Early defeat launched a rapid political climb

The second in a series of occasional articles examining the 2008 candidates for president.

CHICAGO - Defeated, broke, and unsure what life held next, Barack Obama lumbered aboard the Abegweit, an old ferry docked in Lake Michigan off downtown Chicago.

The day, in mid-2000, was luminous, the boat offering panoramic views of the city, the lake, and beyond. But the atmosphere was funereal: Obama had just lost badly in his bid for Congress, and he had organized this small fund-raiser to help retire his campaign debt.

"I felt like they were going to bring a casket out or something," said Dan Shomon, a top aide on Obama's past political campaigns.

Obama had established himself as an up-and-coming black politician with big dreams - a conciliatory figure whose promise held redemptive power for an America eager to transcend the divisive racial politics of yesterday. But his bruising loss to US Representative Bobby Rush in the March 21, 2000, Democratic primary, along with pressure from his wife to pursue a more predictable and lucrative career, left him facing hard choices.

He was a 38-year-old second-term state senator laboring under Republican leadership in Springfield, the state capital. Yet he lacked a clear political alternative. "Is Obama dead?" one Chicago commentator asked on radio. In his soul-search ing, Obama considered what today seems unthinkable: getting out of politics.

"I think he genuinely wondered: Should he even continue to pursue a political career?" said Martha Minow, who had taught him at Harvard Law School and become a friend.

Obama tried to imagine himself in different roles. He considered becoming president of the Joyce Foundation, a Chicago organization that gives out roughly $50 million a year to initiatives on the environment, poverty, violence, and schools. The position was high-profile, well paying, close to home, and appealed to his sense of public mission. Obama knew the foundation's work because he was on its board at the time.

But there was a catch: He would have to leave the state Senate, at least temporarily putting his political ambitions on ice.

"I think he really was at a point where he had to decide whether, look, am I going to be a behind-the-scenes policy guy, or am I going to follow up on Springfield with political actions?" said Carin Clauss, a Joyce Foundation board member at the time.

The foundation job was one of several alternatives to politics Obama weighed, including a full-time teaching job at the University of Chicago Law School, returning to full-time law practice, and even joining friends in the business world. None felt right.

"I think, in my heart, I wanted to continue in public service," Obama said in an interview.

Some of Obama's friends and advisers say he was morose after the loss to Rush; others recall his resilience. The congressional campaign gave him reason to feel both: He got a glimpse of what he could be as a political leader, but he had chosen the wrong race to break into national politics and not run a strong campaign.

"Barack didn't come out of this with a whole rosy picture," said Aldophus Kindle, a field operative for Obama in 2000 and 2004 who has known him for 20 years. "He was [angry] at himself, I believe, for committing to a race he didn't go ahead and deliver, and go ahead and win. It wasn't like Obama was sitting at the dinner table saying, 'OK, what next?' "

Obama's half-sister, Maya Soetoro-Ng, with whom he is close, said: "He sort of agonized for a time about whether to give [politics] another shot, and at the same time, I think he felt a stirring within and the sense that he was destined for something bigger."

His destiny was hardly clear that day on the ferry. But what became clear, as the sting from the 2000 loss wore off, was that Obama and those behind him knew he had some political life left in him, knew he felt called to serve. He just needed a place to do it.

A POLITICAL EDUCATION

Obama's journey has cut an unlikely path, beginning in Hawaii and taking him to Indonesia, Los Angeles, New York, Cambridge, and finally Chicago, his home base for much of the past two decades.

He was born in Honolulu on Aug. 4, 1961 to a black Kenyan goatherder-turned-economist, Barack Obama Sr., and a white, aspiring anthropologist from Kansas, Stanley Ann Dunham, who met at the University of Hawaii. His parents soon separated, and Obama's father returned to Kenya, leaving young Barack to be raised by Dunham and her parents, whom he called Toot and Gramps.

