Lawrence Lessig seems to make the most sense given that Lessig himself is already considering an Independent campaign of his own, was running more to promote his Citizen Equality Act rather than to become President, and could help Webb appeal to more liberal voters. However that would be likely be dependent on Webb 'adopting' the Citizen Equality Act as part of his platform which, given some of its provisions, I find some difficulty seeing. If they can compromise on a water-down version its a possibility.
I would not consider Chafee given he doesn't bring anything to the table, and his one debate performance ended any chance he had of making a positive impression on the national stage, akin to Perry's "Oops" moment; he could try of course, but first impressions are very difficult to dispel.
Huntsman seems a good choice, provided he would accept. He would solidify the ticket as an alternative for centrist voters, but the problem therein lies with the fact that both the Republicans and Democrats are going to be actively courting those voters as well. At least with Lessig for example Webb might have a small base among disaffected liberals. 'Might'.
Agreed on Lessig, but I don't see Huntsman running on the bottom of the ticket. He has an ego that would demand the top spot or nothing.
