The sun is just rising as Rahm Emanuel takes to the sidewalk under the Brown Line stop at Addison. He’ll be there for over an hour, his gloveless hands raw from the cold, greeting the commuters dashing for their trains.

He’s there, he says, because he wants to meet the constituents of the Fifth Congressional District. Actually, he’s there because he has to be. Emanuel–a legendary wheeler-dealer, one of President Clinton’s chief political operatives throughout the 90s–has come out of the back room to run for Congress in the March 19 Democratic primary. And that means gripping and grinning and hanging out with the hoi polloi. “It’s not so bad,” says Emanuel. “I’m getting into this. Really. I love meeting the people.”

Despite his protestations, the 42-year-old Emanuel is an unlikely candidate for the seat. For one thing, he’s not from the district, at least not in the conventional sense. Most Chicago politicians push the notion that they’re neighborhood guys. They point to the parks where they played, the high schools they graduated from. But Emanuel isn’t a neighborhood guy. He didn’t grow up in Ravenswood, North Center, Albany Park, Portage Park, Dunning, Belmont Cragin, or any of the other communities that make up the Fifth District. He didn’t play ball at Welles or Portage or Hamlin park and didn’t go to Lane Tech, Steinmetz, Lakeview, Roosevelt, or Prosser. He didn’t even attend a local college or university. No, he grew up in Wilmette, graduated from New Trier West, and went to Sarah Lawrence College, where he studied ballet and got a liberal-arts degree.

He came to Chicago after graduating in 1981–hardly a major political disadvantage, since so many voters in the district, including many of his seven opponents in the race, didn’t move to town until after college. Except that once here, he never ran for office, he never led a local grassroots movement, he never joined a community group. He never participated in any citizen fight against the bureaucracy, a misguided zoning decision, or a rapacious developer. His children don’t attend public schools, and he’s never sat on a local school council or been engaged in any of the ongoing school-reform battles.

He even pretty much sat out the greatest political campaign of the last 20 years–Harold Washington’s 1983 mayoral race. As he recalls, he voted for Richard M. Daley over Washington in the Democratic primary. “But then,” he says, “I voted for Washington over [Bernie] Epton in the general.”

At the time he was 23 years old, living in a Lakeview apartment and working as an organizer for the consumer group Illinois Public Action Council–going door-to-door on the north side, signing up members and asking for contributions. It was through the council that he met some of the most influential people in his life, including another young activist, David Wilhelm. He and Wilhelm went to work as organizers in the successful campaigns of Congressman Lane Evans and Senator Paul Simon. By 1989 he was Mayor Daley’s chief fund-raiser, a relatively easy gig, since most donors knew that Daley was the only political game in town.

Given the Daley connection, it was only a matter of time before Emanuel went national, and in 1991 he joined Bill Clinton’s fledgling presidential campaign as a fund-raiser. He moved to Little Rock, where he joined James Carville, George Stephanopoulos, and the rest of the brain trust working out of the “war room.”

In some ways Clinton and Emanuel made an odd couple. Clinton was, of course, the Elvis Presley of national politics–warm and endearing, with his ingratiating aw-shucks, I-feel-your-pain, down-home style. Emanuel was, by all accounts, brash, arrogant, and caustic. While Clinton could listen to people talk about their problems for hours, Emanuel showed no patience for chitchat. The world, he let it be known, was divided into those who had money to give to the campaign and those who did not. And unlike Clinton, he didn’t care if people disliked him. “Making enemies is inevitable,” he told a reporter in the early 90s. “If your goal is to get things done, and get them done quickly, yes, you’re going to have them.”

These traits served him well as a fund-raiser. He didn’t ask–he demanded. And he refused to take no for an answer. He’d call people once, twice, or three times if he had to. “If somebody gave $100, he would call back and say, ‘How about $200?'” Wilhelm told reporters.

Clinton clearly appreciated those talents. And why not? Emanuel raised about $71 million for Clinton’s first presidential campaign, keeping the money flowing during the dark days of the New Hampshire primary, when Clinton was mired in the Gennifer Flowers sex scandal. After Clinton won he tabbed Emanuel to organize his inauguration, then hired him to work in the White House as a chief strategist.