When his mother remarried, Obama moved with her and his stepfather, Lolo Soetoro, to his stepfather's native Indonesia, where he lived until he was about 10. He then returned to Hawaii to live with his mother's parents. In high school in Honolulu, Obama went by the name Barry, liked the beach, and played basketball - but he also had a depth about him, "a rich interior life," his sister said.

After graduating from Columbia University in New York in 1983, Obama moved to Chicago for a community organizing job, inspired by the election that year of the city's first black mayor, Harold Washington, and the political awakening it seemed to represent. He wanted to be a force for change, empowering poor and middle-class families to stand up to the businesses, politicians, and bureaucrats who paid them little heed.

Obama plunged into Chicago's South Side, working closely with churches and community organizations. He tasted the frustrations of trying to make change only from the bottom - frustrations that drove him to Harvard Law School in 1988, with plans to return with a bigger toolbox.

He spent his first summer of law school interning in the Chicago office of the firm Sidley Austin, where his adviser was a first-year associate and recent Harvard Law School graduate named Michelle Robinson. To her, Obama was a talented and caring dreamer; to him, Robinson was a sharp, sensible daughter of the South Side whose more traditional upbringing he envied. They soon began dating.

As their relationship matured, Michelle Obama recalled in a recent interview, she asked her brother, Craig Robinson - the fourth all-time leading scorer at Princeton and now the basketball coach at Brown University - to get him on the court, to see what he was made of.

"I said, 'Well, he plays basketball - loves to watch it, loves to play it, talks a lot of trash about it,' " she said. "It was important to me to see, well, can he play, or was he just talking? Did he have skills, or was this all in his head?"

Her brother returned with a good report: Obama was a team player, confident without being cocky, not a ball hog but not afraid to shoot. That helped seal the deal. He and Michelle were married in 1992 and put down roots in Hyde Park, a multiracial enclave south of downtown Chicago.

After Harvard, where he was president of the prestigious Harvard Law Review, Obama could have written his ticket to just about anywhere - white-shoe law firms, investment banks, possibly a clerkship on the Supreme Court. But his heart remained in community work, in fulfilling the hopeful vision for America he had nurtured since his upbringing: a just, equitable place where everyone gets a fair shake.

In Chicago, he ran a successful minority voter registration program called Project Vote! In 1995, at age 33, he published his first memoir, "Dreams from My Father," a deeply personal meditation on identity, race, and his relationship with his absent father. He began lecturing part-time at the University of Chicago and practicing civil rights law.

"I really have to want to be here," he said in an interview with The Chicago Reader just before the 2000 congressional primary. "I'm like a salmon swimming upstream in the South Side of Chicago. At every juncture in my life, I could have taken the path of least resistance but much higher pay."

Believing he could apply his organizing skills and grass-roots philosophy to government, Obama decided to run for the state Senate in 1996, winning office with an aggressive political move.

Obama ran for the seat of Alice Palmer, a respected activist who had decided to run for Congress and anoint Obama as her successor. But when Palmer's congressional bid fell short, she decided she wanted to keep her seat and tried to get Obama to step aside.

Not only did Obama refuse, his political associates - led by Chicago Alderwoman Toni Preckwinkle and her staff - challenged the validity of Palmer's signatures and the signatures of his other prospective opponents. Many were ruled fake, and in one fell swoop Obama knocked every rival out of the race.

"That's what happens in Chicago," Preckwinkle recalled.

But if Obama had cleared his path to the state Senate, at home it was a different story. Michelle Obama was cynical about politics, particularly the bare-knuckle Chicago variety. It would be the couple's first real taste of the delicate balance between Obama's political aspirations and the demands of home.

"I wasn't a proponent of politics as a way you could make change," Michelle Obama said. "I also thought, was politics really a place for good, decent people?"

