1. He Takes Another Big Risk—and Flops
"Obviously, he took the biggest risk of his presidency with the Osama operation. He took a huge risk and it completely paid off. He was right. But watch out now for the over-confidence that comes with success. Don't try this again with Mullah Omar, the head of the Taliban. It's a common thing for presidents to do, particularly on the basis of a risky success. They think, "Well, that went great, let's try something like that again." The next risky mission could end up being a disaster that will be very difficult for his presidency to recover from. I sometimes think Bush got into Iraq because the original Afghanistan mission seemed to go so easily. It was won in two weeks, with very few troops involved. I think that led to a notion that he could have equally quick success in Iraq. Instead he wound up with something that defined the rest of his presidency. See, presidents often have two modes. One is: 'Hunker down, we gotta be careful.' And the other is: 'Things are great, don't worry about it.' It's when they get in that second mode that mistakes happen."
2. He Thumps His Chest Too Much About Bin Laden
"He's already mentioning it in speeches, and he has to stop. Never ever put the Osama mission in political terms. People are going to want him to put this in ads. Don't. Everybody knows he did a great job! This was a different kind of thing for sure, but after impeachment was over, Joe Lockhart had this great phrase: 'We're in a gloat-free zone.' The president's gotta stay in a gloat-free zone."
3. He Makes a Bush 41 Blunder on the Economy
"Obama no longer has national security as a deficit. He's answered the 3 a.m. call. But health care is still a vulnerability. The deficit is a huge vulnerability. Unemployment is a huge vulnerability. The whole economy is a huge vulnerability. If he doesn't get re-elected, it will be because someone really taps into one or more of those four vulnerabilities. And there are still questions about how in touch he is with people out in the heartland. After the Gulf War, I don't think Bush 41 got cocky. He just wasn't mindful of the economy, and then he had the moment with the supermarket scanner. You always watch out for that moment that symbolizes what might be a negative in the back of everyone's brain. So for Obama, this is not the time for another Broadway date. And the period between now and the election is a Martha's Vineyard–free zone."
4. He Ignores a Big Chunk of His Constituency
"Obama has more support from those making over $200,000 than any Democrat in history. So when he makes the fight about the Bush tax cuts for upper income voters, well, he has nearly as many upper income voters as the Republicans! Which is one of the reasons why, when he didn't agree to the tax-cut deal, the congressional elections turned out so badly. Then, after the election, when he agreed to the deal, his numbers soared. Now he is saying, once again, that one of his priorities is to raise taxes on "that group." "That group" is his voters! Believe it or not, those are his people. It used to be that upper income voters were 3-to-1 or 4-to-1 for the Republicans. Obama does best with people who make the least and people who make the most. So if he returns to the class warfare rhetoric of the budget fight, he is going to be recreating the midterms. And that kind of election is a loser for him."
5. He Acts Like a Presidential Candidate Instead of a President
"Which he's doing already, and that's a mistake. In the beginning of his presidency, he got overexposed. The tendency was—and still is—to throw him out there, for an intensive series of interviews. And I think he got overexposed. He does not want to be overexposed now. He has to be careful. One of the big pitfalls that's already happening here is that he's now making himself a presidential candidate again instead of a president."
6. Shit Happens
"Five-dollar-a-gallon gas. Continually plunging real estate prices. More bank defaults. If any of these things happen, it'd be seen as Obama not handling it. He owns all of this now."
7. A Sex Scandal
"I certainly doubt it with this president. But hey, even Al Gore wound up in one."
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