Emanuel’s sudden rise to the top–at age 31 he was riding on Air Force One and was on a first-name basis with the country’s leading pols and pundits–may have gone to his head. It certainly accentuated the more strident parts of his personality. The profiles of him in the early days of the Clinton White House depict an almost comically vain spoiled brat. The Washington Post called him a “wiry, thin, foul-mouth ballet dancer” whose “brash, punish-your-enemies style apparently reflected a White House in which certitude sometimes outpaced judgment.” New York Times columnist Frank Rich wrote, “If the word oleaginous didn’t exist, someone would have to invent it to describe Rahm Emanuel.”

Mother Jones called him “arrogant, rash and power hungry” and described how he once “sent a rotting fish to a former coworker with whom he had parted ways.” Later in that article an unnamed colleague said, “Nobody says he’s dumb, but everyone says he’s an asshole.” He’d let the Mother Jones writer see his impatience, snapping rubber bands, tapping pencils, and shifting in his seat. He said he saw no point in joining a feeble journalistic expedition to find profound meaning in his life. “I don’t know about you,” he said, “but if I want introspection, I’m gonna pay a hundred dollars an hour.”

The story went on to describe Emanuel indulging for a moment in some recreation–on the bike path in Washington’s Rock Creek Park, shirtless and in tight shorts, shouting “left!” as he zipped past “hapless yuppies and their children. . . . His furious pace doesn’t slow for tight corners or low overhangs. Most people find bike rides relaxing, but Emanuel rides as if he’s being chased by the headless horseman.”

Ironically, despite his reputation for ruthlessness, Emanuel fit right in with an administration known for its middle-of-the-road policies. For all his talk of punishing enemies, he and Clinton were ideological soul mates, in that they were perfectly willing to compromise their political beliefs if that’s what they needed to do to get elected and pass legislation. Like Clinton, Emanuel called himself a “new Democrat,” as distinguished from the social activists in the party’s past. If he had a role model it was, of all people, Lee Atwater, the Republican operative who’d exploited racial fears to help George Bush beat Michael Dukakis in 1988. Like Atwater, Emanuel said he wanted to win by rallying the middle class.

The result was a wasted presidency, at least in the eyes of many progressives. As presidential scholars James MacGregor Burns and Georgia Sorenson write in their book Dead Center: Clinton-Gore Leadership and the Perils of Moderation, Clinton abandoned many of his campaign promises, particularly his national health-care plan, which he couldn’t pass even though the Democrats controlled both houses of Congress during his first two years in office. “Facing an ideological party, he could not be ideological because he was a transactional broker who was not always persistent and skillful enough to make his dealing stick, and was a would-be transforming leader without the deep conviction necessary to that strategy,” Burns and Sorenson write. “No wonder some Americans considered him neither a fox nor a lion, but a chameleon.”

For better or worse, Emanuel had a hand in deciding Clinton’s agenda and in shaping almost all of the major legislation that did pass, including welfare reform, the Brady bill, the Assault Weapons Ban, NAFTA, and the Children’s Health Insurance Program. He in turn was loyal to Clinton, sticking with him through the worst of the Monica Lewinsky scandal, even after it was obvious that Clinton had lied to him–as well as all of his other chief aides–about his affair with the former intern. “I’m not the kind of guy who walks away,” says Emanuel. “I’m very loyal.”

But by 1998 Emanuel and his wife, Amy–who’d just had the first of their three children–had decided that Washington wasn’t where they wanted to raise their family. They decided to come home. They bought a house in Ravenswood, and he went to work doing what most operatives do when they leave the White House–making money, big money. He found a job as an investment banker with the New York-based firm Dresdner Kleinwort Wasserstein, even though he’d never worked in a bank in his life. He laughs at the notion that an investment banker needs experience in banking. In reality, he says, it’s much the same as national politics. “Putting together deals–arranging mergers and acquisitions, which is essentially what an investment banker does–is not unlike overseeing the passage of legislation,” he says. “You bring people together. You keep them talking. You learn when a no really could mean a yes.”

Between 1999 and 2001 he helped put together four major deals, including the merger of Peco Energy and Unicom, Commonwealth Edison’s parent company. For his efforts, he made about $8 million in fees. “I like the job,” he says. “It gave me the economic security to do what I want with my life.”

