updated 8/27/2008 11:39:57 AM ET 2008-08-27T15:39:57

Guests: Norah O‘Donnell, Rachel Maddow, Michael Smerconish, Eugene Robinson, Terry McAuliffe, Kim Gandy, Pat Buchanan, Dee Dee Myers, John Hickenlooper

DAVID GREGORY, HOST:  “I‘m in.  And I‘m in to win.”  Those were Hillary Clinton‘s words in January, 2007, when she launched her bid for the presidency.  Now she‘s on the outside looking in as she prepares to deliver a pivotal speech in support of Barack Obama.

We are at historic Union Station at the Democratic National Convention in Denver, as the RACE FOR THE WHITE HOUSE lands on Hillary Clinton‘s Rocky Mountain plateau. 

And good evening, everybody.  Welcome to RACE FOR THE WHITE HOUSE.

I‘m David Gregory. 

My headline tonight is “The Hillary Clinton Factor.” 

Tonight, Senator Clinton‘s big opportunity to put any convention tension to rest.  But despite clear indications that she will throw her full support behind Obama, some of Senator Clinton‘s are still unhappy with the outcome, with a list of grievances.  Chief among them, of course, Obama‘s failure to pick her as his running mate.

Norah O‘Donnell, chief Washington correspondent, MSNBC host, Senator Clinton will apparently ask her delegates to be released to Obama, but what does she say tonight to put all the grumbling to rest? 

NORAH O‘DONNELL, MSNBC CHIEF WASHINGTON CORRESPONDENT:  She has to say, I want Barack Obama to be president of the United States, back him, and here‘s why.  And she‘s got to draw the distinctions that she did before a women‘s group today that he‘s wrong on the right to choose, abortion rights, and also on equal pay, a lot of things that would move the women voters who still back Hillary who aren‘t yet ready to endorse Barack Obama. 

GREGORY:  It‘s an important point.  And she‘s got to vouch for Barack Obama in a way that says to her supporters, he‘s got what I‘ve got, in effect. 

O‘DONNELL:  And I think she‘s going to do it on substance.  The question, whether the tone plays and whether us watching believe her when she says it. 

GREGORY:  Well, it‘s not just tone, it‘s what she said on the record in the fight for the nomination.  Let‘s look at Senator Clinton when she conceded her nomination fight back in June. 

(BEGIN VIDEO CLIP)

SEN. HILLARY RODHAM CLINTON (D), NEW YORK:  The way—the way to continue our fight now, to accomplish the goals for which we stand, is to take our energy, our passion, our strength and do all we can to help elect Barack Obama the next president of the United States. 

(END VIDEO CLIP)

GREGORY:  So, Rachel Maddow, host on Air America, soon to be host on MSNBC 9:00 each evening, is that the Hillary Clinton that we‘re going to see tonight in tone and in language? 

RACHEL MADDOW, MSNBC POLITICAL ANALYST:  I think so.  It obviously matters, as Norah said, that she say, if you support me, if you accept my leadership, I believe that you should support Barack Obama.  It‘s important that she say that, but it is also important that Senator Clinton represents the pivot, I think, of this entire convention toward McCain, what the stakes are.  If you are still angry about Senator Clinton not winning the primaries or not getting chosen as vice president, if you think about supporting McCain or not supporting Obama, what that would means. 

She has to go after McCain.

GREGORY:  Right.  There‘s still, again, the question of the bruising primary battle, how Senator Clinton‘s words could come back to haunt her.  Here she is back in February mocking Senator Obama. 

(BEGIN VIDEO CLIP)

CLINTON:  Now, I could stand up here and say, let‘s just get everybody together, let‘s get unified.  The sky will open, the light will come down, celestial choirs will be singing, and everyone will know we should do the right thing and the world will be perfect. 

(APPLAUSE)

Maybe I‘ve just lived a little long, but I have no illusions about how hard this is going to be.  You are not going to wave a magic wand and have the special interests disappear! 

(END VIDEO CLIP)

GREGORY:  Michael Smerconish, this is the question: Has she written McCain‘s playbook for him? 

MICHAEL SMERCONISH, RADIO TALK SHOW HOST:  What she needs to do tonight, it‘s not enough to say that she wants Barack Obama to win.  The level of analysis on her words is unprecedented.  People are saying that if you play it in reverse, you hear, “I shot Paul.”  It‘s insanity, what‘s going on here. 

What she needs to do, David, she needs to tee it up against John McCain. 

GREGORY:  Right.

SMERCONISH:  If she wants to earn the respect of all these folks, she becomes the hatchet against McCain.  That‘s her strategy tonight.

GREGORY:  Well, and let‘s talk about McCain, because I see a real parallel here to 2000 if you look back at the kind of language that McCain was using against George W. Bush back in January of 2000. 

Watch.

(BEGIN VIDEO CLIP)

SEN. JOHN MCCAIN ®, ARIZONA:  Governor Bush‘s plan has not one penny for Social Security, not one penny for Medicare, and not one penny for paying down the national debt.  And when you run ads saying you‘re going to taking care of Social Security, my friend, that‘s all hat and no cattle. 

(END VIDEO CLIP)

GREGORY:  So Gene Robinson with “The Washington Post,” is this a matter where this simply is going to take more time than even Democrats are expecting?  It can‘t be solved at this convention?  Just like with McCain, it took him several years before he got right with the right and right with George W. Bush. 

EUGENE ROBINSON, MSNBC POLITICAL ANALYST:  Well, that may be the case, but what I hear from inside the Clinton inner circle this afternoon is that she‘s going to make a really good start on it tonight.  I hear the speech was still being worked on early this afternoon, that the drafts that people have seen do everything we‘ve talked about and more. 

