In August 1999, Barack Obama strolled amid the floats and bands making their way down Martin Luther King Drive on Chicago’s South Side. Billed as the largest African-American parade in the country, the summer rite was a draw over the years to boxing heroes like Muhammad Ali and jazz greats like Duke Ellington. It was also a must-stop for the city’s top politicians.
Back then, Mr. Obama, a state senator who was contemplating a run for Congress, was so little-known in the community’s black neighborhoods that it was hard to find more than a few dozen people to walk with him, recalled Al Kindle, one of his advisers at the time. Mr. Obama was trounced a year later in the Congressional race — branded as an aloof outsider more at home in the halls of Harvard than in the rough wards of Chicago politics.
But by 2006, Mr. Obama had remade his political fortunes. He was a freshman United States senator on the cusp of deciding to take on the formidable Hillary Rodham Clinton and embark on a long-shot White House run. When the parade wound its way through the South Side that summer, Mr. Obama was its grand marshal.
The secret of his transformation, which has brought him to the brink of claiming the Democratic presidential nomination, can be described as the politics of maximum unity.
He moved from his leftist Hyde Park base to more centrist circles; he forged early alliances with the good-government reform crowd only to be embraced later by the city’s all-powerful Democratic bosses; he railed against pork-barrel politics but engaged in it when needed; and he empathized with the views of his Palestinian friends before adroitly courting the city’s politically potent Jewish community.
To broaden his appeal to African-Americans, Mr. Obama had to assiduously court older black leaders entrenched in Chicago’s ward politics while selling himself as a young, multicultural bridge to the wider political world.
“There are some people who say he’s not strong enough on this or that, that he’s wishy-washy, that he’s trying to have it both ways,” said Abner J. Mikva, a former congressman and mentor to Mr. Obama. “But he’s not looking for how to exclude the people who don’t agree with him. He’s looking for ways to make the tent as large as possible.”
Mr. Obama’s ability to replicate the eclectic coalition he built in Chicago and expand it to the national stage has allowed the one-term senator to match the Clintons at their signature game: collecting influential friends and supporters.
An untraditional politician who at times uses traditional political tactics, Mr. Obama, 46, was portrayed in dozens of interviews with political leaders and longtime associates in Chicago as the ultimate pragmatist, a deliberate thinker who fashions carefully nuanced positions that manage to win him support from people with divergent views.
“Most Americans are getting a small glimmer into the rough and tumble world of the South Side of Chicago politics, which is very, very difficult to navigate,” said Representative Jesse L. Jackson Jr., an Illinois Democrat and ally of Mr. Obama’s. But Mr. Obama did it with skill: “It’s very unusual to have various factions agreeing with you and your politics,” Mr. Jackson added.
Others see his deft movements as a politician’s shifting of positions and alliances for strategic advantage, leaving some disappointed and baffled about where he really stands.
“He has a pattern of forming relationships with various communities and as he takes his next step up, kind of distancing himself from them and then positioning himself as the bridge,” said Ali Abunimah, a Palestinian-American author and co-founder of the online publication Electronic Intifada, who became acquainted with Mr. Obama in Chicago.
Even moments that supporters see as his boldest are tempered by his political caution. The forceful speech he delivered in 2002 against the impending Iraq invasion — a speech that has helped define him nationally — was threaded with an unusual mantra for a 1960s-style antiwar rally: “I’m not opposed to all wars.” It was a refrain Mr. Obama had tested on his political advisers, and it was a display of his ability to speak to the audience before him while keeping in mind the broader audience to come.
Perfect for Hyde Park
When Judson H. Miner invited a third-year Harvard Law School student named Barack Obama to lunch at the Thai Star Cafe in Chicago before his 1991 graduation, Mr. Miner thought he was recruiting the 29-year-old to work for his boutique civil rights law firm. Instead, Mr. Obama recruited him.
Mr. Obama made it clear that he was less interested in a job than in learning the political lay of the land from a man who had served at the right hand of the city’s first black mayor, Harold Washington. Mr. Miner, who had helped with the historic 1983 election of Mr. Washington and served as his corporation counsel, proved a willing tutor.
The confident younger man “cross-examined” Mr. Miner about how Mr. Washington had managed to emerge from an election riven by bigotry to form a governing coalition in which he “got along with all these different types of folks,” Mr. Miner recalled.