He could have stayed in investment banking, remaining a behind-the-scenes player, occasionally sitting on public boards and commissions–Daley appointed him to the CHA board. But he had other ambitions few people were aware of. “I wanted to run for public office,” he says.

His reasons were simple. He says he wanted to serve the public, and he thought he’d be good. “I know the system–I know how it works,” he says. “I knew I would be effective, and I knew I wanted to serve. My parents had always taught us the importance of public service. I just didn’t know where. It’s not like I had mapped this whole thing out.”

One day last year it came to him when he was playing in his front yard with his kids. “[Fifth District congressional incumbent] Rod Blagojevich happened to run by–you know, he’s a big jogger–and we started to talk,” he says. “Rod said he was going to run for governor, and I said, ‘Who’s going to run for Congress?’ We kind of joked about me doing it. After Rod left, I started thinking about it. It just seemed to be the right thing.”

On the surface, it might seem like an uphill fight. Emanuel had no strong ties to local organizations or politicians. And his candidacy threatened to upset many elected officials with longtime dreams of serving in Congress, who seemed likely to respond: Who the hell is this guy to jump to the head of the line?

But he quickly assured friends and advisers that running for Congress wasn’t far-fetched. It was an open seat. He wouldn’t have entrenched opposition. True, Nancy Kaszak had already announced that she was planning to run, but she had few powerful backers and little money. Mayor Daley had no candidate in the race, and the area’s most powerful committeeman, Alderman Richard Mell, would be neutral, because Blagojevich is his son-in-law. As one Mell backer put it, “We don’t want to alienate any of the people running for Rod’s old seat.”

As for his campaign strategy, Emanuel could apply the lessons he’d learned during his years with Clinton: he would avoid the liberal label and run as a pragmatic centrist, even though the district is safely Democratic. Certainly fund-raising wouldn’t be a problem–his Rolodex was filled with potential donors (he’s already raised more than $1 million, enough to run TV commercials; Kaszak has raised about $300,000). And he had a solution for his lack of political support: he met privately with Daley and received his blessing, if not outright endorsement–the mayor rarely endorses candidates in a Democratic primary. That was enough to persuade many people that he was, as Emanuel puts it, “the mayor’s guy,” and he went on to get public endorsements from aldermen Pat O’Connor, Bernie Hansen, Tom Allen, and Margaret Laurino, among others.

Of course, there was still the problem of his pit-bull reputation. “Rahm has a lot of strengths as a fund-raiser and a deal maker that are not necessarily enamoring,” says one of his advisers. “Now, I could make the argument–and I think a lot of people would agree–that the district really could use a hard-ass in Congress looking out for its interests. But that’s not an easy sell.”

Following this analysis, Emanuel had to transform his public image, at least during the campaign. He could no longer play the role of the arrogant power broker who didn’t give a damn about the people he insulted. He had to show he cared, not just in a grand public-policy sense, but in a personal way. He had to demonstrate that he understood something about the people whose hands he was shaking. He could no longer divide the world into winners and losers–losers get to vote too. In short, he couldn’t strip to his bare chest and barrel down the bike path of life, screaming at pedestrians to get the hell out of his way. No, he had to be more like his old boss, Clinton, oozing charm and not disdain. He had to apply the lessons he’d learned from the master.

In November, Emanuel announced his candidacy, and the man who stood at the podium in the River Park field house before his parents, his wife, and his children bore little relation to the guy who’d raised money for the Clinton campaign. He didn’t mention his fund-raising days at all; instead he reminded voters of all the programs he’d helped pass. He called to the podium “my Uncle Les, who has been a Chicago police officer for 23 years,” and “Mike Wsol from the Firefighters Union, Local Two.”

After Wsol stood up Emanuel said, “As we all witnessed on September 11, the police and firemen in their selfless acts of courage represent the true character of the American people. I want everyone to take a moment to recognize them for what they have done and what they do every day. In that way, this campaign is not about me–it is about you, your families, the values that bind us together, and the principles we share.”