That they talk about party unity, that they praise and describe Senator Obama‘s values.  That a speech that brings the party together, and that the tone has been described to me as spot on. 

GREGORY:  Let‘s talk to about somebody that knows about this speech very well.  Joining me now, Terry McAuliffe, the former chairman of Hillary Clinton‘s presidential campaign.  He is on the convention floor here in Denver. 

Terry, good to see you.  Welcome.

TERRY MCAULIFFE, FMR. CLINTON CAMPAIGN CHAIRMAN:  Hey, David.  It‘s awful exciting down here. 

GREGORY:  Let me amplify on what Eugene just reported, because sources I‘ve talked to as well said that this is still being worked on this afternoon.  Hillary Clinton is intent on hitting all the chords in this speech. 

Let me ask you the most direct question.  What, specifically, does she say tonight to put all the talk about the bitterness between these two camps to an end? 

MCAULIFFE:  Well, David, she doesn‘t go anywhere near that.  What she‘s going to do, first of all, is thank all of her supporters.  And then she moves to make the case why every single person who supported her needs to support Barack Obama enthusiastically.  And she lays out the reasons why. 

And then, she‘s going to also make the case, eight years of a failed presidency under George Bush, you would have the same thing with John McCain.  So she‘s going to talk, not only get her supporters to support Senator Obama, but also lay the case why we need to have a Democrat in the White House. 

She‘s worked on the speech for a couple of days.  I think she‘s still working on it.

GREGORY:  Terry, what does she say specifically to those supporters who are not where she is?  They are not over it the way she appears to be.  They are not prepared to walk lockstep behind Barack Obama.  She‘s got to speak very specifically to them. 

What does she say? 

MCAULIFFE:  Well, right, and some of those folks aren‘t there yet, David.  But I do believe after her speech tonight, and she lays out the consequences of not supporting Barack Obama and what it means for health care, what it means for the war in Iraq, what it means for education funding, when she finishes that, and then, tomorrow night, when President Clinton gives his speech, and then finally you have Barack Obama on Thursday night—we have a roll call vote tomorrow night, all the boxes are checked. 

It‘s time for everybody to come home, leave here Friday morning pumped up, unified, talking about John McCain. 

GREGORY:  OK.  Let‘s talk about coming home. 

Numerous people that I‘ve talked to who know both Senator Clinton and former President Clinton say that she is on board, she is working well with the Obama campaign.  It is former President Clinton who has yet to feel that he‘s been shown the proper respect by the Obama campaign, that he is not over the primary fight. 

True or false? 

MCAULIFFE:  False.  And I speak to the former president every day.  I just spent eight days traveling around Africa with him. 

I know how he feels.  He is ready to go.  He wants to give the speech of his life tomorrow night.

He is on board.  And a lot of people are trying to create issues.  He had 35 minutes with Senator Obama Thursday night.  He told him, I will go every day on the campaign trail if you want me.  I will do whatever you want me to do. 

The ball is in their court.  We‘re ready to go.  Hillary is ready to go.  Everybody is there.  We‘re doing everything we can to help Senator Obama.

GREGORY:  Terry, this is how Politico‘s John Harris sums up the Clintons‘ mission.  He writes this: “For the Clinton‘s, the politics of the week are simple: Accept the cheers of the many Democrats who will support them, be lavish in their praise for Obama, make sure that if he loses, no one can say it was because they were covertly rooting for that result.”

Fair? 

MCAULIFFE:  You know, I can‘t get into all the psychobabble that a lot of these folks partake in.

Hillary Clinton, from the time she‘s moved out of the race, has done fund-raising, has traveled, has done everything asked of her.  She‘s in it.

Barack Obama‘s the nominee of the party.  Joe Biden is our vice presidential nominee.  They are going to run their campaigns, they‘re going to make the decisions.  It‘s not up to the Clintons. 

They are going to everything they are expected to do.  It‘s up to Senator Obama to get that message out there, convince the American public that he should be commander in chief of the United States.  It isn‘t about Bill and Hillary Clinton...

GREGORY:  All right.  Now, here is the issue, Terry.

MCAULIFFE:  ... when we leave this convention.

GREGORY:  Here is the issue for the Obama campaign and for Senator Clinton.  Yes, she can be an asset, is an asset for Senator Obama.  She is also currently an asset for the McCain campaign. 

They have released a new ad called “300 a.m.,” and it features Hillary Clinton‘s own words.  Take a look.

MCAULIFFE:  OK.

(BEGIN VIDEO CLIP)

NARRATOR:  It‘s 3:00 a.m., and your children are safe and asleep.  Who do you want answering the phone? 

NARRATOR:  Uncertainty, dangerous aggression, rogue nations, radicalism. 

CLINTON:  I know Senator McCain has a lifetime of experience that he will bring to the White House, and Senator Obama has a speech he gave in 2002. 

NARRATOR:  Hillary is right.  John McCain for president. 

MCCAIN:  I‘m John McCain, and I approved this message. 

(END VIDEO CLIP)

GREGORY:  It‘s an accurate ad, Terry.  Even if she supports Barack Obama, how does she walk that back? 

MCAULIFFE:  Listen, I think, David, people understand in the heat of the primaries, you want to win.  And she‘s made the decision to support Barack Obama.  She‘s going to go out there enthusiastically for him. 

Everybody knows what she‘s going to do for Senator Barack Obama.  Everybody knows she‘s—you know, how she feels on John McCain.  She knows that Barack Obama would be the better choice of president of the United States of America.  They did it with Senator Biden.

