'Countdown with Keith Olbermann' for Monday, July 14
video podcast

Video via MSNBC: Oddball

Guest: Richard Clarke, Chris Cillizza, Michael Ian Black, Howard Fineman

RACHEL MADDOW, GUEST HOST (voice over): Which of these stories will you be talking about tomorrow?

The Taliban killed nine U.S. soldiers, not with a roadside bomb, but in a coordinated attack against a U.S. base in Afghanistan. Barack Obama lays out his plans for getting out of Iraq and focusing in on Afghanistan. But John McCain says Obama's wrong because Iraq is the central part on the war on terror. Where did he get that?

(BEGIN VIDEO CLIP)

SEN. JOHN MCCAIN, (R) PRESIDENTIAL CANDIDATE: That's what Osama bin Laden says. Iraq is the central battleground.

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MADDOW: A reality check on the war on terror with Richard Clarke; the politics with Howard Fineman.

(BEGIN VIDEO CLIP)

DAVID REMNICK, THE NEW YORKER: The purpose of this cover was like the Colbert Report in print.

(END VIDEO CLIP)

MADDOW: The "New Yorker" in full damage control mode over its latest cover. Where is the fine line between satire and the problem that some people find truthiness in the over the top caricature of the Obamas?

The running mate's mates problem. Obama reportedly tells a Clinton donor, Hillary is being considered for veep but there's a little issue of a guy named Bill.

And John McCain officially joins the 20th century, already over with by proclaiming he is learning to get online. No word on whether President Bush has offered him any tips on how to use the Google. Meanwhile South Carolina governor and McCain surrogate, Mark Sanford, goes on the TV machine to tell viewers that John McCain and George Bush are very different.

(BEGIN VIDEO CLIP)

GOV. MARK SANFORD, (R) SOUTH CAROLINA: I mean, for instance, take,

you know, take for instance the issue of, of - I'm drawing a blank -

(END VIDEO CLIP)

MADDOW: It looks like the governor got some coaching from one of his constituents.

(BEGIN VIDEO CLIP)

LAUREN CAITLIN UPTON, MISS SOUTH CAROLINA TEEN USA: And Iraq, and

everywhere like, such as -

(END VIDEO CLIP)

MADDOW: All that and more: Now on Countdown.

(BEGIN AUDIO CLIP)

UNIDENTIFIED MALE: I hate it when I do that.

(END AUDIO CLIP)

MADDOW: Good evening. I'm Rachel Maddow in for Keith Olbermann.

This is Monday, July 14th, 113 days until the 2008 presidential election.

And today, one of the presidential candidates came out with a plan to send more U.S. troops into combat. It was John McCain. The catch -

Barack Obama wants to send these troops to Afghanistan. The war some U.S. troops call "Forgotistan."

In a "New York Times" op-ed today, Obama says, as president, he would send at least two additional combat brigades to Afghanistan. He explains to umpteenth time that he has never said a rigid, unconditional timetable for withdrawal from Iraq and he explained why he thinks leaving Iraq is essential to America's safety.

"Ending the war is essential to meeting our broader, strategic goals," he wrote. "Starting in Afghanistan and Pakistan where the Taliban is resurgent and al Qaeda has a safe haven, Iraq is not the central front on the war on terrorism and it never has been."

Obama will travel with Republican Senator Chuck Hagel and Democratic vice presidential short-lister Senator Jack Reed to both Iraq and Afghanistan this summer.

Under Obama's plan which he reiterated is open to revision. U.S. combat brigades would be removed from Iraq over a course of 16 months ending in the summer of 2010, leaving a residual force in Iraq to perform specific and limited missions like protecting U.S. personnel, hunting al Qaeda, and possibly training Iraqis.

Obama's argument for focusing on the Afghanistan-Pakistan border was underscore this weekend by the deadliest attack on U.S. forces there in years. Nine Americans killed on a coordinated military assault on a U.S. base yesterday.

All this, amid reports of growing military concern about Afghanistan, the Pentagon having already re-tapped to the USS Abraham Lincoln to the region, and military officials reportedly urging Mr. Bush to accelerate troop movements out of Iraq and into Afghanistan and reports that even Bush administration diplomats have now been, quote, "talking about dates for U.S. pullouts in talks with the Iraqis." A path the president previously claimed would - help the terrorists.

Let's bring in a man who knows about real terrorists - former counterterror adviser, Richard Clarke, author of "Your Government Failed You."

Mr. Clark, thank you so much for joining us.

RICHARD CLARKE, AUTHOR, "YOUR GOVERNMENT FAILED YOU": Rachel, it's good to see you for a change.

MADDOW: First, you worked in a two most recent administrations on the issue of counterterrorism. With that expertise, can you weigh in on Senator Obama's piece today whether you think he really gets it, gets the important issues on counterterrorism?

CLARKE: Well, what he said today is, in no way different from what he's been saying for about a year now. For about a year now, he has been sounding the alarm about the real battle against al Qaeda, which has always been Afghanistan and Pakistan. That's where they were before 2001. That's where they still are today.

