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(part 2)


Brimming with confidence, he equated Mr. Rush with “a politics that is rooted in the past” and cast himself as someone who could reach beyond the racial divide to get things done. But it quickly became clear that while he had solidified his support among Hyde Park’s denizens, he had not built enough bridges to the surrounding black communities.

That failure was apparent on the summer day in 1999 when he walked through the South Side during the Bud Billiken Parade and Picnic. Other politicians rode on colorful floats, trailed by throngs. But Mr. Obama was on foot as he made his way through the cheering paradegoers who had shown up to celebrate black pride.

“People were asking, who is he?” said Mr. Kindle, who served as one of his emissaries to the black community. “You could see how humbling it was in his face.”

The campaign, as Mr. Mikva put it, was “a disaster from beginning to end.” Yet in ultimately losing, Mr. Obama learned that he needed to expand his base to be able to bounce back onto a larger stage, according to Mr. Mikva and others. “The beauty of Obama,” Mr. Kindle said, “is that he was willing to be taken to the woodshed” and “allow himself to grow.”

Mr. Obama, who had a reputation in Springfield as standoffish (“He socialized, but he did not hang out,” Mr. Kindle said), began making courtesy calls to black politicians and members of the clergy. He assured them that he had nothing against Mr. Rush and that “it was all cool,” said Ron Lester, who was Mr. Obama’s pollster during the race.

Mr. Jones, the State Senate president who by then had become Mr. Obama’s political benefactor, stepped up to help as well. The two were an unlikely pair: the Harvard-educated lawyer and the former sewer inspector who had risen through the ranks of Chicago ward politics. Mr. Jones let Mr. Obama take center stage on legislation important to the black community, like forcing the police to tape interrogations.

His willingness to negotiate — the interrogation law ended up with a host of exceptions — gained him a reputation as a pragmatist who could sell compromise as a victory to all sides, said Peter Baroni, then the legal counsel to the Republican caucus.

“He took what came into the fray as a very leftist bill, a very leftist proposal, a very non-law-enforcement bill,” Mr. Baroni said, “and he appeased law enforcement and brought everyone around to support it.”

Before his loss to Mr. Rush, Mr. Obama’s typical response for requests for state money would be a lecture, recalled Dan Shomon, a former Obama aide. “He would say something like: ‘You know what, you’re not going to get your money, and you know why? Let me explain the state budget,’ ” Mr. Shomon said. “Then he’d give a 20-minute treatise on how the Republicans wouldn’t raise taxes, so there wasn’t any money to do what they wanted to do.”

Now, Mr. Obama more eagerly met the demands for spending earmarks for churches and community groups in his district, said State Senator Donne E. Trotter, then the ranking Democrat on the Senate Appropriations Committee. “I know this firsthand, because the community groups in his district stopped coming to me,” Mr. Trotter said.

Typical of Mr. Obama’s earmarks was a $100,000 grant for a youth center at a Catholic church run by the Rev. Michael Pfleger, a controversial priest who was one of the few South Side clergymen to back Mr. Obama against Mr. Rush.

Father Pfleger has long worked with South Side political leaders to reduce crime and improve the community. But he has drawn fire from some quarters for defending the Nation of Islam leader Louis Farrakhan and inviting him to speak at his church. Father Pfleger, who did not return calls for comment, is one of the religious leaders whose “faith testimonials” Mr. Obama has posted on his presidential campaign Web site.

David Axelrod, the chief strategist for the Obama presidential campaign, said that Father Pfleger was “remaking the face” of Chicago’s South Side and that all of Mr. Obama’s earmarks went to worthy programs like his.

With his black base more secure, Mr. Obama began in 2002 to contemplate a run for the United States Senate.

“I had lunch with him at the Quadrangle Club, and we were discussing the different bases he had to touch. I said, ‘You have to talk to the Jackson boys first,’ ” Mr. Mikva recalled, referring to Representative Jackson and his father, the Rev. Jesse Jackson. “Because Jesse Jackson Jr. had his eye on that seat. He said, ‘I know. I’m working on that.’ ”

Mr. Obama soon sat down with the younger Mr. Jackson at the 312 Chicago restaurant. Michelle Obama had attended high school with Mr. Jackson’s sister and been close to the family for years, and the congressman had attended the Obamas’ wedding. “He said, ‘Jesse, if you’re running for the U.S. Senate I’m not going to run,’ ” Mr. Jackson recalled.

But Mr. Jackson had already decided against it, and he gave Mr. Obama his blessing.

