Quotes of the Day

On a recent Saturday morning, a middle-aged man worked the produce and deli sections of a South Side Chicago supermarket, ambling past signs touting a half-pound of honey ham for $2.49 and a bulletin board with photos of three teen runaways. In tan chinos, a sports shirt and a well-worn brown leather jacket, he walked up to the African-American shoppers and employees with brisk efficiency, engaged in amiable but brief chats, then turned and headed down the bread aisle, a universe away from the West Wing meeting he'd have been in were it not for a career decision unprecedented in political annals.

"Rahm Emanuel, running for mayor" he said, thrusting out his hand to Chiquita Robinson, 48, a deli clerk who didn't need the introduction. "I'm gonna vote for you," she said, later explaining her preference: "Obama asked him to work for him. He's from Chicago. He's really involved in things, knows a lot of people and will be great."

He doesn't shout, doesn't curse, doesn't tell anybody they're stupid or wrong. For the moment, at least, that vividly profane side of Barack Obama's former chief of staff has been replaced by a disciplined campaigner with some overwhelming advantages: a national profile, a prodigious Rolodex, shock-and-awe fundraising, a triathlete's stamina and a hit man's resolve—plus, of course, the reflected glow of the President of the United States, himself a hometown hero. All of which is upending conventional wisdom about the city's Feb.?22 mayoral election, in which Emanuel is the clear front runner. The change in leadership comes at a perilous moment. The next mayor could either reinstate Chicago's status as a world-class city, or leave it another postrecession victim.

Chicago politics being a blood sport, front-runnerdom has made the slim Emanuel a fat target. Critics wonder if a man known for dropping F bombs like a B-52 has the temperament to be mayor. Emanuel's prime rival raises daily the threat of a "Rahm tax" on services from gym memberships to haircuts. The cops and firefighters pointedly are not endorsing him. People are still muttering about the more than $18 million he earned in less than three years as an investment banker after he left the Clinton White House. And Emanuel had to summon every ounce of his finite patience to endure nearly 12 consecutive hours of public interrogation over whether he even qualifies to be on the ballot as a legal city resident. (He does, according to the state's supreme court.)

In this odd adventure, Emanuel, 51, is something of a trailblazer: there are 17 living former presidential chiefs of staff, yet none have departed the White House for anything quite so humble as a bid for municipal office. James Jones, an Oklahoman who held the job under Lyndon Johnson, went on to serve a few terms in Congress; Dick Cheney, who staffed Gerald Ford, represented Wyoming in the House; and Erskine Bowles, who steered Bill Clinton through the Lewinsky saga, lost two U.S. Senate bids from North Carolina. But it's something different to walk away from Situation Room crisis meetings, visits to foreign capitals, high-stakes budget negotiations and the Sunday-morning talk-show circuit for a rough-and-tumble world in which speedy garbage pickup can make you a hero and unplowed snow can ruin you.

And we're not talking about just any White House chief of staff. We're talking about Rahm, among the most famous and influential occupants the job has seen in years. A man who helped elect Clinton and to shape his White House, then won a hard-fought North Side congressional seat from which he, in turn, recruited and advised the candidates who restored a Democratic House majority in 2006. A man who mused about becoming the first Jewish Speaker of the House, before leaving Congress to work beside America's first black President. And yet here he is this morning at a strip mall in a black working-class neighborhood, fist bumping little kids as surprised shoppers snap cell-phone pictures. The candidate is warm, if not effusive, good with eye contact, then exiting conversations to quickly corral another shopper as if he were a hustling parking-lot attendant paid per car. Emanuel is a decisive man, and he is campaigning in the pursuit of a decisive win on Feb. 22—not just a victory but one big enough to avoid a runoff election.

