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Even in the face of creeping gentrification, Chicago's far South Side is a gritty, dismal place. Low-rise buildings stretch for kilometres across crumbling sidewalks that front shuttered stores long mummified by rusted metal grates. Some churches keep their doors locked all day; visitors must ring the bell. Call a cab and it rarely shows up.

In the 40 or so blocks that make up the city's most hardscrabble neighbourhood, public transportation is scarce. But few people walk, not wanting to chance being hassled in a place where even U.S. postal workers leer at women passing by.

The streets were rougher still in 1985, when a caramel-skinned 23-year-old some called “Babyface” arrived from New York to help tackle social issues hobbling the community. Although he could not have realized it at the time, his arrival marked the beginning of an ambitious journey for someone who had been raised mostly in Hawaii.

He looked like an African American, but with a mother from Kansas and father from Kenya, Barack Obama did not really know what it meant to be black in urban America until he reached Chicago. He decided to get to know his new surroundings – on foot.

Rev. Alvin Love, head pastor at Lilydale First Baptist Church, was sitting in his office when “Barack rang the doorbell. I looked out the window. I didn't see a car. I go down, I see this skinny guy with big ears.”

The clergyman was surprised, but impressed. “The very fact that he was walking through the community said to me he was someone who, if he didn't know the community, at least was trying to get a feel for it – and wasn't afraid.”

Mr. Obama soon captivated Mr. Love with his novel ideas about how to mobilize people, how to knit together ethnic and religious groups that had never before co-operated. “He said to me, ‘Your issues of unemployment and crime in the community are the same issues the Baptists are having and the African Americans are having. Let's put all the other things aside. If we're going to tackle issues … let's see if there's a common ground for all of us.'

“That really was unheard of. To actually just sit down over issues … and do that with ethnics and Catholic priests, that was something.”

Over the years that followed, Mr. Love watched as Mr. Obama used the South Side almost like a laboratory as he honed what has, two decades later, become his trademark: an ability to solve problems by bridging what seem like insurmountable gaps between opposing factions.

At the same time, he became steeped in African-American culture and found something he had searched for since childhood – a clear sense of his own identity.

Now, at 47, Mr. Obama is threatening to eclipse the favoured Hillary Clinton for the Democratic Party's presidential nomination, a prize that could very well make him the first black person ever to reside in the White House.

As one long-time adviser says, he's “made to be president … This is an individual who transcends politics.”

PART 1: WHERE THE ROAD BEGINS AND ALMOST ENDS

Barack Hussein Obama's earliest memories of the country he wants to lead are set against a backdrop of the next best thing to paradise: tall, swaying palms and the pounding surf of Hawaii.

To those who knew his mother, Mr. Obama's birth was a surprise. Ann Dunham was raised largely in Kansas by working-class parents who eventually wound up moving to the 50th state. She was 18 and just starting out at the University of Hawaii in 1960 when she met a provocative Kenyan exchange student named Barack Obama.

He already had a wife and child back home, but said he was divorced. The two fell in love and defied convention by running off to marry in secret. Six months later, on Aug. 4, 1961, Barack Obama Jr. was born in Honolulu. But by the time he had turned 2, his parents' marriage had begun to fray. His father won a scholarship to Harvard University, but there wasn't enough money to bring his family along. So Ann stayed in Hawaii with young “Barry.” A year later, the Obamas divorced.

Many years later, Mr. Obama said the departure of his father affected him deeply. “Every man is trying to live up to his father's expectations, or make up for his mistakes,” he told his biographer, David Mendell. “In my case, both things might be true.”

At the time, however, life was too much of a whirlwind for the loss to hit home. By the time Mr. Obama was 6, his mother had fallen in love with another exchange student. Lolo Soetoro, an Indonesian Muslim, was a budding businessman when he whisked the family off to Jakarta, young Barry's first brush with real poverty. Universal electricity had arrived only a few years earlier; many homes were just bamboo huts.

There were few foreign families in their neighbourhood and Barry spent about four years there. When he was 10, his mother, concerned about his future, sent him back to Hawaii to live with his grandparents.

He was enrolled at the elite Punahou School, a private institution north of Waikiki Beach on the outskirts of Honolulu where cars are banned and teachers traverse the lush 76-acre campus in golf carts. Other famous students over the years have included America Online co-founder Steve Case, eBay titan Pierre Omidyar and golfer Michelle Wie.

The school was an easy five-block walk from his grandparents' 10th-floor apartment in a building that, since the launch of his presidential campaign, has been overrun with journalists. (Recently, one reporter was nabbed shimmying up an outdoor pole in an attempt to gain access to the upper floors.)