Within a few days his first mailing hit the street. Multicolored and slick, it makes no mention of his time as a Clinton fund-raiser or investment banker. Instead, it contains pictures of his grandparents beneath the headline “Always remember where you come from” and devotes a full page to his Uncle Les. As in his announcement speech, Emanuel’s voice is humble, not brash.

“My grandfather–my mom’s dad, Herman–came to the United States from Eastern Europe in 1917 when he was only 10 years old,” the flyer reads. “His family sent him to Chicago to escape religious persecution. On a wall in my parents’ house, my folks placed pictures of all the members of our family who didn’t make it to America. That wall came to mean two things to my brothers, sister and me. One was how lucky we were to be Americans. The other is that we should never forget people who are left behind. It’s a lesson I’ll always remember.”

Running for office meant dealing with reporters. Here too he changed his ways, taking all questions, no matter how annoying, with a clenched smile.

Do you run the risk of looking like a carpetbagger?

“Why would anyone say that?”

Didn’t you grow up in Wilmette?

“Well, it’s true that I went to junior high and high school there, but my formative years were spent in Chicago. We lived at Winona and Broadway until I was in fourth grade. I lived in Chicago long enough to root a Chicago identity.” Besides, he added, it’s not like he doesn’t have family from Chicago. His mother grew up here. Her family lived somewhere on the west side, though he wasn’t quite sure where. “I think she went to Von Steuben High School–I’ll get back to you on that.”

Why did the family move to Wilmette? Again, he wasn’t sure. “But some of the family stayed in Chicago,” he says. “My mother’s brother, my Uncle Les, lived here. He’s a Chicago police officer, a sergeant in the 17th District. My family came to Chicago all the time when I was growing up. We used to get together Sunday nights at my grandparents’ home. It was next to this big park. I don’t have the address.”

He went on, “To tell you the truth, I don’t think my connection to Chicago is an issue. I’ve lived here almost my whole adult life. My father came here from Israel in the 50s, when he was a young man. He had a pediatric practice for 40 years on the north side. For 20 years he was on Lincoln Avenue. After that he was on Peterson and Cicero. He’s now retired from the practice, but he still volunteers for the city at their north-side clinic.”

He also says it doesn’t matter that he’s made millions as an investment banker; “I think I helped structure those deals to save jobs,” he insists. And it doesn’t matter that he ruffled feathers during his days in the White House: “I had a job to do. I was serving my country, my president.” Besides, he says, he’s changed as he’s grown older and had children, and his bratty, tempestuous days are behind him. “We aren’t the same people we were ten years ago,” he says. “No one is.”

What really matters, he says, are the political convictions he’s forged over the years. “I grew up in a home that was very involved in politics,” he says. “We were Democrats–always. From my grandfather forward. I can remember arguments around the table about Henry Wallace having split the ticket. There was never a moment when I was tempted to vote Republican.”

In answer to the criticisms of James MacGregor Burns and other progressives, Emanuel says that he and Clinton did the best they could in the face of withering Republican opposition. “Think of all we accomplished–the Brady bill, a ban on assault weapons. No one said it could be done. Everyone said it’s suicide to take on the NRA. We got the Children’s Health Insurance Program passed–that means guaranteed health insurance for the children of working families. I can remember negotiating with Congress on that. One of the big differences between Republicans and Democrats is that the president had eye and dental care in [his plan], and the Republicans did not have it in theirs. But we stuck with that fight, and we kept it in. And do you know something? I had a woman come up to me on the campaign and say, ‘My son has eye care thanks to that program.’ That makes a difference. That fight meant something. Going against the Republicans and the insurance industry was the right thing to do.”

He promises that if he gets elected, he’ll deliver similar goodies for his district. Like what? “How about expanding the Ravenswood line to O’Hare–though I haven’t worked out all the details,” he says. Or “cleaning up the Great Lakes,” though he’s not specific here either. He does promise to personally oversee every constituent complaint and request his office gets, no matter how mundane.

Many local political observers are cracking up at Emanuel’s makeover. “Please, if I hear one more word about his father the doctor–excuse me, the pediatrician–or his uncle the cop I’ll puke,” says a northwest-side politico who’s working for Kaszak. “This guy’s no saint. He was Clinton’s fucking hatchet man, for Christ’s sake. I’d have a lot more respect for him if he was honest and said, ‘I’m a prick, but I can deliver.'”

