While the Illinois senator has never been accused of wrongdoing, some of the associations he formed as a community organizer and politician in Chicago may provide fodder for attacks, Democratic and Republican political experts say.
Besides his relationship with indicted businessman Antoin Rezko, Obama might face Republican criticism over contacts with a former leader of the Weather Underground, a banker with ties to a convicted felon and even his church.
``He has had relationships with individuals who are controversial, he has had relationships with individuals who are in trouble,'' said Cindi Canary, director of the Illinois Campaign for Political Reform.
Canary says that ``there has been no link whatsoever that ties him to their troubles.'' Even so, that may not immunize him from attack. In 2004, Massachusetts Democratic Senator John Kerry, the presidential nominee, was subjected to unfounded criticism about his service in the Vietnam War.
`Inevitable'
``I think that it is inevitable that the media and Republicans will try to resort to these tactics,'' said Julian Epstein, a Democratic strategist who isn't affiliated with any campaign.
Alex Conant, the Republican National Committee press secretary, said that if Obama ``wants to be commander-in-chief, he's going to have to answer to his record in Illinois.''
Nothing in Obama's 11 years in public office rises to the level of the scandal that embroiled the likely Republican nominee, Senator John McCain of Arizona, in the 1980s. McCain, 71, was among five senators who took contributions from savings- and-loan executive Charles Keating, and were then accused of seeking favors from regulators for him. The Senate Ethics Committee reprimanded McCain, though it cleared him of wrongdoing.
Still, Obama's past endorsements and donors may give opponents material to work with. One target might be his 2006 backing of Democrat Alexi Giannoulias, who was elected Illinois state treasurer.
Loans to a Felon
During the campaign, the Democratic speaker of the state House and other party leaders criticized Giannoulias because of loans his family bank made to Michael ``Jaws'' Giorango, a convicted felon. Obama stuck with Giannoulias after the revelations, though he did call on him to explain the matter.
``I'm going to ask Alexi directly what is happening,'' Obama said in April 2006, according to the Chicago Tribune.
More recently, Obama has conceded it was ``boneheaded'' of him to buy a home in June 2005 for $1.65 million with the involvement of Rezko, who was under federal investigation at the time. Rezko was indicted 16 months later on unrelated corruption charges, and is awaiting trial in jail. Over the past year, Obama, 46, has returned about $85,000 in campaign contributions given or raised by Rezko.
When Obama bought the home in Chicago's Kenwood neighborhood, Rezko's wife, Rita, purchased, for $625,000, adjoining land that the house's owners insisted on selling at the same time. Seven months later, she sold the Obamas one-sixth of her lot, for $105,000, so they could expand their yard.
`Vetted'
New York Senator Clinton, 60, points to the Rezko controversy as evidence that Obama may be more vulnerable to criticism than she because her longer tenure in the spotlight means she has been ``vetted.''
``I understand exactly what is coming at me, and there isn't any new information,'' she said Feb. 11 in an interview with the Politico and an ABC-TV affiliate. ``I don't think we can say that about my opponent.'' Still, the Clinton campaign has had its own embarrassments: In September, it was forced to return about $800,000 raised by Norman Hsu, who was arrested on charges stemming from a 1991 fraud case.
Besides Rezko and Giannoulias, Obama could face questions about his relationship with William Ayers, a former member of the radical group the Weather Underground who is now a professor of education at the University of Illinois in Chicago. Ayers donated $200 in 2001 to Obama's Illinois state Senate campaign and served with him from 1999 to 2002 on the nine-member board of the Woods Fund, an anti-poverty group.
A Series of Bombings
The Weather Underground carried out a series of bombings in the early 1970s -- including the U.S. Capitol and the Pentagon. While Ayers was never prosecuted for those attacks, he told the New York Times in an interview published Sept. 11, 2001, that ``I don't regret setting bombs.''
Bill Burton, Obama's spokesman, said Ayers ``does not have a role on the campaign.'' Ayers said he had no comment on his relationship with Obama.
Even the candidate's church, the Trinity United Church of Christ, and its pastor, Jeremiah Wright, have come under scrutiny. Last month, Obama ``strongly'' condemned anti-Semitic comments made by Louis Farrakhan after the church's magazine published an article praising the leader of the Chicago-based Nation of Islam.
In what may be a preview of the attention to come, the church has been barraged with so many questions about its association with Obama that it now responds with an automated e- mail that describes the candidate as a member ``for nearly two decades.''
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