In his memoir, Dreams from My Father: A Story of Race and Inheritance, Mr. Obama says his exploration of what it means to be black in America began at Punahou, which boasted a diverse student body but only a handful of black faces (even now only 2 per cent of Hawaiians are African-American). Annual tuition is about $15,000 although, like him, many students attended on scholarships.

Still, there were no obvious signs that Barry had trouble fitting in. Yearbook pictures show a smiling, happy-go-lucky student. “He was a smart, active, funny guy …” recalls Tom Kreiger, a fifth-grade classmate. “He told people he was an African prince. We believed him.”

In high school, however, cynicism and confusion over his racial identity intensified. He grew more rebellious, experimenting with drugs and allowing his grades to slip. “Pot helped, and booze; maybe a little blow when you could afford it,” he wrote, adding: “Not smack, though.”

Basketball was a welcome distraction. Although Mr. Obama spent much of his time on the bench, Dan Hale, a teammate who now coaches basketball at the school, has vivid memories of how Barry would step in to break up fights when pickup games overheated.

He seemed to dislike confrontation, others have said, but Mr. Hale remembers him as “an intellectual … worldly,” and says that playing basketball on a multiracial team likely “helped Barry see that it was possible for people from all walks of life to get along.”

And, in fact, Mr. Obama writes in his memoir that “at least on the basketball court, I could find a community of sorts, with an inner life all its own. It was there that I would make my closest white friends, on turf where blackness couldn't be a disadvantage.”

Even so, some of his old acquaintances say they were surprised to learn of the angst he was feeling. “I had no idea what he was going through,” says Eric Kusunoki, his old home-room teacher. “He certainly never wore it on his sleeve. He was always very upbeat, very personal.”

According to Mr. Kusunoki, “We are all minorities here. We grow up pretty comfortable with each other. So I think Barry was able to experience more freedom than he might have had elsewhere, and thus he was able to be himself, work things out and develop more than he would have, otherwise.”

PART 2: SEEKING ANSWERS ACROSS THE WATER

In his senior yearbook, Mr. Obama thanks the “choom gang” (chooming is island slang for smoking marijuana) and says in his memoir: “Junkie. Pothead. That's where I'd been headed: the final, fatal role of the young would-be black man.”

But somehow he kept his grades high enough to win a scholarship to Occidental College in Los Angeles, where he hung out in coffee houses, took part in rallies and developed the analytical mind he seemed to have inherited from his intellectual father. “He seemed to have gotten some purpose in life during those two years at Occidental,” his grandmother, Madelyn Dunham, has suggested.

Yet he soon tired of Occidental, and in 1981 transferred across the country to Columbia University in New York. There, while sharing an apartment on the Upper West Side, he received a call from an African aunt, who informed him that his father, by then an alcoholic, had died in a car accident. The news was a mighty blow even though the two had seen each other only once since the divorce – a visit his father made to Hawaii when his boy was just 10.

After that, Mr. Obama spent much of his time at Columbia soul-searching. He took up jogging and lifting weights, and adopted a solitary lifestyle.

“I spent a lot of time in the library. I didn't socialize that much. I was like a monk,” he says in a 2005 Columbia alumni magazine.

But by the time he graduated in 1983, Mr. Obama had finally chosen a career. “I decided to become a community organizer,” he writes. “When classmates in college asked me just what it was that a community organizer did, I couldn't answer them directly. Instead, I'd pronounce on the need for change. … Change won't come from the top, I would say. Change will come from a mobilized grassroots.

“That's what I'll do. I'll organize black folks. At the grassroots. For change.”

Yet it was more than a year before he found a satisfying job changing things. First, to start paying back his loans, he joined Business International Corporation, a New York consulting and research firm where he was surprised to find himself tantalized by the lure of corporate life.

“Sometimes, coming out of an interview with Japanese financiers or German bond traders, I would catch my reflection in the elevator doors – see myself in a suit and tie, a briefcase in my hand – and for a split second I would imagine myself as captain of industry, barking out orders, closing the deal, before I remembered who it was I had told myself I wanted to be, and felt pangs of guilt for my lack of resolve.”

Perhaps propelled by that guilt, Mr. Obama left the company after about a year, did some half-hearted community organizing in Harlem and felt somewhat uninspired.

Then, one day, he saw an ad in The New York Times that would change everything. The Calumet Community Religious Conference, a community organizing agency financed by Catholic churches, was looking for an African American willing to run – for little pay – a program for the South Side's black community, which was being hurt badly by the collapse of the steel industry.

Although not especially religious (he now carries a Bible when campaigning), Mr. Obama decided to inquire. Already his natural charisma was winning people over.