At the Addison el stop the commuters come in batches, darting down the sidewalk, heads lowered, faces grim, worried about being late for work.

David Blitstein, Emanuel’s driver and campaign aide, positions himself to the west of the entrance, handing out flyers as the commuters pass. Emanuel holds open the door to the station and says “Hello” or “Good morning.” Or, noticing a novel one woman’s holding, “Nice book.” Or “Great hat.” It goes on like that for over an hour. By 8:30 it’s time for a break. So Emanuel, Blitstein, and Josh Galper, his press secretary, head over to the Lincoln Restaurant, a diner on Lincoln Avenue near the corner of Damen and Irving Park.

Inside, he circles the room, shaking hands, greeting diners, the cashier, the waitress, the cook. Once at his table he orders eggs, hash browns, toast, and coffee. He’s hungry, he says. He went swimming–a mile’s worth of laps–at 5:30: “I swim three times a week.”

After breakfast he’ll be off to Hiawatha Park on the far northwest side to meet with a group of seniors. “Something my good friend Alderman Bill Banks helped set up,” he says. “Then it’s back to the office on Belmont. From there, it’s–hold on.” He reaches in his pocket for his cell phone, which is apparently vibrating. “Yeah,” he says. “Uh-huh. Well, keep me posted.”

He explains that he ordinarily doesn’t like to interrupt face-to-face conversations with cell-phone calls, “but I’m waiting for an important announcement.” He knows the local AFL-CIO is about to throw its support behind one of the candidates. He already has the support of the Chicago Teachers Union, but he admits there’s a chance the AFL-CIO might go to Kaszak. He was up late last night strategizing with aides about it. He didn’t get to bed until after midnight and got only five hours of sleep. But that doesn’t matter. “I don’t need a lot of sleep,” he says.

The food comes, and he digs into his eggs, talking between bites. “The morning el work energized me–it always does,” he says. “I love meeting my constituents. I love campaigning. I’ve been to el stops, Jewels, Dominick’s, bingo games. You know, I learned a lot of stuff from watching President Clinton. He was the greatest campaigner.”

The waitress returns with the check. Emanuel looks up at her and smiles. “Thanks for the coffee,” he says. “The coffee’s great.” He holds up his finger. It’s the phone again. “Yeah,” he says into it. “Yeah! All right! We got the AFL-CIO endorsement!”

“All right!” says Blitstein as he high-fives Emanuel.

Emanuel’s so happy he leaps to his feet, embraces me, and rubs his knuckles over my head. “Let me give my new good friend a noogie,” he says.

At the counter four big guys in work clothes are waiting to pay their bill. “Hello, my name is Rahm Emanuel, and I’m running for Congress,” he tells them. Then he motions toward me. “Watch what you say–we’re with a reporter.” They stare blankly at him.

Back in the car, we hurtle west toward Hiawatha Park, Blitstein whipping from one lane to the next.

“David, please–what’s the hurry?” says Emanuel. “You keep this up, and we won’t be able to hold down breakfast.”

Blitstein slips a Bob Dylan CD into the player. Galper is on the cell phone, trying to set up a visit by Clinton. He’s coming to town in three days to make a formal endorsement, but they haven’t selected a site for the press conference. Emanuel whips out his own cell phone. “Details, details,” he says, as he dials his office.

They reach Hiawatha Park right on time, but the guy Alderman Banks supposedly sent over to greet them, a guy named Pete, is nowhere to be found. Emanuel walks into the gym, where 100 or so seniors sit at tables playing cards, bingo, or other games of chance. Then he walks back out to the front desk. “Any sign of Pete?” he asks the man sitting there.

The man shrugs. Emanuel sighs. So much for Alderman Billy Banks and his much-vaunted support. Emanuel has to decide: Does he deliver some remarks without Pete’s introduction? Or does he merely work the crowd? He goes with option B. “I don’t want to seem like I’m intruding,” he explains. “I don’t want to interrupt their event.”

And so he works the room, slipping from one table to the next. “Hi,” he says to one lady in a pink sweater. “How ya’ doin’? Good? OK?”

“I’m sort of tired,” she says.

