Meet the New Boss

Tattered finances, broken schools, rampant crime—Rahm Emanuel is taking on an entrenched bureaucracy and a legacy of corruption to fix the problems that American voters care about most deeply. Can the mayor of Chicago make the city that works work?
Tim Klein

I was walking around my sister’s Near North neighborhood in Chicago recently and came upon a small patch of green called Bauler Park. Paddy Bauler was the rollicking tavern owner and 43rd Ward alderman who in 1955 famously shouted, upon hearing of the election of Richard J. Daley as mayor: “Chicago ain’t ready for reform!”

More than half a century later, the man who not long ago represented Bauler’s neighborhood in Congress insists that Chicago is finally ready. Rahm Emanuel, who succeeded old man Daley’s son Rich as mayor last May, has to be careful not to repudiate the Daleys, who helped nurture his rise. And “The Missile,” as the Chicago journalist James Warren dubbed him, is hardly a good-government “goo goo.” “Taking the politics out of politics is like taking the money out of capitalism,” Emanuel told me during his mayoral campaign. But in locking on to his three high-value targets—the city’s tattered finances, a murder rate twice that of New York, and schools that aren’t preparing Chicago’s future workforce—Rahm (as he’s known everywhere) is bent on wholesale reform of “the Chicago Way.”

Ever since the film The Untouchables popularized the term, there’s been some misunderstanding about what the Chicago Way means. In the movie, Sean Connery’s Irish cop describes to Kevin Costner’s Eliot Ness how to get Al Capone: “He pulls a knife, you pull a gun. He sends one of yours to the hospital, you send one of his to the morgue! That’s the Chicago Way!” And that will be Rahm’s way, at least some of the time. But in practice, this vague urban modus operandi is less about vengeance than venality—payoffs, kickbacks, and ghost-hiring, not to mention the destructive if perfectly legal tradition of cozy union contracts and the newer “pinstripe patronage” of sketchy bond deals and privatized city functions. In its mid-century heyday, the Chicago “machine” often delivered services along with the corruption, but the parts got rusty. In the decade following the first Mayor Daley’s death, in 1976, the city’s political structure broke into warring factions, which beginning in 1989 were brought into a surprisingly sturdy alliance by his son, who developed strong ties to the black and Latino communities.

Richard M. Daley has a lot to show for his 22 years in office. He built the spectacular Millennium Park, began school reform in a system that in the 1980s was considered the worst in urban America, and helped revitalize fading neighborhoods that had long been the backbone of Chicago. But he did much of it on borrowed money, and by 2010 his profligate spending, a declining population, and the economic downturn combined to send the city $637 million into the red. Low-income kids were still getting shot every day; the schools were still a mess; and grumbling grew louder about the mayor using half a billion a year in economic-development money like a piggy bank for pet projects. With the failed bid for the 2016 Olympics, a sense of ennui set in, something Rahm recalls as “the most dangerous thing … the sense of capacity being scaled back and questioned, second-guessed.” Daley announced in September of 2010 that he wouldn’t seek reelection, and Rahm jumped into the race.

For months, Rahm waited for a final ruling on his eligibility, which was challenged on the dubious grounds that he wasn’t really a Chicago resident. But his decision to descend on Chicago from his perch in Washington had its advantages. His loyalty to President Obama gave him immediate street cred with African Americans, who make up 40 percent of the vote. And his stature as a national figure helped him prevail without the support of the usual party hacks, plugged-in local contractors, and intransigent unions. (Much of his campaign money was raised in big donations—just before the law changed to limit them—from local CEOs, out-of-town hedge-fund managers, and Hollywood moguls.) A tactical thinker known for advocating small-bore or symbolic initiatives in both the Clinton and Obama White Houses (for instance, he begged Obama to back incremental, not large-scale, health-care reform), Rahm is more strategic nowadays, and intensely focused on his sweeping vision for the future of Chicago. He knows that to achieve it, he must extinguish many of the old ways of doing business.

