What Exactly Is Barack Obama's Association With Ex-Weather Underground Member William Ayers?

This is a rush transcript from "The O'Reilly Factor," May 12, 2008. This copy may not be in its final form and may be updated.

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BILL O'REILLY, HOST: In the "Factor Follow-up" segment tonight: We've been looking into the political situation in Chicago where Barack Obama rose to prominence. Obviously, his association with Reverend Wright has hurt him. And there's also been bad publicity about William Ayers and Bernadine Dohrn, two radicals associated with the violent Weather Underground back in the '60s. In 1998 Connie Chung spoke with Ayers and Dohrn on ABC News.


CONNIE CHUNG, ABC NEWS: A lot of people out there are probably saying: "I would love to hear them say, 'We were young. We were idealistic. We were foolish, and we were probably stupid. We made mistakes, and we're sorry about it. We're grown up now.'"

WILLIAM AYERS, FORMER WEATHER UNDERGROUND MEMBER: Well, I would say we were young, we were idealistic, we were foolish and we made mistakes.

BERNADINE DOHRN, FORMER WEATHER UNDERGROUND MEMBER: We made mistakes, and we'd do it again. I wish that we'd done more. I wish we'd been more militant. I wish a lot of things. But taken as a whole, we were so lucky to be born into that moment in history.


O'REILLY: Now, both Ayers and Dohrn were charged with crimes. Dohrn was convicted of aggravated battery. Joining us from Chicago, John Kass, a columnist for the Tribune, and Sandy Rios, FOX News analyst and radio talk show host on WYLL.

Sandy, I begin with you. Obviously, these are unrepentant people. They, for whatever reason, feel that setting bombs off and destroying infrastructure in America is legitimate. They teach now at the University of Illinois at Chicago. And they are, or were, in Barack Obama's political sphere. Now, do you know any more than that? Was there a personal relationship among the three?

SANDY RIOS, RADIO TALK SHOW HOST: Well, I think a case could be made, yes. David Axelrod himself said they have a very friendly relationship. But I think part of the center of their relationship, Bill, officially, is the Woods Foundation. William Ayers and Barack Obama both are directors or were directors at the same time of that foundation.

O'REILLY: What is that foundation?

RIOS: Well, the Woods Foundation funds all kinds of things, and some of them not so good, including community organizing, which is another word for Saul Alinsky, the radical of the '60s who wrote "Rules for Radicals." And his organization method of agitating something that Barack Obama is expert at. He came to Chicago not only to study Alinsky but to be an instructor. They call it community organizing.

But the Woods Foundation paid for that. They paid $25,000 to bring him out. He later served as a director on their foundation. We know that Bernadine Dohrn was also an organizer. We know that William Ayers and Barack Obama served on the board at the same time that William Ayers was pictured on the cover of the Chicago magazine standing on a crumpled American flag with the title "No Repentance." We know that...

O'REILLY: Mr. Kass, but let's try to put it in some kind of perspective. The south side of Chicago politics, in which Barack Obama rose to prominence, is notoriously left. Some would say crazy left. Obama had to know that. Reverend Wright, Ayers, Dohrn, a whole bunch of people. OK. Now, do you believe that he understood that later, as he rose into the U.S. Senate and now running for the presidency, this would come back to bite him?

JOHN KASS, COLUMNIST, CHICAGO TRIBUNE: I don't think so. He was punching his ticket. He hangs out with — he finds Reverend Wright. He goes to Reverend Wright's church. He punches his ticket. He's getting his political resume in order.

He shows up in Chicago not knowing many people. He hangs out with Dohrn and Ayers. He punches his ticket. It's another ticket punch. He's getting his resume, left — left center, far-left bone fides in order. That's what he did.

O'REILLY: Now, did he do that out of ideology or opportunism?

KASS: It's probably opportunism. The more I think about it, less ideology and more opportunity.

O'REILLY: You see, that's how I see it.

KASS: I don't know what his ideology is.

O'REILLY: I don't either, but we're going to find out.

Sandy, that's how I see this. I mean, it looks to me like a guy shows up, as Mr. Kass just said, in Chicago. He knows he's going to run on the Democratic liberal side. Those people dominate that area. You know that in Chicago. It's very far left. The machine. And he signs onto the machine, and he rises up. Now, does he believe this stuff? Is there, you know, is there any evidence to say that he does?

RIOS: Well, the only thing we know is just I think we can tell a lot about what he believes through studying what Saul Alinsky taught, because as I said, he came to start community organizing and be an instructor. One of those things is go with the seat of power.

We know, also, what is the thing with the flag? We have got William Ayers standing on a crumpled American flag. We've got Barack Obama running for president saying he doesn't want to wear a flag pin because that's displaying patriotism.

O'REILLY: I don't know, Sandy. That's a stretch to me.

Mr. Kass, last question to you. This is going to hurt Barack Obama. All of these associations is going to hurt him. Would you agree?

KASS: Yes, but what will really hurt him later is when the national media starts figuring out that Barack Obama is not only — has been supportive of leftist figures but that he is basically coming out of the Chicago political machine run by Richard M. Daley and that that machine has Republicans and Democrats, David Axelrod, the far left, the far right, everyone working together to push this young knight in shining armor into the White House.

O'REILLY: All right.

KASS: Once the national media figures that out…

O'REILLY: I don't know. You see, I don't know. It might be too much for the regular voter to grasp. But Chicago is a very unique — and I think that's the best word — political place.

KASS: Why don't you come on over and do your show from here for a while? Check it out.

O'REILLY: Trust me, trust me. We are all over this story.

KASS: Come on.

O'REILLY: By November, Sandy, we're going to bring you back, of course. You stay on it. Because you've been doing a lot of investigation. By November, we're going to know everything about this. This is just the first...

RIOS: I hope so.

O'REILLY: We will. Ms. Rios, Mr. Kass, thanks very much.

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