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Fresh from what should have been a relaxing vacation in Mexico in late January, America’s most powerful Democratic mayor seemed to be an emotional wreck. His voice cracked. His face was flushed. He looked miserable. “As I stand before you today, I am embarrassed, I’m angry, and I’m disappointed, because I feel I have let the people down,” said Chicago’s mayor, Richard M. Daley, during a press conference to address the growing scandal surrounding the city’s Hired Truck Program.
The members of the City Hall press corps—a hard-boiled bunch not easily moved by emotional outpourings from the mayor—were hard pressed to remember when Daley had seemed more aggrieved over allegations of corruption in his administration. Reporters on hand “thought he was on the verge of crying several times,” wrote the Chicago Sun-Times columnist Mark Brown. “He seemed angrier than usual, disappointed,” recalls Craig Dellimore, political editor for WBBM Newsradio 780. “And you don’t often hear the mayor say he’s sorry.”
Daley had good reason to be upset. In a series of stories called “Clout on Wheels,” the Sun-Times had detailed how mayoral cronies and Mob-linked contractors, among others, were getting fat off the city’s $40-million-a-year Hired Truck Program, in many cases by getting paid to do little or no work. In the Chinese water torture of follow-up stories, many themes that have plagued Daley in scandals past seemed to converge: There were waste and inefficiency, apparent favoritism extended to clout-heavy cronies and campaign contributors, abuse of the city’s set-aside program for women and minority businesses, and even a whiff of nepotism, given that one of the mayor’s brothers, Cook County Board member John Daley, had provided insurance for some of the program’s participants.
What also became clear was that the Hired Truck mess had been allowed to fester long after warning bells sounded. When problems in the program first surfaced, in 1997, the city had hired a consultant to conduct an audit and recommend improvements. Yet six years later, the program appeared more corrupt than ever. For Daley, who has gotten so much mileage out of being portrayed as a hands-on manager immersed in the nitty-gritty of the job—if he notices a pothole, he mobilizes Streets and San—there was no way to plead ignorance and shrug the whole thing away, as he had done with so many previous scandals. At best, Daley had taken his eye off the ball. At worst, he had tolerated a corrupt program that wasted perhaps tens of millions of taxpayer dollars. Either way, he looked bad.
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Stumbles such as the Hired Truck scandal certainly are not what made Daley, by any measure, an extraordinarily successful big-city mayor. He has held office on the fifth floor at City Hall for 15 years, longer than any other Chicago mayor except his father. And his popularity among voters has only increased over that time. Last year’s “race” for mayor looked more like a battle between Seabiscuit and Mister Ed—Daley won it going away, with 79 percent of the vote.
A quick glance around town reveals plenty of reasons for Daley’s electoral dominance. The streets are cleaned. The garbage is hauled. The snow gets plowed. The street lights work. The trains run on time. Crime is down. In other words, The City That Works works pretty well.
Beyond delivering the basics, Daley can boast a litany of other successes that would do any mayor proud. He has forced improvement on a public school system once disparaged as the worst in the nation. He has torn down public-housing high-rises that were among his father’s most ignoble legacies. He has made sure basic city services were more evenly distributed to minority neighborhoods, and employment in city government was more inclusive to minorities. And he has seen to it that the city looks great, thanks in no small part to those ornamental wrought-iron fences that the mayor adores, and to those picturesque flower beds gussying up the city’s boulevards.
But as sure as the tulips bloom on Michigan Avenue each spring, new scandals seem to sprout like crabgrass on Daley’s watch. Often these scandals involve people with close connections to the mayor receiving juicy no-bid contracts or getting cut in on plump deals as lobbyists or consultants, creating the appearance that clout and favoritism remain the guiding forces in determining who does business with City Hall.
Not all of the scandals are created equal, of course. They have ranged from the merely venal to the possibly criminal. And over the years Daley has insisted—sometimes indignantly, often implausibly—that clout plays no role in his administration; that he would never compromise the best interests of the taxpaying citizens of Chicago or jeopardize his reputation for the sake of enriching a friend or relative or generous campaign contributor.
Still, the sheer volume of apparent conflicts of interest and ethical lapses that have clouded Daley’s tenure should trouble anyone who cares about the city. Beyond that they raise a puzzling question: Why does Daley allow them to happen? With all his power and influence, why does he risk his legacy as a great mayor by not cracking down on clout and cronyism in his administration? “That’s the $64,000 question,” says one legislator who has observed the workings of the Daley administration.
It’s a question as much about Chicago as about its leader. After all, the city has a history of tolerating—sometimes celebrating—a certain level of boodling. One school of thought even presumes that corruption is the grease that makes Chicago work. Yet, in the past decade or so, other big cities have revived and thrived under dynamic mayors without being plagued by the clout-related scandals that regularly erupt here. After a while, it’s hard not to conclude that the solid, taxpaying citizens of Chicago are being duped. Wouldn’t Daley like to cement his reputation by campaigning to clean things up?
To find answers, I set off on a quest of inquiry and discovery. City Hall rebuffed my efforts to speak directly with the mayor on the subject (he did provide written answers to a few general questions; see “Mayor Daley Responds,” page 63). But I did talk to more than two dozen other people, from current and former public servants to consultants, academics, journalists, wonks, watchdogs, and others who get paid to think about the workings of Chicago politics and government. Some of my sources have worked for Daley in the past, and some work with him today. Many acknowledge that Daley could curtail the clout and the cronyism and the ethically tortured dealings tomorrow if he chose to. Their explanations for why he doesn’t range from the self-evident—voters have not punished Daley at the ballot box—to the biological—the existing system of political rewards and favors is so deeply encoded in Daley’s DNA that he literally sees nothing wrong with it.
“This mayor is very similar to his father—personally honest, not taking any money himself,” says the legislator quoted above (to maintain working relations with the mayor, several people quoted in this article insisted on remaining anonymous). “But all the Bridgeport childhood pals and political cronies and siblings and big campaign contributors—they’re all feeding at the trough and getting inside deals and making him look bad. And it goes on and on and on. At some point you’ve got to say, ‘This is what he believes in. It’s part of his philosophy of government. He wants it this way.’”
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