That was once thought to be impossible. Given the large (six-candidate) field, and the deep ethnic fragmentation of America's third largest city, insiders doubted that anybody could pull more than 50% to win outright. The bookmakers expected a runoff between a white candidate and a black or Latino contender. Yet here in one of the nation's most segregated cities, not one African-American shopper or worker during this morning's supermarket swing privately voices a preference for the leading black candidate, former U.S. Senator Carol Moseley Braun. No matter that in 1992 Chicago catapulted her to the U.S. Senate — the body's first and only African-American female. To these voters, a sense that Emanuel has the power and prowess to deliver results matters more: "He could pull strings to do the city good," says Lucas Redmond, 69, a retired refrigeration engineer who voted for Braun back then but associates her with wasted opportunity. Chimes in a dairy-department employee: "I voted for her, but it seems when we go with race, it doesn't do us any good. He's better qualified."

City hall has been run since 1989 by Richard M. Daley, the king of American mayors. Daley leaves Chicago having overseen the city's transformation from declining Rust Belt bastion to world-class metropolis, with a flourishing arts scene, innovative financial markets and commerce-fueling transport services. With its dazzling sculpture and architecture, the 24.5-acre (10 hectare) Millennium Park, opened in 2004, not only anchors downtown but makes it one of the great public spaces anywhere.

Chicago's problems, however, are also daunting. There's the city's $500 million deficit, which amounts to nearly 10% of its annual budget. Several pension funds face the prospect of going under, with little help likely from a state whose own financial predicament is precarious at best. The city's basic infrastructure, especially mass transit, is in rapid decline. The school system is in crisis, with a high school dropout rate that exceeds 50%. Only the cities of Detroit, Milwaukee and Newark, N.J., are more segregated. According to a recent analysis of economic growth in 150 metropolitan areas worldwide by the Brookings Institution and the London School of Economics, Chicago placed a listless 82nd. Chicago's substantial black population in particular endures crushing unemployment and persistent crime. "You can have a world-class ballet and opera," says Emanuel (a former ballet dancer). "But if half your kids aren't graduating, you can't be a world-class city."

Which brings us to the obvious question: Why? Why leave the grand arena of national governance for a circus of pothole fixing, tree trimming, water-main repair, subway-line extensions and fights over which alleys drivers can use as thoroughfares? Why subject yourself to a city-hall press corps whose cynicism can make its White House counterpart look decorous and fawning? "I loved the White House. I loved working for both President Obama for two years and for President Clinton for six years," Emanuel tells me after somehow arriving just five minutes late to a downtown diner in a blizzard that has paralyzed the city. "But I love with a greater amount of emotion and strength also being the mayor of the city of Chicago, a city I grew up in and I would want my kids to call home. I think it's facing some serious challenges... Every city faces these challenges. I want to be the first to solve them." In other words, Emanuel is a gut-level kind of guy with a gut-level passion for Chicago. He loves it for the grit and grandiosity that has produced everything from Saul Bellow's greatest novels to Michael Jordan's six NBA titles to the epic Daley-family political machine. "I give you Chicago," wrote the newsman-essayist H.L. Mencken. "It is not London and Harvard. It is not Paris and buttermilk. It is American in every chitlin and sparerib. It is alive from snout to tail." Emanuel's vision is less lyrical but just as devout. "It's the most livable big city," he says, "with all the potentials of a big city and the management of a smaller town. This is what makes it, from a lifestyle question, unique. It's the only inland city with an international economic focus."

The Road to City Hall
No one expected Daley to leave when he did. But Emanuel wasted no time assembling an organization that has operated with the discipline and stealth of a presidential incumbent with a lead. Famous for his invective and epithets, Emanuel knew that the image of a coarse hothead might be useful in a fixer but could unnerve voters choosing an executive. Thus the man who once sent a dead fish to a pollster has been on his best behavior, taking extreme care not to flash his trademark temper in public. (Though he can still occasionally get snippy, as he did during an appearance at a charter school, curtly telling one loquacious host to stop talking so that he could hear from the teachers.) He won't engage rivals in rhetorical combat—Emanuel has skipped several candidates' forums—and prefers to appear, much like a President does, at only one message-specific public event per day. He is selectively minimalist about when to engage with the press.

