Disqualifiers?
One blogger focuses on Webb's downside:
Webb has said that "-women can't fight' because they are biologically unsuited for combat; he called the Naval Academy "-a horny woman's dream'; he derided the Navy's attempt to clean up its act after the infamous 1991 Tailhook sexual harassment scandal. Jim Webb for Secretary of Defense, maybe, but not for vice president.
Yeah, the minute Webb was nominated, somebody would probably trot out those red herrings. But Obama's already got the women's vote, and it's hard to fathom those women switching to a pro-life dinosaur because of remarks made years ago (that have since been recanted). What Webb brings to the party are those, umm.... "rural" voters who Hillary so famously courted ("hard working white Americans...") who could potentially put Obama ahead in states that McCain might otherwise expect to win.

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