The 5 Best Big-City Mayors

Richard Daley / Chicago
Richard the Second
He wields near imperial power, and most of Chicago would have it no other way. Two years ago, Richard Daley was re-elected to his fifth term with 79% of the vote. His annual budgets are routinely passed with only token opposition. He controls public housing, public schools and the city council. He is cozy with Big Business, is a master at the ward politics of fixing streetlights, and he speaks with a blunt, blue-collar brio that Chicagoans find endearing.

"There's never been a [U.S.] mayor, including his dad, who had this much power," says Paul Green, professor of policy studies at Chicago's Roosevelt University. And he's used it to steer the Windy City into a period of impressive stability, with declining unemployment and splashy growth.

From the days of Daley's legendary father, sometimes known as Richard the First, Chicago's national reputation as a bare-knuckle city of backroom deals by the Democratic faithful and their labor-union allies has always held a lot of truth. But Daley has professionalized the city by hiring skilled managers and burnished its business-friendly image by strengthening connections to global firms like Boeing, which relocated its headquarters to town, and to white-shoe industries like banking, financial services and law.

In his 16 years at city hall, Daley, 62, has presided over the city's transition from graying hub to vibrant boomtown, with a newly renovated football stadium, an ebbing murder rate, a new downtown park, a noticeable expansion of green space and a skyline thick with construction cranes. As federal and state dollars flowing to the city have dried up, he has used his influence to persuade corporations and the wealthy to kick in for big-ticket attractions, like the $475 million Millennium Park, nearly half of which was paid for by private donations.

Daley's unchecked power sometimes short-circuits public debate. In 2003, under cover of night, he unexpectedly dispatched wreckers to demolish Meigs Field, a tiny downtown business airport that he called a security risk but preservationists had been fighting to save.

Allegations of financial corruption have caught up some of his political allies, although Daley has personally avoided implication.

With so much political capital at his fingertips, the mayor has been able to take big risks. The city is in the midst of knocking down its old high-rise housing projects, which concentrated the poor in pockets of crime and privation. Many of the former tenants are being relocated to better, low-rise housing that blends into existing neighborhoods. Since Daley took over the school system in 1995, he has brought graduation rates up from 51% to 54%, but he's not stopping there. Last year he launched a reform plan in which old, failing schools are to be replaced with new ones that have more autonomy over their curriculums. So far Daley has $24 million in private commitments to fund the program. The best way to minimize crime and poverty in a city, Daley believes, is to keep the middle class from fleeing to the suburbs. "Education is the complete answer to all these other social issues," he says. "The key for all cities is whether you turn public schools around."