Emanuel has also brought a political version of Colin Powell's concept of overwhelming force to bear on the race. The nearly $12 million he raised in just the three months following Daley's September decision dwarfed the combined total funding of his rivals. It was five times that of his prime critic and opponent, Gery Chico, a wealthy lawyer and former Daley aide whom Rahm has managed to recast as a compromised insider. Moguls such as Steven Spielberg, Steve Jobs and Chicago hedge-fund billionaire Ken Griffin help finance an all-star team of local consultants and young sharpies lured from the Obama Administration. Entertainers such as Jennifer Hudson and Jeff Tweedy of Wilco have headlined fundraisers. The comedian Andy Samberg, who memorably impersonated a cartoonishly obnoxious Emanuel on Saturday Night Live ("Do I lack even basic social skills? Absolutely"), stumped for Emanuel at a train stop in January, declaring that Emanuel would be "the most overqualified mayor of all time."

Behind the scenes, meanwhile, Emanuel employs the most cutting-edge techniques. A focus on social networking and demographically targeted e-mails is part of "using the Internet in ways not previously used in a municipal campaign," says Chicago-based Democratic consultant Eric Adelstein. Emanuel is harnessing Google Analytics to micro-target voters based on their Web surfing. "So you look for 'Chicago Bears' and there may be an Emanuel message that might interest you, a sports fan between the ages of 40 and 60," Adelstein says. While Emanuel has more than 40 paid staff members, a well-known Latino candidate, city clerk Miguel del Valle, has six. And the control Emanuel's team exerts can sometimes befit a national candidate: when a local television news station recently interviewed his parents, the campaign insisted that its own crew film the interview as well. And then there are the effective TV ads, one featuring Obama and another, Bill Clinton.

The shrewd, muscular campaign is the natural product of a career that has always been somewhat exceptional. Born to a hard-driving pediatrician father who served in a Jewish paramilitary organization that operated in Palestine and a psychiatric-social-worker mother, Emanuel moved to the Chicago suburbs as a youth with his equally ambitious and successful brothers, prominent Hollywood agent Ari and bioethicist-oncologist Ezekiel. He attended summer school in Israel and, eschewing a scholarship with the Joffrey Ballet, attended Sarah Lawrence College and quickly found his place in Chicago politics, working in 1989 as chief fundraiser for Richard Daley's first winning mayoral bid. (The revolving Daley-Obama door now features Daley's younger brother William, who hired Emanuel for that 1989 fundraising job, replacing him as White House chief of staff.)

Emanuel's ascent to the national scene began when he was one of the first hires at Clinton's fledgling Little Rock, Ark., presidential headquarters in 1991. He proved a prodigious fundraiser and joined Clinton as a White House adviser for six years; next came those two-plus lucrative years in investment banking, in which he impressed many with his contacts, judgment and capacity for work. In 2002 he won the congressional seat vacated by Rod Blagoje-vich, who went on to glory and then disgrace as governor. Emanuel took on what he calls "a job nobody wanted," he says, as chairman of the Democratic Congressional-Campaign Committee, where he was praised for selecting mostly moderate candidates and shepherding the party's 31-seat gain in 2006. It seemed entirely possible that Emanuel would succeed Nancy Pelosi as House Democratic leader until Obama asked him to take his mix of White House and Capitol Hill expertise into the Oval Office.

For a man barely acquainted with failure, the mayor's race could have been a humbling experience. Yet fortune shone upon him. His strongest potential white rival blinked and didn't run. The city's black political elite chose Braun as its "consensus" candidate, a move that proved disastrous: Braun has been uninspiring and erratic, most notably when she declared at a February candidates' forum that a black female rival had previously been "on crack." The public's attention has been elsewhere — the Bears' playoff run, the epic blizzard — drowning out the attacks of rivals like Chico, who has sought to exploit the vagueness of Emanuel's proposal to broaden Chicago's tax base. (Chico calls it "the largest sales tax in the city's history"; Emanuel counters that his plan would not raise overall taxes.)

