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Can Rahm Emanuel Fix Chicago’s Problems?

THE NEW MAN ON FIVE: In his first few months as mayor of Chicago, Rahm Emanuel has moved at breakneck speed to tackle long-neglected problems and drag a torpid bureaucracy into the 21st century. But the biggest battles lie ahead. Does he have what it takes to save the city?

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Rahm Emanuel
“I feel the sense of responsibility,” says Emanuel. “I think the public has expectations. I don’t want to let ’em down.”  Photograph: Nancy Stone/Chicago Tribune

Rahm Emanuel removes his blue suit jacket, puts on dark sunglasses, and hops into the back of his black SUV. He squirts a blob of Purell sanitizer onto his palms—virtually a job requirement for glad-handing politicians—and then takes a big swig of bottled water.

Emanuel is slight of build, but his cocksure swagger makes him seem bigger. He has a tanned complexion, with salt-and-pepper hair—mostly salt—cropped fairly short and perfectly coifed, as if he just left the barbershop. Deep, dark bags encircle his eyes, the result of little sleep and the breakneck schedule he keeps. But right now he is feeling loose and relaxed—like a school kid who knows he aced a test. Which he has just done, more or less. The new mayor, 46 days in office at this point, has spent the past hour fielding questions submitted via Facebook during a live televised town hall meeting filmed at Kennedy-King College in Englewood. He pretty much nailed every question without breaking a sweat and artfully dodged two or three trickier ones.

Rock music plays on the radio in the background, just the way the mayor likes it, as we start the nine-mile drive back downtown to City Hall. Emanuel reclines a bit in his seat, one of the few opportunities he has in his long workday to relax. He betrays a slight annoyance at my presence in the back of the SUV—as if he were unhappy at being dragged into this car ride. Famously prickly, Emanuel at first spits out staccato answers to my questions. But the more he talks, the more revved up he gets, and pretty soon he is waxing expansive on the joys of the job and on all of the things he wants to accomplish in his first 100 days, first year, and first term—most of it boilerplate stuff he repeated ad nauseum during the campaign.

Suddenly he practically leaps out of his seat. From his window, he notices that we are approaching a private road that runs through a tunnel at McCormick Place—a route that the mayor’s security detail sometimes uses as a shortcut to the Loop.

“All right!” Emanuel calls out excitedly as we enter the tunnel. “I’m like Batman! I’m going down the Bat Cave! The Bat Road!”

He turns to Chris Mather, his communications director, seated next to him, and cracks, “We’re going to rename it. I want a sign made—‘Bat Road.’”

“We got rid of those,” Mather replies, in the obliging straight-woman role. (A couple of weeks earlier, Emanuel had put an end to displaying the mayor’s name on city signs, a practice, he explained, that wasn’t worth the cost, given the city’s financial woes.)

“Are you kidding? I can donate a sign,” says Emanuel, who likes to have the last word.

We pull up to a gate at the tunnel’s entrance. “Music louder!” Emanuel calls out to his driver. “This is the Bat Road!”

Chicago is a damsel in distress, in serious need of a superhero. The city is losing residents—more than 200,000 over the past decade, according to the latest census—and, just as significantly, many thousands of businesses and jobs with them—more than 30,000 between 2009 and 2010 alone. Not only is Chicago at risk of becoming the fourth-largest U.S. city, slipping behind Houston, it is careening toward bankruptcy. Next year, the city will be $635 million in the hole, not including unfunded pension obligations. Double that if you count the more than $700 million of red ink from Chicago Public Schools, which Emanuel also oversees but whose budget is separate from the city’s. And let’s not even get started on the Chicago Transit Authority, which is in similarly poor fiscal health.

Beyond the dire finances, there is also the stagnant housing market, an economy that is still in the tank, and a murder rate that is three times as high as that of New York City, which has nearly triple Chicago’s population. For some time now, the city’s spirits have seemed lower than the 76-foot hole dug for the never-built Chicago Spire. That gaping void has become a sad monument for a city that is not on the move but on pause—or worse, spiraling downward.

Rahm Emanuel wants to be Chicago’s savior, its Batman. “I feel the sense of responsibility,” he tells me. “I think the public has expectations. I don’t want to let ’em down.”

Since taking over as Chicago’s 46th mayor in May, the 51-year-old Emanuel has projected energy, urgency, and confidence. He has brought a more professional, West Wing–like management style to City Hall, which had felt increasingly anachronistic in the waning years of Richard M. Daley’s reign. (Emanuel’s office wasn’t even wired for Internet service when he moved in.) With brass-tacks candor, he has sent a clear and unmistakable message that the old order—presided over by Daley, with whom Emanuel will inevitably be compared—is gone. As the deputy mayor, Mark Angelson, said to union officials who were locked in a battle this summer with Emanuel’s administration over work-rule changes and layoffs: “There’s a new sheriff in town.”

