• Paul John Higgins

These are the moments a City Hall reporter lives for: My girlfriend and I were having dinner at a downtown restaurant recently, and we couldn’t help but overhear the couples in the next booth kvetching about Chicago’s parking meter lease deal.

“Boy, the city really blew that one,” said one of the guys.

“They really did,” said one of the women. “And it’s all on Mayor Daley.”

While the private company now running the meter system has jacked up rates to maximize its profits, she went on, the city has already spent most of the $1.2 billion it received in the deal—money that was supposed to last for the next 74 years.

“I never thought I’d see the day when Daley was vulnerable,” she concluded. “But he is.”

And she’s not the only one who sees it.

Despite the myths propagated by his administration—and received as fact by many news outlets, including, most recently, the New Yorker—Daley is not overseeing a smoothly running, contented city. (See Ben Joravsky’s column in this issue for more on that.) Every day I hear CTA riders bitching about the decline of rapid transit, which Daley appointees have overseen for the last two decades. At community policing meetings people talk about daily gunfire down the block from their homes; cops, meanwhile, quietly rage about how the police department has cut hundreds of officers from its ranks in the last couple years. Aldermen have been fretting aloud about the vacant homes and empty storefronts pockmarking their neighborhoods, and they say they’re inundated with calls from constituents wanting to know why the city isn’t doing more to get rid of squatters and drug dealers. Then there are all the complaints about potholes, poorly maintained parks, and struggling schools. Community activists wonder why the city has doled out hundreds of millions of dollars in corporate subsidies when it can’t find the money to maintain basic city services. And scores of people around town are, like my fellow diners, irked that the city sold its street parking system to an investment bank.

Voter anger waxes and wanes, but in Chicago this time around Mayor Daley is a primary target. Last fall a Tribune poll found that just 35 percent of Chicagoans approved of his performance—his lowest rating since he was elected in 1989. And the poll was conducted before Chicago lost its bid for the 2016 Olympics, before Daley decided we’d use the parking meter “rainy day fund” to plug holes in the 2010 budget, before one of his chief City Council allies, Isaac Carothers, pleaded guilty to bribery and tax evasion, and before one of his erstwhile critics, Toni Preckwinkle, won the Democratic primary for county board president by promising reform (though she was wily enough to seek his endorsement).

With just a year before the next municipal election, Daley seems to be in trouble—so much so that some have predicted he won’t even run. Many observers have speculated that what may push him off the fence is the health of his wife, Maggie, who has been battling cancer.

There’s no doubt his stock has fallen. But Daley isn’t just any politician. I predict his poll numbers and popularity on the street will have little bearing on whether he runs again—and even less on whether he can win.

For starters, he’s not the type who would give up his throne to live out his days on the golf course. And it’s not as though he hasn’t dealt with PR nightmares before—he’s waded through scandals that would eat other pols alive, over things like his friendships with contractors who won millions of dollars in city business by fraudulently claiming their firms were led by minorities and women; the millions of taxpayer dollars paid to trucking companies that bribed their way into contracts and then did no work; and illegal patronage hiring by some of his top aides. By now Daley knows what to do: find a fall guy, rant about him on camera, give him the ax, declare the problem solved, and return to his aggressive downtown flower-planting campaign.

Nobody wants bad press, but Daley seems to like a fight. More to the point, he likes a win, as much as Michael Jordan ever did. And he’s not interested in eking one out—he likes to win big. He gets annoyed when even a handful of aldermen vote against something he’s pushing. He likes to be dismissed as inarticulate, provincial, or weak—and then to outmaneuver his critics again so he can gloat a bit. In 2006, when Daley was preoccupied with that federal investigation into patronage hiring in his administration, mayoral irritant Joe Moore got the City Council to pass a ban on foie gras. Two years later the mayor refused to let Moore speak (and the alderman’s mike conveniently cut out) as mayoral allies used a parliamentary trick to overturn the ban without a moment’s debate. Afterward the mayor paraded around City Hall wearing the smug smile of a 14-year-old bully. Who can imagine that guy delivering a “You won’t have Richie to kick around any more” speech?

So far Daley has offered only the vaguest answers to questions about his plans. “I don’t know why you already put me in the grave,” he told reporters last fall when someone dared to ask if he would run for reelection.

Most took his response to mean that he shouldn’t be counted out. I took it to mean he’ll quit when he’s dead.

The way I see it, Daley is more Ahab than Nixon. He’s operating on his own logic, and he’s not going to change his course for anybody, even if it takes the ship down.

Maybe I’ve got it wrong. But I’ve talked about Daley’s future with dozens of elected officials, campaign manager types, and other political insiders—some loyal to the mayor and others seething with resentment toward him. Every one of them has told me the same thing, often down to the word: “All indications are that he’s going to run again.”

