updated 5/20/2008 2:38:32 PM ET 2008-05-20T18:38:32

Guest: Michelle Cottle, Eugene Robinson, Rachel Maddow, Michael Smerconish

DAVID GREGORY, HOST:  Tonight, he’s talking like the nominee, and tomorrow he will likely meet an important milestone.  So when and how will Barack Obama declare victory and look forward to the fall?

THE RACE FOR THE WHITE HOUSE rolls on. 

Welcome back to THE RACE.  This is where we never leave the race. 

We’re happy to have you.  I’m David Gregory.

You have made it for your stop for the fast-paced, the bottom line, and every point of view in the room. 

Tonight, it is Obama/McCain, round two on Iran.  Later, in “Three Questions” tonight, what would an Obama diplomatic surge toward Iran actually entail? 

Inside the War Room tonight, what went wrong inside the Clinton campaign?  A special take based on an intriguing new piece from “The New Republic.”

The foundation of the program, of course, a panel that comes to play. 

With us tonight for the first time, Michelle Cottle, senior editor of “The New Republic.”  And joining Michelle, Gene Robinson, columnist and associate editor of “The Washington Post,” also an MSNBC political analyst; Rachel Maddow, host of “The Rachel Maddow Show” on Air America, also an MSNBC political analyst; and Michael Smerconish, radio talk show host on WPHT in Philly, and columnist for both “The Philadelphia Inquirer” and “The Daily News.” 

OK.  Welcome all. 

We begin as we do every night with everyone’s take on the most important political story of the day.  It’s “The Headline.” 

I’ll get us started here tonight.  My headline, “Look Who’s Talking to Tehran.” 

The diplomatic dustup over direct talks with Iran has become a central issue in the early general election debate between Obama and McCain.  What is clear is that both sides want this fight to drive home a central theme of their campaign. 

Here’s McCain.

(BEGIN VIDEO CLIP)

SEN. JOHN MCCAIN (R-AZ), PRESIDENTIAL CANDIDATE:  Senator Obama has declared and repeatedly reaffirmed his intention to meet the president of Iran without any preconditions.  Such a statement portrays the depth of Senator Obama’s inexperience and reckless judgment.  These are very serious deficiencies for an American president to possess. 

(END VIDEO CLIP)

GREGORY:  Today, Obama clarified that he does consider Iran to be a grave threat to the United States, but he chided McCain for following what he called the Bush playbook. 

(BEGIN VIDEO CLIP)

SEN. BARACK OBAMA (D-IL), PRESIDENTIAL CANDIDATE:  For all their tough talk, one of the things you have to ask yourself is, what are George Bush and John McCain afraid of?  I’m not afraid that we’ll lose some propaganda fight with a dictator.  It’s time for America to win those battles, because we’ve watched George Bush lose them year after year after year. 

(END VIDEO CLIP)

GREGORY:  The real question in all of this that we will tackle later in the program is, what is to be gained from speaking to Iran directly?  And has Obama laid out a real policy for all of that? 

That’s what I’m thinking about tonight.

Rachel Maddow, what’s your headline tonight?  You’re also thinking about Iran and hypocrisy.

RACHEL MADDOW, MSNBC POLITICAL ANALYST:  I am indeed, although I think my headline might work better in print than in speaking.  But here’s the idea: “Pot Meet Sharp”—no, wait, wait.  Kettle—no. 

How does it go?  “Pot Calling the Kettle Charlie Black.” 

GREGORY:  There we go.

MADDOW:  Yes, it’s one of those things that works way better in print.  But the point is that Senator McCain has got two simultaneous stories going on in politics right now. 

There is his attack on Senator Obama for wanting to meet Iran, for wanting to talk with Iran, for wanting to engage in diplomacy with that country.  At the same time, his chief strategist, Charlie Black, has not only been talking to governments that the United States considers unsavory, he’s been on their payroll as a lobbyist for governments like the Burmese military junta and would-be dictators from countries like Angola and Zaire. 

So, to have the Charlie Black scandal sort of still hanging over his campaign while he’s making these allegations about meeting with Iran is an awkward coincidence right now in the news cycle for John McCain. 

GREGORY:  But Charlie Black wouldn’t determine whether or not there’s engagement with Iran and a McCain presidency.

MADDOW:  No, but it’s hard to say we ought not engage with these unsavory countries when you have got your chief strategist for your campaign is a guy who was on the payroll, not just to engage with those countries, but to convince America that those countries are much better than they actually are. 

He was literally paid to burnish their image.  In some ways I think that’s a lot worse than engaging in diplomacy with one of our enemies. 

GREGORY:  All right.  More on this to come. 

Michelle Cottle, what is your headline?  You’re also thinking about the McCain campaign and some difficulties it has today.

MICHELLE COTTLE, “THE NEW REPUBLIC”:  That’s right.  And Rachel has set me right up for my memo to McCain, which is: you better clean that house from top to bottom. 

This week he has seen the fifth resignation from the campaign over this dustup over too close of ties with lobbyists.  This time it’s the national fund-raising co-chair, finance co-chair, Tom Loeffler.  I mean, this is a man who’s entire candidacy is based on his character. 

McCain is the reformer.  He is the special interest scourge.  And for him to have all these problems with these lobbyists is just a prime opportunity for Obama to tee up on him for the entire general election campaign. 