I grew up near Wrigley Field, amused by the lore of machine precinct captains reminding residents to “vote early and often.” I skipped school every Election Day to canvass for earnest reform candidates, but loved the roguish charm of the city’s politics and inhaled books with titles like Clout, Boss, and Don’t Make No Waves, Don’t Back No Losers. Younger generations of Chicagoans are not so enamored. “They’re cynical about City Hall, post-Blago,” Rahm tells me, referring to the recent sentencing of Rod Blagojevich, who is the second Illinois governor now behind bars (George Ryan is the other) and the fourth in 40 years. The best-known charges against Blagojevich involved his efforts to win favors in exchange for naming someone to fill Barack Obama’s Senate seat after Obama became president. Rahm spoke often on the phone with the governor in that period, and grew so suspicious that the FBI was wiretapping the calls that, as he later bragged, “I didn’t drop the fucking ‘f bomb’ once!” (Rahm was never implicated in any wrongdoing.)

For all the attention given to Obama’s Senate seat, most of the rap against Blagojevich involved depressingly routine “pay to play” shakedowns, in which the governor was nailed for being unsubtle in the way he demanded campaign contributions from those aiming for state contracts. The same thing had gone on less brazenly at the city level under Rich Daley, who was untouched by scandal personally but, like his father, often turned a blind eye to the influence-peddling around him.

Rahm quotes an iconic Chicago line to make his point on reform: “We don’t want nobody nobody sent.” His aim, he says, is to build a Chicago where everybody is a somebody, even if nobody sent ’em. The mayor’s office says that it has recorded more than 6.4 million total visits to the city’s new Web site, which, among other new transparency measures, posts all government salaries. During the debate over last year’s budget, more than 40,000 Chicagoans commented online about where to make cuts. Paddy Bauler is cursing Twitter from the grave.

“We are known as ‘the city that works,’” Rahm says. “You gotta make sure it works for everybody and not just a few.” He insists that the deeply entrenched system is already beginning to change: “One mother having difficulty with CPS [Chicago Public Schools] posts something on Facebook about schools. She got called that day by CPS. When the fuck did that ever happen around here? Another person tweeted about a pothole on her street and the Chicago Department of Transportation was at the pothole the next day, filling it!”

Sitting in his cavernous office on the fifth floor of City Hall, Rahm lowers his outstretched, empty palms, then raises them above his waist. “If you have your hands above the table, you can’t deal from the bottom of the deck,” he says. When he sees that this gets a smile out of me, he warms to his new metaphor.

“Stop putting your hands below the table!” he exclaims, as if addressing the ghosts of boodlers and ward heelers past, the ones who in the 1960s led the great columnist Mike Royko to propose changing the motto on the seal of Chicago from Urbs in Horto (“City in a Garden”) to Ubi Est Mea (“Where’s Mine?”). To encourage better table manners, the mayor has required the posting of all no-bid contracts (“The no-bidders know: don’t fuck with this”) and launched innovative “reverse auctions,” wherein bidders bid down the cost of construction projects and the city saves money. “Rather than sealed bids,” Rahm explains, “Jonathan Alter Inc. will post his bid online, and now Chris Mather LLC [his communications chief at the time, sitting nearby] will say, ‘Okay, I can beat Jonathan; here’s mine online.’”

Reverse auctions are but one of a hundred Missile launches since Rahm took office.

Rahm may have been a risky purchase, but Chicagoans are lining up to buy him. Last summer, his approval ratings from his private polls (leaked by him) hit 79 percent, and his polls show him down only about 10 points since then. So far, almost everyone—except members of the Chicago Teachers Union, the Amalgamated Transit Union, and the American Federation of State, County and Municipal Employees and their backers—likes Rahm’s performance.

“Rahm is what the city needs. You gotta have a tough manager,” former Illinois Governor Jim Thompson, a moderate Republican, tells me, expressing a representative view of the downtown business community. Steve Chapman, a conservative Chicago Tribune columnist who lambasted Rahm when he was White House chief of staff, wrote a column last fall saying that so far there was little reason to criticize the mayor. I found this perspective common among my liberal friends, too. Don Rose, a longtime voice of progressive Chicago and a tough man to please, is concerned that Rahm has no major anti-poverty plan yet, but says he’s doing a good job modernizing “slovenly government functions.”

The good feeling will fade with various flaps, feuds, and freak-outs to come. It always does. In May, the city will host the NATO summit, and protesters from around the world have promised a “Chicago Spring.”* Rahm has already had to back off his tough new ordinances that would have increased fines for resisting arrest, a sign that he might lack the finesse to get through the summit without ugly clashes. Sooner or later, he’ll face bruising strikes and have his rocky innings with Illinois Governor Pat Quinn and power brokers like Michael Madigan, speaker of the Illinois House, and Ed Burke, the Chicago City Council’s finance-committee chairman, who plotted against him during the campaign. He is already at odds with Joe Ferguson, the city’s inspector general, over whether a mayor obsessed with accountability for others should apply it to himself and let the IG be independent (Rahm argues the position falls under the mayor’s office).

