Many on the lefty blogs really like Webb as Obama's VP candidate. I think choosing him would be a major disaster, for several reasons, but especially because of what he once wrote about women in the military:
[Women's] presence at institutions dedicated to the preparation of men for combat command is poisoning that preparation. By attempting to sexually sterilize the Naval Academy environment in the name of equality, this country has sterilized the whole process of combat leadership training, and our military forces are doomed to suffer the consequences. … [T]he system has been objectified and neutered to the point it can no longer develop or measure leadership. …
He also wrote this:
Military leaders are at best passive and at most often downright fearful when confronted by activists who allege that their culture is inherently oppressive toward females and that full assimilation of women depends only on a change in the mind-set of its misogynist leaders.
Webb has had many opportunities to clarify or to explain his views but he has not bothered. And this means that having him as the VP candidate would be very much like spitting in the eyes of all those women who voted for Hillary Clinton in the primaries. It would be a political gaffe of the highest order, because it would indicate that it's really true that the guy politicians are completely blind and deaf when it comes to what makes the female voters tick.