You could begin to understand Daley, 68, by watching him operate in his City Hall lair, as he meets with officials of Colombia. They weren't talking cocaine or heroin, but bargaining over yellow roses and pink carnations.
Daley wanted Colombia, the largest exporter of cut flowers to the U.S., to shift its headquarters for shipments to Chicago from Miami. He made the case for the superiority of O'Hare International Airport and, having done his homework, knew the Colombians don't like the pace of Customs inspections in Miami. He informed them that the Department of Homeland Security has already posted a second flower inspector at O'Hare.
It was a tiny window into Daley's drive to replace a blue-collar Rust Belt manufacturing economy with one whose essence is not even understood by locals. James Heckman, a Nobel prize-winning economist at the University of Chicago, notes that in the last decade Chicago has inspired important new financial markets and instruments, like trading in foreign currencies, insurance risks, and other complicated uncertainties. Gone is the city's reliance on the wheat, corn, and soybean futures. Chicago is a leader in specialized services for heavy industry, industrial-scale agriculture, and the logistics of industrial-scale transport systems, all of which come with a raft of related legal, design and other white-collar services.
Daley's Colombian plotting also reflects an acuity that is often underestimated, especially given his frequently inarticulate ways and petty and self-defeating (and, lately, escalating) feuds with media. When it comes to dealing with Washington, he's a master of pulling levers even while publicly voicing disdain with virtually anything associated with the capital.
"The ink wasn't even dry on the stimulus bill when he was literally in my office; very organized, comprehensive and specific," says Transportation Secretary Ray LaHood. A month later, LaHood called Daley to wish him happy birthday as he passed through Chicago, only to then find himself in Daley's office for 90 minutes, listening to more details of the city's transportation needs. In 2009, Chicago received more than $1.3 billion in transportation funds, according to department figures.
Daley has been a whatever-works non-partisan in a one-party town of homogenous if distinct elites and well-known fixers ("the smallest major city anywhere," says politician-turned developer Bill Marovitz) and a chum of presidents of both stripes. He was wired to the Clinton administration, even if a distinct moral streak prompted disdain for Bill Clinton's personal life. George W. Bush and he were buds, surely seeing themselves as underestimated children of great men.
And while his father left the country just twice, Daley's traveled overseas dozens of times; he adores France, Switzerland and China. He reads the South China Morning Post and Financial Times, two of six or seven papers he peruses in the morning and often clips for top lieutenants. Chicago has a vibrant Sisters Cities program with 28 partners including Shanghai, Prague, Amman, Paris, Bogota, Busan, Accra and Osaka.
His successor better understand how he navigated an essentially weak mayor/strong City Council system and a nasty, balkanized Illinois political universe with sophisticated opponents and competing centers of power along the way exhibiting a sneaky and downright cosmopolitan intelligence. The legendary columnist Mike Royko once wondered "whether he's got the brains to tie his shoes." In fact, Daley is a smart guy whose city has a burgeoning library system and more than 12,000 kids learning Chinese in 44 schools.
Daley inherited a Chicago in marked decline, with manufacturing and the white middle class exiting to the suburbs and Sunbelt. He slowed the middle class and business flight by marketing "quality of life" to compete with the burbs (thus the millions of dollars in flowers). He impressed them with operational efficiency. The snow and garbage get picked up. He cut enough deals to keep the underlying system of cronyism and sweetheart pacts greased and running; impressing whites with new schools but capitulating to the teachers union on almost every major issue.
He accommodated the self-interest of various factions and formed de facto non-aggression pacts with rivals such as Alderman Edward Burke, a long-potent finance committee boss. And when he felt he had to act imperiously, he did, most notably in the unannounced, midnight bulldozing of a private airstrip along the lakefront so he could turn it into a park and concert venue.
Remarkably, the city's population has grown slightly since 1989, to 2.85 million; modest by Sunbelt standards but far outpacing other Heartland cities like Cleveland and Detroit, which have lost big numbers. Immigration, and more births (mostly Hispanic) than deaths, offset an accelerating and still-worrisome exodus. What remains is a more diverse city, with the non-Hispanic white population (now 31 percent) down by 15 percent since his first election, the Hispanic population (28 percent) 50 percent greater and the black population (35 percent) roughly the same. If the 2010 Census shows an actual population increase during the previous decade, the reason will be Hispanic births.
