I think Webb is going to be the choice. The main barrier to his pick will be getting Kaine's okay ... because Obama owes Kaine big time for the early endorsement. But I think Gov. Kaine will be fine with it.
If Obama/Webb wins, the Senate seat opens up. Now, it's a tricky situation ... Gov. Kaine will have to appoint someone, but then there will be a special election in 2010 ... and then a regular senate election in 2012. Kaine's gubernatorial term expires Jan 2010, so my guess is that he would rather finish out his term than jump to the Senate in 2009 ... Virginians don't like their governors messing around with their one term in office.
But if Kaine wants to run in 2010, he'll need to appoint someone who will promise to step aside. The perfect person to serve as a two-year fill in is Doug Wilder, capping his career with a two-year stint as a U.S. Senator.
So there's my theory ... Webb to VP, Wilder as interim Senator, Kaine to the Senate in 2010.
This is the most important election of our lifetime because the very survival of the principle of three equal branches of government with checks and balances hangs in the balance. The enormous powers the Bush/Cheney administration has usurped for the Executive must be decisively repudiated by defeating the Bush clone, McCain.
Jim Webb was talking about this unconstitutional accumulation of power in his campaign here in Virginia, so he understands and can articulate the issue of abuse of executive power.
Webb's rational and pragmatic approach to foreign relations, including when and how to use military force is the perfect contrast to the McCain/Bush irrational and illegal actions and policies.
The Senator's military career in Vietnam and subsequent service at the Pentagon gives him the credentials to formulate, advise, understand, and carryout national security policy.
Jim Webb will stand his ground and hit back when the Republicans try to swiftboat. E.g., he is not afraid to give the President a piece of his mind in person at the White House about the Iraq war, when Bush asked about his son then serving in Iraq.
Webb resigned on principle, as Sec. of the Navy, I think, when he did not agree with a Reagan decision. This indicates to me that he will not be a career politician because he wants to get things done, and his personality is not suited for an extended stay in the slow moving Senate. Therefore, now is the perfect time to tap his abilities for this crucial role in the history of American politics.
The time is now, because to Senator Webb's credit, it is likely he will not stay available as an elected politician very long.
Honestly, if Webb stays in the Senate, my money's on Kaine for Secretary of Transportation after he leaves Richmond.
Great minds...
Personally, I'm a little nervous about Webb's ability to retain the seat in 2012, given his disdain for campaigning and retail party building (where was he at the JJ?). I think he is a FANTASTIC Senator, but only a perfect storm got him elected.