pilsen neighborhood, said Chicago liked Daley because he mangled sentences and still teared up when asked about his 2-year-old son three decades after the boy died.
And residents liked the fact that the mayor was up at 6 a.m., riding around the city looking for lots filled with seagulls, rats running through alleys and any other thing that needed to be fixed to keep Chicago "The City That Works."
"It's a city where a person will brag that my father worked at the steel mills. That whole family connection is important in Chicago and Mayor Daley exudes that," he said. "Whoever the next mayor is, they need to connect to that."
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