I hope, David, they spent (ph) a lot of money on these ads, because people understand, we had a primary fight, now we are into the general.  Reset it.  We start off again.  And they understand it, they get it. 

GREGORY:  All right.  We will leave it there. 

MCAULIFFE:  We‘re going to talk here in this hall about the issues that affect—OK, David. 

GREGORY:  All right, Terry.  Terry McAuliffe, we‘re out of time. 

Thanks very much. 

MCAULIFFE:  Thanks, David.

GREGORY:  Good luck tonight.

MCAULIFFE:  All right.  Thank you.

GREGORY:  Coming next, America meets Michelle Obama.  So how did she do in her big introduction? 

RACE FOR THE WHITE HOUSE, live from the Democratic convention in Denver, is back on MSNBC.

(COMMERCIAL BREAK)

(BEGIN VIDEO CLIP)

MICHELLE OBAMA, BARACK OBAMA‘S WIFE:  They‘ll tell them—they‘ll tell them how this time, we listened to our hopes instead of our fears. 

(APPLAUSE)

How this time, we decided to stop doubting and to start dreaming.  How this time, in this great country where a girl from the south side of Chicago can go to college and law school, and the son of a single mother from Hawaii can go all the way to the White House... 

(END VIDEO CLIP)

GREGORY:  That was Michelle Obama, of course, last night in her speech, the headline speech to the convention.  An important cornerstone in yesterday agenda to define, who is Barack Obama? 

So, Gene Robinson, how did she do?  What message did she deliver?

ROBINSON:  Well, I thought it was a great speech.  It was not just about him, it was also about her, it was about the family. 

You know, just talking to people today, of course the moment everyone remembers was at the end, after the speech, when Sasha and Malia came out, the two daughters, and had that charming exchange with Obama via satellite. 

GREGORY:  Right, which we‘ll show in just a moment, but I want to focus on her for now.

ROBINSON:  Right.  But, you know, I thought she did everything she had to do and more in that speech.  The way she—I thought it was well delivered, and it gave us an idea of who she is.  And that she‘s not some sort of forbidding figure. 

GREGORY:  You talked about the moment with the daughters.  Let‘s show that.  This is when Barack Obama was beamed in from Missouri. 

Watch.

(BEGIN VIDEO CLIP)

UNIDENTIFIED FEMALE:  Daddy, what city are you in? 

SEN. BARACK OBAMA (D), PRESIDENTIAL CANDIDATE:  I‘m in Kansas City, sweetie. 

And Malia, Sasha, how do you think mom did? 

UNIDENTIFIED FEMALE:  I think she did good. 

OBAMA:  All right.  I think so, too. 

(END VIDEO CLIP)

GREGORY:  You know, if I boil down, Norah, what that presentation was about, this kind of made-for-television family portrait is about saying, you know us, we‘re like you. 

O‘DONNELL:  Right.

GREGORY:  And that is not something that the Obamas have been able to do successfully enough before now. 

O‘DONNELL:  I think a lot of people look at people‘s family structure, look at their children, and get a sense of who they are.  And that moment gave a sense of, wow, those are really cute kids.  They really love their dad.  That‘s a nice family structure, they must care about each other a lot. 

And I think that did more, in many ways, that moment, than even her speech, in some ways, to sort of give people a sense of, oh, I kind of like them.  It was a likeable moment.  Even Barack Obama telling that phrase (ph) that he brought her out for an ice cream on their first date and how persistent he was about getting a date with her. 

GREGORY:  Right.

O‘DONNELL:  I mean, it was sort of silly, but it made all of us sort of giggle. 

GREGORY:  But Rachel, I think there was not as much lightness to the speech, right?  I mean, there were a lot of family moments. 

This was—I described it this morning as a rebuttal in many ways.  You heard a lot about working class background, her love for America.  This was a way of saying, I am not who I have been made out to be, America.  That‘s about me, and I‘m the window into you understand Barack Obama. 

MADDOW:  Yes, there is political strategy to doing a speech like this.  And the strategy here is to take away the ability of the McCain campaign to make a demon out of Michelle Obama and to make the Obama family something other, alien and threatening. 

I think the most important part of this speech was that she was making the case that they are a product of meritocracy.  That they—that both Michelle and Barack Obama worked hard, played by the rules, and that‘s how they got to where they are.  And that‘s something that every American identifies with.  That‘s the basic American value.

GREGORY:  But has the McCain campaign been guilty of creating a caricature of Michelle Obama?

SMERCONISH:  Well, somebody who has access to a “send” key has certainly created a caricature of Michelle Obama.

David, I didn‘t focus so much on what she was saying as I did the way in which she was saying it last night.  I said here yesterday that I believed she needed a softening moment.  And I think she got that. 

She looked beautiful.  And she delivered in a very comfortable set of remarks that—I thought it went over well.  Any objective observer would have to say that she knocked it out of the park.  That‘s the bottom line. 

GREGORY:  But who is she trying to reach?  Again, this is not about reaching the core Obama supporters. 

SMERCONISH:  The middle.

GREGORY:  It‘s reaching the middle, it‘s reaching swing voters.  It may be reaching values voters who don‘t feel like they connect with the Obama family.

SMERCONISH:  I think in large part, people are just now beginning to pay attention.  I think the slate has been wiped clean.  We‘re all junkies; we love this.  The rest of the country, in large part, I think tuning in for the first time.

GREGORY:  Is there a danger, Rachel, in spending too much time defining Obama? 

MADDOW:  Yes.  Yes.  You have four days at the convention. 

GREGORY:  Right.

MADDOW:  You probably should have spent half a day of those four days defining Obama, and the rest of the time defining the choice between Obama and John McCain.  I think they probably did—they probably should have had one more hard-edged speech last night about John McCain, to include that in last night‘s program (ph). 

