Barack Obama knew nothing of the city's bare-knuckle politics, but he was a good listener and a quick learner. And he liked to talk about social change.
He entered politics on the very bottom rung of the ladder. As a low-paid community organizer, he agitated for jobs in a depressed steel community, better city services, anything that would help poor people improve their lives.
Now a generation later, Barack Obama, the one-time outsider who not long ago was knocking on doors and pounding the pavement just to be heard, is making history -- as the presumptive Democratic presidential nominee and first black candidate representing a major party.
It is a giant leap in his already improbable journey from the exotic corners of Hawaii and Indonesia to the halls of privilege of Cambridge, Mass., the poverty-wracked streets of Chicago and finally, the corridors of power on Capitol Hill.
But it is here in Chicago that Obama learned to put together coalitions, understand the value of compromise and the need to bridge gaps -- all things he says will work in the White House.
It was here that Barack Obama, activist, became Barack Obama, politician.
He did it by relying on his experience as an outsider, always finding ways to meld with worlds that were not his own.
"He was a stranger but he made his way," says Mike Kruglik, who worked with Obama as an organizer. "He could see himself in other people."
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From the very beginning, Barack Obama has blended cultures.
His father, also named Barack Obama, was a black scholarship student who traveled from his small village in Kenya to attend the University of Hawaii. His mother, Stanley Ann Dunham (her father always wanted a son), was white and just 18 when they met in a Russian class.
Barack -- "blessed" in Arabic -- was born on Aug. 4, 1961. His parents' marriage was short-lived.
His father left his family to study at Harvard when his son was 2, returning just once when his son was 10. Obama wrote poignantly about that visit in his memoir -- remembering the basketball his father gave him, the African records they danced to, the Dave Brubeck concert they attended.
Obama never saw his father again.
By then, Obama had already lived in Indonesia -- homeland of his stepfather, Lolo Soetoro, another university student his mother had met in Hawaii. For the young Obama, it was an exotic environment: He learned to eat snake meat and grasshopper, had a pet monkey, Tata, and saw the harsh realities of Third World poverty.
After four years, Obama returned to Hawaii, first living with his mother, then with his maternal grandparents: Gramps and Toot or Tutu (Hawaiian for grandmother) -- all transplants from Kansas.
Today, Maya Soetoro-Ng sees traces of all three family members in her half-brother.
From their mother, she says, "he gets his ability to build bridges, to keep an open mind ... his taste for adventure, his curiosity and his compassion."
From their grandmother, Madelyn: "his pragmatism, his levelheadedness, his ability to stay centered in the eye of the storm."
From their grandfather, Stanley: "his love of the game. My grandfather ... pursued life with great zest and enthusiasm and a great sense of possibility."
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In Hawaii, Obama was typical. And atypical.
He was a scholarship student at the prestigious Punahou School, a private academy in Honolulu where he was "intelligent, but not overly intellectual," says his half-sister. He was outgoing, laughed easily and wasn't above showing off.
Obama -- then known as Barry -- had a rebellious streak. One friend remembers they both got in trouble in seventh grade for pitching quarters on school grounds.
The chubby kid who collected Spider-Man and Conan the Barbarian comics grew into a teen who listened to jazz saxophonist Grover Washington Jr. and Earth, Wind & Fire, tooled around in Gramps' old Ford Granada, golfed, played poker, sang in the choir and joined Ka Wai Ola, the school's literary journal.
Obama also loved basketball and as a forward dubbed "Barry O'Bomber," he favored a left-handed double pump shot. During his senior year, the varsity team captured the state championship.
Obama was both a fierce competitor and a sensitive friend. His buddy, Mike Ramos, says if he missed several baskets during pickup games, "Obama was the guy to say, 'Keep shooting. Don't worry. It'll drop.'"
There also was an introspective side to Obama, the outsider grappling with his biracial roots.
Though he had a diverse group of friends, he and two others among Punahou's few black students met weekly for what became known as "ethnic corner."
"It was more about learning from one another, other than it's the only place we feel safe," says Tony Peterson, one of the three. They discussed interracial dating, education -- and, he says, probably "whether we would see a black president in our lifetime."