Mr. Obama, who had spent time in Chicago as a community organizer in the 1980s and already knew he wanted to run for office, openly weighed the pros and cons of working for the law firm. On the one hand it was beloved by many of the city’s liberals and black leaders for its work on issues like voting rights and housing equality. On the other, the firm had clashed with Chicago’s powerful mayor, Richard M. Daley, who presided then and now over the city’s sprawling Democratic organization.
“During the course of our talking, it came out that people who knew he was having lunch with me were trying to convince him that this was the worst place for him to go. He shared this with me — he was amused,” Mr. Miner said, laughing. “This isn’t where you land if you want to curry favor with the Democratic power structure.”
It was, however, exactly where an aspiring politician might land if he happened to want to run for office from Hyde Park, a neighborhood with a long history of electing reform-minded politicians independent of the city’s legendary Democratic machine. Mr. Obama chose to put down roots in the neighborhood after graduating law school and marrying Michelle Robinson, a Chicago native and fellow lawyer.
A tight-knit community that runs through the South Side, Hyde Park is a liberal bastion of integration in what is otherwise one of the nation’s most segregated cities. Mayor Washington had called it home, as did whites who marched with the Rev. Dr. Martin Luther King Jr. and wealthy black entrepreneurs a generation removed from the civil rights battles of the 1960s.
At its heart is the University of Chicago; at its borders are poor, predominately black neighborhoods blighted by rundown buildings and vacant lots. For Mr. Obama, who was born in Hawaii to a white Kansan mother and an African father and who spent part of his childhood in Indonesia, it was a perfect fit.
“He felt completely comfortable in Hyde Park,” said Martha Minow, his former law professor and a mentor. “It’s a place where you don’t have to wear a label on your forehead. You can go to a bookstore and there’s the homeless person and there’s the professor.”
Mr. Obama quickly grounded himself in the community. He led a successful drive that registered nearly 150,000 black voters for the 1992 campaign. He became a part-time professor at the University of Chicago Law School. And, in 1993, he finally decided to join the law offices of Miner, Barnhill & Galland.
The choice sent a signal that Mr. Obama was “allying himself with the independents, which is what you have to be if you’re going to be elected from the Hyde Park area,” said Don Rose, a longtime Democratic political consultant.
The decision to accept Mr. Miner’s job offer quickly paid off. By the time Mr. Obama announced his candidacy for the Illinois Senate in 1995 — at the very Hyde Park hotel where Mr. Washington had kicked off his mayoral campaign — he had cultivated a network of influential supporters.
Mr. Miner was “enormously helpful” in introducing Mr. Obama to the liberal coalition of blacks and whites that had helped elect Mr. Washington, said Valerie Jarrett, a longtime friend and close adviser. “It brought in a whole new circle of people.”
Mr. Obama cultivated clients like Bishop Arthur M. Brazier, the influential pastor of an 18,000-member black church and founding president of the Woodlawn Organization, which focuses on improving conditions for blacks in a neighborhood adjacent to Hyde Park. The two men began talking politics over tennis games at Chicago’s elite East Bank Club, Mr. Brazier recalled.
Mr. Obama also worked on housing redevelopment projects involving Antoin Rezko, who became one of Mr. Obama’s most generous donors. Mr. Rezko is currently on trial for corruption charges unrelated to Mr. Obama.
It was through the law firm that Mr. Obama met Marilyn Katz, who gave him entry into another activist network: the foot soldiers of the white student and black power movements that helped define Chicago in the 1960s.
As a leader of Students for a Democratic Society then, Ms. Katz organized Vietnam War protests, throwing nails in the street to thwart the police. But like many from that era, Ms. Katz had gone on to become a politically active member of the Chicago establishment, playing in a regular poker game with Mr. Miner while working as a consultant to his nemesis, Mayor Daley.
“For better or worse, this is Chicago,” said Ms. Katz, who has held fund-raisers for Mr. Obama at her home. “Everyone is connected to everyone.”
Mr. Obama was comfortable attending performances of the Chicago Symphony Orchestra with city scions like Newton N. Minow, the father of Martha Minow. Mr. Minow, who had served in the Kennedy administration and managed the white-shoe law firm of Sidley Austin when Mr. Obama worked there after his first year of law school, began introducing him to Chicago’s business titans.