And you look at what he says today, it's the same thing. He said, "I would send two more brigades, perhaps, three, into Afghanistan and I would start pulling brigades out of Iraq at the rate of about one a month." And there's exactly the same statement as he made throughout the primary campaign as what he said today.

MADDOW: July is on track, sadly, to follow May and June as a month in which Afghanistan may be deadlier than Iraq for U.S. troops. Do you think that we are now finally getting to a point where we can dispense with the myth that this administration's focus on Iraq hasn't cost us in terms of our goals in Afghanistan?

CLARKE: Well, I think so. I mean, we have the chairman of the Joint Chiefs of Staff, Admiral Mullen, the highest ranking officer in the U.S. military, saying he wishes that he had more brigades in Afghanistan today and the reason he doesn't is that they're in Iraq. And that's exactly what Barack Obama has been saying for over a year.

So, if Barack Obama is a military amateur, as some people are saying, I guess the chairman of the Joint Chiefs is, too.

MADDOW: This is going to sound like a simple question and I don't mean it rhetorically at all, I mean it seriously. Do we know at all what the Bush strategy is in Afghanistan? Do we know what the Bush administration's goals are in Afghanistan and what they're doing to try to meet those goals and do we know of any difference between McCain and Bush on those issues?

CLARKE: Well, McCain hasn't said much about what he would do in Afghanistan and Obama has talked about a comprehensive plan involving not just military activity, but development aid to cut back on the opium crops, to get the people there some alternative other than the Taliban.

And when you look at the McCain statements, they're kind of vague. Frankly, the Bush statements are kind of vague, too, because the obvious conclusion is you have to send more troops. His military leaders, his secretary of defense even, has been saying that, but he hasn't been because he can't send more troops right now because of this war in Iraq.

MADDOW: The conservative commentator, Bill Kristol - consider the source here - but he did recently report that President Bush feels the big problem heading into the next presidential administration is neither Iraq nor Afghanistan, but Pakistan. Our supposed ally where al Qaeda has very real safe havens where Admiral Mullen has spent a lot of time lately, as you mentioned, but where the government still does not want our troops, this weekend reiterating, yet again, that they do not admit the presence of U.S. troops anywhere in Pakistan nor do they want them.

Where are the candidates on Pakistan and are you hearing any sort of cogent policy out of Washington toward Pakistan at all?

CLARKE: Well, we're not hearing anything out of the Bush administration other than they're going to keep pressing them. But there's no policy to convince the Pakistani government to actually go after al Qaeda, which has a free haven up in the northwest territories.

Obama began almost a year ago saying that we had to do more. He said during the debates that if there were a high-value al Qaeda target on the other side of the border in Pakistan, he would authorize for us to go after them. He was attacked for that, and then four times, Rachel, four times this year - quietly the Bush administration did exactly what Obama had said should be done.

So, I find - this is kind of interesting phenomenon going on. Obama is saying things that turn out later to be obvious and true and even the Bush administration has to admit it and start doing what Obama was on to months before they were. And, yet, McCain is the national security expert?

McCain, remember, wanted to go into Iraq in 1998. He started advocating the invasion of Iraq in 1998 and he has no plan to get out. Obama, at least, is saying if everything goes as expected, U.S. troops, major combat units, will be out in the summer of 2010. That's pretty specific.

MADDOW: Richard Clarke, former national counterterrorism adviser, the author of "Your Government Failed You," it's a pleasure to see you and have you here. Thanks for joining us.

CLARKE: Thanks, Rachel.

MADDOW: There's also a lot of ground to cover tonight on the politics of war and national security.

For that, we turn to MSNBC political analyst Howard Fineman, senior Washington correspondent for "Newsweek" magazine.

Hi, Howard.

HOWARD FINEMAN, MSNBC POLITICAL ANALYST: Hi, Rachel.

MADDOW: In his op-ed today in the "New York Times," Obama mentions the possibility of tactical adjustments to his 16-month plan for withdrawing from Iraq. Is Obama courting the flip-flop label again, or at this point, is there starting to be a little political shine on the idea of listening to the folks on the ground, considering facts on the ground, instead of sticking to the plot line no matter what?

FINEMAN: Well, it's a fine line, as you know, between one man's grounded realism and another's flip-flopping. I think what Obama is trying to do here with this op-ed and with the speech he's going to give tomorrow, Rachel, is to try to reassert control over an issue that defined him, that really put him on the national stage to begin with, which was his opposition to the invasion of Iraq all these many years ago.

As Richard Clarke said, Obama has had a knock for seeing over the horizon on some of these issues, even though he doesn't seem to have the experience on the ground to do so. He's trying to say here are the next steps I want to take, asserting the need to put more troops in Afghanistan, which is a bold move in and of itself, and basically trying to say, "Look, this is where I've been, this is where I'm going to be. I'm going to be realistic."

