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A Series of Fortunate Events

Obama gathers his thoughts before speaking at the Iowa First Congressional District Democratic Caucus workshop in Peosta, Iowa, in July 14.
Obama gathers his thoughts before speaking at the Iowa First Congressional District Democratic Caucus workshop in Peosta, Iowa, in July 14. (Jeremy Portje - Associated Press)

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Obama laughs, now, hearing that anecdote. He doesn't remember the exchange, but adds, "If the conversation did come up, and I said that I was interested in electoral politics . . . my aspirations would have been higher than being an alderman."

Craig "should have said, 'Don't tell Michelle!'" says Michelle Obama, who initially tried to talk her husband out of running for office. He persuaded her, she says, by arguing that they had a responsibility to work on behalf of people less privileged than they are.

"You know, Barack is very convincing and very passionate," says Michelle, who says she was naive in the beginning about the impact it would have on their family life, which now includes two young daughters, Malia and Sasha. "So I eventually said: 'Sure, let's do it. Okay, you win.'"

"And then," she concludes, "you're in."

Barack Obama's first opportunity came, as opportunities would with striking frequency, when somebody else's personal life got messy.

In the fall of 1995, Mel Reynolds, 43, who represented Illinois' 2nd Congressional District, was forced to resign when he was convicted on charges related to having sex with a 16-year-old campaign volunteer. There were several contenders in the special election to replace him, including Alice Palmer, a progressive state senator who represented Hyde Park and urged Obama to run for her state Senate seat. But when Jesse Jackson Jr. won the primary, Palmer decided she wanted her old job back. Obama did not step aside. More than that, according to the Chicago Tribune, when Obama's staffers looked at the petitions she'd hastily garnered, they saw irregularities and challenged them before the board of elections. Then, noting irregularities in the petitions of his other primary opponents, Obama knocked them all out of the race. He went on to win and was sworn into the state Senate in January 1997, and started commuting to Springfield.

His ambition, now, was as visible as a radio tower. Invited by Harvard political scientist Robert Putnam to participate in the Saguaro Seminar, a network of thinkers who met around the country to discuss community issues, Obama talked so openly about his political future that the group began referring to him, teasingly, as "Governor."

"He was transparently and lovably ambitious," says Putnam, author of a seminal work on the withering of community in American life, Bowling Alone: The Collapse and Revival of American Community. "He was always talking about running for office and the importance of being in politics."

The group stoked his sense of potential. "I remember, after the second or third meeting, a crowd gathered around him and said, 'When are you running for president?' recalls Martha Minow, who was also a Saguaro member. "I try to remember: Why did we think this? It was his way of listening astutely to the conversations, offering an embracing, objective view: Here's how what everybody says fits together."

Lacking ties to any ward machine, or the street credibility of leaders who had ascended the ranks, Obama ingratiated himself with Emil Jones, who would become president of the Illinois state Senate after the Democrats assumed control. Jones became a mentor to Obama, entrusting him with overseeing reforms of welfare, campaign finance and the criminal justice system. Among Obama's achievements was a law requiring that murder confessions be videotaped. In all of this he displayed what Mikva, who became another of his mentors, calls his characteristic "knack for getting people to bargain seriously." Not everybody liked him; one Senate colleague described him as so ambitious that given the chance, he'd run for "king of the world."

After just a few years, Obama was talking about running for Congress, and thought he saw an opportunity. In 1999, black congressman Bobby Rush had challenged Richard M. Daley for mayor, and lost. Obama conducted a poll, says then-campaign manager Dan Shomon, and it suggested that some voters, particularly white ones, were looking for an alternative to Rush. "I was a little bit questioning about whether Rush was vulnerable at all, but Barack was sure that he was," Mikva says.

Obama paid a price for trying to depose a member of the African American power structure: During the race, the suggestion was subtly advanced that Obama was not "black enough." Then, that October, Rush's adult son was murdered in a street shooting, and Obama shut down his campaign for several weeks to show compassion. His campaign lost momentum, and he lost badly in the March 2000 primary.