GREGORY:  Well, you know, it‘s interesting, because, Norah, I talked to a couple of Democratic officials today who said a couple things.  One is that choice will become clearer, particularly with Mark Warner, who is running for the Senate from Virginia, and his headline speech tonight.  Hillary Clinton will get the attention, but Mark Warner is going to talk about the choice in terms of Obama being a bridge to the future and McCain being about the past. 

O‘DONNELL:  Right.

GREGORY:  That kind of contrast is going to be important in this convention. 

O‘DONNELL:  I‘ve talked to a lot of Democrats who said there wasn‘t enough red meat last night.  Now, that wasn‘t the goal for Michelle Obama.

GREGORY:  Right.

O‘DONNELL:  But maybe they could have put Senator Claire McCaskill for 5 or 10 minutes in between there, and then she could have—because she‘s had some great lines, and she‘s a wonderful advocate for him.  They‘ve got to do that tonight.

There is some concern though that Mark Warner‘s speech tonight is about building the bridge to the future and not enough though about those one-liners that will replay over and over again that draw those deep distinctions with McCain that this party believes Barack Obama is not tough enough to do. 

GREGORY:  All right.  Well, I‘ve got to take a break here.  We‘ll talk more about that as we continue. 

Coming up next, we‘ll see what else is on THE RACE‘S radar tonight.  What caused Joe Biden to choke up today, an appearance before the Delaware delegation?

A little bit later on, all eyes on Hillary Clinton as she takes center stage tonight.  What does she have to say to bring an end to the drama?  One of Clinton‘s most ardent supporters will share her thoughts.

(COMMERCIAL BREAK)

GREGORY:  And we are back, live from Denver, with a look at what else is on THE RACE‘S radar tonight. 

Tonight on the radar, vice presidential candidate Joe Biden got a little emotional in Denver today.  He was talking to the Delaware delegation about the future and his past. 

Watch this. 

(BEGIN VIDEO CLIP)

SEN. JOE BIDEN (D), VICE PRESIDENTIAL CANDIDATE:  It‘s a great honor being nominated vice president of the United States.  And it is an honor, and I‘m proud of it.  I don‘t mean in any way to diminish it.  But it pales in comparison to the honor that I‘ve had representing you. 

(APPLAUSE)

You know, I look—I look—I look at—and I apologize for getting a little emotional. 

(END VIDEO CLIP)

GREGORY:  You know, Smerc, when I watched that today, I actually watched it on the Web this afternoon, and a couple of things struck me.  One is that he is opposite of cool and aloof and hard to get to know.  And he lets it hang out.  And this is the first time he was at the convention and addressing a group where reporters were there as well.  And it‘s an emotional time for him.

SMERCONISH:  Joe Biden wears his heart on his sleeve.  He‘s not a poll-driven, finger to the wind kind of a guy.  And I think that‘s what‘s endearing about him, even when he makes foibles, even when he offers those gaffes and makes mistakes.  He comes across as the kind of guy that you‘ve had a beer with or you‘d like to have a beer with, and that‘s what‘s endearing about him.

GREGORY:  It‘s interesting, Norah.  He talked as well, without being specific about it, about the tragedy that befell him, the loss of his young daughter and his wife when he first got to the Senate.  And he talked to these supporters today and said, look, I didn‘t always handle myself as well as I might have back then.  And it seemed like he might have been making an allusion to some of his malapropisms or long-windedness.

But it was intensely personal.  And t went back to the very beginning of his political career. 

O‘DONNELL:  There‘s an authenticity about him and the sharing of his personal life that many people Barack Obama needs to do a little bit more of.  It will help connect with voters.  I mean, that is an amazing story.  His wife was out looking for a Christmas tree when they were hit by a drunk driver, and he lost his wife and his daughter.

I think the showing of emotion by Joe Biden shows how privileged he feels he is to have been nominated to this ticket.  And I think he really wants to do a good job for Barack Obama. 

And his speech on Wednesday night I‘m looking forward to, because I think that this is going to be—given what he said on Saturday, I mean, it is going to be a barn burner.  There was not that much applause in the convention center last night.  Wednesday night, I think, is going to be a big night.

GREGORY:  All right.  I‘m certain he‘s going to stick to the 2000 words as well.

Coming up next, how is Obama doing defining John McCain?  We‘re going to go inside the war room when RACE FOR THE WHITE HOUSE returns.

We‘re live from Denver.  And we‘re back right after this.

(COMMERCIAL BREAK)

GREGORY:  Two political dynasties, the Kennedy‘s and the Clinton‘s; last night, an emotional appearance by Senator Ted Kennedy.  Tonight, a different kind of emotion and a pivotal moment in the convention, with Hillary Clinton on center stage.  THE RACE FOR THE WHITE HOUSE is live in Denver at the Democratic National Convention in windy low-down, lower downtown of Denver. 

All eyes are on Hillary Clinton as she takes center stage tonight.  What does she have to say to bring an end to the drama?  Some of Clinton‘s most ardent supporters are still very disappointed that Clinton was not named the vice presidential nominee.  My next guest is included among those.  Joining me now is the president of the National Organization for Women, Kim Gandy.  Kim, welcome.  Thanks for being here. 

KIM GANDY, NOW PRESIDENT:  Glad to be on the show. 

GREGORY:  Senator Clinton made it clear that she supports Barack Obama.  She‘s moved on.  Why haven‘t you? 