The only problem he's got, I think, was timing. I think to have this op-ed piece today in advance of going to Iraq, and to once again committing himself to that 16-month timetable before he actually goes back to Iraq, I think, shows that there was a political task to be done with this op-ed, which is to reassure the left-wing of his own party that he still was the guy that they first fell in love with a few years ago.

MADDOW: I saw in the op-ed real effort to try to make a timeliness claim, I think, about the fact that Maliki and others in the government are saying, "We are ready for you to plan to leave" if not leave already. He's trying essentially to say, "There's is an opportunity here for a pivot point on Iraq policy. There's an opportunity here where America has a choice. Do you want to make the Bush/McCain choice or do you want to make the new choice?"

And it maybe that it's just political timing that's been driven by - for lack of a better phrase - by the conditions on the ground there.

FINEMAN: I think that's right. He hasn't seen them up close himself, but you're absolutely right. I think Maliki's statements about wanting the American troops to be on a timetable for withdrawal played directly into Barack Obama's hands and he wanted this op-ed piece to try to get control of this issue again, Rachel. I can't state it more specifically than that.

He's got to get control of it. That's the reason for the op-ed, the interviews he's given on this topic and this big speech he's going to give tomorrow, to show that he has a broader vision for what to do going forward that's better and shrewder than John McCain's.

MADDOW: Back to the issue of McCain for a second, because McCain can no longer criticize Obama for not going to Iraq - in his speech today, McCain said Obama should also visit South America. McCain, also, referred to Czechoslovakia today, which is a country that hasn't existed for 15 years or so. He has cited Czechoslovakia before on the campaign trail.

McCain has had this, "I have been in the Senate longer and have more stamps in my passport" line of attack against Obama. Is that undercut by McCain frequently, and surprisingly getting details, like this, wrong?

FINEMAN: Well, it's true that he's better traveled, as you say. It's true that he has more stamps in his passport but a presidential campaign is not a contest about airline miles. It's about judgment. And Obama has made some pretty shrewd calls - on the dangers of Afghanistan, on the problems of Pakistan, on the exhaustion of the troops, on the overstretching of our budgets - and that's got to be Obama's claim.

McCain comes from the warrior class, nobody denies him that. If you read his books, if you know his story - son and grandson of admirals, I mean, the guy knows war. He knows a lot about the world.

But what Obama is saying is, "I offer a new kind of global leadership in which I know how to listen, in which I'm open to understanding other cultures on their terms and not seen through military eyes, but through the eyes of individuals to individuals." That's what Obama's saying. Obama's challenge is to make that not look naive, but make it look smart.

MADDOW: One last question, Howard. If Obama didn't make plans to visit Iraq, he would be criticized by McCain for it. We'd seen that already. If, when Obama does visit Iraq, he concludes the U.S. needs to formulate withdrawal plans, he would be criticized by McCain for that - we can see that coming.

If Obama, hypothetically, went to Iraq and decided we need to stay there for 100 years, he would be criticized by McCain for changing his position to side with McCain. There's no scenario on which he's not going to come under attack on the issue of Iraq. Senator McCain likes to talk about Iraq.

Do you see the Obama campaign figuring out that it doesn't help to try to make decisions based on anticipating criticism because he's going to get criticized no matter what he does?

FINEMAN: Yes, that's what the speech tomorrow is about. I talked to David Axelrod, the guy who's really running the Obama campaign, I said, "What's going on?" He said, "Look, this speech tomorrow, we're going to try to show that there is no broad plan for the whole world on the McCain side. We have a comprehensive view of the world and we're going to lay that out starting tomorrow."

So, yes, the Obama campaign is trying to quit looking that McCain sort of bomber buzzing around Obama's head and give a longer statement of where they hope to take the country and the world.

MADDOW: Howard Fineman of "Newsweek" and MSNBC, thanks for joining us tonight.

FINEMAN: Thank you, Rachel.

MADDOW: As far as covers go, it definitely has people talking, but does the "New Yorker" cover satirizing rumors and slurs about the Obamas have people talking about the right thing?

Meanwhile, is Obama really considering Hillary Clinton for vice president? He allegedly tells one Clinton donor that Bill would be the big sticking point.

And John McCain is learning how to use the Internet. It turns out, they're not a big truck; they're a system of tubes.

Details ahead on Countdown.

(COMMERCIAL BREAK)

MADDOW: The "New Yorker" calls it's latest cover a satire. Both campaigns denounce it but as the outrage over the meter of red line, the outrage-o-meter, have we reached a point where the only safe jokes are ones that you can guarantee everyone will get?

And, is there really chance it will be an Obama-Clinton ticket?

And in Bushed, taped evidence suggests that access to senior Bush administration officials is for sale if you donate to Bush's library.

That and more: Ahead on Countdown.

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MADDOW: The details hidden in the "New Yorker" cover drawing of Senator Obama and his wife Michelle aren't the story. The outrage over the "New Yorker" cover isn't the story either.