The Tribune believes that for all the promises of transparency, “the mayor’s office is opaque” and doesn’t let the public see how decisions are made, as the hard-charging reporter David Kidwell told Rahm in a confrontational and sarcastic (on both sides) February interview. The Tribune, suspicious that the city was expanding the use of speed cameras at traffic intersections more to raise revenue than to increase safety, asked for 165 internal e-mails on the issue and received only 25, none of them from the mayor. (He views e-mails as comparable to private phone conversations and staff meetings and thus sees no need to make them all public.) To win support for the cameras, Rahm had claimed publicly that Chicago was among the worst big cities for pedestrian fatalities, when in fact it’s among the best. The newspaper, for its part, virtually ignored a study showing that cameras had cut fatalities by 60 percent in the areas where they’d been tried. He got the better of this argument, but because he can be as petulant as Rich Daley, he will offend plenty of people before long. They will lie in wait until his popularity wanes, then pounce.

And yet, I can’t help holding out hope that Rahm’s success in his first year gives him a fighting chance to have not just a good run as mayor but a historic one. He has established useful precedents for dealing successfully with Springfield, where he helped lobby through a model school-reform bill, and with the City Council, where against all expectations—including Rahm’s—his first “austerity budget” was approved 50–0. And his relentlessness about measuring success and staying connected to voters (he takes the “L” to work a couple days a week, to chat with commuters) will serve him well.

While raising expectations can breed disappointment, as President Obama has found, it can also build momentum for even more-ambitious change. More than a year ago, I stood in a union hall on the Near West Side and heard Rahm give his Election Night victory speech. After the platitudes and self-congratulation, he turned unusually serious. “We have not won anything until kids can go to school thinking of their studies and not their safety,” he told the crowd. Then he repeated it for emphasis: “We have not won anything.” Rahm knew that gangs terrorize kids every day across broad swaths of the South and West Sides. He was aiming high and daring Chicago to remember.

Rahm Israel Emanuel was born in 1959, two years after me, and as Chicago Jews immersed in politics, we have superficially similar backgrounds. But he returned to the city to work on campaigns after getting his degree from Sarah Lawrence, then gravitated home after stints in Washington. I go back mostly to visit family.

My parents met Rahm before I did, and disagreed with each other about him. My mother, the late Joanne Alter, was a feminist reformer who went to the first Mayor Daley in 1972 and told him that it was the 20th century and he must let women into the Democratic Party. Daley, clever about neutralizing opposition, slated her for a position near the bottom of the ticket, commissioner of the Water Reclamation District, and she became the first woman elected to public office in Cook County. Later, she turned down a young Rahm Emanuel for a job on one of her campaigns because she thought he was arrogant and obnoxious, the kind of guy, she said, who was always looking over your shoulder to see if someone more important was in the room (although she would have loved his present-day focus on cleaning up the riverbanks of the Chicago River, one of her pet causes). My father, Jim Alter, a retired Chicago businessman, has long admired Rahm’s political skills. He was impressed that his congressman managed to both offer outstanding constituent services and rise in just four years to the House leadership. It didn’t hurt when Rahm arranged for a local documentary to be made about World War II veterans in his district that featured my father’s exploits as a combat aviator.

I’ve been writing about Rahm periodically since 1992, when he broke national Democratic Party records as a fund-raiser for Bill Clinton’s presidential campaign. He was notorious that year for threatening millionaires twice his age that they’d be screwed if they didn’t max out now, a threat that, even when unspoken, should keep his campaign coffers overstuffed in the years ahead. After impressing Clinton with his management of the inauguration, Rahm proved so annoying in the White House that Hillary Clinton tried to fire him. He simply refused to go, rehabilitated himself by shepherding the 1994 crime bill and other Clinton initiatives through Congress, and proved that he was one of only a handful of people in Washington who could actually get something done.