Most fortuitous of all was the strange battle over the basic question of whether Emanuel was, in fact, a Chicago resident eligible to run for mayor. A lawsuit, whose source of funding remains mysterious, argued that he'd lived in D.C. too long to call himself a Chicagoan. Weeks of legal wrangling culminated on Dec. 14 in nearly 12 consecutive hours of testimony from Emanuel that included a discussion of items stored in his Chicago basement (including his wife's wedding dress). After an appeals court ruled against Emanuel, the Illinois Supreme Court unanimously decreed him a legal resident. A saga that threatened to embarrass not only gave him endless free publicity but, thanks to his uncharacteristic self-restraint in the face of goading by a pack of hostile citizens, softened the caricature of volcanic Rahmbo. It made him out to be the victim and underscored an implicit campaign theme: Emanuel as patriot who left his post in Congress to serve his President and now longed to return home. Especially in the African-American community, the notion of a powerful white man sacrificing for a black man is potent.

Training for a Tough Job
Much credit surely goes to the candidate himself, a paragon of fitness and energy. On Mondays, Wednesdays and Fridays he starts at 5:45 a.m. by swimming a mile at the elite, perfect-for-networking East Bank Club. On Tuesdays and Thursdays he does 25 minutes on a stationary bike ("Level 14," he says), 15 minutes on an elliptical trainer, 100 sit-ups and weights. On Saturdays he hikes 20 miles (32 km) or runs 4 miles (6.5 km), and on Sundays he has private yoga instruction. Then it's off to daylong, mostly unpublicized, appearances, including meet and greets at 100 El stops so far and hours spent feeding his inner wonk by studying the intricacies of school policy, transit, community policing, planning, airports, homelessness, garbage collection, health care and public housing. There are detailed papers on saving health care dollars via wellness programs, semiprivatizing trash pickup, persuading retailers to put supermarkets in the city's many "food deserts" and creating a sprawling, Google-like campus for high-tech innovators and venture capitalists. A serial cell-phone user, he's constantly dialing donors, prospective hires and legislators, like Illinois senate president John Cullerton, who says Emanuel has been the only mayoral hopeful to call.

The hardest part might be when Emanuel ventures into a lion's den: Chicago's firehouses. Few groups are as clannish as the city's firefighters, many of whom have the time to work second jobs. A strong case can be made that there are far too many, especially given the sharp drop in the number of fires (thanks in part to modern construction standards). Emanuel has hinted that this system must change. When he took his message to a North Side firehouse this month, one firefighter (who wouldn't give his name) offered his verdict: "The guys aren't too happy."

For Chicago to survive and flourish, however, hard choices lie ahead. A city with 30,000 employees groans under $12.4 billion in unfunded pension liabilities. Borrowing $245 million for anticipated police and firefighter raises, Chicago shares a fiscal predicament with cities nationwide. Though the school system has become a national laboratory for change, overall progress is incremental, and test scores are uninspiring. Teachers are well paid but work the shortest school day of the nation's 50 largest districts, teacher recruitment and performance evaluation are awful, and principals are not well trained.

That's why Emanuel's critique of city workers in a TV ad titled "Service" infuriates union leaders but seems to resonate with voters. "City government is not an employment agency," he says. "That means making sure everybody that works for the city government knows that they're actually a public servant representing and helping the people that pay them." Unionists may be outraged, but a popular suspicion is that too many have had it too good for too long. Emanuel is proposing various savings of $500 million, although he is withholding some key, politically charged details, like whether he'll go after pension benefits of existing workers.

It is a sign, however, that Emanuel is not interested in merely being a caretaker of the city he loves. Every city in America faces similar problems with its schools, budget and public-employee pensions. But Chicago's example will be especially important. As he has been throughout his career, Emanuel is prepared to make some enemies to achieve his goals. He insists that the story is bigger than one man. "It's about governing, not about me," he says. "The day of reckoning has come. Denial is not a long-term strategy."

• JAMES WARREN