In Chicago, the Dynasty Rolls On

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Scott Olson / Getty

Chicago Mayor Richard Daley, 2006

For a few brief moments last year, Richard M. Daley actually looked vulnerable heading into his current campaign for a sixth — count 'em — term as Chicago's mayor. Four of his closest aides, included his patronage chief, were convicted last summer on corruption charges, while a federal probe of the city's hiring practices continued. Around the same time, a court-ordered investigation detailed an elaborate torture ring operated — and later covered up — by high-ranking Chicago police officials from the 1970s until the '90s. What's more, in an unprecedented show of defiance, the city council broke ranks with the mayor, passing an ordinance to boost the wages that Big Box employers like Wal-Mart and Target would have to pay. In the end, Daley persuaded enough aldermen to reverse positions to ensure his veto wouldn't be overridden, demonstrating that "da Mayor" was still very much the boss.

Daley's chances for retaining his post now seem as predictable as the wintry, gray skies over Lake Michigan this time of year. Here, in the largest U.S. city without mayoral term limits, Daley's fleeting weakness vanished almost overnight following the Democratic takeover of the House of Representatives, when two would-be mayoral rivals, Congressmen Jesse Jackson Jr. and Luis Guttierez, decided it could be a lot more fun to stay in Washington. Political insiders have also suggested that even these ballyhooed potential opponents might not have had campaign operations robust enough or financially equipped to overtake the Daley machine.

In 2003, Daley — facing token opposition, as he does this time — received 78% of the vote. And on Feb. 27, an election date not exactly selected to encourage turnout in the Windy City, he is likely to do just as well. "With every election, Daley wins with higher margins and lower turnouts," says Jay Stewart, executive director of the Chicago-based Better Government Association. Even if his percentage slips a bit, one thing he won't change is his opposition to campaign debates. Daley doesn't engage in them because, plain and simple, he doesn't have to. The result is a generation of young Chicagoans who have never seen their mayor or his opponents articulating their positions on the pressing issues of the day. "It wouldn't be the Lincoln-Douglas debates, but it would be better than nothing," said a frustrated Stewart. Assuming he completes another four-year term, Daley, 64, will have served longer than his legendary father Richard M. Daley, who had been mayor for 21 years when he died in office in 1976.

It is, alas, an axiom of politics in Illinois — and especially Chicago — that voter tolerance for bribery, kickbacks and other stinky political practices is extremely high, as long the trash is picked up on time. And since the mayor himself has been indicted on nothing, he strides on, overseeing everything from public housing and education to the details of an ongoing beautification initiative. It helps that some of his most unpopular moves, like his unilateral decision to demolish a small lakefont airport in 2003 under the cover of night, seem nearly forgotten. Meanwhile, he has accepted blame for not having had a better handle on the rampant job-rigging infractions, in which applicants for city positions who had political connections were favored over those with better qualifications.

He also gets much credit for the city's dramatic downtown revival, with its emphasis on flower planting and condo development. The 2005 opening of the $500 million Millennium Park — exorbitant cost overruns notwithstanding — has been a crowning achievement. His latest endeavor is to imprint the sparkling urban visage on the rest of the world: Daley is currently consumed with luring the 2016 summer Olympic Games to Chicago, and he's already traveled to Beijing, Athens and Barcelona for insights on how those host cities fared.

The city's sponsorship of the Gay Games last summer gave him a taste of the reflected glory that comes from hosting a complex and successful array of international sporting events. Those games "moved without any controversy — and that says a lot," the mayor noted. If Daley does succeed in his Olympics bid, he may well still be in charge when it's time to greet the athletes nine years from now.