Chicagoans like having a rich mayor; it gives them one less thing to worry about. Rahm made his bundle (more than $18 million) in two and a half years in the Chicago office of Wasserstein Perella, largely because he was lucky enough to be there when the investment bank was sold. Against the odds, he got himself elected to the House of Representatives in 2002, with the help of Daley and his own better-than-expected common touch. His legend grew in 2006, after he won control of the House back for the Democrats as head of the Democratic Congressional Campaign Committee, and he set his sights on being the first Jewish speaker. When, just before the 2008 presidential election, Barack Obama asked him to be chief of staff if he won, Rahm hesitated, confiding to anyone within earshot how hard it was to give up the autonomy of elected office. Inside the White House, he helped Obama avoid another depression and amass the most extensive legislative record since Lyndon Johnson, but the job left him exhausted and unfulfilled. Almost from the moment he arrived, he told me and other reporters that he would run for mayor of Chicago in a heartbeat if Rich Daley decided not to seek reelection in 2011.

Rahm knows I find him able and impressively hyperactive, but when I asked him last fall whether he’s too combative to wear well with the public, he proved my point by getting testy. “Don’t stereotype me for how you knew me when I was 24, when now I’m 51 and I’m a different person and I’m a more mature person. Okay? Don’t write within your stereotypes. Okay? I’m smarter about the pitches I have to swing at. When I grew up, I had to swing at them all.” He cites several examples to prove he knows that, as Ted Kennedy liked to say, “Honey works as well as vinegar,” from courtesy calls to labor leaders who opposed him, to what he says is the first-ever reception hosted by a Chicago mayor in honor of Springfield legislators. And instead of trying to strip Alderman Burke of his widely resented 24-hour, four-man security detail, Rahm negotiated a reduction of the detail to two retired police officers. “He’s always known when to step on the gas, but he’s developed the ability to throttle down and work circuitously rather than running through walls,” says David Axelrod, another Chicagoan and now the chief strategist of Obama’s reelection campaign, who remains a close friend. Rahm’s trying to be less profane (at least in public) and is no longer thrilled to be called “Rahmbo,” after the Sylvester Stallone character who invades North Vietnam by himself.

No one ever becomes “a different person,” but greater maturity is always possible. Rahm’s older brother, Ezekiel, an oncologist and medical ethicist who worked in the Obama White House and is writing a book titled Growing Up Emanuel (the third brother, Ari, runs a large Hollywood talent agency), says he hasn’t seen Rahm so content in more than 20 years. “I know the world finds it hard to believe, but he’s calmer now, maybe because of his family. And he’s more articulate about his own thoughts and more willing to break down for others what he knows intuitively. On the other hand, you’ve got eternal truths—he’s impatient, and the most important quality for him is execution. That’s inherited genetically from my dad [a pediatrician who fought in Israel’s War of Independence in 1948]. He was always saying, ‘Get on with it. Get it done.’”

Rahm does seem much happier than he did a couple years ago, when I interviewed him at the White House. After he took office last spring, he joked to his predecessor: “Rich, you lied to me. You said this is a good job. It’s actually a great job. If I’d known how great, I would have primaried you.” These are the kinds of stories that generate affection. Bruce Reed, currently Vice President Biden’s chief of staff and a co-author with Emanuel of the 2006 book The Plan: Big Ideas for America, likes to say that those who don’t hate Rahm love him a lot. Even his intensity can be endearing. “Lunch with Rahm is like speed dating,” Dick Durbin, the senior senator from Illinois, told me. “He’ll bring up 30 items in an hour, and if you’re late, he’ll squeeze the 30 into 30 minutes.”

The mayor’s claims that he has mellowed ring a little hollow, given his track record. He said the same thing when he went to Congress and then when he reached the Obama White House, before the leaks of hair-raising accounts that made him seem like the same old rude guy. But the abuse he delivers has a way of inspiring loyalty. Several former aides compare him to a coach whose tough-love attitude is appreciated only in retrospect. One fed-up White House official told me a couple of years ago that Rahm “treats us all like we’re Lloyd,” a reference to the Asian American secretary on the HBO show Entourage, who is endlessly abused by Ari Gold, the over-caffeinated character based on Ari Emanuel. But the same official later admitted that she missed Rahm’s insult-rich Jewish humor and preferred it to the insular, corporate approach of Bill Daley, who got his job as chief of staff in part because Rahm pushed Obama to hire him.

Any new maturity comes from Rahm’s almost maniacal discipline. But it is frequently tested, as when during the mayoral campaign he faced a grueling all-day public hearing over whether he should be allowed to stay on the ballot. I’d asked him at the time how he kept his legendary impatience in check through several hours of personal invective and conspiracy theories flung at him by a Star Wars–cantina collection of Chicagoans. Rahm says he looked at a picture of his wife, Amy Rule, and their three children that he kept on the hearing-room table and remembered how his family teased his youngest child, Leah, about memorizing a Thomas Paine speech while wearing her retainer. “I kept looking at the picture and hearing my inner voice,” Rahm says. “‘These are the thimes that thiy men’s thouls.’”