But tonight, in our fourth story on the Countdown: The potential consequences of the clearly meant to be satirical cartoon are the story.

First, the details. By now, you have no doubt heard and very likely seen the cover of the magazine which depicts a turban and tribal dress-wearing Obama in the Oval Office fist-bumping his mightily AK-47 touting, combat boot-wearing, mightily afroed wife. Above the fireplace hangs a portrait of Osama bin Laden; in the fireplace burns an American flag.

All of the scare tactics and misinformation about Barack Obama are now available in one handy 8 ½ by 11 location. This afternoon, editor of "New Yorker," David Remnick defended the cover as on-target satire.

(BEGIN VIDEO CLIP)

DAVID REMNICK, THE NEW YORKER: I don't think this satire went too far. It's all about accusations of Obama being insufficiently patriotic, or soft on terrorism, or Michelle Obama somehow being '60s-style revolutionary. All this is nonsense, and that's what the cover is trying to say that it's nonsense. It is an attack on those who would manipulate and lie about him and we are holding a mirror up to that.

(END VIDEO CLIP)

MADDOW: Neither campaign sees it the way Remnick does. When first asked about the cover yesterday in San Diego, Senator Obama is said to have shrugged incredulously saying, quote, "I have no response to that."

Later, his spokesman put out a statement, quote, "The 'New Yorker' may think, as one of their staff explained to us, that their cover is a satirical lampoon of the caricature Senator Obama's right-wing critics have tried to create. But most readers will see it as tasteless and offensive. And we agree."

Even Senator McCain agrees. At least, he agrees that Obama's supporters will find it offensive.

(BEGIN VIDEO CLIP)

MCCAIN: I just saw a picture on television. I think it's totally inappropriate and, frankly, I understand if Senator Obama's supporters will find offensive.

(END VIDEO CLIP)

MADDOW: Lots to talk about with MSNBC political analyst Jonathan Alter, also, a senior editor at "Newsweek" magazine.

Hi, Jon.

JONATHAN ALTER, MSNBC POLITICAL ANALYST: Hi, Rachel

MADDOW: So, the magazine here depicts a lie about Obama because the lie is supposed to be funny. It's supposed to be funny that anybody would believe something so obviously untrue about the Obamas. So, is the problem here that way too many people believe these allegations, essentially that way too many people won't get the joke?

ALTER: Yes. Look, in 1925 when the "New Yorker" was founded, the founder, Harold Ross, specifically said to investors that the magazine was not for, quote, "The little old lady in Dubuque," - which is a kind of a patronizing thing to say.

But, the problem is, there are a lot of people outside of Dubuque really, I think, about 13 percent of the public that believes, at least, some of these lies about Senator Obama. So that when you're doing this, you know, whether it's funny or not, and reasonable people can disagree on that, it has consequences - in terms of the campaign and this is something that, I think, the "New Yorker" probably didn't think through as much as they might have.

It's true that it's kind of silly to get all hot and bothered and cancel your subscription over a cartoon as some people are doing. That's something that extremists in other countries have done about Danish cartoon. We really shouldn't be doing that here. But the fact remains that it is something that goes beyond satire into the actual, you know, marrow of the campaign.

MADDOW: Because of that context that you're talking about with the latest polling, as you said, showing 13 percent of Americans believe that Barack Obama is a Muslim.

Given that, given that has been a factor in the campaign thus far and it will continue to be a factor in the campaign - that mistaken belief about Barack Obama, that the belief that he is a Muslim - even though he is not - given that, do commentators and journalists and people who participate in discussions about politics have a responsibility to state clearly every time this comes up Barack Obama is not a Muslim, it is a mistaken belief?

Because, presumably, some percentage of people hearing these discussions, some percentage of the time, the only words that are really clicking with them are Obama and Muslim and they're not getting what they want (ph).

ALTER: I think you're absolutely right.

You have to state that clearly every time the subject comes up and you have to go beyond that and you have to take all the other lies and distortions about Obama, and actually take the time to refute them, which most often, you know, we can say, do we really need to be taking the time that we would rather use to analyzing campaign issues just refuting lies? The answer to the question is yes, we do need to do that and it's just part of our responsibility to what are called low-information voters - people who are not paying wrapped enough attention to know these things are untrue.

But, I think, it's kind of a mistake to assume that somehow what we tell them is going to be more powerful than an image. Visuals always speak louder and that's why this cover is a problem.

MADDOW: And they stick with us in a way that you can't necessarily always rebut with words. Is part of the problem here - execution? If it were funnier, would this not be as big of a scandal?

ALTER: No, it would still be the same. I mean, I didn't think it was

unfunny. They don't do ha-ha covers, they do sort of dry (ph)

illustrations, which this was and -

MADDOW: Well, how about the context of what magazine this is then? I mean, if this had been a right-wing magazine, if this has been a conservative political magazine, would the reaction be the same, even if they came up with the same argument saying this is satire?