These days, City Hall has the feel of a hot start-up. The suite of offices on the fifth floor where the mayor and his top staff work crackles with high-voltage—if somewhat chaotic—energy. Spend time around the mayor’s office and you can’t miss the small army of 20- and 30-somethings (some of them returning Obama administration veterans) in power suits, clutching their Starbucks cups or BlackBerrys, bouncing around the hallways or busily at work in a hive of cubicles. It is a marked contrast to the perceptible malaise and inertia of Daley’s last years, in which new ideas seemed few and far between and there was a palpable sense of an administration merely treading water.

Emanuel’s changes are more than just stylistic; they are generational. He is astute enough to realize that the old bedrock principle of “good government is good politics”—especially the practice of promising city jobs in exchange for campaign work—is outmoded and unsustainable. The patronage and cronyism that were permissible in the past, he knows, are not only bad government but also very bad politics at a time when Chicago’s unemployment rate tops 9 percent and many residents are exasperated by the corruption, waste, and selfishness that flourish here. Through his rhetoric and actions, Emanuel has positioned himself as a change agent for the future—despite his obvious debts to Chicago’s political past. “We aren’t our parents’ Chicago anymore,” he tells me during one of our interviews. “That’s a good thing. We appreciate what our parents did, but this is different.”

To underscore the point, Emanuel has led a full-on assault against the “status quo”—two words, he has said, he is “banning” from the vernacular of city government. What is the status quo? It is years’ worth of unbalanced budgets, patronage-padded payrolls, and insider deals; a chronically failing public school system; a dysfunctional and, literally, crumbling mass transit system; an undermanned and outgunned police force; and an entrenched and corrupt political culture. At the everyday level, it is waste (three city workers needed to change one streetlight bulb), Rube Goldberg–like inefficiency (40 different firms to process and collect checks), and insider privilege (four taxpayer-funded bodyguards for one alderman, Edward Burke). It is 1,400-plus shootings a year, a high-school graduation rate of 50 percent, and a Red Line train that has difficulty getting from Howard Street to 95th Street trouble-free.

“Some people were telling me, ‘Rahm, don’t run for mayor, why would you want this job?’” says Emanuel. “Well, I love this city. I think it can achieve great things, and I’m ready to put my resources to that.”

One could be forgiven for wondering if Emanuel is some kind of masochist. He spent five years—an eternity when measured in doglike West Wing time—as Bill Clinton’s chief political adviser, remaining through the Monica Lewinsky scandal and the subsequent impeachment saga; he returned to the White House with Barack Obama, smack-dab in the midst of the Great Recession and with two taxing and unpopular wars overseas; and he wanted to be Chicago’s mayor, despite the “shit sandwich,” as Emanuel has privately described the mess, bequeathed to him by his predecessor.

With a self-assuredness that borders on cockiness, Emanuel is confident that he has the right plan and an able leadership team in place to turn things around. A fiery competitor, he seems to want to constantly one-up his predecessor—not necessarily to rub Daley’s nose in it, but because he is never satisfied. (He has a to-do list that he says his staff “lives in fear of.”)

The political-operative-turned-commentator Paul Begala, one of Emanuel’s close friends, gave an apropos description of then congressman Emanuel to Rolling Stone: “He’s got this big old pair of brass balls, and you can just hear ’em clanging when he’s walking down the halls of Congress.”

That same clanging sound now reverberates throughout City Hall, as well as across all 228 square miles that lie within Chicago’s city limits—and can even be heard 200 miles farther south, down I-55, in Springfield.

Emanuel is clearly relishing the role. “This is the best job I’ve had, and I’ve had great jobs,” he tells me. “I jokingly say—and it’s a joke—I always thought it was a great job, but if I knew it was as great as it is, I’d have challenged Rich [Daley] four years ago.”

So far, everything for Emanuel has gone almost like clockwork, perhaps too smoothly. But this is still the prelude, the honeymoon, and the big battles are about to really begin. For starters, his first budget, for 2012, is due in the coming weeks, and he’ll have to somehow erase the city’s $635 million deficit with a lot less money coming in from the state and federal governments. Complicating this task, too, he has promised to do so without raising taxes, cutting police officers, or relying on one-time revenues: tactics that Daley used to balance his recent budgets but that Emanuel calls “cheating.” The painful choices he will have to make are no doubt going to be unpopular with many, especially the unions representing city workers and teachers. Next May, Emanuel will face another huge test when the NATO and G-8 summit meetings, which he helped bring here, come to town, creating a host of security challenges.

Meanwhile, he has his 71-page list of promises he says he intends to keep, come hell or high water. Some are smaller tasks, some are seemingly intractable large-scale problems. But just months into office, one could wonder: Did Emanuel set expectations too high? Can he keep up the frenzied pace? And will his sharp-elbowed manner wear well over time?