After that experience, no one was surprised that Rahm abandoned Rich Daley’s practice of taking town-hall questions directly from voters in favor of questions e-mailed in or submitted on Facebook. His staff says that he interacts daily with average Chicagoans, so why waste time on there’s-a-dog-on-my-lawn complaints? But screening many of the questions plays into the impression of the mayor as a man obsessed with orchestrating events and cultivating his public image. He doesn’t seem to have noticed that even the president of the United States takes questions from all comers at town-hall events.

This doesn’t quite make Rahm the control freak of popular imagination. “He wants to do the right thing, desperately,” says Garry McCarthy, his superintendent of police. “People like that are sometimes prone toward micromanagement. He does not micromanage me. He tells me what he needs, [but] doesn’t tell me how to do it.” McCarthy is learning how Rahm—in Congress, the White House, or City Hall—often practices government-through-newspapers. “He’ll read something in the paper and call me up and say, ‘What is this? I didn’t know about it.’” His M.O. illuminates how crucial a vigorous press is to problem-solving in the public sector. It’s the positive side of his obsession with publicity.

As his brother suggested, Rahm’s quick mind can sometimes be obscured by his tangled tongue. This verbal awkwardness in public (“We have a high unemployment,” and “the Wall Street” bears the blame, he said on Meet the Press) is a trait he inexplicably shares with all recent Chicago mayors except Harold Washington. Otherwise, he represents a major stylistic departure from his predecessors. Nearly every 20th-century mayor was pudgy and from the wards. Rahm is a trim yoga devotee and former ballet dancer raised in well-to-do suburban Wilmette. This somehow fits the new Chicago. As you pass all the hip new restaurants and gleaming downtown office buildings, it’s Rahm who seems to personify the city that Rich Daley built, where the children of ethnics who fled integration in the 1960s are returning from white suburbs to live in some of the same neighborhoods where their grandparents did, only now they’re made up less of immigrants from Poland and Mexico than of young professionals from Northbrook and River Forest.

Traveling around the city, I see Apple stores, J.Crews, and Whole Foods on avenues I remember containing slag heaps, warehouses, and taverns. The rebirth of Wicker Park and Bucktown is old news, but in recent years neighborhoods like Bronzeville (largely African American) and Logan Square (largely Hispanic) are also looking better.

There are still plenty of ethnics—Latinos make up more than 20 percent of the city’s population—but downtown and the North Side have much more of a Manhattan feel than when I was growing up in the 1960s and ’70s. In those days, the world of reformist “lakefront liberals” extended only a few blocks west of Lake Michigan and made up no more than three or four wards on the North Side and one—the 5th Ward, at the University of Chicago—on the South Side.

Now the political map has flipped, and the remaining ward bosses Rahm reels off (“Burke, Cullerton, John Daley …”) number fewer than half a dozen out of 50 wards. “You can count them on one hand, and I’m doing it with my half finger,” he says, making light of when he sliced himself while working at an Arby’s in high school and almost died from an infection that cost him half a digit. He adds that a third of the City Council is new, which gives him a large group with whom to use his legislative skills to build coalitions.

But running the city is harder than it used to be. The dismantlement of the machine began in 1969, with a lawsuit brought by a reformer named Michael Shakman. While the resulting “Shakman Decrees,” which eventually restricted most patronage, have hardly ended hiring and firing based on political connections, a series of rulings has left room for only about 1,000 political appointees out of a city workforce of 33,000. That means far fewer workers like Fraser Robinson, a foot soldier in the first Mayor Daley’s organization whose work as a precinct captain helped him get promoted to pump operator in the Water Department. His daughter grew up to be Michelle Obama.

When I ask about precinct captains like the president’s late father-in-law, Rahm says they don’t even exist anymore. Elections in Chicago are now more like those in the rest of the country, where block organizations are in eclipse. “So when you say ‘Where’s the precinct?,’ it’s at a TV station, okay?”

Presented by

Jonathan Alter, a columnist for Bloomberg View and an MSNBC analyst, is the author, most recently, of The Promise: President Obama, Year One.

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