Obama arrived in the state Senate in 1997 promising to be the "hardest-working senator down in Springfield." He also made a concerted effort to build relationships with lawmakers from rural regions hours away - and worlds removed - from Chicago. Over basketball games and rounds of golf, and at poker sessions with legislators and lobbyists, Obama befriended colleagues from different backgrounds and generations - personal connections that helped him pass bills then, and that are still paying political dividends to this day.

Despite his down-to-earth nature, Obama's ambitions and idealism were apparent.

"I knew I would be in the Illinois Senate longer than he would be, and not in a derogatory way," said Terry Link, who joined the Senate when Obama did and hosted the poker games. "I knew that bigger and better things were ahead for him, and I knew that from Day One."

Obama's Ivy League education, Hyde Park address, and perceived holier-than-thou attitude rubbed some lawmakers the wrong way, at least initially. Black lawmakers from Chicago mocked his pedigree.

Obama helped neutralize the criticism by cultivating a relationship with the powerful Senate Democratic leader, Emil Jones, a former city sewer inspector from a far South Side district. Jones came to view Obama as a son; Obama has called Jones his "political godfather." Under Jones's tutelage, Obama shepherded some major bills through the state capitol during his eight-year tenure.

He won passage of Illinois's first major ethics reform in years, over the objections of many Democrats. He passed legislation making Illinois the first state to require police to videotape homicide interrogations. He helped spearhead racial profiling legislation and death penalty reform. Obama built a reputation as a pragmatist with a genuine interest in reaching across the aisle, a trait that would define him later as a US senator and presidential contender.

"He was willing to work with Republicans, so they didn't see him as some evil figure," said Dick Simpson, who heads the political science department at the University of Illinois-Chicago.

Chicago Mayor Richard M. Daley, who got to know Obama when Obama was in the state Senate, said: "He's not edgy all the time. He's not in your face on an issue."

He was, however, edgy for higher office, and in 1999 he thought he saw his opening.

'WE GOT SWAMPED'

Less than three years into his state Senate career, Obama ignored the counsel of friends and decided to take on Rush, a former Black Panther and longtime fixture in his South Side congressional district. Link, Obama's friend from the state Senate, was one who warned him against it.

"It was real simple," Link said. "I didn't think he was ready for it."

But Rush was considered vulnerable after losing badly to Daley in an ill-conceived bid for City Hall. So on a Sunday in late September of 1999, Obama brought several hundred supporters to the Palmer House, a downtown hotel, to kick off his bid for Congress.

Rush said in a recent interview that he was stunned when he learned that Obama was challenging him.

"I was shocked, disappointed, and, you know, frankly somewhat angry," he said. "If there are 10 issues, we agree on 9.5. . . . I didn't see the rationale for it."

Obama's argument was not so much that Rush had been a bad advocate for the district, but that Obama could be a better one. If Rush represented the Old Guard of black activism, Obama embodied a new generation of post-Civil Rights era leaders less encumbered by the us-versus-them dichotomies of the past. Another state senator from Chicago, Donne Trotter - one of the black lawmakers who ribbed Obama in Springfield - also entered the race.

If Obama's campaign began optimistically, a hard reality soon set in. Polls showed a yawning gap between his and Rush's name recognition. And then on Oct. 18, 1999, Rush's 29-year-old son, Huey Rich, was shot on a South Side street. He died in a hospital four days later. The slaying elicited a wave of sympathy for Rush, forcing Obama to effectively suspend his campaign for a time.

"I think that voters were prepared to give Bobby Rush another look from that point on," said Chris Sautter, Obama's media strategist in that race.

A few months later Obama was on his annual Christmas trip to Hawaii to visit his grandmother. A crucial, close vote on a crime bill came up in the Senate earlier than expected. His daughter was sick, and Obama elected to stay with her instead of flying back for the vote, a decision that drew a torrent of criticism and bad press.

Things never got much better. Obama campaigned tirelessly, appearing without gloves, hat, or thick jacket in the dead of winter on wind-swept El platforms.

