It seems to me like this conversation needs to start from the perspective of where Obama needs help the most, and it seems that he's most lacking when it comes to security and military matters, as well as executive experience. He's also weak experience-wise on foreign policy, but none of the frontrunning GOPs have much more experience at it than does he, and he has good, novel ideas there. On the other hand, Rudy, Romney and Huckabee all have executive experience, and while Obama has run something larger than a coffee shop, saying that you were the President of the Harvard Law Review has not historically tended to enhance a candidate's outsider status, or endear them to middle America.
There was a time when Wes Clark would have seemed an ideal VP candidate--before he started whoring himself out to Hillary, that is. Maybe Obama will choose to be forgiving there, but Clark doesn't have much going for him other than a resume. Ditto Bill Richardson, whose melange of social moderation, fiscal conservatism, and strong opposition to the Iraq War has appealed to--approximately seven percent of likely Iowa caucusgoers, and nobody anywhere else. Bad mix for this campaign year, and Richardson and Clark are poor campaigners. Obama could try to tackle the executive experience angle with either Sen. Evan Bayh or Gov. Brian Schweitzer--the latter of whom might be an inspired choice--but Sen. Jim Webb might just be the best choice available.
Webb is a former combat marine who later served in the Reagan Defense Department and as Secretary of the Navy. He knows the armed forces, he was right on Iraq from the beginning, and unlike John Kerry, he exudes toughness. He's a great campaigner. He's from the all-important state of Virginia. And he's a former Republican, which is no small asset, in my opinion. It would enrage conservatives to see a turncoat on the other side's ticket, and it will allow him to articulate a good case for moderates to abandon the GOP for the Democracy, since he would just be able to relate the factors that led him to take that action. He's a solid progressive with some forgiveable exceptions (like guns) and it seems like he'd be able to appeal to Westerners and Southerners reasonably effectively. He's largely lacking in scandal fodder as well, save some trumped-up Macaca accusations about being anti-woman. Let's not forget that he managed to dethrone George Allen as well, which deserves some reward. Had Allen survived his re-election campaign, it would have been a completely different campaign season, for sure.
