This is a tough question to field, since the word “bold” could very easily be interpreted as either “visionary” or “stupid” depending on the context. With that in mind, I’ll take a shot at this one.
For Obama, my choice might fall into both the visionary and stupid categories, but I would say Bill Richardson. He’s hugely popular in his home state of New Mexico, but this doesn’t really bring much to the table as Obama looks to carry New Mexico handily. Also, there is a risk involved in putting two minority candidates on the same ticket, so it might not be the smartest idea. But it would certainly reinforce the change message, while likely further shoring up Obama’s numbers with the increasingly powerful Hispanic vote. Also, Obama has been seen as waffling a bit on Iraq by his more hard core left wing supporters, and given Richardson’s iron clad stance on ending the war, it might help shore up those numbers. Will it happen? Unlikely in the extreme. But it would certainly be bold, no matter how you define that.
As for McCain, he seems to be giving a close look at a number of the more “boring” choices of “yet another ROWG” candidates. (Rich Old White Guys.) If he were to make a truly bold move and a serious effort at stealing the Hillary dead-enders, he may want to consider a female Veep pick. I think Carly Fiorina is out of the running having never held an office as high as dog catcher. McCain wants to make sure he captures the middle. (The hard core conservatives don’t care much for him, but they like Obama far less, so they’ll swallow their angst and vote McCain.) With all this in mind, McCain could go for a serious dark horse from the moderate stable and pick former New Jersey Governor and EPA secretary Christie Todd Whitman. Again, I don’t see it happening, but it would certainly be a bold choice.