"We called him the Kenyan Kennedy," said Will Burns, a field operative on Obama's campaign. But the district's voters weren't looking for another JFK.

Aides say Obama failed to raise enough money and was helpless in the closing weeks, when Rush enlisted President Bill Clinton - a revered figure among many African-Americans - to do ads for him on black radio.

Despite the years Obama had spent working for black communities, Rush was able to sow suspicion about Obama in African-American neighborhoods, portraying him as the candidate of Hyde Park intellectuals and white liberals. Borrowing a dig from a Curtis Mayfield song, he dubbed Obama "an educated fool."

What Rush didn't say, Trotter did. Days before the primary, Trotter told The Chicago Reader, "Barack is viewed in part to be the white man in blackface in our community."

This harsh critique of Obama from a small group of African-American leaders has dogged him throughout his political career -a price he pays, some supporters believe, for his broad appeal among nonblack voters and willingness to design his own mold as a black politician.

The predominantly black First Congressional District stretched south into white enclaves, and Obama's strategy was to lock up white voters first, figuring they would gravitate to him over Rush. He was right, but he came up well short in the black neighborhoods, whose residents saw no reason to throw out their familiar congressman.

Rush won 61 percent of the vote, Obama won 30.

"We got swamped," Preckwinkle said.

"I think his ambition came crashing into a well-established record," Rush said in the interview.

But if Rush, who is now a supporter of Obama's presidential campaign, expresses confidence today about putting his record up against Obama's, he evidently felt differently back then. Just in case Obama was thinking rematch, Rush made sure, during the redistricting process after the 2000 Census, that Obama's street was carved out of his congressional district.

THE COMEBACK

A few days after the election, Obama was back in Springfield playing cards at Link's house. It was awkward at first, Link said, because what happened in the congressional race was precisely what he and others had predicted.

"Finally it just came out, and he said, 'All right, let's get it over with,' " Link said. "Everybody said, 'OK, we told you so.' We didn't talk about it much after that."

The loss weighed on Obama.

"It's impossible not to feel at some level as if you have been personally repudiated by the entire community, that you don't quite have what it takes, and that everywhere you go the word 'loser' is flashing through people's minds," he wrote in his second book, "The Audacity of Hope," published last year.

Obama's political prospects were fuzzy, and he and his supporters struggled with whether he would run for office again - and where. They discussed a possible statewide campaign in 2002. Some saw him as a potential attorney general, or state comptroller. But Obama was not sure he would run for anything.

"He was rethinking his political future, there was strong pressure from Michelle, and I think he was starting to wonder if he was going to go anywhere," Shomon said.

His wife had had her fill of politics, she said, and was looking forward to him settling into a more stable job like the Joyce Foundation post.

"My hope was that, OK, enough of this, now let's explore these other avenues for having impact and making a little money so that we could start saving for our future and building up the college fund for our girls," she said.

Michelle Obama - with degrees from Princeton and Harvard Law School - said their combined school loan debt exceeded the mortgage on their Hyde Park condo. Even so, like her husband, Michelle had difficulty reconciling competing emotions.

"It's hard to look at somebody with the talents and gifts of Barack and say, 'Go do something smaller than what you could do,' " she said.

Obama today plays down his discussions with the Joyce Foundation, saying the president's job was not automatically his had he wanted it. Former board members say the foundation loved him, but they questioned his interest in the position.

Richard Donahue, a board member at the time, said he remembers telling him: "For God's sake, Barack, this is a great job. But you don't want it."

In time Obama recognized that leading a foundation was not his destiny, not the realization of the dreams he harbored.

"He said, 'I was literally shaking with fear that I would get the job,' " Shomon recalled.

Obama came to understand, as he navigated his many options, that he could not extinguish the spark for politics. His restless spirit and fierce competitive streak wouldn't let him. So he decided to stay in the state Senate and bide his time for the right shot to make his mark.

"My attitude was, it was worth trying one last big race," he said.