He did not take his drubbing well. "He is not a good loser," says Shomon. Obama acknowledges this: "Losing's always miserable."

So miserable, that when Mikva met with Obama, he found him unusually dispirited. "That was the one time he semi-seriously thought about giving up politics. He was frustrated; he had been [in the state Senate] for four years; the pay is very modest. It seemed that whatever his ambitions were, there wasn't going to be a channel for them."

Obama, who didn't want to be a "lifer in the state legislature," agrees that he seriously considered looking for another way to make an impact. "Some doubts entered my mind as to whether some kid from Hawaii named Barack Obama could succeed in a political venue, where a lot of times voters are relying on very little information and making snap judgments based on somebody's name and whether they've got family ties."

But, of course, the loss to Rush would turn out to be more fortunate than it appeared. As Newton Minow points out, had Obama beaten Rush, "he would have been in Congress, not a senator, and he wouldn't have given the speech at the [2004] Demo-cratic National Convention" that would change the trajectory of his career. "Nothing like that would have happened. I'm a great believer in timing. Everything is timing."

And timing, now, was on his side. Just when Obama was despairing, it became evident that Peter Fitzgerald was foundering in the U.S. Senate. "He had some very good characteristics," says Obama now. "But he just didn't seem to enjoy the job much, and wasn't a particularly good politician. I thought that a Democratic challenger could draw a sharp contrast and be effective. I thought I could beat him."

Shomon tried to dissuade him from running, arguing that a Senate campaign would put too much pressure on his personal life. "His counterargument was similar to his counterargument always: We can change politics, we can change the agenda, we can help average people." He said, Shomon recalls, "I'm not going to be able to help people if I'm stuck in the state Senate for 20 years."

"He really felt like this was his opportunity," Shomon says. "Every time Barack saw an opportunity, he felt like it could be his last."

Then in April 2003 -- just a few months after Obama formally entered the primary -- Fitzgerald surprised everyone by announcing he would not run for reelection. This, Obama believes, was his luckiest break of all, because it meant that there was no incumbent. The seat was truly open. "I thought I could beat him, and still think I could have beat him, but the fact that he did not end up running, obviously, left the field wide open."

Ultimately there would be seven candidates in the Democratic primary, but for Obama there were two who mattered. One was Dan Hynes, the popular state comptroller and favorite of the party machine. The other was Blair Hull, a wealthy stock trader who had sold his company to Goldman Sachs for $531 million.

Hull's presence, while formidable, did two things to help Obama. First, it increased the likelihood that the white vote would split between Hynes and Hull. Second, it enabled Obama to raise much more money than he otherwise could have. The newly passed McCain-Feingold campaign finance reform law contained a "millionaire's amendment." In a race against a wealthy opponent who is financing his own campaign, a candidate is permitted to raise significantly more than the normal limit. In this case, Obama could raise $12,000 from each donor instead of $2,000.

"This was a huge advantage; it just made a huge difference," says Mikva. "I gave him more money than I've ever given anyone in my life."

In The Audacity of Hope, Obama writes how put off he was by the magnitude of the fundraising effort a Senate race requires. "I started engaging in elaborate games of avoidance during call time -- frequent bathroom breaks, extended coffee runs." But he steeled himself for the task and learned to set aside "any sense of shame I once had in asking strangers for large sums of money."

He built a diverse group of donors. Among them were black business owners and professionals. He could also take advantage of his Ivy connections, drawing on moneyed Harvard classmates and his wife's super-loyal Princeton connections. He had energetic supporters in Minow and Mikva, as well as David Axelrod, the leading Democratic campaign consultant in Illinois. He appealed to many of Chicago's "lakefront liberals," who occupy a strip stretching from downtown to the North Shore along Lake Michigan, and attracted major benefactors such as the Crown and Pritzker families, big money.

But Hull was still vastly outspending him, and the spending mattered. A poll taken about a month before the primary showed Hull in the lead, with Hynes and Obama trailing.