And he had better start going through those rosters and find out who else has been talking to Burma or Saudi Arabia or anybody else that’s going to not—he’s not going to want these surprises. 

GREGORY:  Well, the other issue, too, is that they’ve had time to deal with all of this.  They have been doing a lot in the McCain campaign preparing for the general when nobody else was looking. 

COTTLE:  This is true.  And it’s—for all the time that they’ve had, suddenly it’s a problem now?  I mean, he has very few days left before this becomes a general issue campaign—or general election campaign, and Obama is going to turn his focus on to the Republicans.  And at that point, there had not—there had better not be any kind of thing that they can latch on to, to say, what—how can he pitch himself as a reformer? 

GREGORY:  Yes.  All right.  A little bit later on we’re going to talk about exactly what kind of Republican McCain is anyway.  That’s in “Three Questions,” in the back half.

Gene Robinson, you’re thinking about Hillary Clinton tonight. 

EUGENE ROBINSON, MSNBC POLITICAL ANALYST:  Yes, David. My headline is, “Hillary’s Bluegrass Encore.” 

You know, at this point, Hillary Clinton is almost like a singer who’s coming back on stage to give her fourth of fifth encore.  But out in the audience, people are getting up and putting on their coats, kind of checking to see where they left the parking stub. 

She—you know, she spent the day in Kentucky, she’s expected to win a big victory in the primary in Kentucky tomorrow.  Yet, the focus is not on Hillary Clinton. 

It’s not on her.  It’s on Barack Obama and the math.  Obama and McCain are conducting the general election campaign already.  And, you know, Hillary Clinton is still belting it out, but we’re really not paying a lot of attention. 

GREGORY:  Right. 

All right.  Smerconish, what’s your headline tonight? 

MICHAEL SMERCONISH, RADIO TALK SHOW HOST:  Hey, David.  Here it is—“Lay Off My Wife.”

Barack Obama tried to set the fall campaign rules today by defending his wife in the face of this Tennessee GOP YouTube moment that manages to mention, let’s see, Ronald Reagan, God, Ellis Island, guns, and a whole host of other Americana ideals in the span of about three minutes’ time.  Will it work?  Well, here’s Senator Obama today. 

(BEGIN VIDEO CLIP)

OBAMA:  If they think that they are going to try to make Michelle an issue in this campaign, they should be careful, because that I find unacceptable.  Whoever is in charge of the Tennessee GOP needs to think long and hard about the kind of campaign that they want to run. 

MICHELLE OBAMA, BARACK OBAMA’S WIFE:  We’re trusting that the American voters are ready to talk about the issues and not talking about the things that have nothing to do with making people’s lives better. 

B. OBAMA:  But I also think these folks should lay off my wife.  All right?  Just in case they are watching. 

(END VIDEO CLIP)

SMERCONISH:  The Tennessee GOP spokesman says, look, it’s fair game.  These are her words.  We didn’t distort the truth.  We’re just turning the tables on things that she’s actually said, and these are real folks.  But in middle America, one wonders how it will all play out and whether John McCain can exercise control if he wanted to over things like this. 

GREGORY:  Right, exactly.

All right.  A lot more to get to.  We’re going to take a break here.

Coming up, the final push and rush heading into tomorrow’s Kentucky and Oregon primaries.  Who’s ahead in the polls, and is tomorrow’s importance more about the margin of victory or defeat than it is about actually who wins or who loses? 

Later on, a play date with the panel is coming your way.  Call us, 212-790-2299, or e-mail us at race08@msnbc.com.

RACE FOR THE WHITE HOUSE comes right back.

(COMMERCIAL BREAK)

GREGORY:  Back on RACE FOR THE WHITE HOUSE now and heading inside the War Room, looking at the strategies at the tactics inside these campaigns to see what’s working and what isn’t. 

Back with us, Michelle Cottle from “The New Republic”; Gene Robinson, Rachel Maddow and Mike Smerconish.

First up, tomorrow’s primaries.  We’re in the final stretch before Oregon and Kentucky.  Now, according to the latest Suffolk University polls, in Oregon it’s Obama leading by four points over Hillary Clinton, 45-41.  And in Kentucky, it’s Clinton dominating, 51-25 over Obama.

Clinton today in Kentucky showing no signs of backing down, making her argument for why this race is nowhere near over.  Listen. 

(BEGIN VIDEO CLIP)

SEN. HILLARY RODHAM CLINTON (D-NY), PRESIDENTIAL CANDIDATE:  I believe that with your help, we will send a message to this country, because right now, more people have voted for me than have voted for my opponent. 

(APPLAUSE)

More people have voted for me than for anybody ever running for president before.  So, we have a very close contest—the votes, the delegates—and this is nowhere near over. 

(END VIDEO CLIP)

GREGORY:  Nowhere near over.  Well, she needed (INAUDIBLE) in South Dakota showing her level of commitment, but when it comes to the popular vote argument, is any of this going anywhere, Rachel? 

MADDOW:  The popular vote argument is one of the more specious moved goalposts that we have seen.  Obviously, if it was the popular vote that counted, not a single state would hold a caucus.  If it was the popular vote that mattered, every state that wanted to have its message heard would allow Republicans and Independents to vote in their primaries.

States don’t set up these contests that the popular vote will be the tally on which they are judged.  It is a made up metric.  I think Hillary Clinton actually has quite a lot of good arguments for staying in the race, but the popular vote one is laughable. 