In mid-2002, Obama began to focus on the upcoming US Senate race. The incumbent, Republican Peter Fitzgerald, seemed beatable, and it was not clear Carol Moseley Braun, who had held the seat before Fitzgerald, would try to reclaim it. Obama and his wife made a deal: This would be, as his wife puts it now, "the last hurrah."

At a few key appearances around Illinois that year, advisers say, Obama felt the magic again.

On a Saturday night in September 2002, the Pierre Menard Democrat Club held its annual membership dinner at a VFW hall in Sparta, where a few hundred party faithful paid $100 to eat roast beef and ham. Obama was a last-minute fill-in keynote speaker. He made the 650-mile round trip in one day, needing to be back for a church event Sunday morning.

That night, Obama delivered a soaring, motivational speech about public leadership, said Barb Brown, a Democratic Party official who helped plan the dinner.

"It was really sort of inspiring us to step up to the plate and make sure all of us in politics, that we're doing it for all the right reasons," she said.

Days later, on Oct. 2, 2002, Obama made one of the most important speeches of his political life. Invited to address a hastily organized protest of President Bush's war plans for Iraq, Obama told hundreds of people in Federal Plaza in downtown Chicago that invading would be a big mistake.

"I am not opposed to all wars," Obama said. "I'm opposed to dumb wars."

That fall, Obama had not yet announced his Senate campaign but began lining up friends, supporters, and donors. He signed up David Axelrod, a well-respected Chicago political strategist and ad-maker, to help plot the race he would run.

As with his campaign against Rush, not all his friends and advisers were on board. One Sunday morning, the Obamas and some friends had brunch at the home of Valerie Jarrett, a Chicago businesswoman who had known them for years. Jarrett, fretting about the impact a run would have on Obama's family, recalled that she "already had my resolve that he shouldn't do it."

"We were saying, well, what if you lose?" Jarrett said. "He said, 'I think the timing is right, I think I have a lot that I can offer, and the worst thing that can happen is that I lose. ' At the end of a two-hour breakfast, I was not only on board but I was chairing the finance committee."

A NATIONAL FIGURE EMERGES

If Obama's decision to run for Congress was impulsive - and, by his own admission now, a little vain - his decision to vie for the US Senate was a studied one.

"In some ways I think I was a better United States Senate candidate because I didn't feel as if I needed to [run] that race simply to stroke my ego, that at that point I was doing it much more because I wanted to talk about the issues that were at stake," he said.

His failed bid for Congress had been a useful dress rehearsal. It proved he could appeal to white voters as well as black ones. It let him audition his message that Washington does not work for all people. And it showed him what to do - and what not to do - to win.

"I think that, plainly, one of the lessons he learned from 2000 was start early, plan well, do the hard work of laying a foundation," Axelrod said.

Formally launching his Senate bid in January 2003, Obama became a savvier and more effective fund-raiser, tapping both the white, North Side crowd he had impressed in 2000 and an emerging base of black professionals, many of whom were eager to support a man who, literally and allegorically, seemed to represent a unified America they longed for.

He also became less eggheadish and more engaging on the stump.

"It doesn't do you any good to run as a professor at the University of Chicago, or to think of yourself that way on the campaign trail," said Preckwinkle, the Chicago alderwoman.

One of Obama's key moves came in the spring of 2003, after Democrats won control of the Illinois Senate and Jones, Obama's political mentor, became Senate president. Obama approached Jones, told him he had the power to make a US senator, and said he wanted to be that senator. Jones agreed, quickly becoming an influential booster whose support lent an important imprimatur.

"You got somebody good," Jones said, "you push him."

Having a powerful figure like Jones out front early helped Obama gain traction in what looked like a tough race. Prospective opponents included Dan Hynes, the state comptroller from a politically connected family; Blair Hull, a former securities trader with millions to spend on his own campaign; and Jack Ryan, a Republican investment banker who became an urban schoolteacher.