The question, then, is whether anyone who can conceivably win is going to run against him. [See Mick Dumke’s companion piece, Mayoral Material? Ten to watch, even as they demur.]

No one can beat Daley if no one tries to. It’s obvious, but in this town the obvious needs to be stated. Daley hasn’t had a serious challenge since warding off Roland Burris in 1995, and even supporters acknowledge that this hasn’t been good for the city. There’s little reason to expect any change from Daley if he keeps getting more than 70 percent of the vote.

When Daley first took office, the city was racially divided after years of coordinated white opposition to the first black mayor, Harold Washington. But Washington died on the job in 1987, and in the special election two years later Daley campaigned as a healer, locked up the white vote, and slipped past his African-American opponents, beating interim mayor Eugene Sawyer in the primary and Alderman Tim Evans in the general. (Municipal elections were divided into a primary and general election then—the primary was eliminated in 1995.) Daley won 54 percent of the vote in both contests.

That’s his worst performance to date. Even his most formidable foes got it worse—Daley beat county commissioner (and future congressman) Danny Davis 63 to 31 percent in the 1991 primary and Congressman Bobby Rush 69 to 27 percent in 1999.

If black opponents have faltered against him, white and Latino opponents have stayed away altogether. Other than a few fringe candidates in the 1990s, Daley hasn’t faced a white challenger since former mayor Jane Byrne ran against him in the 1991 primary. He’s never faced a Latino.

In those elections, though, the conditions favored the incumbent. The local economy was thriving: the city was raking in the tax dollars, and the mayor had plenty of resources to spread around. Favored contractors got rich as new police stations and libraries were built in black and Latino areas that had once vehemently opposed Daley. Churches got city support for social services and affordable housing construction, and pretty foliage was planted in street medians. Even as neighborhoods that used to rely on manufacturing and mill jobs continued to crumble, the Loop was bright, prosperous, and full of energy. Progressive types didn’t want to admit it, but lots of people thought Daley did a fine job of shepherding the city into the postindustrial era.

But the mayor had sticks as well as carrots—namely the armies of old-school patronage workers at his disposal. Anyone who stood in his way—or in his allies’ way—had to face the prospect of being mowed down at election time. In 2003 incumbent 12th Ward alderman Ray Frias dropped his reelection bid after concluding he couldn’t beat a challenger backed by the Hispanic Democratic Organization, a force of hundreds of city workers commanded by top Daley allies.

Daley’s margins soared as he consolidated power. But at the same time, voter participation plummeted. In 1989, 934,049 people voted in the first round of balloting for mayor; in 2007 just 456,765 did. Daley got 324,519 of those votes, or 71 percent. In 1989 he’d received 486,586 votes to constitute his winning 54 percent.

To remain in power, Daley didn’t have to be popular. He just had to be less uninspiring than his foes.

Still, the last election could’ve been different. In the middle of the night on March 31, 2003, without notifying the FAA or any pilots or aircraft owners, Daley unilaterally ordered crews to bulldoze the runway at Meigs Field, the small airport on Northerly Island. He claimed this sudden move would diminish the threat of an airborne terrorist attack, though many remembered that in 1994 he’d unsuccessfully tried to turn the space into a park. Critics called him a tyrant; legal fees and fines levied by the federal government cost the city about $500,000. The mayor shrugged it off, and for the most part the public followed suit. By the following September Northerly Island was a park.

The next rounds of scrutiny weren’t as easy to dismiss. Starting in 2004 U.S. attorney Patrick Fitzgerald zeroed in on the Hired Truck program and then on illegal patronage hiring, the hallowed tradition of trading jobs for campaign support that created armies like the HDO. Before the feds were done, dozens of people had been convicted on fraud and other charges—among them Robert Sorich, the mayor’s patronage chief and family friend from the Bridgeport neighborhood, where they both grew up. Federal investigators interviewed Daley—in the presence of his private attorney—but he was never charged with wrongdoing.

The mayor looked vulnerable, and Congressman Jesse Jackson Jr. took note. Junior began issuing statements, giving speeches, and granting interviews blasting City Hall corruption. He traveled around the city meeting people and speaking to neighborhood groups, raised some money, and even set up a campaign organization—then abruptly opted out of a mayoral challenge, saying the Democrats’ new majority in the U.S. House meant he could do more good in Washington. People close to his campaign also said he was discouraged by the results of polls he’d conducted showing he probably wouldn’t win.

He was probably right. The supposedly weakened Daley raised $6.4 million in the eight months leading up to the election, spent $4.7 million of it, and went on to crush two lackluster opponents, circuit court clerk Dorothy Brown and political activist William “Dock” Walls.