GREGORY:  Hey, Smerc, is the argument about taking on the media and people in the media trying to pronounce the end of her argument?  Is that a smart argument? 

SMERCONISH:  She’s playing the hand that she’s dealt.  I mean, what she’s really saying is that Florida and Michigan are in relative to the popular vote. 

I don’t think it’s so much a media play that she has got left.  Meaning to go out and stake her territory against the media. 

I think that the only hope—I think she has no hope.  But some kind of an allez-oop or a—you know, use whatever metaphor you would like, because I think only if Florida and Michigan are sat would this matter.  And that’s not going to happen.

GREGORY:  Yes.  All right.  Let me move on here.

Next up, even if Obama wins the majority of pledged delegates tomorrow, he will not be declaring victory.  But today Obama seemed to talk about the primary race as if it were all in his rearview mirror. 

Listen to this. 

(BEGIN VIDEO CLIP)

B. OBAMA:  Nobody thought—well, I appreciate you, but let’s face it, nobody thought a 46-year-old black guy named Barack Obama was going to be the Democratic nominee. 

It was pretty tough and hard fought.  Senator Clinton is a formidable opponent.  She was relentless and very effective. 

(END VIDEO CLIP)

GREGORY:  All right, Michelle.  If he’s talking like that today, why wouldn’t he go out tomorrow with the majority and say this race is over, Hillary Clinton, time to pack it in? 

COTTLE:  Well, he has to walk a very careful line here.  I mean, he wants this to shift to the general election, and he wants to kind of start taking on McCain.  But he cannot afford to brass off all those Hillary voters who in the past, you know, have made it very clear they do not appreciate when a woman is underestimated or counted out or anything like that.  He’s got to make nice with all of these voters.

GREGORY:  Yes.

Gene, but the issue here as well is he may be experiencing a pretty bruising defeat in Kentucky as well.  Does this open up another area of vulnerability for him that people will start analyzing?

ROBINSON:  No, I don’t think—I mean, his vulnerability in Kentucky has been kind of analyzed and overanalyzed.  And so we will talk some, I suspect, tomorrow night about white working class voters, and then we’ll talk about whatever happens in Oregon. 

GREGORY:  Right.

ROBINSON:  The last poll puts that contest closer than previous polls have put it.  I suspect it’s not quite that close. 

But I think Michelle is absolutely right.  He doesn’t want to appear to crow, appear to gloat, appear to...

GREGORY:  Yes.

ROBINSON:  ... kind of dance on the grave of the Clinton campaign as long as the mathematics isn’t...

GREGORY:  Right. 

ROBINSON:  Yes, absolutely.

GREGORY:  And then the question is, what does he do the day after?  We know that he’s had some pretty good day after these primaries.  What does he do perhaps to close the deal with another superdelegate endorsement, another big name that’s out there?  We’ll see. 

Moving on, Obama and McCain are still battling it out over Iran today.  We talked about that at the top of the program.  MSNBC’s “First Read” blog, “Presenting the dangers for both sides, candidates to engage in the debate.  For Obama, he risks being portrayed as naive, inexperienced and weak, while McCain risks being painted as too Bush-like.”

So, who is more at risk in the debate of over-stereotyping? 

And Rachel, the point of this is to say they’re both kind of playing to type here, and playing to a type that ultimately could hurt them.  And yet ironically, they both want to argue this is a central part of their campaign. 

Take it on.

MADDOW:  I think this shows remarkable confidence by both candidates, because if this were a different Democrat and a different Republican, I think this would be proceeding on much more predictable lines.  But John McCain seems to be not at all concerned that he would be compared with George Bush on this. 

He’s not at all trying to draw a distinction between Bush.  He’s very confident in asserting that he’s got the right idea about Iran, despite all these complications like the lobbyists on his campaign and his previous statements. 

Similarly, Barack Obama has been incredibly confident on this.  He’s bringing it up all the time.  He looks like this is exactly the fight he wants to be having.  He thinks this is a real strong suit for him to say Democratic ideas on national security are for once not something we need to be defensive about.  I think it’s a pretty exciting change from previous contests. 

GREGORY:  Go ahead, Gene.

ROBINSON:  It’s more than political calculation on both sides.  It’s authentic substance. 

I remember talking to Obama more than well over a year ago.  And this was a central theme, that we shouldn’t be afraid to talk to regimes that we don’t like. 

I think both men genuinely believe they’re right on this, and so I don’t think they’re going to back down because they think they’re...

MADDOW:  And they both see political advantage here, which I think is fascinating. 

ROBINSON:  Yes, they do.

MADDOW:  A real test...

(CROSSTALK)

ROBINSON:  Yes, they do.  But I think regardless of political events, I think they both believe what they are saying. 

GREGORY:  Let me move on to a final War Room item, and that is Obama responding to the tactics from the GOP to make Michelle Obama’s level of patriotism an issue in the general election, warning them sternly that she is off limits.  Again, listen to this. 

(BEGIN VIDEO CLIP)

B. OBAMA:  The notion that you start attacking my wife or my family—you know, Michelle is the most honest, the best person I know.  She is one of the most caring people I know.  She loves this country.  And for them to try to distort or to play snippets of her remarks in ways that are unflattering to her I think is—is just low class. 