Peterson and other buddies say Obama never spoke of the turmoil he revealed in his memoir, "Dreams from My Father," in which he wrote about wrestling with his racial identity and using drugs -- including marijuana and cocaine -- to "push questions of who I was out of my mind."
In a 1999 article written for the Punahou Bulletin, Obama said that as one of the few blacks in the school, "I probably questioned my identity a bit harder than most. As a kid from a broken home and family of relatively modest means, I nursed more resentments than my circumstances justified, and I didn't always channel those resentments in particularly constructive ways."
After high school, Obama attended Occidental College in Los Angeles and had a varied group of friends, including Vinai Thummalapally, a native of India. They became roommates in the summer of 1980 when Obama, still a teen, was already plotting his life's journey.
"I want to get into public service," he recalls Obama saying. "I want to write and help people who are disadvantaged."
Obama later transferred to Columbia University, where he says he became more serious. "I didn't socialize that much. I was like a monk," he said in a 2005 Columbia alumni magazine interview.
After graduation, he spent two years as a writer for a business newsletter and as a coordinator at City College in Harlem for an environmental and consumer advocacy group.
Then he answered an ad for a job in Chicago, sent a resume, and sat down at a coffee shop on Lexington Avenue in New York for a two-hour interview.
Soon, he was packing up for a new home and a city that would shape his life.
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Obama arrived in Chicago in 1985 with a college degree, a map of the city and a new job -- community organizer.
Starting salary: Just over $10,000 plus enough money to buy a beat-up Honda.
Obama was a stranger to Chicago, but living abroad gave him experience as an outsider and a natural empathy for people without money and power, says Gerald Kellman, the man who hired him.
Working for the Developing Communities Project, Obama organized black churches on the industrial South Side, an area crippled by the loss of steel mills and factories.
Obama's task was to mobilize residents to agitate for themselves, whether it was to lobby for a new job training center, remove asbestos from a housing project or arrange a meeting with the mayor.
"He seemed to listen well and he learned fast," Kellman says. But even though Obama worked with people trained by Saul Alinsky, the father of community organizing, he didn't adopt hard-nose tactics.
"He did not like personal confrontation," Kellman says. "He had no trouble challenging power and challenging people on issues. When it came to face-to-face situations, he valued civility a great deal. ... When it came to negotiating conflict, he was very good at that. ... He was not one to get drawn into a protracted conflict that involves personalities."
Obama became close to many of those he organized -- women old enough to be his mother.
"This kid was so bright -- I shouldn't say kid, this man was so bright, but he didn't hit you over the head with it," recalls Loretta Augustine-Herron, a founding member of the communities project. "He was matter-of-fact and smooth. ... He explained things so nobody would be offended."
The women doted on him. They chided him when he would eat just a spinach salad for lunch, laughed when he showed off his dance moves ("He didn't lack confidence, I can tell you that," Augustine-Herron says) and joked about his punctuality and seriousness.
"If we don't hurry up, baby-faced Obama is going to be mad," they'd prod one another as they rushed to a meeting with him.
Yvonne Lloyd says Obama prepared them for dealing with bureaucrats, telling them whom to approach, guiding them on what to say -- then offering critiques.
"He was there, trying and pushing," says Lloyd, mother of 11. "He energized us. When you've been a housewife all your life and all you've done is raise kids, you don't know too much about the outside world. He taught us."
And if there was something he didn't know, he'd find out. "'Let me look into it' were his favorite words," says Lloyd, who still calls Obama "my skinny little boy."
Obama remained close with his half-sister, Maya, who visited Chicago during the summers. When her father died while she was just a teen, Obama, nearly a decade older, took on a paternal role, taking her on tours of college campuses.
Obama also was honing his writing skills, crafting vivid short stories about pastors and crumbling communities, inspired by his Chicago experiences. He showed them to fellow organizer Kruglik, who was impressed by how he had captured the feel of the streets. "I couldn't figure out how he had the time and energy to do it," he says.
His organizing work also made him more pragmatic.
"Barack was no longer naive. He had spent three years on the streets of Chicago in about the toughest political environment you can see in the U.S.," Kellman says. "He had a clear view of what was possible."