ALTER: Well, what would have happened in that case is that, you know, the "New Yorker's" readership is liberal and actually the magazine editorial has been very pro-Obama. So, its readers are outraged. If this had been in a conservative magazine, the readers would have thought it was funny and they wouldn't have cared, but you still would have had the liberal outrage.

I do think it gets a little tiresome to hear all the "cluck-clucking" all the time about how this or that thing is inappropriate in a campaign. People should ease up on that and, you know, recognize that campaigns in America have always been with all kinds of charges and countercharges and cartoons that were out of bounds. This is nothing new in American politics.

MADDOW: Sure. It's kind of a game that everybody has a right to say whatever they want and everybody has a right to complain as loudly as they want to get to. That's their business, I guess.

Jonathan Alter, it's nice to see you.

ALTER: Thanks, Rachel.

MADDOW: Jonathan Alter of "Newsweek" and MSNBC.

The Pentagon launches an internal investigation that - we could solve for them in about 10 seconds. That's ahead in Bushed.

And, two years in a row Miss USA takes a tumble at the Miss Universe pageant. Now, that is where they have investigation.

Countdown continues is just a moment.

(COMMERCIAL BREAK)

MADDOW: Whether or not you think the cartoon portrayal of Michelle and Barack Obama on the cover of this month's "New Yorker" is funny or harmful, clever or dumb, there's one undeniable good thing about it. At least the "New Yorker" has the right to publish stuff like that.

On this date 210 years ago, the sedition act was passed by Congress, making it a federal crime to publish false, scandalous, or malicious writings about the U.S. government. Passed in 1798, the act expired in 1801, and except for a second sedition act resurfacing in 1918 - false, scandalous, and malicious writing about the U.S. government has been flowing freely ever since. God bless America. Let's play Oddball.

(BEGIN VIDEO CLIP)

MADDOW: We begin in Vietnam, site of last night's 2008 Miss Universe Pageant. The United States again snubbed by the universe, as Miss Venezuela was crowned the winner. America's representative, Krystle Stewart (ph), finished eighth. I though I'm no expert on beauty pageants, I think I may know what happened here. Give it up for Miss USA, everybody. Bless her heart, Stewart quickly composed herself and hustled off stage. This is the second straight year that Miss USA has failed in the walking competition. Rachel Smith was the victim last year. Next year fool-proof plan, roller shoes, high heeled roller shoes. So if Miss USA starts to fall again, she can just say she's doing shoot the duck.

Let's go to Alahabad (ph), India where street vendor Ron Baboo's (ph) finger food is flying out of his fryer. Baboo uses a boiling cauldron of oil to cook his delicious doughy fritters. To reduce overhead, instead of a spoon or a spatula, Baboo uses his own hands to pluck the fried dough out of the pot of boiling oil. Baboo then passes the savings and boiled finger skin on to you, the customer.

Baboo says the heat doesn't bother him, that customers love watching him at work, and that once his fingerprints are completely melted off, he will retire to a life of crime. Good luck, Baboo.

(END VIDEO CLIP)

MADDOW: Some blamed Bill Clinton for ruining his wife's chances to be president. Now, is he hurting her shot at vice president?

And political punch lines, John McCain is learning the Internets. Maybe he will use the Google to finally learn that Czechoslovakia isn't a country any more.

But first, the headlines breaking in the administration's 50 running scandals, Bushed. Number three, war, what war-gate, an update. We told you last week about Gina Gray, the Arlington National Cemetery public affairs director who was fired for trying to get media into military funerals on occasions when the family of the fallen had specifically requested that. Now, the Army has ordered an internal review of Gray's firing. A spokesman telling the "Washington Post" that the military wants to strike the right balance between family wishes and the interests of the press. The issue here is that family's wishes were the same as the interests of the press. Families wanted media coverage of the funerals and the media wanted to cover the funeral. Seems like those two things wouldn't be that hard to balance.

Number two, America for sale-gate. Where can a disgraced former dictator turn for help these days? Congressman Henry Waxman will be holding hearings to investigate one answer turned up by the "Times of London" yesterday, reporting that the White House will lend a sympathetic ear in return for cold, hard cash donations to the Bush library in Texas. An undercover reporter asked the lobbyist whether he could rehabilitate the image by Kyrgyzstan former dictator by getting him a meeting at the White House.

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UNIDENTIFIED MALE: I think that could be worked out. I can't promise we can get to the president. But because he doesn't with a lot of former presidents these days. I don't think he meets with hardly anyone. But the situation in Kyrgyzstan is, I think, worse than it was before. That's a given. And I think that some things could be done. I think that the family, children, whatever, should probably look at making a contribution to the Bush Library. How big, I won't know yet. I don't know. It would be like maybe a couple hundred thousand dollars or something like that.

Cheney's possible, definitely the national security advisor, definitely either Dr. Rush or Deputy Secretary is possible.

