Larison wrote:

Choosing Webb is another way of saying, “Yes, Democrats must have a military veteran with culturally conservative attitudes on their ticket in order to demonstrate their fidelity to the United States, which is otherwise suspect.” Selecting Webb and selecting him specifically because of what he represents, rather than what he can do, accepts the judgement that Obama’s patriotism and American-ness need bolstering. This has the risk of being every bit as self-defeating and embarrassing as John Kerry’s “reporting for duty” moment at the national convention.

Antle asks:

By the way, pre-Cheney didn’t major parties always pick their running mates on the basis of what they represented or could at least deliver electorally rather than what they could do?

The answer is: Yes!

And Bush selected Cheney because he represented that chunk of the American population that were not recovering alcoholics, who read books from time to time, who were curious about the world, and who were not manipulated and controlled by strong personalities… The message Bush was sending: “Well, I know that I’m not qualified to be a president. But I’m selecting a VP who is.” And it worked.

In any case, on a theoretical level it makes sense for Obama to choose Webb (for all the reasons that have been mentioned). But it’s also risky (personality, “baggage,” etc.)