(END VIDEO CLIP)

GREGORY:  Smerc, the question for you and your response on this—it was your headline tonight—does the GOP go after Michelle Obama to its peril, or do they do it to try to put the two of them in the context of the kind of, you know, left wing, almost radical views of the Democratic Party? 

SMERCONISH:  Very carefully they need to treat this issue.  And this is another of those where they may not be able to rein in the 527s, because they’ll have a mind of their own. 

Look, I keep giving her the benefit of the doubt.  She said something that she should not have said for the first time in her life.  And we’ve all heard the sound bit by now.

I’d like to think that what she meant to say was, never before has she been as proud of her country.  After all, her husband, an African-American, stands poised to capture the nomination of the Democratic Party in this race for the presidency.  But they are her own words. 

And I think just as he needs to nip in the bud some of these patriotism issues, she could do likewise.  She ought to deliver a stem winder on this kind of an issue. 

GREGORY:  All right.  We’re going to take another break here.

Coming up next, “Smart Takes” tonight.  We may have come a long way since the ‘60s and the civil rights movement, but is race still a factor in politics?  And will it hurt Barack Obama, should he win the Democratic nomination, which appears likely at this point?

“Smart Takes” up next.

(COMMERCIAL BREAK)

GREGORY:  We’re back with “Smart Takes” here on RACE FOR THE WHITE HOUSE. 

We’ve read it all—the newspapers, blogs, magazines.  And we’re bringing you today’s “Smart Takes.” 

Here again, Michelle, Eugene, Rachel and Michael. 

First “Smart Take” in today’s “Wall Street Journal.” 

Former U.N. ambassador John Bolton calls Obama’s proposal to negotiate with Iran “naive and dangerous.” 

To the quote board.

“Negotiation is not a policy, it is a technique.  Saying that one favors negotiation with, say, Iran has no more intellectual content than saying one favors using a spoon.”

“For what?  Under what circumstances?  With what objectives?  On these specifics, Mr. Obama has been consistently sketchy.” 

Rachel, do you agree or disagree? 

MADDOW:  I disagree with Mr. Bolton.  Mr. Bolton’s own career has been the antithesis of diplomacy.  When he was—he was the former U.N. ambassador who famously remarked that if several stories were knocked off the U.N. building, it wouldn’t make a bit of difference.  He’s against diplomacy with anybody with whom we don’t already totally agree. 

I think Obama has been rather specific.  He said, listen, we’re arguing from a position of strength when we sit down with these countries.  We should not be insecure.  Sit down, listen to what they have to say.

We may not find a point of compromise, but we might find a way to reduce tensions, and that would be good for our standing in the world.  I think that seems rather cogent to me.

GREGORY:  Yes. 

But Gene, even on Obama’s talk about preconditions there’s been some movement about there—about whether there would be conditions or not. 

ROBINSON:  Well, it’s his distinction now.  And I don’t know if it’s a distinction with or without a difference. 

It’s preparation as opposed to preconditions.  There actually is a difference I think.  Preconditions means—you know, I take it to mean that we are assured that the Iranians are going to agree to act (INAUDIBLE) before we will sit down and meet with them, or whatever. 

But look, this is an administration.  Both of them have worked for an administration that has sat down and talked with North Korea. 

GREGORY:  Right.

ROBINSON:  They have nuclear weapons.  The object of sitting down with Iran is to keep them from getting nuclear weapons. 

GREGORY:  Right.  Of course, the distinction there, it’s not one-on-one.  It’s part of a group, which is the same way this administration negotiates...

ROBINSON:  Right.  OK.

GREGORY:  ... with Iran as well.  So a debatable point.

Let me move on.

ROBINSON:  But there’s an argument for—I mean, foreign policy, you know, the school of thought on foreign policy that says you give some sort of great imprimatur to a regime if you sit down and talk with it.  Well, I think the Iranians are doing pretty well without our sitting down and talking with them.  So I don’t see how it can hurt a lot. 

GREGORY:  All right.  Let me move on.

Our “Smart Take,” Michelle, you’re up on this.

Dick Morris makes a bold statement in a “Washington Post” piece that Obama cannot get elected because of his race.  And because of that, McCain’s has a shot of winning in a year when Republicans seemed doomed.

To the quote board.

“McCain’s base will be there for him,” he argues.  “Indeed, it will turn out in massive numbers.  Wright has become the honorary chairman of McCain’s get-out-the-vote efforts.  It would be nice to think that race isn’t a factor in America in politics anymore, but it is the growing fear of Obama, who remains something of a bit unknown, that will drag every last Republican male off the golf course to vote for McCain, and he will need no further laying on of hands from either Evangelical Christians or fiscal conservatives.”

Take 20 seconds to respond to that, Michelle. 

COTTLE:  All right.  First off here, of course race will be an issue in American politics just like it’s an issue in American life.  The question is, you know, Obama has distanced himself from Wright and the issue will come back up.  And of course the campaign is going to have to deal with it again. 

GREGORY:  Yes.

COTTLE:  They should be prepared for this.  Now, but, of course, I don’t know that any more Republican men are going to jump up off the couch for Obama than they would have for Hillary Clinton.  So...

GREGORY:  All right.  I’ve got to take a break.

We’ll talk more about Iran after this.

