Democrats cannot defeat today’s GOP in a bidding war over who is more militaristic and irresponsible in foreign policy, just as the GOP can never outbid the Democrats when it comes to making lavish, irresponsible promises about domestic spending. To fight the election on this ground is a losing proposition for Democrats, and this is why efforts to out-veteran the veteran opponent, which is part of the rationale for selecting Webb, will simply draw attention to the “weaknesses” that have been attributed to Obama. It is an attempt to beat the opposition at its own game with a candidate who is uniquely ill-suited to playing that kind of game. Hence he has tried to frame the election in entirely different terms, because once the election is defined along tradiitional lines he probably knows that he will lose.
Suppose he chooses Webb. What then? Each time someone explains why he chose Webb, the answer will come back that he had to choose someone who had served in the military (because he hadn’t) and whom Middle Americans could accept (because they couldn’t accept him), and so each time Webb is mentioned voters will be reminded of the critique of Obama. He has negatively defined himself in ways that are particularly advantageous to his opponent. Instead of destroying or cancelling out the critique, it would strengthen it, and simultaneously play the game of the “old politics” that Obama professes that he wants to escape. Is there an electoral reality that confirms that Obama has political weaknesses with certain constituencies? Of course. The trick, then, is not to dwell on those weaknesses and not obsess over winning over voters who cannot be won over. The larger point would be that if Obama is so unelectable that he cannot put together a winning coalition without accomplishing the impossible and winning over these die-hard anti-Obama Democrats of Appalachia and so forth, it won’t matter whether he chooses Webb or Tony Hawk. Meanwhile, choosing Webb sends the signal that he is going to chase a will o’ the wisp and lacks confidence in his ability to win without that sort of overt symbolic pandering.
There's definitely something to this argument: I think that by picking Al Gore in 1992, for instance, rather than some Dem graybeard with stronger foreign-policy credentials, Bill Clinton sent an effective signal that he wasn't going to play by the GOP's rules, and that he was going to double down instead of the theme of change, both political and generational, that animated his campaign. But the beauty of the Webb pick is that it has the potential to offer the best of both worlds. Yes, it addresses some of Obama's weaknesses (national security, the white working class) and maybe helps him in the potential swing state of Virginia. But it also doubles down on one of his biggest strengths - specifically, the notion that he's the standard-bearer for a post-partisan Democratic Party. After all, what separates Webb from, say, a John Kerry or a John Edwards - both of whom appealed to Democrats because they seemed to (but didn't really) shore up the party's weaknesses on national security and with the white and Southern working class - is that he really is a different kind of Democrat. He isn't a conventional left-liberal who happens to have a military record and/or a Southern accent; he's a more sui generis figure, a cultural (though not social) conservative with heterodox views on a variety of issues.
This is why, were I Obama, I would look at the left-liberal case against Webb - on the grounds that he's too anti-feminist, too pro-military, too skeptical about affirmative action and immigration, too hostile to Hollywood and academia - as an advertisement for the pick. An Obama-Webb ticket wouldn't send just a message that people who share the same ethno-cultural identity as Jim Webb can have a home in the Democratic Party, the way Kerry and Edwards were supposed to show that veterans and Southerners could too be Democrats; it would send a message that people with Webb's views can have a home in the party. It would lend substance to Obama's thus-far insubstantial claim to be something other than a party-line liberal, and in the process it would have the potential to achieve at the national level what the Congressional Dems have successfully done at the local level - namely, expand the definition of what it means to be a Democrat. That's the promise, as-yet-unfulfilled, of the Obama campaign. And that's how you build a lasting majority.
Photo by Flickr user Kalexnova used under a Creative Commons license.