Jones believes his endorsement also helped quell criticism, including from some black political leaders, that Obama was getting too big for his britches. "There were those who said: 'He's new. Who is he? What makes him think he [could run]?' " Jones said.

Obama also got lucky. Moseley Braun elected not to run for her old seat; then Hull and Ryan were badly damaged by revelations about their marriages.

"The US Senate race was the flipside of what happened in 2000," Burns said. "Every break that could go his way in 2004 he got."

Obama emerged from the crowded March 2004 primary as the Democratic nominee, going on to handily beat Republican Alan Keyes, a black, conservative perennial GOP political candidate. Obama's election in November 2004, which made him just the third black senator since Reconstruction, was a rare bright spot for Democrats that fall.

One hallmark of Obama's success, particularly in the primary, was his support in predominantly white areas.

"I'd get these glowing reports back," Axelrod said. "And I'd ask him about it, and he'd say, 'You know, these folks are just like my grandparents from Kansas.' "

Making a play for white voters was, once again, a conscious strategy: His advisers knew that if they made inroads in white communities they would win, because the vast majority of black voters in Chicago would be behind him.

"He perfected what Carol Moseley Braun and Harold Washington had before: a black person who would be acceptable to the white suburbs and people downstate," said Simpson, of the University of Illinois-Chicago.

It was this unique, charismatic figure with a foot in both worlds who, with The Impressions' "Keep on Pushing" playing behind him, crested the stage at the Democratic National Convention in Boston in 2004.

Axelrod likes to joke that people assume Obama was born on stage that night. In the public imagination that is largely true.

The day before Obama's speech, Jones said, he was in the elevator of a Boston hotel with other Democratic delegates, wearing an Obama button.

"[One woman] looked at me and she said: 'Oh, we know where you're from. You're from Alabama,' " Jones recalled. "I said to her, 'No, that's Obama - he's your keynote speaker for tomorrow.' "

Obama's speech the next night began dryly but crescendoed into his now-famous deconstruction of partisanship, a simple but eloquent discourse on the dangers of dividing.

"I'm sitting there, and tears started to run down my face, I felt so embarrassed," Jones said. "We all felt so good for him."

A NEW EXPERIMENT

After that speech, the self-described guy from the South Side with the funny name suddenly became a household name. There had long been whispers among acquaintances that Obama would one day run for president, but that night the whispers became a drumbeat, and no longer just from friends.

In his two and a half years in the Senate, Obama has worked on nuclear arms control, federal lobbying and ethics reforms, and other issues. But his brief Senate career has been largely overshadowed by presidential murmurs.

With the letdown of 2000 and the glory of 2004 both fresh in his mind, Obama summoned friends and supporters to the Old State Capitol in Springfield on Feb. 10 and launched his boldest political experiment yet.

"Look, I recognize there is a certain presumptuousness in this - a certain audacity - to this announcement," he said that day. "I know that I haven't spent a lot of time learning the ways of Washington. But I've been there long enough to know that the ways of Washington must change."

With the primaries now a few months away, Obama's candidacy has ignited a grass-roots movement across the country, reengaged people in the political process who had written off politics completely, and been a powerful role model for untold black youth.

His spectacularly rapid rise has also prompted questions about whether he has the experience to be president. Whether the country is ready for Barack Obama, as his supporters believe, will hinge on whether voters think Barack Obama is ready for the country - whether they see his inclusive message not just as rhetoric, but as a way forward for the country.

It was, after all, just a few years ago - as John McCain was making his first presidential run and Hillary Clinton was on her way to the US Senate - that Obama wondered if politics held a place for him. It is, Obama says, a period in his life he reflects on often.

"I'm constantly reminding myself that a lot of these opportunities that have opened up for me are beyond my control, and that I am not a hundred times smarter than I was five years ago, or a hundred times more articulate," he said. "It's not as if I have changed dramatically."

Scott Helman can be reached at shelman@globe.com.