(END VIDEO CLIP)

MADDOW: Is this a random con man selling meetings he can't deliver. We wish. Actually, that was Stephen Paine, major Bush fund-raiser, member of the Homeland Security Advisory Council, veteran or overseas trips with Bush and Cheney, who was actually paid by the actual dictator of Azerbaijan to arrange an actual meeting with Mr. Bush in April '06. Wonder how he pulled that off.

Number one, serial driller-gate. President Bush today lifted an executive order banning off-shore drilling. It's an order that dates back to the other President Bush. The move accomplishes nothing, because Congress still has its own ban in effect. But that's not the only way we know this is pure politics. According to Mr. Bush's own Energy Information Administration, off-shore production could not even start until five years after the off-shore sites were released. That's 2013. Off-shore sites could not significantly impact U.S. production until 18 years after leasing. That is 2026.

The impact on prices from off-shore drilling when the oil finally starts flowing in 2026? Because oil prices are set on a global market, the EIA says the impact on prices would be, quote, insignificant. But the political impact, priceless.

(COMMERCIAL BREAK)

MADDOW: Barack Obama has a three-dimensional dilemma, or as he calls it a complication, involved in the selection of his running mate. Our third story on the Countdown, Hillary Clinton as an asset with her own potential liability, her husband Bill. Last Thursday, Obama reached out to Democratic donor and ardent Hillary Clinton supporter Jill Iscol. When the conversation turned to Hillary's shot at VP, Iscol says Obama expressed concern over Bill as the second spouse; quote, once you're a president, even if you're a former president, you're always a president.

Complicated, indeed. Obama knows how much the power the Clintons wield in Democratic politics. Remember this from Thursday.

(BEGIN VIDEO CLIP)

OBAMA: Learned from her as a candidate. I'm proud to call her my friend. I know that I desperately need her and Bill Clinton involved in this campaign.

(END VIDEO CLIP)

MADDOW: Desperately. And then this from Saturday.

(BEGIN VIDEO CLIP)

SEN. HILLARY CLINTON (D), NEW YORK: I have participated in and watched ten presidential elections. Democrats have won only three. And I happen to know very well someone who won two of those three over the last 40 years. So I think I know a little bit about how challenging it will be to win.

(END VIDEO CLIP)

MADDOW: Chris Cillizza is a political reporter at WashingtonPost.com.

Chris, thanks for joining us.

CHRIS CILLIZZA, "THE WASHINGTON POST": Thanks for having me, Rachel.

MADDOW: In your estimation, is former President Clinton the biggest barrier to Senator Clinton's chances at the vice presidency?

CILLIZZA: You know, Rachel, I always feel when you talk about Bill Clinton he's both the best asset and the biggest deficit or distraction in almost any conversation. And I think it is true, when you think about Hillary Clinton and the vice presidency. I think the basic rule of thumb for picking vice presidents is, above all, do no harm. You don't want to put someone on the ticket who raises questions or complicates your message. You want someone who bolsters you, hopefully geographically, ideologically or something like that.

But you also don't want to pick anyone who causes you problems. And Bill Clinton is a tremendously talented politician. He's still extremely popular in a number of segments of the party. But the reality is, he's a little bit of a free agent, as we saw during his wife's campaign. He doesn't necessarily stay on message. He doesn't necessarily say the things the campaign wants to say. And so that is, I think, a problem when you are thinking about putting his wife on the ticket.

MADDOW: From Senator Clinton's perspective, we all know there is no real way to run for the vice presidency. If Senator Clinton believes your analysis, if she thinks Bill could be a barrier to her getting the nod, is there anything she can do about it?

CILLIZZA: No. You know, Rachel, I think if she could have had Bill Clinton do exactly what she wanted during the primary, we would not have likely seen what we saw in advance of the South Carolina primary in January, excuse me. Many people within the Hillary Clinton campaign - and I say Hillary, not Bill - the Hillary Clinton world, thought they should pass on South Carolina. It was an unwinnable race. Bill Clinton, really, again, with those strong southern roots, felt like he could go down there and make a difference. He did make a difference. It was just on the negative side for his wife.

I think if you look at the arc of her campaign, it does not seem to me that she is not able to say, Bill, don't do this and yes, do this. I think he listens a lot of the time, but not all the time.

MADDOW: According to the "L.A. Times," Obama reached out to this prominent Clinton donor because he had heard that she was unhappy with how Senator Clinton was being treated. If the "L.A. Times" is right in their reporting on that, wouldn't it make it worse in such a conversation to site Bill as a complication?

CILLIZZA: I can't imagine she will be an ambassador in an Obama administration. It is generally frowned upon, though I encourage it as a reporter, for donors to say what the presidential nominee told you or didn't tell you. Look, I think Barack Obama thought he was having a private conversation. Again, we don't know the full context of the conversation. I always am worried about sort of taking a snippet of one person's side of a conversation. But he thought he was having a private conversation.

