This is a rush transcript of "Special Report With Brit Hume" from May 20, 2008. This copy may not be in its final form and may be updated.

(BEGIN VIDEO CLIP)

SEN. BARACK OBAMA, (D) PRESIDENTIAL CANDIDATE: We are going to reach a milestone today, hopefully, that is very important. It means that we've gotten the most delegates that are assigned by voters in primaries and caucuses.

BILL CLINTON, FORMER PRESIDENT OF THE UNITED STATES OF AMERICA: We've got more voters, more workers, more givers than ever before. But the energy is on our side and the issues are on our side.

(END VIDEO CLIP)

BRIT HUME, HOST: Bill Clinton seemed to be saying that they had the energy on their side, and he had said they had more voters. Barack Obama obviously would dispute that.

Some thoughts on all now this from Fred Barnes, the Executive Editor of The Weekly Standard, Nina Easton, Washington Bureau Chief of Fortune Magazine, Bill Kristol, Editor of The Weekly Standard, and Juan Williams, Senior Correspondent of National Public Radio, all FOX News contributors.

Before we get into this, just a couple of thoughts about Senator Kennedy — it does sound as if there is a lot we don't know about this diagnosis and whether this tumor will be subject to treatment. It doesn't look like they can operate on it.

You can see there that he looks like he is in pretty good fennel. And, apparently, when you have a brain tumor, you feel fine for a while. So I suspect he will be around for a while. Juan, your thoughts?

JUAN WILLIAMS, SENIOR CORRESPONDENT, NATIONAL PUBLIC RADIO: If you were listening carefully and watching FOX, and we had so many of the Senate leaders come out today, I thought the body language was pretty grim.

HUME: Yes, they did seem grim, didn't they — Bill?

BILL KRISTOL, EDITOR, THE WEEKLY STANDARD: Medical conditions are hard to predict. So I hope he does fine.

NINA EASTON, WASHINGTON BUREAU CHIEF, FORTUNE MAGAZINE: It sounds like it's inoperable, which means no matter what he will be coping with chemotherapy and radiation and fighting this thing.

And the timing of it is quite tragic since he's on the verge of seeing a Kennedy-style liberal have a chance at the White House for the first time in a generation. It's not surprising how much he feels connected to Barack Obama.

FRED BARNES, EXECUTIVE EDITOR, THE WEEKLY STANDARD: If all goes well he could be around for a few more years. I wouldn't count him out yet.

And one of the surprising things about Kennedy is he is one of the few liberal Democrats who actually crosses the aisle to try to make compromises with Republicans. Not many of them do. Obama doesn't.

HUME: Obviously his own caucus would miss him, but a lot of Republicans would miss him, too, if he had to leave the Senate.

Let's get into this today. Let's look at the delegate scorecard as of tonight. This is what Barack Obama was really talking about. Of the delegates, not counting super delegates, he has 1,610. He needs about 1,625 to have a majority of the delegates elected in primaries and caucuses.

Obviously, as you can see at the bottom, the total you need more to be nominated is greater than that. That is the victory it he will claim tonight.

And it gets harder and harder to add anything to this because you don't kind of don't know what to say. Nina, you had a good insight last week. Maybe Hillary Clinton is running for vice president. If not, what?

NINA EASTON, WASHINGTON BUREAU CHIEF, FORTUNE MAGAZINE: A power broker on some level. It's very interesting to watch this tonight where you have Barack Obama at this rallying in Iowa, and it sort of feels like a curtain call. Meanwhile, Hillary Clinton is playing the third act still out on the stage.

And I think her game plan right now is to collect as much popular vote as she can, and to keep doing it.

BARNES: That's what I'm going to watch tonight. Oregon and Kentucky, they are roughly the same size, and they are pretty close in population — don't hold me to that. And who wins the popular vote tonight?

Look, we know Obama is 99.9 percent sure of winning the nomination. But here Hillary Clinton, if she wins the popular vote, will have another part of her argument for whatever she wants.

And there were alarming numbers in the Kentucky exit poll for Obama — 50 percent of the Democratic voters say they won't vote for him. We know a lot of them will, but it does suggest, as we have seen in Pennsylvania and West Virginia and again in Kentucky, that there is a large block of working class Democrats who are available to John McCain if he can get them.

KRISTOL: Yes. I think tonight Hillary Clinton is likely to get more votes than Obama, if you add up Kentucky and Oregon. She has done that pretty consistently in the last couple of months, with the exception of the North Carolina/Indiana night when they split the primaries but Obama got more votes —

HUME: That was only two weeks ago.

KRISTOL: I know, but it seems longer.

Here is an amazing fact — it is longer from tonight to election night than the time from New Hampshire to tonight. A lot can happen.

HUME: Will anything ever seem this long?

WILLIAMS: I would say one thing that seems to be changing is if you look at the Gallup tracking poll, there is now a larger and larger lead for Barack Obama among Democrats nationwide, who have the sense that Obama is the nominee.

So I think there is a sense of conclusion reached on the body politic of the Democratic Party.

The other part of this is Patty Doyle and David Axelrod getting together and talking about where there might be opportunities for —

HUME: Patty Doyle is who?