A Pivotal Moment

Betty Lu Saltzman, a Democratic doyenne from Chicago’s lakefront liberal crowd, convened a small group of activists, including Ms. Katz, in her living room to organize a rally to protest the United States’ impending invasion of Iraq. It was late September 2002, and Mr. Obama was on the top of Ms. Saltzman’s list of desired speakers.

She first met him when he ran the black voter registration drive in the 1992 election, and was so impressed that she immediately took him under her wing, introducing him to wealthy donors and talking him up to friends like Mr. Axelrod. But with just a few days to go before the rally, Ms. Saltzman was having trouble reaching Mr. Obama. Finally, she said she left word with his wife.

But before Mr. Obama called her back, he dialed up some advice.

With his possible run for the United States Senate, he wanted to speak with Mr. Axelrod and others about the ramifications of broadcasting his reservations about a war the public was fast getting behind. An antiwar speech would play to his Chicago liberal base, and could help him in what was expected to be a hotly contested primary, they told him, but it also could hurt him in the general election.

“This was a call to assess just how risky was this,” said Pete Giangreco, who along with Mr. Axelrod described the conversation. When Mr. Obama tossed out the idea of calling it a “dumb war,” Mr. Giangreco said he cringed. “I remember thinking, ‘this puts us in the weak defense category, doesn’t it?’ ”

The rally was held on Oct. 2, 2002, in Federal Plaza before nearly 2,000 people. On the podium before speaking, Mr. Obama joked about the dated nature of crowd-pleasing protest songs like “Give Peace a Chance.” “ ‘Can’t they play something else?’ ” Ms. Saltzman recalled his saying.

The speech, friends say, was vintage Obama, a bold but nuanced message that has become the touchstone of his presidential campaign: While he said the Iraq war would lead to “an occupation of undetermined length with undetermined costs and undetermined consequences,” he was also careful to emphasize that there were times when military intervention was necessary.

“What’s fascinating about Barack is what he’s trying to do is reframe and change the discourse so you build support for liberal alternatives within the electorate,” said Will Burns, a former aide whom Mr. Obama also consulted on the speech. “He has an ability to frame stuff so it’s not an all or nothing proposition.”

Still, Mr. Obama’s refrain about supporting some wars perplexed some in the crowd.

An event organizer, Carl Davidson, recalled that a friend “nudged me and said, ‘Who does he think this speech is for? It’s not for this crowd.’ I thought, ‘This guy’s got bigger fish to fry.’ At the time, though, I was only thinking about the U.S. Senate.”

Straddling Two Worlds

As Mr. Obama moved closer to running, he paid a visit to James S. Crown and his father, Lester, billionaire investors who presided over a sprawling Chicago business dynasty and prominent leaders in the Jewish community.

As the meeting ended, the younger Mr. Crown said, his father — who is “fairly hawkish” about Israel’s security — was noncommittal about Mr. Obama. But, James Crown said, “I pulled him down to my office, and I said, ‘Hey, look, I think you should run, and I want you to win.’ ”

In courting families like the Crowns, Mr. Obama was gaining entree into the upper echelon of the city’s corporate boardrooms, a ripe source of campaign money. But he was also seeking to broaden his appeal to Jewish voters, and he was wading more deeply into one of the touchiest issues in American politics: the Israeli-Palestinian conflict.

For years, the Obamas had been regular dinner guests at the Hyde Park home of Rashid Khalidi, a Middle East scholar at the University of Chicago and an adviser to the Palestinian delegation to the 1990s peace talks. Mr. Khalidi said the talk would often turn to the Middle East, and he talked with Mr. Obama about issues like living conditions in the occupied territories. In 2000, the Khalidis held a fund-raiser for Mr. Obama during his Congressional campaign. Both Mr. Khalidi and Mr. Abunimah, of the Electronic Intifada, said Mr. Obama had spoken at the fund-raiser and had called for the United States to adopt a more “evenhanded approach” to the Palestinian-Israel conflict.

Still, Mr. Khalidi said ascertaining Mr. Obama’s precise position was often difficult. “You may come away thinking, ‘Wow, he agrees with me,’ ” he said. “But later, when you get home and think about it, you are not sure.”

A.J. Wolf, a Hyde Park rabbi who is a friend of Mr. Obama’s and has often invited Mr. Khalidi to speak at his synagogue, said Mr. Obama had disappointed him by not being more assertive about the need for both Israel and the Palestinians to move toward peace. “He’s played all those notes right for the Israel lobby,” said Mr. Wolf, who is sometimes critical of Israel.

During the Senate campaign, Mr. Obama joined in a “Walk for Israel” rally along Lake Michigan on Israel Solidarity Day. The Crowns and other Jewish leaders raised hundreds of thousands of dollars for him. Several days before the primary in 2004, some of his Jewish supporters took offense that Mr. Obama had not taken the opportunity on a campaign questionnaire to denounce Yasir Arafat, the leader of the Palestine Liberation Organization, or to strongly support Israel’s building of a security fence.