Then, in late February 2004, Blair Hull had a very bad day. There had been rumors of an ugly divorce from an ex-wife; when the court records were released, they contained allegations of domestic abuse. Shomon remembers Obama's reaction. He feared that if Hull dropped out of the race, Hull's support would shift to Hynes. But Hull stayed in the race, and hung onto about 10 percent of the vote.

This may not have mattered as much as it seemed. In the end, Obama, preaching a message of unity, did much better with white voters than anyone had anticipated. After Hull's disaster, Hynes's numbers edged up slightly, while Obama's soared. "Much to our shock and surprise," says Axelrod, "he won with 53 percent of the vote." They were incredulous -- and ecstatic. Obama won in the most unlikely places, including portions of northwest Chicago, where Harold Washington once had been treated so venomously that it made the national news. He was, it now became clear, a genuine crossover politician, something that put Obama on the national map. William Finnegan profiled him in in the New Yorker, Scott Turow wrote a piece in Salon, and the newsweeklies took notice.

Now the cherries were falling into place furiously. Obama's Republican opponent was Jack Ryan, another very wealthy opponent, well-regarded. And the Democratic Party -- finally taking notice -- decided it would give Barack Obama some help.

It would ask him to make a speech.

In early summer of 2004, organizers of the Democratic presidential convention were faced with some challenges, chief among them the fact that no Bush-bashing would be allowed among convention speakers. The Kerry campaign didn't want to alienate swing voters by speaking ill of Republicans. So the convention needed speakers who could present an upbeat message and still sound compelling.

There were some givens. Bill Clinton would be the prime time speaker Monday night; the third and fourth nights would feature John Edwards and John Kerry, respectively. On Tuesday they wanted a keynote speaker in the tradition of the great keynoters of the past: Barbara Jordan, Mario Cuomo, Ann Richards, "people who inspired hope," as Donna Brazile puts it, "and not only inspired hope, but laid a framework for the party."

There were a number of criteria as planners began proposing candidates. Youth was desirable, and freshness, and diversity. "We were trying to think creatively of the next generation of leaders," says one campaign official. They came up with a list of Democratic governors that included Mark Warner of Virginia, Bill Richardson of New Mexico and Tom Vilsack of Iowa: solid choices, but a list that, as the official put it, "didn't get us where we wanted to go." Jennifer Granholm, the photogenic new governor of Michigan, was also on the list. And Kerry campaign manager Mary Beth Cahill, who had read some of the coverage following Obama's primary victory, proposed Obama.

It was an appealing idea. Obama was known to be a speaker who could get a crowd going. He was a Midwesterner from a major industrial state, providing a demographic complement to Southerner Edwards and Northerner Kerry. But these things were also true of Granholm.

Weeks before the decision was made, David Axelrod heard "scuttlebutt" that Obama was being considered. Axelrod told Obama, who says he found it a bit hard to believe. "I have to say, I was skeptical," Obama says. "Traditionally -- obviously -- that slot is not given to a state senator." Obama did not lobby directly, but Axelrod did, saying, "My case was that he was a transcendent figure who could deliver a unifying message and had just won a spectacular victory."

According to an official involved, the decision came down to the fact that Obama, unlike Granholm, was still trying to win an election. Just a few weeks before the convention, it would emerge that Obama's opponent, Jack Ryan, had tried to talk his wife at the time into performing public acts at a sex club. Ryan would eventually withdraw, and there was talk that some marquee Republican, possibly former Chicago Bears coach Mike Ditka, would enter the race. The balance in the Senate was 51-48 in favor of Republicans. "We needed his Senate seat," says the official. So Obama it was.

Kerry gave Obama's selection an enthusiastic thumbs up. "I was impressed by him," Kerry says. "I had met him and . . . campaigned with him in Illinois, and thought on a personal level he would be able to convey the kind of message I wanted to convey out of my convention: a message of inclusiveness and change, a new view about how we can make our politics more relevant to people and, in a sense, just put a little bit of different language in front of folks."

In The Audacity of Hope, Obama portrays it as a total surprise when Cahill called to invite him to deliver the keynote. "The process by which I was selected as the keynote speaker remains something of a mystery to me," he writes, saying that after he received the call in his car, he marveled to his driver, "I guess this is pretty big."