He also came to see his father's experience as a civil servant in Africa as a cautionary tale.
"He had this sense of his dad being too idealistic and not practical enough ... and not accomplishing what he wanted," Kellman adds. (Obama later wrote that his father -- who was killed in an automobile accident -- had died "a bitter man.")
Obama said in his memoir that during those years in Chicago, he "broke out of the larger isolation" he had when he arrived and discovered that sharing life stories with people "gave me the sense of place and purpose I'd been looking for."
He was ready to move on -- to Harvard Law School.
But he promised he'd return.
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Obama entered Harvard older than many classmates, stepping into an incubator for America's elite -- future Supreme Court justices, Fortune 500 leaders, U.S. senators and presidents.
Former classmates and professors remember him as an intellect with mature judgment, a conciliator who could see both sides of an issue.
"He wasn't someone that you simply wanted to read his class notes or hear his voice," says Charles Ogletree, a Harvard law professor who served as a mentor to Obama and other black students. "You wanted to hear him thinking. There was something special about him."
The law school had plenty of achievers trying to edge out their competition but that wasn't Obama's style, says Laurence Tribe, a professor who hired him as a research assistant.
"He was not at all about credit but results," Tribe says. "He would often give credit to others that he did the work for."
Tribe says Obama also could deal with very smart people "in ways that didn't bend them out of shape. He learned how to move through those circles ... made few waves and got things done."
Obama had two pivotal moments during his Harvard years: One came during his first summer when he worked at a large Chicago corporate law firm and met another Harvard law graduate, Michelle Robinson, who would become his wife and the mother of their two daughters, Malia and Sasha.
The other was a professional triumph: Obama made headlines when he was elected the first black president of the Harvard Law Review, perhaps the most prestigious legal journal in the nation.
"For us, it was a real major celebration, a real milestone, a real landmark," says Earl Martin Phalen, a black classmate. "It didn't have the same meaning for him. ... He did not take that pound-on-my-chest attitude, 'Look at me, I'm the first one.' He was conscious of the historical significance but understood ... there was a responsibility."
With graduation, Obama became a hot commodity. High-powered job offers flooded in. He chose another direction.
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Back in Chicago, Obama joined a small civil rights firm, ran a voter registration drive and lectured on constitutional law at the University of Chicago Law School.
In 1996, he won a state Senate seat representing Hyde Park -- the South Side neighborhood that encompasses the prestigious university as well as pockets of deep inner-city poverty.
Obama later wrote that he understood politics was "a full-contact sport and minded neither the sharp elbows nor the occasional blind-side hit." But in Springfield, the state capital, he was known as a pragmatist who'd cross party lines, working with Republicans as well as other Democrats.
Obama helped change laws governing the death penalty, ethics and racial profiling, and he won tax credits for the working poor. But he failed in his campaign for universal health care.
As a newcomer in the clubby atmosphere of Springfield, Obama also encountered cold shoulders. Some lawmakers initially thought he was a bit arrogant.
"It took him a while to prove that he was a real guy," says state Sen. Kirk Dillard, a Republican who appeared in an early Obama campaign commercial. "For the first couple of years, there was some healthy skepticism. ... It was especially true among his fellow African-American legislators."
Obama's roots and his style -- he avoids the racially tinged rhetoric some black politicians use -- have long stirred debate about his racial identity. Some black leaders and commentators have questioned whether he is "black enough."
Obama says there never has been any question about his being black.
"If you look African-American in society, you're treated as an African-American," he said in a CBS "60 Minutes" interview last year. "And when you're a child in particular that is how you begin to identify yourself. At least that's what I felt comfortable identifying myself as."
But Obama also said in that same interview that his racial identity is "not the core of who I am."
The issue of race, though, took center stage this spring after incendiary remarks by Obama's former pastor, the Rev. Jeremiah Wright, threatened to derail his campaign. In a pivotal speech in Philadelphia, Obama addressed the controversy in broader terms, talking about black and white resentments and calling on the nation to break the "racial stalemate we've been stuck in for years."
