Alex Massie makes it here:
An Obama-Webb ticket closes a circle. Much has been said, some of it overblown but enough of it with a kernel of truth to justify the hype and optimism, about how electing Barack Obama would be an act of historic significance, in some way atoning for the original sin of slavery and reconciling the darker elements of American history. As I say, a good deal of this is trite: a President Obama is not going to magically close the divide between white and black America, but there's enough to this to make the hope it inspires understandable.
Putting Jim Webb on the ticket completes this process. like John McCain, Webb can plausibly claim that his ancestors have fought in almost every American war. Unlike McCain, Webb is a creature of the white working class. He believes his people - the Scots-Irish of Appalachia - remain misunderstood, under-appreciated and disparaged by America's elites. If Obama is a "wine track" candidate, Jim Webb is definitely "beer track". He's quite happy - proud in fact - of his "redneck" stock. ...
Perhaps it's the romantic in me that finds Jim Webb the most appropriate subordinate for Barack Obama - politically and historically. If circles are to be closed they might as well be closed properly and completely. And what better symbol could there be for a campaign largely predicated upon symbolism?
Is there such a thing as too much symbolism for a single campaign? If so, this probably approaches it. But I agree that an Obama-Webb ticket would be something to behold.