This seems disingenuous. "There is no doubt that that call was expected," says Michael Duga, chief of staff to former senator Max Cleland, who also was involved in the planning. Axelrod doesn't dispute this: "We heard shortly before he got the call that he was likely to get it." So, he acknowledges, "we did get a little bit of a heads-up."

Obama knew what he wanted do with the speech, says his communications director, Robert Gibbs. He wanted to tell his life story as an American narrative. He wanted to offer himself as an embodiment of what's possible. And he wanted to write the speech himself, which he did, stuck in Springfield during votes, sending drafts by e-mail. But Gibbs also did research. Listening to past keynote speeches, he realized that there were two basic models. One was the 1988 Ann Richards punch-line model -- you deliver a one-liner, and there is wild applause, and you deliver a one-liner, and there is wild applause -- and the other was the 1984 Mario Cuomo model, a visionary declaration that the audience doesn't punctuate with clapping, because it's rapt. That's the model Obama went for.

On the night of the speech, Gibbs and Axelrod stayed in the greenroom with Obama and his wife beforehand, then went down to watch on the convention floor, with thousands of delegates, reporters and spectators. Another 9 million people saw the speech on the cable channels covering the convention.

Obama began by talking about his mother and father, the diversity of his heritage, how "in no other country on Earth, is my story even possible." He spoke about issues -- better government, health coverage, better care for veterans -- then delivered his famous call for unity and compassion: "We are all connected as one people. If there is a child on the South Side of Chicago who can't read, that matters to me, even if it's not my child," he said, dismissing the idea of "red states for Republicans, blue states for Democrats . . . We are one people, all of us pledging allegiance to the stars and stripes, all of us defending the United States of America."

On the floor, Gibbs recalls, he and Axelrod sensed the rapture of the crowd and looked at each other "like two kids at Christmas."

"Sometimes you know it's a home run at the crack of the bat," says Axelrod. "As soon as he swung, you knew that the ball was going to go over the fence."

The full impact of the speech became clear to Obama's staff days later, when they embarked on a whistle-stop RV tour of downstate Illinois. Obama, Shomon says, was furious when he saw the schedule. He was exhausted and wanted to spend time with his family. But at the first town on the first day, there were 500 people instead of the 100 that had been expected. The same thing happened again, and again; then one day they drove into a state park to see 1,000 people crowded into an open-air amphitheater. "Everyone knew exactly what everyone else was thinking," say Gibbs. "Wow."

This continued. "You'd hear [Democratic] party people talking: Not only was it the biggest crowd we ever saw, it's new people, not just the usual suspects -- we don't even know who these people are," says political analyst Charlie Cook.

The speech vaulted Obama into mega-celebrity. "It's like walking around with Michael Jordan now," says his brother-in-law Craig Robinson. As for money: "It wasn't a matter of fundraising anymore," says one of his consultants, Joe McLean. "It was just a matter of collecting money."

And they didn't even need all of it. The next cherry clicked into place when the Illinois Republican Party, having taken more than a month to find a replacement for Jack Ryan, had the extraordinary bad sense to import Alan Keyes, a loose cannon and perennial candidate from Maryland. Obama won with 70 percent of the vote. "You'd have to be appointed to get an easier ride than that," says Cook. "How many people get elected to the U.S. Senate without having a single negative ad run against them?" Ron Walters, a political scientist at the University of Maryland, agrees. "You could argue that if the Republicans had had a viable candidate, there would be no Barack."

The country happened to be uniquely poised to receive Obama at the precise moment when he materialized, says Andrew Kohut, president of the Pew Research Center. In 2004 -- and even more, now -- the country was deeply unhappy with the status quo. "They're looking for political change, and he certainly personifies change," says Kohut, who conducted a poll showing that when people hear the name "Barack Obama," the words that come to mind are "new," "young," "charismatic" and "smart."

Then again, "inexperienced" is another word that comes to mind. Kohut's polls show that the second thing voters want is competence, and they see this in Hillary Clinton more than Obama. "And that," says Kohut, "is why we have a horse race."