“Better get more coffee,” he says.

He calls one lady “honey” and one man “my pal.” He shakes hands and passes out flyers, pointing to pictures of his children. He tells them about the clinic his father ran on Peterson Avenue and the hundreds and hundreds of children he delivered. He tells them about his Uncle Les, the police sergeant, and he reminds them that he has Alderman Banks’s endorsement.

The people seem to like him. They’re friendly. They take the stuff he hands out–nail files, key rings, and flyers–but they’re clearly more focused on their games. After about 30 minutes he darts out the door.

Back in the car, Blitstein barrels down Addison, even faster than before. Galper gets back on his cell phone, still scouting locations. Blitstein pulls out his phone and dials, steering with one hand. Dylan sings about the gates of Eden.

Emanuel turns to me. “I want to give my new best friend all my attention,” he says, grinning.

“Why didn’t you run in Wilmette?” I ask.

“Wilmette!” he says. “What’s with you and Wilmette? I don’t live in Wilmette. I live in Chicago.”

“I know, but you grew up–”

He raises his hand. His phone is vibrating. “Hello,” he says. “Hi, honey. How’s everything? Great? Good. How are the kids? Good. Tell them I love them. OK. I love you.”

After he puts away his phone I ask, “Was that your wife?”

He rolls his eyes. “No, it was an intern.” He shakes his head. Then he looks up almost in panic. “That’s a joke, you know. About the intern. Of course it was my wife. It was a joke. Hey, you can’t print that–that joke’s off the record.”

Three days later the master comes to Chicago to endorse Emanuel. The setting’s an infant health clinic on North Halsted, an ideal location to emphasize the Children’s Health Insurance Program Emanuel helped Clinton pass. It’s one of those carefully scripted affairs, with a band of children sitting off to the side of a large waiting room, ringed by a horde of reporters, camera operators, and radio and TV technicians.

By the time Clinton and Emanuel arrive it’s after 4 PM. They’re 35 minutes late, and the crews have been grumbling. But as soon as Clinton enters the room–with Emanuel bounding behind him–the grumbling stops.

Clinton doesn’t apologize for being late. And he shows no sign that he notices the 60 or so adults with cameras, notepads, and tape recorders standing in the room. He heads straight for the kids. He shakes their hands. He asks, how are you doin’? He talks to them as though they’re alone, even as the cameras whiz, whirl, and snap.

“What book are you readin’?” asks Clinton.

It turns out to be a kids’ biography of Bill Clinton. “Great book,” he says. “I’ve read it 100 times.”

Then he starts reading Where the Wild Things Are to the children. After he’s finished he takes questions.

“I want to be president,” one kid says. “How do you become president?”

“You have to learn about different kinds of people,” Clinton says, “because America is a land of many different people.”

Another boy asks if he misses his old job.

“I miss the work. I loved the job. But no one gets to do it forever.”

Then up to the podium they go, and Clinton delivers a stirring plea for Emanuel’s candidacy. “Rahm helped me be a much better president,” he says. “He brought values of Chicago neighborhoods, the toughness of this great city.”

Then he acknowledges Emanuel’s bad-boy reputation. “People used to talk about how tough Rahm Emanuel is. Well, you don’t need a shrinking violet in Congress. I have never worked with anyone in public life who is more consistent. What are we going to do today to solve a problem?–that’s how Rahm approached life. He kept his Chicago values in the White House, so I know he will do it in Congress. He will be a breath of fresh air blowing at gale-force speed. I’m honored to be here with him.”

In the back Emanuel is beaming, his eyes glistening. Later he steps to the podium with his own remarks. “Thank you, Mr. President,” he says, his voice cracking. “I was always at your side, and I will always be at your side.”

From there it’s off to a private fund-raiser, with donors paying $1,000 a pop. Then it’s to a party at the Park West, attended by a few hundred up-and-coming young professionals. Clinton never slowed–shaking hands, laughing, kibitzing until the wee hours.

Emanuel stayed until the end. But the next morning, inspired by the master, he was up early, ready to hit the road and greet the shoppers at Jewel and Dominick’s stores throughout the district.

Art accompanying story in printed newspaper (not available in this archive): photo/Jon Randolph.