On the last day of June, the day of the Facebook town hall, I was invited to ride along with Emanuel. I was instructed to meet the mayor and his entourage beforehand at the Sheraton, where Emanuel was spending the morning schmoozing with CEOs and government officials who were in town for a Clinton Global Initiative conference. As I waited for Emanuel in the lobby in front of Shula’s Steak House, where the mayor had dropped by to speak to a group of UBS bankers, Mather, the communications director, approached me.

“Stay close,” she cautioned. “When he moves, we move. Fast!”

Sure enough, Emanuel soon charged out of the restaurant’s glass doors, like a racehorse bolting free of the paddock, blowing past me with a curt “Hello.”

To say Emanuel’s first few months in office have been similarly fast paced would be an understatement. Less than an hour after being sworn in, he had already signed six executive orders to reform some of the city’s ethics rules and cut $75 million from the 2011 budget. Hardly a day has passed since his inauguration—since Election Day, really—without Emanuel announcing some new policy or program. “At any given moment there seems to be six Mayor Emanuels announcing six different initiatives,” the New York Times columnist David Brooks observed in late June.

Notoriously impatient, Emanuel says he wants to go even faster. “If you think this is fast, wait—we’re going to pick up the pace,” he boasts. He is so focused on the job at hand and in such a hurry to get things done that once, when Sean Parker, the billionaire founding president of Facebook, was in town and was taken to meet him, Emanuel, according to a witness, hurried by him without stopping, barely even looking back to tell Parker, “I can’t talk to you now—I’ve got work to do.” Parker, incidentally, had cut Emanuel a $100,000 check for his mayoral candidacy.

Emanuel has already racked up significant legislative successes in both the City Council and in the Statehouse (not unlike how, as chief of staff for President Barack Obama, he led the charge on Capitol Hill to win approval for funding for the Troubled Asset Relief Program [TARP] and the health care overhaul legislation). He also cleaned house at the Chicago Board of Education, replacing all seven members, and eliminated and consolidated city departments. He took away credit cards from city workers and cut the lucrative stipends for two city boards and commissions, and he ordered a review of the pay for all appointees. He has used his connections to court companies—from United Airlines and Walgreens to Motorola Solutions and Chase—and to lure jobs, 4,200 of them and counting, into the city. He redeployed 650 police officers from desk jobs to heavy-crime areas and partially privatized and expanded the city’s recycling program. The list goes on.

Emanuel’s frenetic pace is reminiscent of the small-ball brand of politics he championed in the Obama administration and, years earlier, in the Clinton White House, when he spearheaded efforts to pass NAFTA, the crime bill, and welfare reform: a guiding philosophy of doing a lot of accomplishable things, one step at a time, that add up to a much bigger record of accomplishment. The little victories create a sense of momentum—or, as Emanuel likes to say, a feeling that “confidence breeds capability.”

It appears to be working. Emanuel’s job performance has won widespread plaudits—so much so that he is already generating 2016 presidential speculation. (Emanuel dismisses such talk in typical fashion. When, for instance, one reporter asked him a day before his inauguration if he had presidential ambitions, Emanuel brandished his middle finger at the reporter and said, “That’s the dumbest thing in the world.”) Practically wherever he goes, passersby want to shake his hand or give him a high-five, or they hold up their phones to snap pictures. Part of this reaction certainly has to do with his celebrity. Since his stint as White House chief of staff, he has been one of the most visible figures in American politics—even satirized on Saturday Night Live.

Emanuel is not a natural retail politician. He does not have Bill Clinton’s gift of feel-your-pain empathy or Barack Obama’s rhetorical flourishes. But he is a workhorse, and during the campaign and as mayor, he has spent untold hours at el stops, grocery stores, firehouses, and churches across the city, pressing the flesh and, more important, just listening to what’s on residents’ minds. He has also reached out to Chicagoans through Facebook and Twitter and through websites that his office has set up to solicit feedback and ideas. He has reportedly even personally called some residents who offered ideas that intrigued him.

So far, Emanuel has been rewarded for his efforts, earning glowing press and, more significantly, support from the public. An internal poll conducted by his political shop in late August showed a job approval rating of 79 percent, huge numbers by political standards. (Another poll, taken in June, showed similar results.)

His popularity was on full display one sunshine-filled Saturday morning in mid-August, at the Bud Billiken Parade in Bronzeville. Upon his arrival, Emanuel was mobbed by paradegoers. Before the festivities began, an alderman, Walter Burnett, followed Emanuel around like a pestering little brother. “Can I walk with you?” Burnett kept asking. “I don’t run this show,” Emanuel told him. Emanuel took a hero’s stroll—actually a jog—down the two-mile route along King Drive, zigzagging from one side to the other to shake hands, kiss babies, and soak up the adulation from spectators shouting, “Rahm!” and “We love you!”

