a best-selling author; a screenwriter (Rules of Engagement, and another in the works); an Emmy-winning documentary producer; the author of a large number of articles and book reviews; an Annapolis graduate; a boxer (he lost a legendary and controversial championship match at Annapolis against Oliver North); an autodidact who grew up a military man's son and indifferent student but on his own became a passionate reader of history; a first lieutenant and Marine rifle platoon commander with Delta Company in Vietnam, where he won the Navy Cross for heroism (the second-highest award in the Navy and the Marines), the Silver Star, two Bronze Stars, and two Purple Hearts; a graduate of Georgetown Law School who then worked on the staff of the House Veterans Affairs Committee; a teacher of English literature at the Naval Academy; and an assistant secretary of defense and then secretary of the Navy during the Reagan administration.
Not to mention his achievement in wresting his Senate seat from a near-certain Republican incumbent. A Virginian who has written a book about his Scots-Irish heritage and who bristles at the word 'redneck', Webb could help Obama to win over those white, working-class voters who seemingly flocked to Clinton in the primaries.
Webb may turn out to be too unpredictable a proposition for the Obama campaign to handle. But his occasional eccentricity is what many find appealing about him, as in this anecdote recounted by Drew:
The sense in Washington that he was—well—different was enhanced by his famous first encounter with President Bush after the election, when at a November White House reception for newly elected members of Congress, Webb refused to shake Bush's hand. Bush then sought Webb out and asked him about his son, who was serving in Iraq, "How's your boy?" and Webb replied, "I'd like to get them out of Iraq, Mr. President." "That isn't what I asked," Bush snapped. "How's your boy?" Webb responded, "That's between me and my son, Mr. President."