Image: Obama
Steve Helber  /  AP
Democratic Presidential candidate Sen. Barack Obama, D-Ill. gestures as he speaks during a town hall meeting in the library of Granby High School in Norfolk, Va., Wednesday, Nov. 10, 2008.
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msnbc.com
updated 9/10/2008 12:01:05 PM ET 2008-09-10T16:01:05
ANALYSIS

No, Barack Obama was not making fun of Sarah Palin when he talked about some Republican putting “lipstick on a pig.”

He was trying to be colloquial, and John McCain’s campaign knew as much – even as it was going theatrically ballistic.

That’s not to say that Obama hasn’t made mistakes. In fact, he’s made – and is making – a lot.

For two years, Obama played the golf course of presidential politics with the ice-cold self-assuredness of a Tiger Woods. But since securing the Democratic nomination, he’s made a series of strategic errors that could jeopardize his chances in November.

After traveling with him on the trail, watching him in Denver and talking to Democratic operatives and insiders, here’s my list of his errant shots:

Declining to take federal financing for the general election
This mistake is two-pronged. Obama stands accused of flip-flopping on the matter, saying in 2007 that he’d accept those funds and the cash limits that come along with it. In relying solely on private money, Obama appears to have ceded some higher ground to McCain, who, with his public funding, appears slightly more immune to interest groups. On a more practical level, Obama will have to leave the campaign trail more often to headline fundraising events. He’ll likely spend more time than he should in New York, San Francisco and Los Angeles and less than he needs in Cleveland, Pittsburgh and Detroit.

Declining McCain’s offer to hold ten town hall debates
When Obama was leading the race in leaps and bounds, he blew off this GOP proposal. Too bad. Had Obama locked in that deal, he would now be able to confront McCain face-to-face about some of the Republicans’ more aggressive – if not to say cynically manipulative – recent television advertising claims. An Obama-McCain series would also have drawn attention away from Gov. Palin, the autumn cover girl. Video: Obama blasted for ‘pig’ comment

Failing to go all the way with the Clintons
Yes, I know, Bill and Hillary got prime speaking roles in Denver. And yes, I know, the Clintons are difficult to deal with and probably hope Obama fails. Still, it’s Obama’s task to latch on to them, even against their will. But he was too proud. Although he’s going to see the former president this week, Obama should have broken bread with Bill months ago. Obama needs the Clintons to defend and work for him. They are not eager to do so, but it was still Obama’s task to trap them into displays of political enthusiasm. It’s just my guess, but I think Mr. Clinton would have been open to the wooing – if for no other reason than to recapture his reputation as an avatar of the civil rights cause. Obama also neglected to court Clinton fundraisers and supporters in places like Los Angeles. All they want from Obama is a phone call. They would swoon.

The 22-state strategy
For months, the Obama campaign invested advertising time and organizing money in an impressive array of red states that haven’t been on the Democrats’ radar in recent elections. This made for great press clippings. But, for the most part, it was a waste of assets. Except for perhaps Virginia, most out-of-the-way states do not seem likely to end up in Obama’s fold. He’d be more successful focusing on traditional battlegrounds.

Failing to state a sweeping, but concrete, policy idea
It is not enough to be for change – everybody is, or is trying to be. To make it stick, Obama needed, and needs, to put forth an easy-to-grasp grand proposal, one that would encapsulate what his central message. That tagline? That he is dedicated, body and soul, to advancing the economic interests of hard-working, average Americans. He has the makings of such a proposal – his tax cuts for low and middle-income families. But he has yet to package that, or anything else, in an easy-to-grasp, hard-number plan for voters. Instead, he’s got more of a laundry list than an actual rallying cry.

Remaining trapped in professor-observer speak
When you listen to Obama, it sometimes feels like you’re hearing a smart but distant analysis of the political scene. He sounds like a writer or teacher, but not the leader of a political crusade. Obama has been far too “meta” – a detached commentator on his own situation and his own country. Voters want an action plan, not an exegesis.

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Failing to attack McCain early
Obama was wary of attacking a man who had suffered so much during the Vietnam War – an understandable emotion. But that wariness, combined with Obama’s natural inclination to be seen as the nice guy (one who lets others do the knifing) lead to an unfortunate result. It gave two free months for McCain to build up a head of steam as a war hero, as opposed to what Obama needed to paint him as publically: a man beholden to corporate interests and a likely clone of George W. Bush. 

Does all of this mean that Obama is somehow doomed? Of course not. He is a quick study and a fast learner, and the team of McCain and Palin is capable of making their own set of mistakes.

But if I were an Obama partisan I would be worried that his mistakes have a common thread - pride.

Obama seems to want to do things on his own, and on his own terms. It’s understandable. Obama has his own crowd – from Chicago, from Harvard, and from a new cadre of wealthy, Ivy-educated movers and shakers.

“He’s an arrogant S.O.B.,” one of the latter told me today. “He wants to do it his way, and his way alone.” But politics doesn’t work that way. And has Obama should know, or is about to find out, that everyone needs a little help.

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