“I remember thinking, ‘Man, he's very young' …” says Loretta Augustine-Herron, who interviewed him. “he had so much knowledge, it was amazing – we knew he was the one for us.”

He had spent a mere four years on the mainland, much of it in academe, so he also had much to learn. “His background did not make it automatic that he would understand this group of people,” recalls Greg Galluzzo, a Calumet employee who was his mentor. “He had to stretch himself. He had to learn what it's like to grow up in an African-American working-class community.”

Mr. Galluzzo feels that the early challenges taught the future politician some valuable lessons. “In organizing, your first job is to build relationships and bring large groups of people together to act coherently on a common project,” he explains. “The only thing you've got working for you is your personality and ability.”

In his first few years on the street, Mr. Obama claimed many small victories that, more than 20 years later, still stand out. He helped residents of Altgeld Gardens, a notorious housing project, have toxic asbestos removed from their apartments; he landed a job-training office for the area, and helped with such basics as having potholes filled and garbage cleaned up.

Eventually, he also persuaded people to band together and became known for arranging meetings between community members and city officials, then excusing himself to sit at the back of the room and watch what happened.

“He was really was into leadership building,” Mr. Love says. “His real idea was, ‘I'm here to facilitate this, but this is your baby. If you don't do something in your community it's never going to happen.' ”

Mrs. Augustine-Herron thinks that Mr. Obama succeeds because “he listens. … Some people listen and they hear what they want to hear. He actually understands what your issues are, what you feel the problem is.”

She also sees a personal payoff. “I think he needed to do that for himself as much as for us. I think he needs to feel good about what he can do.”

In 1987, a more personal quest for his fulfilment led him to join the South Side's high-profile Trinity United Church of Christ, whose motto is “unashamedly black and unapologetically Christian.” A black Jesus looks down from the stained-glass window.

At the time, it was run by Rev. Jeremiah A. Wright Jr., who writes on the African roots of Christianity and often preaches in a dashiki, the colourful garb of West Africa. He predicted that uniting the local churches was impossible, but Mr. Obama stayed anyway, some say to satisfy his craving to belong to black society.

That year, he also a suffered a personal loss when Harold Washington, the first African-American mayor of Chicago he had come to idolize, had a heart attack and died in his office. Before long, he decided to leave and study law at Harvard. “He realized that, if he didn't expand his horizons … he would not be able to bring about the changes he wanted to bring about,” Mrs. Augustine-Herron says.

Although he recalls Mr. Obama as a bit “young and impatient,” Mr. Love was surprised that he moved on so soon. “I think what he wanted to see was drastic physical change in the community. What he actually did was he taught people to make change. We kept the movement going.”

PART 3: CRIMSON BRINGS OUT HIS TRUE COLOURS

He didn't take long to make an impression when he arrived on the fabled campus, with his leather bomber jacket, his pack of cigarettes and rough edges from Chicago.

He developed a reputation for his remarkable ability to synthesize mind-boggling issues. Former classmates often recall how, rather than try to dominate an intellectual debate, he would listen quietly, vacuum up all that he could and only then speak his mind.

Michael Froman, a classmate and informal adviser, told The Washington Post that Mr. Obama stuck out for “his ability to lead, to guide a group of politically diverse – and divisive – people toward a common goal, to wrestle intellectually with some of the most difficult and complex problems of the day, understand different perspectives and take a position based on principle but made all the more sound by his appreciation of alternative points of view.”

During his first summer break, back in Chicago working at a law firm, he met Michelle Robinson, a Harvard grad from a black, working-class family on the South Side he would eventually marry. (They now have two young daughters.) By the time he returned school, dating was ruled out, giving him more time to study. In 1990, he made history by being appointed the first black to head the prestigious Harvard Law Review – a post that garnered him media attention as well as a contract to write the memoir that appeared five years later.

He also drew fire for adding conservative students who had supported him to the Review's masthead – once again unafraid to bring opposites together.

Then another coup: Lawrence Tribe, regarded as the premier U.S. constitutional scholar, made Mr. Obama his research assistant. In a recent interview with Time magazine, Prof. Tribe said that “I've known senators, presidents. I've never known anyone with what seems to me more raw political talent. He just seems to have the surest way of calmly reaching across what are impenetrable barriers to many people.”

After his four years at Harvard, Mr. Obama could have had his pick of top-flight legal jobs. Instead, he struck up a relationship with Judd Miner from a small constitutional and civil-rights firm in Chicago. “The fact that he was thinking about us suggested income was not the first order of business in his mind,” Mr. Miner says. For one thing, he didn't seem to want to spend his whole life was be a lawyer. “What drove him was a desire to be involved in policy.”

