The more I think about it, the more it just makes sense to me. Jim Webb has the foreign affairs/military experience that Senator Obama so sorely lacks (and badly needs against McCain). Webb's a moderate Democrat who supports gun-owners' rights, yet he'd still appeal to the lunatic wing since he's had his own bout of Bush Derangement Syndrome. And I suspect that he'd even appeal to most white, racist Hillary supporters because, well...he's white (not that Barack has much of a choice there since Barack is the only black guy in the Senate, but you get the drift). Reihan Salam of The Atlantic agrees:
As Barack Obama considers his vice presidential options, he would be very wise to take Jim Webb seriously. By now the idea that Webb could help Obama connect with the Scots-Irish voters of Greater Appalachia is familiar to most of those who follow the presidential horse race. And Webb's military experience, together with his years in Ronald Reagan's Pentagon, give him national security expertise that few leading Democrats can match. Yet there is another reason the Virginia Senator would make an excellent vice presidential nominee. As he's demonstrated this week, Webb can be a masterful legislative tactician.
Though no one will ever mistake Webb for a gladhanding backslapper, he has mobilized an extraordinary coalition of Democrats and Republicans behind a dramatic expansion of veterans' educational benefits. After passing by an overwhelming margin in the House, Webb's Post-9/11 Veterans Educational Assistance Act won 75 votes in the Senate. Because the measure was attached to the Democrats' Iraq War spending bill, which included a number of other spending proposals favored by Democrats and opposed by the Bush White House, there is good reason to believe that the entire package will be vetoed. But there is also good reason to believe that something like Webb's proposal will eventually be made law, thanks in no small part to the measure's overwhelming popularity among veterans and military families.