GANDY:  Well, we—obviously, we were terrific supporters of Hillary Clinton.  Our political action committee was waiting to see who the vice presidential nomination would be before we took a position.  We‘ve been listening to Hillary Clinton and also talking to our own supporters about what a terrific supporter of women‘s rights Barack Obama is.  Obviously, we‘d love to have Hillary Clinton, but we think Barack Obama is a great supporter of women‘s rights and would be a terrific president.

GREGORY:  So why a level of disappointment that amounts to what could be a protest vote, delegates casting their vote for Hillary Clinton instead of doing everything you can do to get party unity at this stage? 

GANDY:  I think it‘s important to note that historically there have been these roll call votes.  Senator Kennedy had a roll call vote when he ran against Jimmy Carter.  Paul Tsongas, even without a lot of delegates, had a roll call vote.  I was a Mondale delegate, but Gary Hart‘s 1,200 delegates got their roll call on the floor.  So there were a lot of delegates who said, wait a minute.  Why now that we have a woman on the floor, why does she not have the honor of getting her name in nomination so that we can cast our votes?  In other words, the men got it, why would it be taken away from Hillary? 

GREGORY:  On the Republican side, there‘s no expectation of a delegate vote for either Mike Huckabee or Mitt Romney. 

GANDY:  I don‘t know that the Republicans have a history of doing that in the way that the Democrats do?  The Democrats have a history of the delegates being able to state their position at the convention.  I think the Hillary delegates really wanted some closure for this.  They wanted the opportunity to say, I was elected a Hillary Clinton delegate, and I‘m casting my vote on the first roll call for Hillary. 

GREGORY:  What does Senator Obama have to do at this stage to get Hillary Clinton supporters behind him without reservation? 

GANDY:  I think he‘s doing the right things.  I think one of the first things that he needed to do was say, yes, this is historic.  Her supporters should have a chance to put her name in nomination and to vote for her on the first ballot.  I think that was hugely important step.  That was something he needed to do to say to her supporters, she has the respect of this candidate and this campaign.  We‘re not going to deprive her of the honor of having her name put in nomination.  That was very important. 

The second thing he‘s done that is very important is to have a platform that addresses women‘s rights issues.  It‘s probably the best platform since 1980. 

GREGORY:  This issue, though, the issue of Hillary Clinton supporters being disappointed that Biden is on the ticket, that Hillary Clinton is not, it still raises the questions: where are supporters like you going to go?  You have John McCain making the argument that Hillary Clinton supporters should go over to him.  Is that really going to happen?

GANDY:  There is no question in my mind that any supporter of women‘s voters could not think about casting a vote for John McCain.  Absolutely not possible.  He is a complete cipher when it comes to women‘s rights issues.  There‘s no question that Barack Obama is absolutely a supporter of women‘s rights.  There‘s no question about that. 

Disappointment, sure.  But her supporters are looking to her for where she‘s going and what she‘s—I‘ve heard her speak twice today already.  And both times she has spoken, she has said, to those of you who supported me, to those of you who worked for me, I want you to work every bit as hard for Barack Obama as you did for me. 

GREGORY:  Kim Gandy, thank you very much.  We‘ll wait for Senator Clinton‘s speech tonight and your reaction afterwards.  Thank you very much. 

GANDY:  Thank you.

GREGORY:  We are going to turn to some of our dream team now to go inside McCain‘s war room.  Has the Obama campaign had success in redefining McCain in the past two days.  Rachel and Smerc, overall, what do you think?  This had been more biography than it has been contrast, Smerc.

SMERCONISH:  Not yet.  I don‘t think they have yet picked up the gauntlet.  I think that last night was a night of feel good, particularly surrounding the emotional appearance by Senator Edward Kennedy.  The, of course, it belonged to Michelle Obama.  But tonight is the night when the lumber should be swung.  I maintain that the best person to do it would be Senator Clinton, because she‘s served with John McCain.  This is her opportunity to unify the party by being the attacker in this scenario. 

GREGORY:  It is interesting.  I‘m told by people close to Senator Clinton that she will create that contrast with McCain, but she‘s going to be more diplomatic about it. 

MADDOW:  She‘s also been put on the spot in a very big way by the McCain campaign, as you mentioned.  The McCain campaign is running these very hard hitting ads, essentially portraying Hillary Clinton as an endorser of John McCain against Barack Obama.  Once you have been put in that position by the opponent to the candidate you have endorsed, you have a very particular responsibility to not only disown it, but hit back hard in a way that makes them never want to use you again. 

GREGORY:  Key issue, commander in chief test.  That‘s a big part of this convention.  On the convention floor last night, I asked Senator John Kerry, the nominee back in 2004 for the party, from Massachusetts of course, if Obama should be using the campaign and this convention to close the gap and define John McCain in a way that Kerry didn‘t effectively do to define Bush four years ago.  This is what he said.  It‘s interesting.

(BEGIN VIDEO CLIP)

SEN. JOHN KERRY (D), MASSACHUSETTS:  He obviously needs to define the differences with John McCain.  But people in America need to understand, Barack Obama is older than John Kennedy, older than Bill Clinton, older than Teddy Roosevelt were when they became commander in chief and president.  Barack Obama, in fact, has made the right judgments.  What I care about, as a former soldier, is the commander in chief going to make the right judgments about where they send those troops. 

Barack Obama was right about Iraq.  He‘s been right about Afghanistan. 

I believe he‘s shown the right judgment.  John McCain has not. 

(END VIDEO CLIP)

GREGORY:  Smerc, that was tough on a couple of fronts.  First of all, he came right out and said John McCain is old.  He‘s going to be an older commander in chief than some of these historic presidential figures, former presidents.  Then he made the point that this has to be a contrast between judgment and experience.  Experience shouldn‘t win the day. 