Obama appeals most to well-educated college graduates, Kohut says, the same demographic group that supported Gary Hart, Bill Bradley and Howard Dean in previous campaigns. People with college degrees tend to be driven by hope and idealism. In contrast, as Cook explains, "downscale Democrats" tend to focus more on economic issues and are more likely to have fond memories of Clinton-era prosperity. "They're more survival oriented."

Robert Putnam, the Harvard political scientist, believes Obama's appeal springs from the fact that the country feels more fragmented than it is comfortable with, and there is a "hunger for connection and for unity." It also helps, Putnam believes, that Obama is not identified with the 1960s, nor does he carry the baggage of past campaigns, as both Edwards and Clinton do.

But most important, Putnam believes, is Obama's biography: the racial unity he represents and an upbringing that enables him to speak to blacks and whites alike. "He's black, but not just black," says Putnam. "A large number of Americans would like to feel they're in a country where someone like that could be president."

The racial question is, of course, complicated and heated. Some commentators, including Debra Dickerson and Stanley Crouch, have revived the idea that Obama is not authentically "black," in that he is not the descendant of slaves and thus lacks this classic part of the African American experience. He has also never been what Dickerson calls "black for a living." He's never worked for the NAACP or any advocacy organization whose goal is taking on the white power structure.

Dickerson points out that, early in his career, Obama did a number of crucial things to neutralize this problem of authenticity. He married a black woman, and he joined an inner-city, mostly black church, Trinity United Church of Christ, led by the charismatic pastor Jeremiah Wright. "I'm not saying he doesn't love her, and I'm sure he believes with all his heart," says Dickerson, but both moves helped shore up his credentials. For black politicians, to begin a speech by praising God is "the black secret handshake," she says. "It's like saying, 'Joe sent me.'"

But it's equally important, Dickerson says, that Obama does not speak like Jesse Jackson or Martin Luther King Jr. It may be good that his keynote speech wasn't delivered in King's majestic cadence, because then he might have been too authentically African American. To appeal to whites as well as blacks, he can't do "the whole Southern preacher thing." And appealing to whites is crucial; Clinton does almost as well as Obama among black voters, for whom, Dickerson says, 2008 presents a "delicious" choice.

"If you're looking for how does Barack Obama win the nomination, he needs to win [the African American vote] by a big margin," says Charlie Cook, and also enlarge that base. "He's got to have a broader base of support than he has now." As in Illinois, he has to be a crossover candidate. And his mannerisms, his credentials, his white mother all help. "He doesn't look like a sub-Saharan African, and he doesn't have an accent," Dickerson says. "If he were sub-Saharan-African-looking, with the same résumé, we would not know his name right now."

In her most controversial assertion, Dickerson argues that Obama appeals to white voters because he enables them to support a black man without having to confront the legacy of slavery. Because Obama is not confrontational; because he describes himself as "being rooted in the African American community, but not limited to it," he permits whites to support a black and feel self-congratulatory. This may or may not be true, but it does seem that -- in the wake of Abu Ghraib and Guantanamo -- part of Obama's appeal is the opportunity to send the world a different message about American racial tolerance at a moment when this seems more important than ever.

"His election would do so much to restore people's faith and belief in the U.S. around the world," says Meg Hirshberg, an influential New Hampshire political donor who recently threw her support behind Obama. "Can you imagine them being president and first lady? It knocks me out, as far as what we would be saying to ourselves and to the world. He's not a descendant of slaves, but she is. I think it would be a remarkable moment in American history."

He also represents biracialism -- what one supporter calls "the emerging majority demographic," the face of what all America will look like someday: brown. No surprise, then, that he appeals more to young voters than do the other Democrats. Twentysomethings are more likely to think biracialism is cool; more likely to be biracial; more likely to have parents who are immigrants. This support may or may not get Obama where he needs to go. Younger voters are enthusiastic, but they are not, as Tony Bullock puts it, "the most reliable loading dock."