(COMMERCIAL BREAK)

(NEWS BREAK)

GREGORY:  Welcome back to RACE FOR THE WHITE HOUSE, I’m David Gregory.  Happy to have you.  Now, the back half, we ask the three biggest questions of the ‘08 race.  Still with us, Michelle Cottle, senior editor of “The New Republic.”  Joining Michelle, Eugene Robinson, columnist and associate editor of the “Washington Post,” also an MSNBC political analyst, Rachel Maddow, host of the “Rachel Maddow Show,” also an MSNBC political analyst, and Michael Smerconish, radio talk show host on WPHT in Philadelphia and columnist for both the “Philadelphia Inquirer,”  and “The Daily News.”

First up tonight, Barack Obama’s foreign policy; today, Obama and John McCain traded sharp attacks over whether America should engage Iran directly.  Listen. 

(BEGIN VIDEO CLIP)

OBAMA:  For all their tough talk, one of the things you have to ask yourself is what are George Bush and John McCain afraid of?  Iran, Cuba, Venezuela, these countries are tiny compared to the Soviet Union.  They don’t pose a serious threat to us the way the Soviet Union posed a threat to us.  Yet, we were willing to talk to the Soviet Union. 

MCCAIN:  The biggest national security challenge the United States currently faces is keeping nuclear weapons out of the hands of terrorists.  Should Iran get nuclear weapons, that danger would become very dire indeed.  They might not become a superpower, but the threat the government of Iran poses is anything but tiny. 

(END VIDEO CLIP)

GREGORY:  First question then, tonight, what would talking directly to Iran achieve?  Smerc, take it on. 

SMERCONISH:  It reminds me of one of those old Charles Atlas print ads.  They’re trying to kick sand in the face of Barack Obama.  Much to his credit, he’s on the exercise program.  He’s not going to stand for it.  I would have a problem with Senator Obama, President Obama, sitting down Ahmadinejad, particularly in the aftermath of what he just said relative to Israel only a week ago.  By the same token, I really don’t like—I think I speak for many, because I get the calls and letters.  I really don’t like the idea of isolationism, relative to even Iran.  Somehow, there’s got to be at least some back channel communication that I think has been lacking in the current administration.  I’d like to think that’s what he’s talking about. 

GREGORY:  Michelle, do you think, sitting down with him Ahmadinejad, assuming he’s actually got enough power to make some sort of decision, does it accomplishes something?  Does he persuade him to back off of his nuclear program in some way? 

COTTLE:  I think the question he’s going to ask, that Barack Obama is going to ask, is have the policies that Bush and McCain looked at, in terms of not engaging at all, served us very well.  I think most people who have looked at what the Bush administration have done are going to say no and they’re ready to try a little bit different approach. 

MADDOW:  David, I just jump in briefly; I think that what’s interesting here is that probably both of these candidates would agree with McCain’s assertion there about the risk of Iran obtaining nuclear weapons technology, the idea not just that they would become a nuclear armed state, but that they would proliferate to terrorist groups, the way that we’ve seen, for example, Pakistan do. 

The question, the difference, and what’s fascinating here—I think Gene points out rightfully it’s a really substantive difference—is how these guys think, how these candidates think you prevent Iran from getting them.  Obama is saying you prevent them from getting to that doomsday scenario in part by talking.  McCain is saying not by talking, but we’re still waiting to here how he thinks you keep them from getting to that point, other than just going to war. 

GREGORY:  Rachel, that might be right.  But what we don’t have an appreciation of is the level of thinking in the Obama camp to differentiate between Ahmadinejad, who has been proven to be a state sponsor of terror, and who speaks in the same kind of rhetorical, hate filled flourishes that a leader of Hamas speaks in, calling Israel a stinking corpse, and his refusal to sit down with the likes of Hamas.  Trying to understand that difference is what becomes important here. 

ROBINSON:  The difference—he said, if I may, David.  He has said that the difference is that Iran is a state, that Hamas is—well, it has power and Gaza, is not a state to sit down and talk with. 

GREGORY:  Yes. 

MADDOW:  It should be noted that John McCain said that when Hamas got elected in the Palestinian territories, that we would have to engage with Hamas as a government at that point, even though he didn’t want to engage with them before.  So, there’s definitely nuance here, in terms of what counts as a state, what doesn’t count as a state, who is too evil to talk to, who do you aggrandize by talking to.  But If talking is part of it or talking is not part of it, that’s an interesting place for the debate to start about how we get our way in the world. 

GREGORY:  Moving on now, McCain’s lobbying purge.  Since Team McCain implemented its conflict policy last week, at least five McCain campaign advisers have resigned for lobbying or ties to independent 527 political groups.  It comes at time when Republicans are looking to the so called Maverick nominee to clean up and rebrand the party’s image.  Second question, what kind of Republican is John McCain?  Michelle, it’s interesting, you hear those closest to McCain talking over the weekend, saying he’s not your average kind of Republican.  He’s a different kind of Republican, which is what they said about George W. Bush as well in 2000.  Is John McCain different? 

COTTLE:  Well, he better hope that he can convince people he is different.  You always want to run as a change candidate when things are going bad, and to separate yourself from the current failed policies.  At this point, in terms of foreign policy, I’m not sure there is any indication that he would have a different sort of Republican.  We’ll have to get into more of that in the general and as they go on down the road.  But no, not that we see at this point. 

GREGORY:  But Smerc, there’s no question that McCain is a much different figure from a mainstream Republican on all sorts of issues, from campaign finance reform to pork barrel spending to other stands he’s taken, except for, particularly at the end here, his proximity to Bush on the war, his proximity to Bush on the policy toward Iran. 