I for one don’t think Jackson should be condemned for not wanting to be a political martyr. Yet I’m not sure he realized how much he might have changed the dynamics of the Daley era, even in losing.

If someone as sharp and charismatic as Junior had launched a full campaign, crisscrossing the city to hammer away at waste and backroom deal making, it could have forced the mayor to adjust the way he does business at least a little. Perhaps more significant, it could have made the simple but profound statement that such a campaign was possible: that someone could take on Mayor Daley, scrutinize his record, draw him into an open debate about the issues, enliven the electorate, and establish a modest tradition of competitive democracy in Chicago.

Instead Junior as good as told everyone that he didn’t think Chicago was ready for a modern, issue-based campaign against Daley, and within a year he’d undertaken a ruinous behind-the-scenes effort to get himself picked to replace Barack Obama in the U.S. Senate. Jackson ended up with a damaged reputation and a new nickname, “Senate Candidate Five,” after federal court filings revealed that he’d discussed the seat with Rod Blagojevich while the governor was allegedly trying to sell it to the highest bidder. Jackson hasn’t been accused of any wrongdoing, but he’s too politically damaged to run for anything besides his current job.

The mayor emerged from his 2007 triumph cockier and more insulated than ever. He pushed budgets through the City Council that raised fees and fines while cutting services. He mobilized business leaders and city resources around his obsessive quest for the 2016 Olympics, made plans to privatize Midway Airport, handed off the meter system with no serious deliberation or public input, and let aldermen know they might not get much-needed investments in their wards if they didn’t play along.

But lately, unlike in years past, Daley has been unable to persuade the public that the City That Works is working. Strapped for cash, the CTA has reduced its already unsteady bus and train service. The Park District keeps hiking fees as its facilities decline.. The school district is facing a billion-dollar budget gap. The city, unable to keep pace with its infrastructure demands, is reportedly hearing proposals to turn over more city assets—including the water system—to private companies.

Even Daley’s been forced to acknowledge that there are problems—but he’s blamed them all on the devastated economy. “Cutbacks, layoffs, you know it’s going to get worse every year,” he said in 2008, at the first signs of a downturn. “So we’re in the same dilemma. It’s not going to go away. It’s going to get worse and worse.”

Yet how the city has reacted to the recession is a mess of Daley’s own making. As those people in the next booth suggested, nothing is more revealing than the parking meter deal.

It was presented to the public as an answer to some of the city’s budget woes—deficits of half a billion dollars a year in 2009 and 2010. By taking the $1.2 billion up front, Daley aides said, the city would be able to cover some short-term expenses while socking away hundreds of millions of dollars to help stabilize finances for decades to come. But the deal wasn’t carried out with the public in mind. It was conceived and executed behind closed doors by city officials and connected lawyers and financial advisers who worked to figure out what they could get for the meter system rather than what they should get. They acted with the mayor’s blessing and consent.

In the end the city got its $1.2 billion cash injection, but evidence suggests we should have reaped at least twice as much. A private company now makes more than a million bucks a week on the parking system and requires the city to compensate it every time meter locations, hours, or rates are changed—even for public festivals or road construction.

Worst of all, the Daley administration will have spent most of the money, including the “rainy day fund,” by the end of next year. For the subsequent seven decades the city will be robbed of millions of dollars a year in interest that should have been available to fund public safety, infrastructure, or social services.

Last August the mayor and his top aides made their annual show of accountability by sitting through three public hearings on the budget in which citizens were free to address them. I attended the one in South Shore. It was remarkable: the mayor and his team remained impassive as a parade of people stepped to the mike to complain about crumbling streets, high crime, failing schools, shuttered public health clinics, nonexistent recycling services, and high taxes.

“I’ve come before you three years,” one woman said. “There’s nothing I can say to you, mayor, or nothing I can do to you, mayor, that would compare to what God has in store for you if you don’t choose to honor this village’s request and do right by these Chicago citizens . . . I ain’t too proud to beg, but I am too black to keep coming here and kissing your behind.”

Daley didn’t respond. In fact, he looked bored. Minutes later, while another citizen was speaking, he got up to stretch his legs in a side room.

Politicians, activists, and other observers say voters have grown angrier in the months since. “The mood of the people, the neighborhood people, the people out of work, the people who don’t feel government is representing them, they’re hot, they’re agitated, and it doesn’t have anything to do with the economy,” says 38th Ward alderman Tom Allen, who’s recently been critical of Daley’s management of the budget. “It has to do with respect and people feeling they’re being ignored.”