One reason even cognoscenti were taken aback by his decision not to seek re-election is that Daley has never faced a credible, well-financed minority opponent. None loomed this time, either, though there remains grinding poverty and unrelenting crime in minority areas. He's been far more democratic than his father in allocating resources, both co-opting potential opponents and gaining the trust of groups suspicious of him, notably blacks (he got 2 percent of the black vote in 1989 but a majority in 2007). He was the first big-city mayor to takeover an awful school system - closing chronic failures, building a few superior public high schools, and starting charters and other experiments. Overall progress: slow but evident. Chicago is the laboratory other school chiefs study.
Downtown has been an obsession (160 high-rises built or underway just since 1998, which is more than one finds in all of St. Louis, Detroit or Milwaukee). Revitalization has been assisted by adroit and debatable use of Tax Increment Financing, a gambit meant to spur growth in blighted areas via revenues from property value growth in those areas. This engine of development may be necessary but it's often been woefully lacking in transparency.
He's boosted forgotten neighborhoods with new police stations, fire houses, playgrounds and so many new libraries that even Harvard's Robert Putnam, whose celebrated "Bowling Alone" asserted an increase in American civic alienation and fragmentation, points to Chicago's branch libraries as a hopeful antidote, spreading literacy and community interaction. In turn, the public investment generated private investment throughout many wards, replete with its inevitable rewards (political donations) to increasingly compliant local aldermen.
Culturally, Daley has overseen a renaissance, with high-brow stalwarts like the symphony, opera and art museums loved by the elite competing with burgeoning theater companies; thousands of free concerts and shows produced by the city; hundreds of miles of bike routes; a strong convention industry and a sharp increase in tourism, with 44 million visitors last year; and high-end restaurants (Gourmet magazine cited Alinea as the nation's best, while Mexican food impresario Rick Bayless won Bravo network's first "Top Chef Masters" contest).
Given this penchant for success, it's no surprise that Daley has long been a magnet for the ambitious and talented. David Axelrod, now an advisor to President Obama, hooked up with Daley early and was a critical strategist, softening Daley's rough image and fashioning him as a sincere healer after years of race-driven City Hall tumult during and following the brief tenure of Harold Washington, the city's first black mayor. Emanuel, spurned by Bill Daley when he sought to manage Richard's 1989 campaign, proved a champion fundraiser, with city workers then playing no small role when Emanuel ran successfully for Congress in 2003. Daley is close to Emanuel in ideology and temperament. If Emanuel were to run and win the mayor's job, Daley would be assured of scant criticism from his successor.
Valerie Jarrett, Obama's closest adviser after his wife, served as a top aide before Daley cut her loose as the planning and development chief, displaying what even loyalists concede is a brutally cold personnel style. In Jarrett's case, Daley bowed to unhappy developers and a then-close mayoral confidant who simply didn't like her. But, as one of 11 former chiefs of staff notes, Daley may be petty and callous, almost never delivering bad news himself, but he's not hateful. He doesn't crush you and make an enemy.
Relations with Obama were complicated. The promise of Harold Washington drew Obama to the city as a community organizer before he enrolled at Harvard Law School. After he returned and entered politics, Daley was mayor and could have backed him at two key moments----when he ran for U.S. Congress against Bobby Rush in 2000 and when he ran in the U.S. Senate primary in 2004---but did not. Obama succeeded despite Daley's lack of attention.
"I think he's doing a tremendous job," a clearly sincere Daley told me, "nationally and globally." As far as his own White House alumni club, he swears he's not in regular contact. "You deal with David, Rahm and Valerie. But I can't just pick up the phone, saying, 'I need this, I need that. They're busy people."
Chicago has thrived under Daley in part due to his administration's bag of financial tricks. In tight times, he has sought to privatize virtually everything except snow and Lake Michigan. He leased the Chicago Skyway, a 7.8-mile tollway, to an Australian-Spanish combine for $1.8 billion, four downtown parking garages to Morgan Stanley for $563 million and parking meters to the same firm for nearly $1.2 billion. Plans to privatize the second airport, Midway, for around $3 billion fell through but likely will be completed one day.
The parking meter deal inspired outrage. Daley rushed it through the often lapdog City Council (he's personally picked 17 of the 50 members as a result of criminal convictions and other exits), only to find citizens furious as they fumbled for quarters as rates zoomed. His white political base, including city workers, was especially angered. Matters were made worse as he furloughed workers and cut services.
Daley needed the Olympics for what were arguably shrewd longterm development plans, especially on the South Side of the city's lakefront. As New York's Bloomberg notes, an Olympics permits you to do things you probably couldn't otherwise, notably with basic infrastructure like subways.
As for naysayers, who assumed huge projects would inspire cronyism with contracts and the specter of future grand juries, Bloomberg declares, "Nobody remembers that Central Park was a bad economic deal, over budget and (with) lots of corruption. You can't imagine New York without Central Park.