Mr. Obama also fit in at Hyde Park’s fringes, among university faculty members like Bill Ayers and Bernadine Dohrn, unrepentant members of the radical Weather Underground that bombed the United States Capitol and the Pentagon to protest the Vietnam War. Mr. Obama was introduced to the couple in 1995 at a meet-and-greet they held for him at their home, aides said.
Now, along with Mr. Obama’s former pastor, the Rev. Jeremiah A. Wright Jr., Mr. Ayers has become a prime exhibit in the effort by Mr. Obama’s presidential rivals to highlight what could be politically radioactive associations. In 2001, Mr. Ayers said he did not regret the Weatherman bombings. Even so, in Hyde Park, he and his wife were viewed favorably for their work in addressing city problems. Mr. Ayers was just “a guy who lives in my neighborhood,” Mr. Obama said recently.
The two men were involved in efforts to reform the city’s education system. They appeared together on academic panels, including one organized by Michelle Obama to discuss the juvenile justice system, an area of mutual concern. Mr. Ayers’s book on the subject won a rave review in The Chicago Tribune by Mr. Obama, who called it “a searing and timely account.”
Running and Winning
Mr. Obama further expanded his list of allies by joining the boards of two well-known charities: the Woods Fund and the Joyce Foundation.
These memberships have allowed him to help direct tens of millions of dollars in grants over the years to groups that championed the environment, campaign finance reform, gun control and other causes supported by the liberal network he was cultivating. Mr. Brazier’s group, the Woodlawn Organization, received money, for instance, as did antipoverty groups with ties to organized labor like Chicago Acorn, whose endorsement Mr. Obama sought and won in his State Senate race.
On the campaign trail, Mr. Obama hewed closely to liberal orthodoxy, positions that have become controversial in the presidential race. A candidate questionnaire from one liberal group, for instance, detailed his views on hot-button issues like the death penalty (opposed) and a ban on handguns (in favor).
Today, Mr. Obama espouses more centrist views and says a campaign aide had incorrectly characterized his views on those issues — a shift that does not sit well with some in the group, the Independent Voters of Illinois Independent Precinct Organization.
“We certainly thought those were his positions,” said David Igasaki, the group’s chairman, who noted Mr. Obama had also interviewed with the group. “We understand that people change their views. But it sort of bothers me that he doesn’t acknowledge that. He tries to say that was never his view.”
In any event, the group endorsed Mr. Obama, and he was easily elected to the State Senate in 1996.
In the state Capitol in Springfield, Mr. Obama was guided through the political thicket by powerful mentors. It was not long into Mr. Obama’s first term when Mr. Mikva recalled getting a telephone call from Paul Simon, the recently retired United States senator. Mr. Mikva had become friends with Mr. Obama after returning from a stint as White House counsel for President Bill Clinton to teach law at the university.
Mr. Simon suggested Mr. Mikva play matchmaker between Mr. Obama and Emil Jones Jr., the powerful Democratic leader of the State Senate. For the better part of a quarter century, Mr. Mikva had played in a golfing foursome that included Mr. Jones.
“ ‘Say, our friend Barack Obama has a chance to push this campaign finance bill through,’ ” Mr. Mikva recalled Mr. Simon’s telling him. “ ‘Why don’t you call your friend Emil Jones and tell him how good he is.’ ”
Mr. Mikva obliged, and in 1998, Mr. Obama passed one of his signature achievements in the Illinois Senate: sweeping legislation that banned most gifts from lobbyists and the personal use of campaign money by state lawmakers. His Hyde Park base applauded, but Mr. Obama would soon learn the limits of his appeal.
Learning His Lessons
The next year, Mr. Obama called Mr. Minow, his former boss, asking to see him. Mr. Obama was eyeing the Hyde Park Congressional seat held by Bobby L. Rush, a former Black Panther leader. “Are you nuts?” Mr. Minow recalled telling the younger man. “Barack, I think this is a mistake.”
Mr. Minow flipped through his Rolodex, calling black businesspeople and asking them if they would help finance Mr. Obama’s bid. He said he received a uniform answer: “No — let him wait his turn.” Nevertheless, the impatient Mr. Obama jumped into the race.
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.