As I'm trying to spark some more debate here, I thought I'd give some more substantial thoughts on my short list of favorite VP choices and try to get your responses. I probably won't do all of them at once, so as to promote some real debate on each candidate.
First, I need to add some criteria for selecting a VP. Clearly, the criteria I used before are clearly short-term political considerations. That's fine since we do want to win this election and shouldn't leave a potentially winning card on the table. Yet, getting Barack Obama is certainly not the only job a VP will be tasked with (nor that for which a running mate will be most important, unless I'm forgetting about how John Edwards helped Kerry sweep the Carolinas). Obviously, becoming Vice President drastically increases one's odds of later becoming President (at least since 1808-1824, in which every election was one by either the sitting Secretary of State, or an incumbent president who had first been elected as the sitting Secretary of State). So, we should ask ourselves a couple of questions.
The first is obvious, would this person make a good President? That is, of course, the million dollar question with every potential President. It's virtually impossible to know with any appreciable level of certainty. But there are clues in each potential candidate's background and record. The other difficulty is deciding how good of a President we are talking about here. To be fair to these potential candidates, but without setting the bar too low, I'd compare my expectations for each of them to the reality of the Clinton administration. An important note here is that this question is totally devoid of politics. Virtually any Democrat who isn't totally self-obsessed would compared favorably to the Clintons in their potential impact on our politics. Instead I'm just asking, would the country be better off with this person as President, and would that improvement be substantial enough to warrant calling them a better than average President.
The second question is wholly political. Is this the kind of person we would want as the face of the Democratic party in 4 or 8 years or should something happen to Obama? To me, this is a bigger question than that of whether someone could function well as a President. The legacies of FDR, Reagan, and Clinton are largely related to how they reshaped the political landscape and they should be. An administration can set policy for a few years. An electoral coalition does it for a generation.
1) Good President? Maybe. But I'm not convinced that he would be. For one thing, his Senate record paints him as a bit uninterested in anything non-military. And his populist rants seem to be more of a obsession with social class struggle than any drive to improve the lives of the poor. I'm not saying he isn't with the party on a lot of those things (and he isn't always), but I have a hard time seeing a President Webb push hard enough to get universal health care, for example. He's also a notorious hot head, which doesn't bode well for his abilities to work with more progressive Congressional leaders.
2) The new face of the party? God no. On his strongest suit, his foreign policy credentials, I've yet to see him offer anything that looks like a new Democratic foreign policy. On domestic issues he lacks vision. Sure I have a soft-spot for his inequality-bashing fetish, but it doesn't get us anywhere. Indeed, on domestic issues, Webb reminds me of Bill Clinton cerca early 1992.
3) Other stuff. Does he help in VA? His decent approval rating among Republicans suggests he might. But the 2006 election results show that he won because of NoVA, where Obama is already golden. And for a guy who's hailed as the Reagan Democrats' wet dream, Allen's 2-1 spanking of him among white protestants, and even more striking 4-1 thrashing among white evangelicals, looks rather weak. Webb the man might be more like Appalachia Democrats than anybody else we can get (except Strickland, damn him for not wanting it), but his electoral coalition looks pretty much like Obama's.
My verdict: There's got to be somebody better out there.