SMERCONISH:  I interviewed Evan Bayh today and addressed this same issue.  What Senator Bayh said to me, and something, frankly, that Senator Obama said to me when interviewed him once before, is don‘t misunderstand my opposition to the war in Iraq as me being weak on terrorism.  I just happen to think we ought to be fighting that front in a different country.  He‘s thinking tribal areas.  He‘s thinking Afghanistan, in particular.  That‘s what he has to do.  He‘s got to get up there and convey to folks, he‘s not about to let sand get kicked in the face of the United States.  He‘ll be tough in the circumstances that call for it. 

GREGORY:  Let‘s also talk about McCain, some of the heat he‘s been taking because of a slip that occurred during an interview last week when he couldn‘t remember how many homes he owned.  He fired back on “The Tonight Show” with Jay Leno last night.  Watch. 

(BEGIN VIDEO CLIP)

JAY LENO, “THE TONIGHT SHOW”:  For one million dollars, how many houses do you have? 

SEN. JOHN MCCAIN ®, PRESIDENTIAL CANDIDATE:  Could I just mention to you, Jay, in a moment of seriousness, I spent five and a half years in a prison cell.  I didn‘t have a house.  I didn‘t have a kitchen table.  I didn‘t have a chair.  I spent those five and a half years, not because I wanted to get a house when I got out. 

(END VIDEO CLIP)

GREGORY:  Rachel Maddow, were you convinced? 

MADDOW:  This is the only thing John McCain could do to reduce the political salience of the way he served his country for those five and a half years.  If he, himself, cheapens by using it as a political crutch to bring up—to deflect any criticism on him on any unrelated issue, that is the only way that issue could become politically less powerful to him.  He‘s doing it to himself.  I‘m mystified by it. 

GREGORY:  But, Smerc, there‘s a different way I think you can analyze it, which is to say this is somebody who is pushing back against the idea that this is a symbol of privilege and being out of touch.  This is a guy who know where he is, where he‘s come from, and hasn‘t been lost in the privilege of America because his father-in-law was very successful. 

SMERCONISH:  Cindy McCain‘s father‘s story is a heck of a Horatio Alger story, the way in which he built that business.  I think it would be prudent for John McCain to stress that.  This is a man, not McCain, who fought for his country, comes home, starts that business on a shoe string, and builds it into a huge distributorship.  That gets lost.  That‘s a story he should tell. 

MADDOW:  But how can you make a political point out of that when then what John McCain did was marry it.  It isn‘t his story. 

SMERCONISH:  There‘s nothing to be embarrassed about the wealth of the family.  I don‘t why he should run from it. 

GREGORY:  What I‘m getting at is the idea that he can‘t remember how many homes there are, which is a slip, is used to say, look, this guy is out of touch.  He‘s just a product of privilege.  Is it not germane to say, look, you know who I am, where I come from.  I‘m not some out of touch rich guy here, or somebody who married into family wealth. 

MADDOW:  You can absolutely say it.  Listen, I was tried beyond all human understanding.  That was where my character was forged.  That was where I proved my love of my country.  But that does not actually come in as germane in any way to the question of whether or not he understands what it is for most Americans right now to be in this economy with the worries that most of us have. 

GREGORY:  All of this, part of the contrast that I think we‘re going to see more of tonight with Mark Warner‘s speech and certainly with Hillary Clinton.  OK, we‘ll take another break here.  Dueling dynasties; the Kennedy‘s making a comeback, lending their family‘s gravitas to Obama.  But where does it leave the Clintons, the other prominent Democratic family?

Former Clinton White House press secretary Dee Dee Myers and Pat Buchanan will join me next.  RACE FOR THE WHITE HOUSE returns live from Denver today.  Don‘t go away.

(COMMERCIAL BREAK)

(BEGIN VIDEO CLIP)

SEN. TED KENNEDY (D), MASSACHUSETTS:  This November, the torch will be passed again to a new generation of Americans.  So with Barack Obama and for you and for me, our country will be committed to his cause.  The work begins anew.  The hope rises again.  And the dream lives on. 

(END VIDEO CLIP)

GREGORY:  That was Senator Ted Kennedy, of course, last night, with echoes of his 1980 DNC speech.  We are now looking ahead to night two of the Democratic National Convention.  Here in Denver, former Obama rival Senator Hillary Clinton with a prime time address this evening.  She will hit the theme renewing America‘s promise, but will also set out with another goal, protecting the Clinton legacy, as the Clintons and the Kennedy‘s step out of the spotlight and cede the political stage to a new generation. 

Former presidential candidate and MSNBC political analyst Pat Buchanan is here, as well as former press secretary to former President Clinton Dee Dee Myers. 

DEE DEE MYERS, FMR CLINTON PRESS SECRETARY:  Lots of former going on.

GREGORY:  Yes.  Welcome to both of you.  Thanks for being here.  “New York Times” reporter Patrick Healy, with the “New York Times,” did an analysis this morning that talked about these two families moving into a different phase of their political identity.  This is how he put—we‘ll put it on the screen: “as one political dynasty was celebrating its legacy and ceding the political stage on Monday night, the other dominant family in the Democratic party was struggling to protect its legacy and accept its own exit from the spotlight.  Senator Hillary Rodham Clinton and Bill Clinton had once hoped this convention would be there‘s, an exultation of past and future Clinton White Houses.  Instead, they were coming face to face with shrunken supporting roles.”

Dee Dee, not easily. 