While deciding his future, Mr. Obama returned to his old community project to help arrange a voter-registration drive. Yet, even with close confidants, he rarely expressed any desire to run for office. Some Harvard classmates recall him talking about becoming Chicago's mayor, but Mr. Miner says that, in all of their discussions in 1992 (the two had many lunches before Mr. Obama finally joined the firm), there was no real indication that his new colleague was eyeing the Illinois Senate.

Part 4: THE LONG-AWAITED POLITICAL DEBUT

Only three years later, in September, 1995, Mr. Obama announced his candidacy for the state Senate. With few political connections, he drummed up support the same way he started his old organizing job: He set out walking.

Night after night, he knocked on South Side doors and told anyone who would listen why he thought he had enough experience to run. “What if a politician were to see his job as that of an organizer, as part teacher and part advocate, one who does not sell voters short but who educates them about the real choices before them?” he asked one reporter.

“As an elected public official, for instance, I could bring church and community leaders together easier than I could as a community organizer or lawyer. … We must form grassroots structures that would hold me and other elected officials more accountable for their actions.”

His lofty ideals helped him win the seat, but when he arrived in Springfield, he learned that he would have to be more of a realist to accomplish anything in the capital.

“He came with high credentials and he had to live up to them,” recalls Chicago lobbyist Paul L. Williams, an occasional Obama adviser. “Barack was the Harvard Law School guy, the smart guy, the ideological guy. He wasn't your old-time back-slapper. Barack wouldn't allow you to buy dinner for him, those kinds of things. He was on the up and up. He always felt he was going on to greater things.”

In his office, he hung paintings of Abraham Lincoln, Mahatma Gandhi and Martin Luther King, now making no secret of his ambition.

Dan Shomon, then a middle-aged political adviser assigned to help the young senator develop a legislative strategy, said their first meeting made him weary. “I have no time for Obama,” he now recalls telling his boss. “He wants to pass 500 bills and change the world.”

He and Mr. Williams agree Mr. Obama's big challenge was figuring out how to function within the political culture he encountered. He “struggled early on with frustrations with the slow process,” Mr. Shomon says, but soon was up to speed, joining a legislative poker league and playing golf. The biggest lessons involved colour. “I don't think he ever looked at somebody, thinking they were black or white,” Mr. Shomon says. “That's something he had to learn.”

Soon, he began to get things done, and recently told The New York Times that was when he learned that “if you're willing to listen to people, it's possible to bridge a lot of the differences that dominate the national political debate. I pretty quickly got to form relationships with Republicans, with individuals from rural parts of the state, and we had a lot in common.”

But in 2000, his ambition led to his first big setback. He was trounced when he made an impulsive bid for a seat in the U.S. Congress and the election turned nasty. “The undercurrents were that Barack wasn't black enough,” says Mr. Shomon, who managed the campaign. “He did have to learn to manoeuvre the minefield of black politics.”

The defeat “rattled” Mr. Obama, but, “looking back, I think it was the best thing that ever happened. The 2000 race was really his initiation. If he had not been through that, everybody believes he would not have been ready for the 2004 Senate race.”

PART 5: A STAR IS BORN

When Mr. Obama tentatively launched his run for a U.S. Senate seat in 2003, friends could sense that the mark left by his embarrassing loss three years earlier had yet to fade. “When you're running in your early stages, there is this gnawing concern that maybe you're going to go to … an event and no one is going to show up,” says Judd Miner, the lawyer. “In the early days, my wife and I would get a call, would we go to an event and bring some friends, just in case.

“You could watch him, and it was clear he got better, and audiences got more receptive.”

The following July, he was given a golden opportunity: to give the keynote address to thousands of Democrats who had gathered to make Senator John Kerry their presidential candidate. A virtual unknown when he took the stage of Boston's FleetCenter, he seemed light-years away from any run for the White House – this was just a litmus test to see if he could get into the Senate.

“In no other country on Earth,” he told them, “is my story even possible.” Then, as he delivered his message of nationalism and unity, the crowd seemed to catch fire.

Approaching his climax, he declared: “The pundits like to slice and dice our country into Red States and Blue States. … We are one people, all of us pledging allegiance to the Star and Stripes, all of us defending the United States of America.”

The next day, newspapers announced that the Democrats had a new star. The question went from would Mr. Obama win a Senate seat to would a Senate seat be enough?

To his old friends back in Chicago, the answer has been obvious for almost 25 years.

“After working with him that first year, I just absolutely knew,” insists Loretta Augustine-Herron, who conducted that pivotal first interview. “We used to talk about it. We'd say he's going to be the first African-American president.”

Jessica Leeder is a Globe and Mail writer based in Toronto and Rod Mickleburgh is a member of the paper's Vancouver bureau.