The lesson here, when you're running for president in this modern political age, where everything winds up becoming public, you're never really having a private conversation.

MADDOW: What is the political impact of this having be leaked? How do these comments play for Obama in the election?

CILLIZZA: Well, you know, I think he's going to - he knows that he needs to reach out to the Clinton folks. The reality, Rachel, is that bill Clinton and Hillary Clinton are both something Barack Obama needs, but also something he has to deal with. There's the positive and negative that always goes along with the Clintons. This will complicate it with some people who say, why are you bad mouthing the former president of the United States. Eight years of prosperity, he brought the Democratic party back.

So, in some circles it's not going to help, but the truth of the matter is those circles are the ones that were always going to be the hardest for Barack Obama to convince, because they're the most loyal to the Clintons and have been for a decade or several decades.

MADDOW: For them, the message they may be most amenable to may be an anti-McCain message, more than a pro-Obama message.

CILLIZZA: Exactly. They may not even be reachable.

MADDOW: Chris Cillizza, who authors "The Fix" on WashingtonPost.com, thanks for your time tonight.

CILLIZZA: Thanks, Rachel.

MADDOW: If John McCain is finally learning to use the Internet machine, did whoever is teaching him explain to him that you don't watch websites.

And the tragic loss of Tony Snow turns into political fodder by a newspaper owned by his former boss. That's ahead. This is Countdown.

(COMMERCIAL BREAK)

MADDOW: Our second story on the Countdown, sad news from Washington, D.C., where Tony Snow died of colon cancer this weekend. The founding host of "Fox News Sunday," he joined the White House as President Bush's third press secretary in May 2006, resigning in September 2007, and contributing to CNN up until his death. Snow was widely respected throughout political and media circles, even by those with whom he disagreed.

As our own Keith Olbermann said upon hearing of his death, "Tony Snow was an optimistic, funny and courageous man who could set aside his politics and inspire others to do the same. It might surprise many at all political points, but while we could not have disagreed more on policy, we were in frequent contact, even during his days as press secretary. Even as I was criticizing his work, and he was, in his own words, yelling at the screen as he watched. It was with great sadness that I heard of his death today, and with sincerity I extend my condolences and my staff's to his family. In the best of us, there is a difference between the message and the messenger and Tony Snow epitomized that."

While most people across the political spectrum have rightly paid their respects to Tony Snow since his death, one organization is trying to use the tragedy of his death. "Page 6" of Rupert Murdoch's "New York Post" actually called MSNBC today to claim that, quote, people close to Tony say, end quote, say Keith didn't know Tony Snow at all. We called Keith on vacation today for a comment and response. In his words, the Post is sick to use Tony Snow's death in such a sad, political manner.

We should also not that Keith first acknowledged his correspondence with Tony Snow on air more than a year ago.

(BEGIN VIDEO CLIP)

KEITH OLBERMANN, MSNBC ANCHOR: This may seem improbable, but Tony Snow and I are e-mail correspondents. Baseball has been our primary topic. He says he watches this newscast, says he enjoys it, and can even resist the temptation to yell at the screen. We're honored to have him.

(END VIDEO CLIP)

MADDOW: Of course, no one close to Tony disputed that back in 2007. Keith tells us today he's happy to share his emails with Mr. Snow with anyone who wants to see them. Even though right now is a time to mourn Tony Snow's passing, not to fend off politically motivated lies. Tony Snow is survived by his wife, Jill, and their three children, Kendall, Robby and Christy. He was just 53 years old. His funeral will be held this Thursday.

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MADDOW: In 2006, President Bush proudly told a cNBC interviewer, who asked about his computer usage, quote, one of the things I have used on the Google is to pull up maps. Little did he know that two years later the presumptive Republican nominee to succeed him would make Bush look like the super hacker hero kid from Tron. In our number one story on the Countdown, big news from Senator John McCain's presidential campaign, the senator is now officially moving into the late 20th century, saying that he's learning to get online.

In a wide-ranging interview with the "New York Times" last Friday, the subject of political blogs was broached - more on that in a moment - but Senator McCain was asked if he went online himself. Quote, they go on for me, the senator answered. I am learning to get online myself and I will have that down fairly soon, getting on myself. I don't expect to be a great communicator. I don't expect to set up my own blog. But I am becoming computer literate to the point where I can get the information I need.

Nice to have that warning from Senator McCain that he will not be a great communicator. Lots to look forward to in an uncommunicative McCain presidency. And the McCain camp might want to consider stopping certain supporters from trying to communicate on McCain's behalf. The guy we're thinking of specifically is South Carolina Governor Mark Sanford. The issue here is McCain's economic plan versus President Bush's economic policies.

(BEGIN VIDEO CLIP)

WOLF BLITZER, CNN ANCHOR: Are there any significant economic differences between what the Bush administration has put forward over these many years, as opposed to now what John McCain supports?