SMERCONISH:  There’s no doubt he has to highlight those maverick tendencies and not get caught up in this movement to placate the more extremes of his party, of my party.  I think the vice presidential selection that he makes is going to be a key determination in that regard.  Look, David, I think the base of the GOP isn’t going anywhere.  The best way to win this race is to maintain the maverick tendencies and make a direct appeal to moderates and independents.  But if he begins and placate the right, then this race is over. 

GREGORY:  Yes, all right, finally; the long Democratic primary finally coming to a close.  But Clinton’s female base may not be ready to jump on the Obama bandwagon.  Interviews in today’s “New York Times” reveal just how deeply offended many Clinton women feel right now.  One female voter said women are being “told to sit down, shut up and get to the back of the bus.”  Another said the nomination was, quote, stolen.  And former Democratic VP candidate Geraldine Ferraro, who resigned from Clinton’s campaign in March after making a purportedly racist comment about Barack Obama, saying that his race was helping him, slammed him for sexism.  Ferraro told the Times, quote, I think Obama was terribly sexist,” and says she may not even vote for him in November. 

The third question then today, how does Obama make up with Clinton’s female base and what can Clinton say to convince her supporters to support him?  Rachel, take it on.

MADDOW:  I think in terms of what Clinton says to her female supporters, she says a lot of the same things that she’s been saying when people ask about the Democratic party unity already, which is essentially to not go out of her way to praise everything wonderfully about Barack Obama, but instead to talk about the risks posed by John McCain.  I do think that you will hear specifically a lot of reference to what John McCain’s promised in terms of his judicial nominations, his judicial appointees, in terms of abortion rights in this country.  That will be a big part of it. 

You don’t even necessarily have to talk about Obama to make the case.  You just talk about McCain. 

GREGORY:  Michelle, is tone what is so important here, and the way he declares victory? 

COTTLE:  Absolutely.  One of the big hits against Obama in general has been that he’s too arrogant or that he thinks he deserves this and he’s been disrespectful of Clinton and her voters.  I think he’s stepped back from that and he’s making an effort to be much more approachable, and make it very clear that he wants these people on his team.  So I think yes, tone is going to be a huge deal with this. 

GREGORY:  Got to take another break here.  Coming up next, speaking of Michelle here, a behind the scenes look at what went wrong in the Clinton campaign.  That’s her piece from the “New Republic.”  And we’re going to go out with a laugh here.  John McCain made an appearance on “Saturday Night Live” here on NBC over the weekend.  He had advice for the Democrats. 

(BEGIN VIDEO CLIP)

MCCAIN:  Democrats, I have to urge you: do not, under any circumstances, pick a candidate too soon. 

UNIDENTIFIED MALE:  So you don’t think Hillary should drop out? 

MCCAIN:  Absolutely not. 

UNIDENTIFIED FEMALE:  I told you. 

UNIDENTIFIED MALE:  Cool it. 

UNIDENTIFIED FEMALE:  You cool it. 

MCCAIN:  That’s right, fight amongst yourselves. 

(COMMERCIAL BREAK)

GREGORY:  We’re back.  We have a special second edition of the war room tonight.  Back with us, Michelle Cottle, Eugene Robinson, Rachel Maddow and Michael Smerconish.  This round, we’re going to go inside Clinton’s war room.  We’re going to take a close look at an exclusive piece in “The New Republic” online by our panelist Michelle Cottle.  Michelle examines the real inside story of the fall of Hillary Clinton’s campaign.

First up, problems for the Clinton camp from the outset.  Staffers now blaming the state of the campaign on one, going negative too late, including failing to attack Obama his associations with Reverend Jeremiah Wright and Weather Underground member Bill Ayers.  Two, the hubris; one saying, quote, running as the inevitable candidate was probably our biggest mistake, particularly in a time when the country is really hungry for change.  Three, fuzzy delegate math; the campaign wrote off smaller states that allowed Obama to rack up the 100 plus delegates that he now has today. 

Michelle, start us off here, the tie of all those thing is Hillary Clinton not thinking she had a real opponent here. 

COTTLE:  One of the things that you find across the board is people agree that they ran as an incumbent, as an inevitable candidate.  They underestimated Obama, and it went downhill from there.  They didn’t plan for the long haul.  They didn’t do substantive differentiation early enough.  Everything kind of fans out from there.  Yes, they are totally kicking themselves at this point. 

GREGORY:  Gene, it’s interesting.  In terms of attacking Barack Obama, there was such a line that was being thread there, very carefully, about racism.  Bill Clinton got in so much trouble for what he said down in South Carolina, comparing him to Jesse Jackson.  If they knew about this Reverend Wright issue, that they were happy to exploit later on among working class voters, they didn’t use it earlier.  Would it have been too dangerous to have done that earlier? 

ROBINSON:  Perhaps, just to bring up the Reverend Wright issue, you know, in the middle of the campaign, that might have been dangerous.  But there’s those in the Clinton camp who do believe they should have, in various ways, gone negative on him earlier and challenged him on all sorts of matters of substance and experience, in a much more frontal way and much more aggressive way, before this got out of hand, from the Clinton point of view. 

By the time we got to Iowa, it was out of hand.  And the Clinton’s spent all the money. 

