A newly formed conservative political group is spending $2.8 million to air the first tough general election ad attacking Barack Obama, questioning his relationship with a founder of the 1960s terrorist group Weather Underground.
Obama's aides denounced the spot, calling it illegal. They likened it to the 2004 Swift Boat Veterans for Truth assault on John Kerry's military service, which some Democrats believe cost Kerry the election, and charged that Republican John McCain was behind it.
In fact, Christian Pinkston, a Washington-area consultant who serves as spokesman for the new nonprofit group, American Issues Project, worked on the Swift Boat campaign.
American Issues Project is a nonprofit political organization that is required to operate independently of the campaign.
Edward Failor Jr., a member of the American Issues board, is an Iowa political operative who worked for McCain's presidential campaign in the state. Failor oversaw President Bush's Iowa campaign four years ago, the first time in 20 years that a Republican carried the state.
"The fact that John McCain dispatched his paid consultant to launch this despicable ad from a so-called independent committee shows how desperate he is to change the subject from his shocking disconnect with the economic struggles of the American people," Obama's campaign said in a statement.
McCain's spokesman denied any involvement and said Failor hadn't worked for the campaign in months.
The 60-second ad opens with Obama giving a speech, then asks how much voters know about the Illinois senator. From there, it bores in on his relationship with University of Chicago education professor William Ayers, who more than 30 years ago was deeply involved in radical leftist politics.
The spot notes that the Sept. 11 hijackers failed to crash one of the hijacked jets into the U.S. Capitol and says that 30 years earlier the Weather Underground detonated a bomb in the Capitol.
"Why would Barack Obama be friends with someone who bombed the Capitol and is proud of it?" the ad asks.
The ad links the bombing to Ayers, who has acknowledged involvement in bombings but was never convicted of terrorist acts.
Ayers and his wife, Bernadine Dohrn, a Northwestern University professor who also was part of the Weather Underground, spent years on the run. After Ayers surrendered in 1980, charges against him were dropped because of prosecutorial misconduct.
Obama has deplored Ayers' conduct but pointed out that it took place decades before the two met.
In an interview Thursday, Pinkston and Failor refused to reveal the ad's financial backers. But Pinkston said the group was spending $2.8 million to air the spots in the battleground states of Ohio and Michigan for the next week.
"It is a big buy, intended to go through the Democratic convention," Pinkston said.
Failor is active in an Iowa group opposed to abortion rights. He is also a leader of Iowans for Tax Relief, which lobbies in Des Moines and has a political action committee involved in Iowa state campaigns.
Failor donated $1,250 to McCain last year and was paid at least $50,000 by McCain in the months leading up to the Iowa caucuses.
"I'm not questioning his patriotism," Failor said of Obama in an interview. "I'm simply questioning his judgment."
Failor criticized Obama for his "friendship with someone who doesn't like this country and is an unapologetic terrorist."
Frank Chiodo, a Democratic activist who was among Obama's early backers in Iowa, said Thursday that he counts Failor as a friend. But he also called him a tough operative.
"He is very, very good," Chiodo said. "He will gut you and show you your heart, and smile at you. He plays for keeps."
Rumors have circulated for months that an ad focused on Obama's links to Ayers would air during the presidential campaign. Hillary Rodham Clinton had warned that Republicans would raise the issue.
Ayers and Obama have known one another for more than a decade. As a state senator, Obama represented the Hyde Park district that encompassed the University of Chicago and Ayers' residence. Ayers hosted a house party for Obama early in Obama's career and gave him a $200 campaign donation.
Earlier this year, when his acquaintance with Ayers was raised, Obama said he "deplored" Ayers' actions more than 30 years ago and noted that he was 6 or 7 years old when Ayers was a radical.
"By the time I met him, he is a professor of education at the University of Illinois," Obama said in a "Fox News Sunday" interview in April. "We served on a board together that had Republicans, bankers, lawyers focused on education."
In the past, McCain has criticized independent groups that enter into the political fray. Spokesman Brian Rogers repeated the criticism Thursday but also echoed the ad's criticism of Obama.
"Barack Obama's long friendship with an unrepentant terrorist raises serious questions about his judgment," Rogers said.