Obama's willingness to befriend Palestinian Americans and to hear their views also impressed, and even excited, a community that says it does not often have the ear of the political establishment.
Among other community events, Obama in 1998 attended a speech by Edward Said, the late Columbia University professor and a leading intellectual in the Palestinian movement. According to a news account of the speech, Said called that day for a nonviolent campaign "against settlements, against Israeli apartheid."
The use of such language to describe Israel's policies has drawn vehement objection from Israel's defenders in the United States. A photo on the pro-Palestinian website the Electronic Intifada shows Obama and his wife, Michelle, engaged in conversation at the dinner table with Said, and later listening to Said's keynote address. Obama had taken an English class from Said as an undergraduate at Columbia University.
Ali Abunimah, a Palestinian rights activist in Chicago who helps run Electronic Intifada, said that he met Obama several times at Palestinian and Arab American community events. At one, a 2000 fundraiser at a private home, Obama called for the U.S. to take an "even-handed" approach toward Israel, Abunimah wrote in an article on the website last year. He did not cite Obama's specific criticisms.
Abunimah, in a Times interview and on his website, said Obama seemed sympathetic to the Palestinian cause but more circumspect as he ran for the U.S. Senate in 2004. At a dinner gathering that year, Abunimah said, Obama greeted him warmly and said privately that he needed to speak cautiously about the Middle East.
Abunimah quoted Obama as saying that he was sorry he wasn't talking more about the Palestinian cause, but that his primary campaign had constrained what he could say.
Obama, through his aide Axelrod, denied he ever said those words, and Abunimah's account could not be independently verified.
"In no way did he take a position privately that he hasn't taken publicly and consistently," Axelrod said of Obama. "He always had expressed solicitude for the Palestinian people, who have been ill-served and have suffered greatly from the refusal of their leaders to renounce violence and recognize Israel's right to exist."
In Chicago, one of Obama's friends was Khalidi, a highly visible figure in the Arab American community.
In the 1970s, when Khalidi taught at a university in Beirut, he often spoke to reporters on behalf of Yasser Arafat's Palestine Liberation Organization. In the early 1990s, he advised the Palestinian delegation during peace negotiations. Khalidi now occupies a prestigious professorship of Arab studies at Columbia.
He is seen as a moderate in Palestinian circles, having decried suicide bombings against civilians as a "war crime" and criticized the conduct of Hamas and other Palestinian leaders. Still, many of Khalidi's opinions are troubling to pro-Israel activists, such as his defense of Palestinians' right to resist Israeli occupation and his critique of U.S. policy as biased toward Israel.
While teaching at the University of Chicago, Khalidi and his wife lived in the Hyde Park neighborhood near the Obamas. The families became friends and dinner companions.
In 2000, the Khalidis held a fundraiser for Obama's unsuccessful congressional bid. The next year, a social service group whose board was headed by Mona Khalidi received a $40,000 grant from a local charity, the Woods Fund of Chicago, when Obama served on the fund's board of directors.
At Khalidi's going-away party in 2003, the scholar lavished praise on Obama, telling the mostly Palestinian American crowd that the state senator deserved their help in winning a U.S. Senate seat. "You will not have a better senator under any circumstances," Khalidi said.
The event was videotaped, and a copy of the tape was obtained by The Times.
Though Khalidi has seen little of Sen. Obama in recent years, Michelle Obama attended a party several months ago celebrating the marriage of the Khalidis' daughter.
In interviews with The Times, Khalidi declined to discuss specifics of private talks over the years with Obama. He did not begrudge his friend for being out of touch, or for focusing more these days on his support for Israel a stance that Khalidi calls a requirement to win a national election in the U.S., just as wooing Chicago's large Arab American community was important for winning local elections.
Khalidi added that he strongly disagrees with Obama's current views on Israel, and often disagreed with him during their talks over the years. But he added that Obama, because of his unusual background, with family ties to Kenya and Indonesia, would be more understanding of the Palestinian experience than typical American politicians.
"He has family literally all over the world," Khalidi said. "I feel a kindred spirit from that."
Ties with Israel
Even as he won support in Chicago's Palestinian community, Obama tried to forge ties with advocates for Israel.
In 2000, he submitted a policy paper to CityPAC, a pro-Israel political action committee, that among other things supported a unified Jerusalem as Israel's capital, a position far out of step from that of his Palestinian friends. The PAC concluded that Obama's position paper "suggests he is strongly pro-Israel on all of the major issues."
In 2002, as a rash of suicide bombings struck Israel, Obama sought out a Jewish colleague in the state Senate and asked whether he could sign onto a measure calling on Palestinian leaders to denounce violence. "He came to me and said, 'I want to have my name next to yours,' " said his former state Senate colleague Ira Silverstein, an observant Jew.
As a presidential candidate, Obama has won support from such prominent Chicago Jewish leaders as Penny Pritzker, a member of the family that owns the Hyatt hotel chain, and who is now his campaign finance chair, and from Lee Rosenberg, a board member of the American Israel Public Affairs Committee.
Nationally, Obama continues to face skepticism from some Jewish leaders who are wary of his long association with his pastor, the Rev. Jeremiah A. Wright Jr., who had made racially incendiary comments during several sermons that recently became widely known. Questions have persisted about Wright in part because of the recent revelation that his church bulletin reprinted a Times op-ed written by a leader of Hamas.
One Jewish leader said he viewed Obama's outreach to Palestinian activists, such as Said, in the light of his relationship to Wright.
"In the context of spending 20 years in a church where now it is clear the anti-Israel rhetoric was there, was repeated, that's what makes his presence at an Arab American event with a Said a greater concern," said Abraham H. Foxman, national director for the Anti-Defamation League.