As Oliphant says:
It is widely speculated that Obama will need to choose a vice presidential nominee versed in national security matters, perhaps with a strong military background, to attempt to blunt the edge his opponent, John McCain, carries in those arenas. Webb seems made-to-order...A decorated war hero, a "Reagan Democrat" who has been an outspoken critic of the Iraq War (and by extension, President Bush), and the man who beat the hapless George "Macaca" Allen in 2006, Sen. Webb would bring a much needed balance to the Democratic ticket; and would more than assure that Viriginia, where Obama is already holding his own against McCain, is in the Democratic column for the first time since 1964.