At one point along the route, when Emanuel ran over to hug and high-five a group in the crowd, I overheard one police officer tell another, “He ain’t like Daley, huh?”

Emanuel has a joke about how he can tell if he’s popular or not: “My test of this—my joke—is when [people] wave, all five fingers are still up in the air. You always know how you’re doing whether they drop any of those fingers.”


Not that there haven’t been stumbles or embarrassments. For one, Emanuel’s otherwise flawless unveiling of his cabinet faltered when it mattered, in his two most important appointments: his choices for school superintendent and police superintendent. Emanuel scrambled into damage-control mode after Jean-Claude Brizard, his pick to head up Chicago Public Schools, came under heavy fire for exaggerated graduation rates at the school district in Rochester, New York, that he had just left and for two federal discrimination lawsuits filed against Brizard during his three-year tenure. Was there a flaw in the mayor-elect’s vetting process? the local press wondered. Similarly, a week after Emanuel chose Garry McCarthy, the police chief of Newark, New Jersey, as Chicago’s new police superintendent, the U.S. Justice Department announced that it was launching an investigation into hundreds of complaints that the Newark police force had violated civil rights—including false arrest, discrimination, and excessive force—and simply swept the allegations under the rug.

Emanuel also took criticism when, on Memorial Day, city and police officials abruptly shut down North Avenue Beach, citing excessive heat. (It was 88 degrees that day.) News reports soon surfaced casting doubt on the official story. It turned out that the police had gotten a slew of 911 calls about gang fights at the beach, and many people suspect that Emanuel and McCarthy cleared the area not on account of the weather but because they didn’t want to suffer the negative publicity that would ensue if the violence got out of hand.

Then there’s the story Emanuel likes to repeat (he did so with me at least twice, and I heard him tell it again at other public outings) about how, during a classroom visit to South Loop Elementary, an inquisitive first grader asked him about his proposal to lengthen the school day and school year. The mayor was so impressed by the little boy’s question that he invited the child to join him at the bill-signing ceremony a couple of weeks later. The part he doesn’t mention: His office invited the wrong student, a girl, who stood with Emanuel at the event. “Oops!” read the Sun-Times headline the next day.

Emanuel’s rush to make his mark is in part self-serving: He wants to escape Daley’s long shadow as quickly as possible. He has a tough, if not impossible, act to follow. Love him or hate him, Daley was a transformative mayor. For nearly a quarter of a century, he changed Chicago in ways large (Millennium Park) and small (wrought-iron fences), and he helped keep the city from becoming another Rust Belt casualty.

Daley and Emanuel go way back. They are political allies and personal friends. A fresh-faced Emanuel rose to political prominence as the chief fundraiser for Daley’s successful mayoral campaign in 1989, and many years later, in 2002, Daley’s political muscle helped Emanuel win his congressional seat.

Early on during Emanuel’s transition as mayor, when a reporter wondered if he was “walking a tightrope” in his comments about Daley, Emanuel just grinned—or maybe he was gritting his teeth—and cracked, “Thank God I had some ballet training.” He quickly changed the subject.

In private settings, though, Emanuel has been more candid, says one close supporter who asked not to be named. According to the supporter, Emanuel once kvetched to him about how the city was in worse shape than he had originally thought. “Rahm feels there was a lot broken that no one was calling Rich on,” the supporter tells me. “But he thinks it doesn’t do any good to say, ‘Look at the mess [Daley] got us in.’”

Some among the political cognoscenti have tried to read between the lines of Emanuel’s rhetoric about the city’s problems and have concluded that he is attempting to pin the blame on Daley, subtly, of course. In late July, for instance, when Emanuel released his administration’s report on the financial health of Chicago—a highly damning analysis of the city’s fiscal stewardship over the previous ten years—James Warren, a columnist for the Chicago News Cooperative, described the report as “the equivalent of a superficially alluring velvet shiv” stuck into Daley’s back.

Others allege that people in the new administration—possibly even Emanuel himself—have been going out of their way to feed the press stories to protect the new mayor from being battered over anything remotely scandalous that might have occurred on his predecessor’s watch.

A prominent Chicago political insider, for one, points to a Sun-Times article published in early June that revealed that Daley’s son, Patrick, had collected $708,999 from a Chicago-based wireless Internet company less than a year after the company signed a 2006 contract with the city to provide Wi-Fi at Midway and O’Hare. The article was based on newly obtained company documents.

“After all these years trying to catch the mayor’s kid’s fingers in the cookie jar, some information suddenly becomes available?” the insider asks rhetorically. “It was just too convenient. It was a direct message being sent [to Daley]—‘Make sure your people behave themselves. I hold the keys to the kingdom. The king is dead. Long live the king.’”

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