WILLIAMS: She was the former campaign manager for Senator Clinton's campaign. David Axelrod is a senior advisor to Senator Obama's campaign. And this is the first time we have seen of any kind of high- level interaction between the two.

So it looks like you might have some sort of positioning. You have one set of issues taking place in Kentucky and Oregon, but maybe you have some things happening behind the scenes that would suggest some healing.

KRISTOL: It's interesting — never in modern American history has the presumptive nominee lost by 40 points as Obama did to Clinton in West Virginia last week, and, according to the latest polls, by something in the range of 30 points in Kentucky. It hasn't happened.

People can pretend that Obama is the nominee and who cares about Kentucky and West Virginia. They are states, however, that the last Democrat to win the presidency, Bill Clinton, carried two times. They are not exactly outlier states.

HUME: And if John Kerry had carried West Virginia in 2004 he would be president.

BARNES: On the other had he lost by 16 points.

HUME: No, if Gore had carried West Virginia —

KRISTOL: All I am saying is that they are tough states obviously for a Democratic in a presidential year, but it is meaningful that Obama is getting clobbered in those states.

HUME: When we come back, John McCain hits Barack Obama on U.S. policy towards Cuba. That issue next.

(COMMERCIAL BREAK)

(BEGIN VIDEO CLIP)

JOHN MCCAIN, (R) PRESIDENTIAL CANDIDATE: He also wants to sit down unconditionally for a presidential meet with Raul Castro — an unconditional meeting with Raul Castro.

BARACK OBAMA, (D) PRESIDENTIAL CANDIDATE: I have never said that I would somehow have meetings with these folks right away, that there wouldn't be any preparation for them.

(END VIDEO CLIP)

HUME: Well, there you have a debate. John McCain says that Barack Obama wants to sit down and have a meeting with Raul Castro, among others, and Barack Obama said wait a minute, I wouldn't say I would do it right away. Raul Castro, of course, is the success to his brother down there in as the head of Cuba.

So is this an issue — I guess there are a lot of people in America, particularly Democrats, who think that our policy with Cuba hasn't worked very well. The Castro regime has continued as even does today. Why not try something new? Is this a winning issue for McCain or not?

BARNES: McCain obviously is on offense. And just from the byte you saw Obama is on defense. Obama said I didn't say this, I'm for preparation and so on. And McCain, after attacking him on meeting with the Iranian president and others, now he jumped on him on Cuba. And no doubt there will be others that will suggest he will jump on him for agreeing to meet with.

So this is offensive politics.

HUME: Well, what the question he was asked that led to all of this was a debate question — would you be willing to meet separately without preconditions during the first year of your administration in Washington or anywhere else with the leaders of Iran, Syria, Venezuela, Cuban, and North Korea in order to bridge the gap that divides our countries. Obama's answer was "I would."

And he went on to say that not talking to countries doesn't punish them and it doesn't work.

BARNES: Big mistake.

EASTON: It is not, as a lot of Democrats have pointed out, it is not as if Cuba closed has promoted democracy there. And John McCain is somebody who is very — he likes to emphasize what works in foreign policy and in military policy.

He, back in 2000, said he supported normalizing relations if there are steps toward democracy.

HUME: Those are known as "preconditions."

EASTON: This is all about domestic politics. This is about a key voting block in a swing state.

Al Gore in 2000 got 19 percent of the Hispanic vote nationwide — I'm sorry, 76 percent nationwide, 19 percent of the Cuban vote, and he lost Florida by 537 votes. Barack Obama potentially has the opportunity to peel off some younger Cuban voters if he makes his case that he has something different that works.

KRISTOL: Two points — Obama is now saying well, there will be preparations. He was asked would you be willing to meet in the first year without preconditions with the leaders of Cuba, Venezuela, Iran, North Korea, and he said I would. And then he reiterated that answer a couple of times.

So I don't know what he is now talking about.

HUME: Maybe "preparation" is code for preconditions?

KRISTOL: He said he would meet right away. And somehow it is our fault, our foolish policy that is preventing democracy from prevailing in Cuba.

And having said that, people shouldn't obsess too much about talks or no talks, obviously. The question is the substance of policy.

HUME: The question is would as the president sit down with a leader like Raul Castro.

KRISTOL: Exactly. And, at the same time, Latin America is very important to the United States. Obama is against the free trade deal with Colombia. Colombia is an actual ally. Uribe is an actual Democrat who has been elected and who is fighting narco-terrorists and fighting Chavez.

Obama's current position is no favors for Uribe, no free trade deal, but I'll sit down with Chavez and Castro.

WILLIAMS: I think it is terrible politics on Obama's part.

But the real problem for Obama is that McCain is able to point to a questionnaire in which Obama was asked some time ago whether he favored normalization, and he said he did, and he thought it would help the oppressed people in Cuba, and he thought it would open the door once Fidel Castro went away to better U.S.-Cuban relations.

Now he has changed his position somewhat. He is saying yes, but only with these preparations, preconditions, whatever. And, as Nina said, John McCain is the one who has changed his position.

So I think what you are seeing is a lot of political lies in the atmosphere in a political year.

But the big point to me is this — it's Florida politics, but it's also the John McCain strength in the general election with Barack Obama has to do with ability to protect the United States against terrorism and his foreign policy experience.

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