One evening early this summer, Obama was on the floor of the U.S. Senate while a series of complicated votes were taking place on President Bush's ill-fated immigration bill. Between votes, Obama milled around, chatting with colleagues. He is a touchy kind of mingler; he tends to put his hands on an arm or shoulder while talking, in an easy, friendly, intimate way. Watching him provided stark evidence of just how rare a person of color is on the Senate floor; apart from him, there were a few black staffers. He is a living testament to how hard it remains for a black politician to win a statewide race, let alone a national election.

After his keynote speech, he was asked, over and over again, if he would run in '08. Diane Sawyer asked. Oprah Winfrey asked. Tim Russert asked. Wolf Blitzer asked. The answer: He would serve out his six-year Senate term.

"The first conversation about the presidential campaign was that there was not going to be a presidential campaign," says Axelrod. Obama agrees. "We very deliberately tried to tamp down expectations," he says. "I didn't do any national interviews until Katrina. I tried to be very deliberate in terms of the work that I did here in the U.S. Senate. I didn't file a lot of symbolic bills -- like a universal health-care bill or other legislation that I wasn't in a position to pass because we were in a minority party."

In October 2006, however, Russert asked again, and this time Obama said, "I have thought about it." Then, this February, he announced. He would run. In '08.

What changed? First, The Audacity of Hope was published in 2006. While on book tour, Obama did a lot of campaigning for other candidates, helping Democrats win control of Congress. During that campaign, the war emerged as a key factor in Obama's favor, points out Ron Walters. In 2002, Obama had made a powerful speech opposing the Iraq war as "rash" and "dumb," and it was probably just as well for him, at the time, that few people had heard of him. But now the country had caught up with his views. The majority of voters, particularly Democrats, think the war was a mistake and want U.S. troops withdrawn.

Last summer Obama also went to Africa, visiting Kenya and South Africa, and speaking out against the violence in Darfur. The crowds he attracted gave him, Axelrod says, "a heightened sense of what he could accomplish."

Shortly before Christmas 2006, he met with Minow and Mikva to discuss whether to run. "He was very worried about what this was going to do to his family," says Minow. "I think Michelle at that point was very dubious, not at all enthusiastic about his running." The two men, who have six adult daughters between them, said they thought it made more sense to run when Obama's children were young and relatively insulated.

The opportunity, in the end, was irresistible. Obama says that what tipped the balance was the crowds. "After seeing the response I was getting around the country, I had to step back and ask: Is there something about my message that is sufficiently unique and could potentially be useful enough to moving the country forward?" he says. "And, ultimately, the answer was yes."

Obama also understands, more than most, the significance of an open seat. For the first time in more than 50 years, there is no incumbent president or vice president running for the White House. An opportunity like that is priceless. "You can't choose the times," says Axelrod. "The times choose you."

Is there a downside? Obama says the biggest one "is personal. It's relinquishing your privacy. As much attention as I had gotten as U.S. senator, I could still hop in my car, drive myself to the grocery store, take my kids to the zoo." Not anymore.

Politically, the risk is that there will be a negative attack that sticks, that Obama will be, in some way, swift-boated. "I will never be more popular than I am as a potential presidential candidate," he says he told a friend before announcing. "Because it was inevitable that the moment I ran, suddenly those of you in the fourth estate would start, you know, chipping away at this image that you guys have created. And so I was mindful of that. The easier thing for me to do would have been to stay put; continue to enjoy nice things being said about me; potentially get on some short list for vice president, which, even if I wasn't selected, would be sufficiently flattering; and see if something came up, some opportunity came up to run for president later."

"This is always a risky enterprise." But, he says, "I just got a sense that the country is in this ferment right now, that everything's up for grabs. Those moments in our politics don't come that often, where -- it really is possible in this election, in a way that might not be four years from now, or eight years or 12 years from now, to help redefine our politics and help point the country in a fundamentally different direction. So, I believe I made the right decision to run. But it was not a slam dunk, to quote George Tenet."

Now there are only 2,181 more cherries that have to click into place for Barack Obama. That would be the number of delegates a Democratic candidate needs to win the party's presidential nomination.

Liza Mundy is a Magazine staff writer. She can be reached at She will be fielding questions and comments about this article Monday at noon.

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