MYERS:  No, first of all, it‘s not easy to lose a contested primary by the most narrow margin in history, and to earn more votes than anybody in history, except the guy who beat her by a very narrow margin.  So for Hillary Clinton, and I think even more difficult for her supporters who put their hearts and souls into this and maybe haven‘t lost in the past.  So it was difficult, but I think Hillary Clinton has really hit all the right notes in the last couple weeks. 

I think she‘s ramping up for a speech that is going to do two things tonight.  One is really appeal to the party and particularly to her supporters for unity, and talk about how important that is.  Also, I think, to do what she did so well at the end of the campaign, which is talk about the different economic challenges we face and the differences between these two parties in addressing the kitchen table concerns of Americans who have seen their homes lost or values shrunk, their jobs threatened, rising gas and energy prices.  There‘s really deep concern in the land.  I think she‘s the perfect person to address it.

GREGORY:  Pat Buchanan, necessarily the party is passing the Clinton‘s by for a new voice, for a new figure.  It‘s important, however, that they do everything right to set her up for a potential run, right? 

PAT BUCHANAN, MSNBC POLITICAL ANALYST:  That‘s exactly right.  The Kennedy‘s are the blood royal of American politics, because of John F.  Kennedy‘s assassination, Joe killed in the war as a hero, Bobby assassinated in 1968.  And Teddy had the last real shot at this generation getting the presidency.  He lost it 28 years ago. 

But they did possess the torch.  It looked like that was being handed off to the Clinton‘s, Bill Clinton and Hillary going out in Martha‘s Vineyard, that area, out there on the schooners and things.  All of a sudden, Ted Kennedy, this year, the older man, the old lion, hands the torch to this young generation, takes it away from the expected winner, Hillary Clinton, who was going to have a Clinton dynasty.  You have a real bitterness, I think understandably, of Bill Clinton for Teddy Kennedy having done that, undeniably.  There‘s no doubt about it, the Kennedy‘s have moved to the, if you will, Obama dynasty. 

GREGORY:  You talk about Senator Kennedy whose son Patrick reacted to his father‘s remarks last night.  Watch. 

(BEGIN VIDEO CLIP)

REP. PATRICK KENNEDY (D), RHODE ISLAND:  It gave me great pride, obviously, to see my father up there.  I have had headaches from the altitude, trying to drink enough water.  Here my dad comes in.  He‘s had radiation, chemotherapy.  He gets up there and knocks the speech right out of the park, and once again illustrates that this is the time, it‘s the summit of his political career. 

(END VIDEO CLIP)

GREGORY:  Norah O‘Donnell, as you listen to Patrick Kennedy, and the symbolism of last night, of the Kennedy family saying the party belongs to the Obama family now.  That‘s the new beginning, if not a dynasty, necessarily, but certainly they are the face of this party. 

O‘DONNELL:  If the dream still lives then the dream lives on in Barack Obama.  That‘s what‘s so powerful in his remarks last night.  That initial endorsement by the Kennedy‘s right before Super Tuesday was the kind of momentum he needed where he eventually got more delegates than she did on February 5th.  So it‘s significant. 

GREGORY:  I have always sensed, analytically here Gene, that what‘s been difficult for the former president, who served with such distinction, who faced controversy with the Lewinsky scandal and impeachment—he did not live in a 9/11 era.  He did not govern in a 9/11 era.  And that Clintonism, he thought, could have been vindicated as a political force beyond his generation with the election of Hillary Clinton.  That has been denied the Clinton family. 

ROBINSON:  The thing that I thought most upset the former president about the primary campaign was when Barack Obama said he wanted to be a truly transformational president like Ronald Reagan, in a way that Bill Clinton was not.  I think that really got under his skin.  It diminished the Clinton era.  I think we will hear some degree of self-vindication of that.   

GREGORY:  Pat. 

BUCHANAN:  Bill Clinton, of course, he had that terrible ending of his administration, sort of in disgrace and all the rest of it.  Here was the opportunity for a second Clinton administration, vindication in every way, getting all that behind them, and them being the future again, as they were in ‘92.  Again, to see Teddy Kennedy before Super Tuesday, as Norah said, to go out and say the torch, no, it doesn‘t belong to you, the front-runner; it belongs to a new generation, and to pass over this generation for Obama must really be very difficult and it must be permanent bitterness. 

MYERS:  I don‘t think they totally accept it.  I think the Clintons think, a little bit, not so fast.  I think that‘s what tonight and tomorrow are about to some degree, is saying, you know what, Hillary Clinton is still a force in this party.  Bill Clinton is still the only Democrat in the last half century to be elected and then reelected.  The Obama juggernaut, powerful and impressive as it is, still has a ways to go. 

BUCHANAN:  Isn‘t that why she‘s got to give—the Reagan speech in ‘76, he came down there and he gave such a terrific speech, people said, hey, did we nominate the wrong person here.  If I were her, I would do such a high level speech, no vindictiveness, try to bring them together.  Every positive thing you can think of. 

GREGORY:  That leads to the question, Dee Dee, is there a decision on how she precedes, what her future is?  Does he start tonight to work down that path? 

MYERS:  Yes, I‘m not sure that the entire strategy has been hammered out in detail.  But yes, tonight is the beginning of the next chapter of her life.  She needs to rise to that occasion with grace, with compassion, with energy and commitment.  She needs to show the country that she really is over it.  If she can do that, I think there will be—

BUCHANAN:  And prayers that somebody doesn‘t win this fall.

MYERS:  -- opportunity for the Clinton brand to move on. 

GREGORY:  All right.  We‘re going to leave it there.  Suffice it so say, we will be watching.  We can‘t wait.  Thanks, Norah, Eugene.  Up nest, three hours until Hillary Convention takes the stage at the convention.  What our panel will be watching for tonight.  And one of the hosts of the show, the mayor of this great city of Denver, joins us when RACE FOR THE WHITE HOUSE returns live from Denver.