GREGORY:  Moving on to personnel, problems inside the Clinton camp; some say, quote, Hillary assembled a team thin on presidential experience, that nobody was truly in charge, and nobody truly accountable.  So who were those in the inner circle who were to blame.  Staffers now pointing a finger at Patty Solis Doyle, complaining that the former campaign manager was, quote, in over her head.  It’s worth noting that Politico is reporting today that the Obama camp has been in talks with Doyle to work for Obama in the general election.  She knows David Axelrod. 

Others accusing pollster Mark Penn, a divisive figure in the Clinton camp.  One staffer criticizing him for running a, quote, out of touch, corporate run campaign.  Penn resigned from the campaign in early April amid a Columbia lobbying controversy.  Finally, Bill Clinton, one insider blaming his behavior in South Carolina for marking the beginning of the end and lamenting that it became more about him than her. 

Back to Michelle.  Again, interesting about Mark Penn, that he was opposed to the idea of really humanizing her.  He wanted her to run a front-runner campaign, almost an incumbent campaign, and it rendered her role as a woman in this campaign, and how historic that was as a change agent—it rendered it somehow subservient to Obama being the first African-American. 

COTTLE:  Absolutely.  This is a debate that goes back to her Senate races when there was the discussion over whether or not they needed to humanize her or whether they wanted to stick with the policy issues and strength and experience.  That is what you saw squabbling among the top leadership in this campaign over.  Mark Penn generally had the upper hand, people say, with the whole, we have to prove, especially because she’s a woman, that she’s strong enough for this job or we’re not going to get anybody to listen to us on any other points. 

GREGORY:  Rachel, there were times in this campaign early on when this seemed like exactly the right strategy, the idea that Bill Clinton would say it’s a roll of the dice to vote for Obama.  It seemed like that kind of experience argument made a lot of sense. 

MADDOW:  The experience argument, right?  But I think that inspiration piece is really, really important.  I think when Hillary Clinton does talk about gender, when she does talk about her candidacy in almost civil rights terms, in terms of being the first woman, it does move a lot of women supporters.  Maybe it doesn’t move them in terms of numbers, but it certainly moves them in terms of passion.  That could be important.

Mark Penn not only undermined that as a strategy, he personified the opposite of that.  When Mark Penn would go on camera as the CEO of Burst and Marsteller (ph), essentially the PR campaign for evil incorporated, he would undermine any inspirational quotient that the Clinton campaign could ever summon up.  He was the antithesis of that sort of feel good thing that Clinton really could have run with much earlier on. 

SMERCONISH:  David, can I just make a quick point on this.  I love the piece.  Michelle did a great job with it.  But I disagree where she comes to the conclusion—folks came to the conclusion in telling her that Bill Clinton should have been chained and kept in the basement.  That was the mistake.  I think his bad behavior was born of frustration because he was being chained and kept in the basement.  I think the reason is that some folks thought it was going to be demeaning to Senator Clinton as a female if, all of a sudden, he assumed that co-status.  That’s where he should have been.  The strong suit was experience.  By keeping him in the basement, they threw that card out the window. 

GREGORY:  This is truly tough.  You do have a former president and she wants to assert herself on her own behalf.  This is why managing Bill Clinton, not just in this campaign, but back in ‘04 and for Al Gore in 200 has always been tricky.  Let me get to a couple of other things, problems with execution that Michelle writes about. 

First, insiders blaming the message that, some say, was, in fact, working up until September, but the campaign was not nimble enough to change when it was no longer working.  Two, poor post-Iowa strategy, namely on the ground, field work operations.  Third, financial mismanagement.  One staffer complaining that it was, quote, bordering on fraud.  Further saying, quote, a candidate who raised more than a quarter of a billion dollars had to pump in millions more of her own money to stave off bankruptcy. 

Gene, the reality is there was a sense they would never have to get to this point, where Barack Obama was really prepared for it, to go into the trenches and win across the country in these caucus states. 

ROBINSON:  Yes, I think it really started from under estimation of Obama.  It was a poorly planned and poorly executed campaign strategy, not to go into the caucus states almost at all, to kind of write them off.  It was all going to be wrapped up before the had to go in.  By the time it was clear that it was not going to be wrapped up, they had neither the resources nor the staff nor the know how to rush into those caucus states, and try to keep Obama from that string of 11 victories in a row, that really appears to have won the nomination for him. 

GREGORY:  Michelle, I want to move on to this final one, problems with the candidate.  One charging, that you talked to, that the campaign did not do enough to show voters the real Hillary Clinton, saying, quote, what they are dying for is to know a little bit more about her.  Two, Clinton’s non-answer to the driver’s license question at the Philadelphia debate reinforced voters’ views that she would say or do anything to get elected.  Three, her speaking style was too dense, too wonky.  In other words, she just didn’t do a great job connecting, Michelle, until she got into real trouble.  Then she seemed to sort of strip away some of those layers. 

COTTLE:  Exactly.  As we saw, people responded to that.  The big question with Hillary Clinton is always, who is she?  Is she this complete conniver who will do or say anything to get elected?  What really motivates her?  What does she care about?  Is she a real person?  They never quite address that well enough.  When you had a stumble, like she did in the Philadelphia debate, where she didn’t really answer the driver’s license question, it was all too easy for the narrative to become, well, see, she doesn’t know what she thinks.  She’s just whatever is convenient and politically of the moment. 