But in a sign of how far Mr. Obama had come in his coalition-building, friends from the American Israel Political Action Committee, the national pro-Israel lobbying group, helped him rush out a response to smooth over the flap.

In an e-mail message, Mr. Obama blamed a staff member for the oversight, and expressed the hope that “none of this has raised any questions on your part regarding my fundamental commitment to Israel’s security.” Mr. Abunimah has written of running into the candidate around that time and has said that Mr. Obama told him: “I’m sorry I haven’t said more about Palestine right now, but we are in a tough primary race. I’m hoping that when things calm down I can be more upfront.”

The Obama camp has denied Mr. Abunimah’s account. Mr. Khalidi, who is now the director of the Middle East Institute at Columbia University, said, “I’m unhappy about the positions he’s taken, but I can’t say I’m terribly disappointed.” He added: “People think he’s a saint. He’s not. He’s a politician.”

Mr. Crown, for his part, could not be more pleased. Since Mr. Obama was elected to the Senate Mr. Crown said that even his father had been won over, helping to arrange meetings for Mr. Obama in a visit to Israel. James Crown said he had “never had even the slightest glimmer of concern that Barack wasn’t terrific” on Israel — a view that Mr. Obama jokingly reinforced at a meeting last year in Mr. Crown’s office.

As Mr. Mikva recounted it, after discussing a lukewarm response by more conservative Jews to some of Mr. Obama’s comments, “I turned to Barack and said, ‘Your name could be Chaim Weizmann, the founder of the Jewish state, and some of these Jewish Republicans wouldn’t vote for you.’ ” And, Mr. Mikva said, “He joked, ‘Well, you know my name is “Baruch” Obama.’ ”

But for all of Mr. Obama’s attentiveness to Jewish concerns about Israel, Republican Party officials have made it clear that they think this is an area of vulnerability. Though Mr. Obama has condemned Hamas, a militant Palestinian group, as a terrorist organization, just last week Senator John McCain, the presumptive Republican nominee for president, suggested that the group wanted to see Mr. Obama in the White House. Mr. Obama denounced that suggestion as a “smear.”

Embracing the Machine

When Mr. Obama delivered a now-famous speech at the 2004 Democratic National Convention that catapulted him onto the national stage, sitting in the audience was Mayor Daley of Chicago.

As Mr. Obama spoke, Mr. Daley and other Illinois officials “were just as wide-eyed as the thousands of conventiongoers,” said James A. DeLeo, a Democratic leader in the Illinois Senate.

The mayor and the senator had some ties, but they had never had a close relationship. Mr. Obama’s friend Ms. Jarrett had worked for Mr. Daley, and had hired Michelle Obama into the administration in the early 1990s. Yet Mr. Obama had run multiple times as a candidate without the mayor’s help.

Now, as Mr. Obama ascended to the larger stage, he also took the final step in his evolution from Hyde Park independent to mainstream Chicago politician, establishing an overt alliance with Mr. Daley. “Over the years, Senator Obama and I have been like-minded in most of the issues facing Chicago,” the mayor said in a statement.

His former chief of staff, Gary Chico, said the mayor’s alliance with the senator was “based on mutual interest and what the mayor saw in the man. They’re both pragmatic.”

But Mr. Obama’s closer relationship with the mayor, coupled with some of his endorsements of Democrats who championed the kind of patronage politics Mr. Obama had once denounced, left some supporters feeling as though he was straying from his roots in the reform movement.

Last year, Mr. Mikva said he took Mr. Obama aside to complain about his endorsement of an alderwoman who had supported Mr. Obama in his United States Senate run and was the focus of newspaper reports about questionable spending on a $19.5 million cultural center. Mr. Mikva said Mr. Obama’s response was simple: “Sometimes you pay your debts.” Early last year, Mr. Obama endorsed Mr. Daley in his re-election bid, asserting that Chicago had blossomed during his tenure.

Mr. Miner, the mentor who had brought Mr. Obama into his law firm in the early 1990s, said he remained an enthusiastic Obama supporter. But, when it comes to some of Mr. Obama’s endorsements, “I don’t know who he’s listening to,” Mr. Miner said.

“I’ve thought sometimes that I should have picked up the phone and called him,” Mr. Miner said. “Why did he think he needed to do this?”

Just before Mr. Obama complimented Mr. Daley, the mayor did something unusual, as well. He broke with his tradition of remaining neutral in Democratic primaries and threw his support behind Mr. Obama’s presidential bid.

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