(COMMERCIAL BREAK)

GREGORY:  Welcome back to THE RACE.  The Democrats invade Colorado.  The state could turn blue for the first time since it elected Bill Clinton president back in 1992.  Now, Colorado is in play big time again.  It‘s time to go one on one with Denver Mayor John Hickenlooper.  Mayor, good to see you.  Thanks for coming by. 

JOHN HICKENLOOPER, MAYOR OF DENVER:  Glad to be here.

GREGORY:  First, as you know, I have a great love for this city.  How is the city holding up with the convention, with security, with all the media here?  How is the city performing? 

HICKENLOOPER:  It‘s been great.  We worked 18 months planning and then training.  Now we‘re executing.  It‘s been going fine.  I think people are excited to be here.  People have been telling me here, police officers are friendly.  You‘ve got taxi cab drivers.  The city is so clean.  Look at all the housing downtown.  It‘s almost been like a Chamber of Commerce booster program. 

GREGORY:  I‘m staying in lower downtown.  This city has done such remarkable work down here. 

(CROSS TALK)

HICKENLOOPER:  This is my old neighborhood.  It‘s where my cabin was.

GREGORY:  This is great.  Let‘s talk politics.  Colorado is in play.  You know, Barack Obama wants to make a big stand here come November.  It‘s a dead heat here.  What are his prospects? 

HICKENLOOPER:  I think he‘s going to do pretty well.  I think the fact that we have more independents here than Republicans or Democrats—I think people here look at individuals.  As Barack becomes better known—we are the kind of place.  I spent almost 20 years in the tavern business.  People want to sit down and have a beer with the candidate.  They want to vote for someone they feel comfortable with.  I think as people get to know Barack, I think they will move towards him in that sense. 

GREGORY:  You have a lot of independents in this state who may not like George Bush, President Bush, but they‘re not yet sold on Barack Obama.  What would you tell him he has to do to close that sale? 

HICKENLOOPER:  I think he has to, A, come out here a few times, but also make sure that he is expressing himself, who he is as a person.  Pretty much anyone I know who has sat down and had dinner or spent serious time with him comes away that he‘s a listener.  He‘s asking questions.  He cares about other people.  He‘s not full of himself.  I think as people get to know him, they will vote for him. 

GREGORY:  Mr. Mayor, thanks very much.  Continued good luck and success this week. 

HICKENLOOPER:  Thank you. 

GREGORY:  Turning to the headliner tonight; Hillary Clinton will take the stage in just a few hours.  Her speech and Bill Clinton‘s speech tomorrow will likely be the most parsed of this convention.  Dream team members tonight Rachel Maddow, Michael Smerconish are back with me.  They‘re watching for tonight as she takes center stage.  Rachel, I‘ll start with you.  Again, what are we looking for? 

(CROSS TALK)

MADDOW:  -- I think would be Senator Clinton going on at length about her own accomplishment, particularly accomplishments won at the expense of Barack Obama.  If you see that, that‘s a problem.  If you see Senator Clinton trying to define the Clintonian legacy in a way that is designed to protect it from Barack Obama running against it, that will also be a problem.  We don‘t see either of those things, I think it‘s clear sailing.  She has to make sure she hits McCain and make sure she reiterates her firm support for Obama. 

GREGORY:  We‘ve got some video of her on the convention floor tonight.  Hillary Clinton doing a walk through this afternoon, getting a chance to rehearse with the teleprompter and get a sense of everything with her daughter, Chelsea Clinton, who will introduce the senator tonight.  There will also be a film, a tribute, an homage to the Clinton‘s.  She got a chance to see some supporters on the convention floor tonight.  Smerc, is this about the Clinton‘s tonight or is it about Barack Obama? 

SMERCONISH:  It‘s about the Clintons tonight.  The intrigue that surrounds Senator Clinton is this: does she really want him to win?  And it‘s not enough for her to say, I really want him to win.  In order for her to prove her mettle on that issue, she needs to go after her old friend, Senator John McCain.  Everybody knows that friendship exists.  That‘s how she‘ll have some skin in the game. 

GREGORY:  Can she, as of tonight, Rachel, deliver?  I don‘t mean her core supporters who are her, who want her to be on the ticket.  I mean her supporters in states like Pennsylvania, West Virginia, the white working class voters who have alluded Barack Obama so far.  Can she deliver them, starting tonight? 

MADDOW:  You know, she may be able to.  I think this is more than personality.  I think this is, in part—the reason that you saw especially the class split in the primaries, the way people voted for Obama versus Clinton, because people aren‘t sure what the next stage of Democratic politics is after Clintonian politics, triangulation and things like NAFTA.  I think, in part, she needs to define herself as part of the future of the Democratic party, to say, I stand with Barack Obama as we move to the next chapter after Clintonism.  It‘s going to be good for the working man in this country. 

GREGORY:  Final thoughts?  Ten second. 

SMERCONISH:  There‘s a tendency on all of our parts to think that folks can be delivered by anyone.  Barack Obama has got to deliver that constituency in the end. 

GREGORY:  All right.  The coverage is here, starting in just a few minutes on MSNBC, the place for politics.  That does it for RACE FOR THE WHITE HOUSE tonight.  I‘m David Gregory.  See you back here live from Denver tomorrow night.  Stay where you are.  Keith Olbermann and Chris Matthews will lead MSNBC‘s special convention coverage.  It all gets started right now. 

THIS IS A RUSH TRANSCRIPT. THIS COPY MAY NOT BE IN ITS FINAL FORM AND MAY BE UPDATED.

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