GREGORY:  Let me make one other point here as we get to a break.  The issue that you bring up about dealing with the press is so interesting to me, because there was a disconnect, not only their style, but in terms of allowing members of the press to get closer to her, to get a sense of who she really was.  There are generations of reporters who were not around for the first Clinton administration and she might have been able to show what she was really about.  Your play date with the panel, next.

(COMMERCIAL BREAK)

GREGORY:  Finally here on THE RACE, remaining moments, your play date with the panel.  And still with us tonight, Michelle, Eugene, Rachel and Michael.  First up, Trudy called us with this question.  It’s a good one.  Listen.

(BEGIN VIDEO CLIP)

CALLER:  I was wondering if the panel would think Hillary Clinton would make a great secretary of state, if that would solve the problem with her having a great position, and if that would solve the problem with Bill Clinton, because I don’t remember ever seeing the secretary of state’s spouse with them on the job. 

(END VIDEO CLIP)

GREGORY:  Well, you know, Smerc, it’s intriguing because it raises the point of whether she could do something else besides being the number two, assuming she would want to.   

SMERCONISH:  Are you sure this is not one of my callers from Philly?  Let me understand this.  In other words, this woman is saying, let’s make her secretary of state, because she won’t bring Bill along for the ride?  Is that length we have to go to make sure he’s not involved.  He should be involved.  That’s my point. 

GREGORY:  Right, but the idea, Gene is would she do anything other than be a vice president?  Could she play a big and effective role elsewhere? 

ROBINSON:  Could she?  Of course she could.  But would she?  We have no idea.  We don’t even know if she would take the second spot on a ticket with Obama.  Her attitude is still that she’s going to win the nomination.  She’s certainly not willing to think about anything like that now.  I’m not sure that secretary of state—you know, it might be a job she’d be interested in.  I doubt it.  I’m a little doubtful about that. 

GREGORY:  I can see Obama going through the roster.  How do you feel about the EPA?   

(CROSS TALK)

GREGORY:  -- Illinois e-mailed this: “Can anyone explain why Barack Obama doesn’t seem to be spending any time in Kentucky?  I thought that after such a huge loss in West Virginia, he would have realized that he can’t just give up in these states is greatly favored.  I really thought he was going to give it a good try.” 

Rachel, I guess his thinking is he came off the West Virginia thing OK with John Edwards endorsing him the next day.  It didn’t really sting him.  Why do you think he’s ceded the ground in Kentucky. 

MADDOW:  I’m with Trish on this one.  I think it’s a little bit weird.  There’s the nuts and bolts argument, which is that it will be time and money wasted.  He’s never going to win that state anyway.  It’s throwing good money after bad.  It’s true, he’s not going to win Kentucky no matter what he does there.  But I do think there’s a case to be made—interestingly, Pat Buchanan has been making this argument, and I find myself agreeing with it, which makes me feel like I’m in a “Twilight Zone.”  But he’s saying, listen, it would mean something for Obama to go and say, you know, I know you’re Clinton voters and I know I’m not going to win here.  I know you’re not standing for me, but I’m standing for you.  I want to be the president for all Americans and for the entire Democratic party.  Even though I know you’re not going to be there for me on Tuesday, we need to see eye to eye and I respect you. 

GREGORY:  That’s an intriguing idea.  Mark from Wisconsin writes something that interests me; “if Barack Obama wins this fall, can we finally put the term Reagan Democrats to bed and make a reference to a new demographic, the Obama Republican?” 

Michelle, what interests me about this—I know this is all anecdotal, but I have talked to some Republicans that I know, pretty tried and true Republicans, who have said to me, you know, whether it’s McCain or Obama, either one I’m actually pretty confident in.  I can see voting for either one.  This is really the recipe Obama that is after, if there are enough of these kinds of voters, and presumably a lot of independents who are really moderate Republicans, who might swing to Democrats now.  It could be his bread and butter. 

COTTLE:  Certainly.  This is the kind of thinking that I’ve talk to some Democrats on the Hill who would to see Obama as the nominee.  They are figuring he and McCain can get in the middle and battle over those independents.  I think the term is Obamacans, what they’ve already come up with.  People have already been thinking of this. 

GREGORY:  All right, real quick, Jim from North Carolina writes this: “it’s abundantly clear to me that Senator Clinton stopped campaigning for delegates before North Carolina.  All she is hoping for out of this race are the bragging rights to the popular vote.  The beauty of it is that Senator Obama can’t contradict it without appearing inelegant.”

Look, this is a hard fought race.  It is relatively close in the grand scheme of things.  But I think he’s still going to argue that he’s won it on points and the points that is matter. 

That’s going to do it for us tonight.  You can play with the panel every night here on MSNBC and RACE FOR THE WHITE HOUSE.  Call us, e-mail us, we’ll get you on the air.  Thanks to a great panel tonight.  We’ll see you tomorrow night for our special coverage of primary night.  “HARDBALL” is next.

Content and programming copyright 2008 NBC.  ALL RIGHTS  RESERVED. Transcription Copyright 2008 Voxant, Inc.  ALL RIGHTS  RESERVED. No license is granted to the user of this material other than for research. User may not reproduce or redistribute the material except for user’s personal or internal use and, in such case, only one copy may be printed, nor shall user use any material for commercial purposes or in any fashion that may infringe upon NBC and Voxant, Inc.’s copyright or other proprietary rights or interests in the material. This is not a legal transcript for purposes of litigation.

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