In his book, "The Audacity of Hope," Obama spoke personally about how race has shaped his own life.
Being a senator, he wrote, has spared him from some of the "bumps and bruises" many black men endure. But he also noted he has faced the "litany of petty slights," including security guards trailing him in department stores and white couples tossing him keys outside restaurants, mistaking him for a valet.
"I know what it's like to have people tell me I can't do something because of my color, and I know the bitter swill of swallowed-back anger," he wrote.
But all through life -- from his childhood in Hawaii to his legislative days in Springfield -- Obama has counted on a racially mixed group of friends and political alliances.
As a state senator, some of his closest friends were suburban and rural white lawmakers. Obama also found a powerful ally in Emil Jones, the state Senate president, an old-school Chicago Democrat known for cutting deals, punishing enemies and having several family members on the state payroll.
In Springfield, Obama would join Democrats and Republicans alike for a weekly Wednesday night poker game. It was a chance to socialize and show he could be just one of the guys -- even though he was the son of an African goat herder, a Harvard-educated lawyer, an author and professor.
"Barack knows what he has to do to fit in and he has the capability to do it," says state Sen. Terry Link, his longtime friend and occasional poker host during those days. "He tries to make it where he doesn't stand out."
Three years into his legislative career, Obama, both restless and ambitious, challenged U.S. Rep. Bobby Rush, a veteran who had an approval rating of about 70 percent and deep roots in the community, dating back decades to when he was a Black Panther.
During that campaign, Obama was dogged by the same question -- whether he was "black enough" for the district. His academic credentials mattered little to some voters who felt Rush better understood them.
Obama was trounced, losing the primary by 31 percentage points. When he arrived at his victory party, the race had already been called for Rush.
"Barack was perceived as an outsider," says Link, the state senator. "He wasn't one of the boys."
He wasn't deterred.
Two years later, he began plotting his next move -- a campaign for the U.S. Senate.
By then, he had a network of friends and supporters in Springfield, including his poker buddies who saw similarities in how he approached his work and the game.
"He was a very calculated player," Link says. "If he was going to play the hand, he knew it was a hand he could win. That's his politics, too. He's not going to do it just to do it."
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Obama launched his national political career with what some dubbed The Speech -- a stirring 17-minute keynote address at the 2004 Democratic National Convention.
Obama was little known outside Illinois when he was tapped for the high-profile appearance. But he had impressed John Kerry, then the Democratic presidential nominee, after the Massachusetts senator heard him speak at a fundraiser and then campaigned with him in Chicago that spring.
Obama walked on the convention stage an unknown. He walked off a star.
The buzz began that very night. Commentators and politicians touted him as a possible White House contender -- even though he was still a state lawmaker.
Four months after the convention, Obama, buoyed by some lucky breaks, won the U.S. Senate seat in a landslide. He became the third black U.S. senator since Reconstruction.
He seemed to have the Midas touch: Two best-selling books, two Grammy awards for recording them, magazine covers, TV appearances, invitations galore.
At first, he said he had no intention of running for president. But he changed his mind after two years in the Senate.
On a blustery February day last year, Barack Obama returned to Springfield to the steps of the Old Capitol, where his hero Abraham Lincoln was a legislator, for another big speech: He announced his candidacy for the presidency.
And so began a 16-month endurance test.
He filled giant arenas on the campaign trail, wooing voters with his soaring oratory, his message of "change we can believe in" and vows to end the war in Iraq.
He racked up large majorities among black, young and college-educated voters but had a much harder time winning over seniors, working-class voters and many women who were hoping for a different kind of history -- the first female in the Oval Office.
Along the way, his campaign collected nearly $265 million -- an unprecedented amount -- from about 1.5 million contributors, most of them ponying up small amounts online.
But Obama stumbled, too. He faced repeated questions about his judgment because of his association with his controversial former pastor and finally denounced Wright's comments as "divisive and destructive." And he had to backtrack when he called small-town residents bitter -- comments his critics said were elitist.
By early May, his campaign was back on track. Obama made a visit to the floor of U.S. House.
He was swarmed by well-wishers, shaking his hand, patting him on the back.
Some were even calling him "Mr. President."