James Oliphant writes a profile of Jim Webb that includes this not so flattering comparison:

Like Obama, Webb is his own sort of political phenomenon, a Reagan Democrat who switched sides. But unlike the first-term Illinois senator, Webb has the reputation of a maverick who heeds no counsel but his own, who in the past has frustrated Democrats and Republicans alike with his outspokenness. [empasis added]

A tough as nails military veteran with a reputation as a maverick? Hmm. Sounds familiar. Obviously, one of Obama's challenges is trying to find a running mate who can help shore up his vulnerabilities on national security without making him look small in the process. The last thing Obama wants is to create a gravitas gap on his own ticket, though given the history of the lack of influence generated by VP selections I suspect it may not matter much in the end.