Race may not play into the next mayoral election the same way it has in the past: Allen represents a predominantly white ward in the northwest-side bungalow belt, an area that’s always backed Daley—to the tune of 86 percent in 2007. South Shore, where the mayor’s behind was brought into the conversation, is much different, a predominantly black, once-prosperous community that—like many on the south and west sides—has been slammed by disinvestment and crime. Daley has also fared well in these neighborhoods in the last few elections. But right now “there are a lot of people in the African-American community looking for a candidate,” says Cliff Kelley, a former alderman who hosts a popular call-in talk show on WVON radio (1690 AM). “Folks want this guy out, and they don’t care what the next guy looks like.”

There’s also been a burst of independent activism in some Latino parts of the city. In February Jesus “Chuy” Garcia defeated incumbent Joseph Mario Moreno in one of the Democratic primaries for Cook County commissioner. While Moreno is allied with Democratic “regulars”—those who make up what used to be called the machine—Garcia would be making his first return to office since the HDO knocked him out of the state senate in 1998. Already some of his supporters are pushing him forward as a leader of a progressive resurgence.

So voters of all stripes might be ready for a choice other than Daley next February. But the path to a first-rate challenge is littered with obstacles.

The first is money. Anyone who wants to be taken seriously will need to be able to afford a sustained ad campaign, primarily on television. Analysts tell me this would require at least a couple million bucks. “I wouldn’t want to go into it with less than four or five million,” says one local pol—who, like many others I spoke to for this piece, didn’t want to be identified because he feared retribution by the mayor.

But where’s the money going to come from? Maybe a wealthy independent candidate like New York’s Michael Bloomberg could pull it off. But area business leaders have been big supporters of Daley through the years and are unlikely to endanger that relationship as long as there’s a chance he’s running—and the mayor will probably delay any announcement for months. Who would want to risk future business prospects by taking on Daley—or even backing someone else taking on Daley?

What about progressive unions, which ponied up millions of dollars for favored aldermanic candidates in 2007? “I don’t see anybody out there who can do it,” says Jerry Morrison, executive director of the Service Employees International Union’s Illinois state council. “So I have no reason to believe there’s going to be a mayoral race, and the unions aren’t going to support anyone who’s not a serious candidate.”

Any formidable challenger will also need to build a first-rate political organization. With the decline of patronage there are few existing organizations with reach beyond a single ward—I can’t think of more than a couple—and they’ve always been aligned with Daley. The mayor doesn’t have the troops he once did, but he’s still got the funds to hire people. Anyone running citywide will have to spend the money and time to recruit and coordinate volunteers, craft and spread a message, and gather the 12,500 valid signatures needed to get on the ballot. The clock is already ticking. “The more time passes, the more likely it is that we know the result of the election next year,” says another local elected official who didn’t want to be named.

Adds a local political consultant: “What thousand people do you need to call? You want to be out there. You want to be ready to hit summer festivals, food tents. You want to sit down with people and say, ‘Do you live in the city? Tell me what’s wrong.’ You need to hit block clubs and community meetings. You start with where your base is demographically and geographically and then start extending from there. Talk about issues particular to your part of town and then move outward to the rest of the city. It’s like spreading asphalt—eventually you want to cover the whole driveway.”

And that’s just the offense. Challengers need to build name recognition as broadly and as soon as possible, but they also have to think about how to do it without being undercut, backstabbed, or crushed before the contest is even under way. “Whoever does run has to be braced for the fact that they’re going to be fucked with,” an alderman told me.

“You have to be willing to see your political career go down in a blaze of glory,” said another.

And hey, don’t all jump in at once—seriously. Analysts say the mayor can only be beat if he’s faced with one or two serious challengers—any more will dilute the anti-Daley vote. That’s what happened when three challengers came up short against a weakened Old Man Daley in 1975. “The challenge is to keep other people out of it,” says the political consultant. “Make him fear the one-on-one fight. Identify the stalking horses.”

Last but not least, anyone who runs has to come in with a record of accomplishment and a sincere desire to run the city, neither of which is a small thing. “As much as people have been critical of Mayor Daley, myself included at times, it’s a hell of a job,” says state senator Kwame Raoul, a pragmatic progressive who emphatically adds that he’s not interested. “It’s a real headache. There are times, like now, when there’s nothing you can do right.”

Some pols and operatives don’t believe anyone can give Daley a real challenge. “Is the anger out there? Sure, but I’ve seen it before, and on Election Day people say, ‘Well, OK, fine,'” says an elected official who’s considered his own mayoral prospects. “People have to actually see you as someone who can do a better job—and then they have to take a chance on you. There’s no one in Chicago who’s done what’s necessary to get into that position.”

“But we’ve got to have somebody run,” says Second Ward alderman Bob Fioretti. He worries that if voters and elected officials don’t start contemplating life after Daley, the city will descend into chaos when he’s gone—whether he leaves of his own accord or not. “At some point this comes to an end, whether it’s through death or otherwise,” Fioretti says. “And I know the fear out there about what happens then.”   v

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