GOV MARK SANFORD (R), SOUTH CAROLINA: Yes. I mean, for instance, take - take for instance the issue of - of - I'm drawing a blank. I hate it when I do that, particularly on television. Take, for instance, the contrast on NAFTA.

(END VIDEO CLIP)

MADDOW: Guess who's not going to be vice president. That made us wonder if the South Carolina governor and a different kind of contender from that same state might have a wee bit in common.

(BEGIN VIDEO CLIP)

BLITZER: Are there any significant economic differences between what the Bush administration has put forward over these many years, as opposed to now what John McCain supports?

SANFORD: Yes. I mean, for instance, take, you know -

UNIDENTIFIED FEMALE: I personally believe - that U.S. Americans are unable to do so - some people out there in our nation don't have that -

SANFORD: Take for instance the issue of -

UNIDENTIFIED FEMALE: Education, like such as in South Africa and the Iraq, everywhere like such as. Our education over here in the U.S. should help the U.S.

SANFORD: I'm drawing a blank and I hate it when I do that, particularly on television.

UNIDENTIFIED MALE: Thank you very much, South Carolina.

(END VIDEO CLIP)

MADDOW: Let's bring in comedian Michael Ian Black, author of the new book "My Custom Van," and also the host of a new show on Comedy Central, "Reality Bites," which premiers on July 17th. Michael, congratulations on the new show. Thanks for joining us.

MICHAEL IAN BLACK, AUTHOR, "MY CUSTOM VAN": Thanks for having me.

MADDOW: Senator McCain is learning to get online. Will this be a seminar, a continuing education class, or will it be like a crash course and will Senator McCain require a tutor?

BLACK: Look, Rachel, I think maybe you're making too big a deal out of this. Every president has blind spots in their education and there's a learning curve when you attain the presidency. Some are maybe a little short on the economy or foreign affairs. In Senator McCain's case, it's just everything that has been invented in the last 35 years. And the way I think what we'll do is we'll educate him slowly. We'll start with technology he's familiar with, the telegraph, for example. And then we'll slowly work our way up to say the CB radio, right?

then maybe the Speak 'n Spell. OK? And then eventually in maybe the second McCain administration, we will go to the personal computer, or PC as the kids call it, President McCain.

MADDOW: Do you think it would be helpful if we, the computer using public, sent Senator McCain tips about how to get online?

BLACK: You know, it's not that easy to get online. It really isn't. First of all, you have to know how to turn the computer on. That's not easy. It's not like there's a magic button that you push and suddenly the computer turns on. So there's that. And a lot of people, they're just pressing the keyboard over and over, just pressing G, G, G. Nothing's happening. You have to know where the magic button is.

So we have to teach him where the magic button is. And then once you get online, there's all these sounds that happen. There's visuals that pop up. It's incredibly complicated. Then, if you get that far, you have to double click on the web browser. I'm sorry, there's not a lot of 72-year-old men out there these days who can double click anything.

MADDOW: In this same interview, Senator McCain was asked what websites he looks at regularly. His answer was, quote, Brook and Mark show me Drudge, obviously. Everybody watches, for better or for worse, Drudge. Sometimes I look at Politico, sometimes Real Politics, sometimes.

Everybody watches Drudge? Is he getting the Internet machine mixed up with the TV machine?

BLACK: You're not understanding something, Rachel. This is where Senator McCain is actually ahead of the curve. As we all know, television and computers will eventually merge. So, eventually, we will all be watching computer. You see? He's living in the future, Rachel. You're living in the past.

MADDOW: I could imagine the spin happening right now on that subject. By the way, Senator McCain today said he was concerned about Russia reducing the energy supplies to Czechoslovakia, even though that country hasn't existed in over 15 years. He made this similar mistake before. Maybe this is one of those pesky facts he could look up once he's comfortable with the Google.

BLACK: Look, do we really expect our president to know which countries exist and which countries don't exist? That's a lot for any man, OK? Maybe he could suggest that Russia reduce its energy supplies to Narnia. It would be basically the same thing.

MADDOW: Last question, does the governor of South Carolina, Mark Sanford, finally cited NAFTA as a difference between Bush and McCain, then later explained he didn't really mean that; they're the same on that, too. Should we at least give Sanford credit for the stammering honesty thing?

BLACK: Absolutely. I think we're looking at this the wrong way. Senator McCain shouldn't be running from the Bush economic plan. If you look at it in a certain light - think about it this way, right now there are billions of people all over the globe who can't afford 4.50 gallon of gasoline. We've got millions of Americans who pay for that every single day. We're the richest country in the world and we should be proud of that.

MADDOW: Comedian Michael Ian Black, host of a new show on Comedy Central, "Reality Bites," author of the new book "My Custom Van," thank you very much for joining us.

BLACK: Thank you, Rachel.

MADDOW: That's Countdown for this the 1,902nd day since the declaration of mission accomplished. I'm Rachel Maddow in for Keith. You can catch me every week night at 6:00 p.m. Eastern on Air America Radio. Thanks for watching.

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