Now this may sound shallow, but I assure you I am not a shallow man and this is based completely on objective analysis: Hillary won't win because (a) she's a woman and (b) shes dispised by other older women because her husband didn't drink from his own well. Lieberman doesn't have a chance because (a) he's Jewish and (b) he even looks Jewish (stereotypical elfish miserly type). McCain won't win because he's openly talked about his PTSD - he's "weak". Obama actually has a chance for a few different reasons: (a) he's handsome, (b) he works the media like a pimp, (c) he's relatively unknown so people are curious - striking the imagination of people, and (d) he's younger and not crotchety like all the others. - That last point is a positive and a negative, though, because while there is another generation who are just now becoming socilly responsible enough to vote and are looking for commonality in a world of crooks, the elderly are the biggest voters and might have a problem with his "checkered" past and the fact that he isn't 100% for cutting taxes. In either case, Hillary is a fool to run against him, or any other Democrat - they don't have that much of a lead in national favor to compete amongst themselves.
The pitiful thing about all the above is that absolutely none of it matters as far as ability to lead and run the country goes. but hey, that's as deep as mass politics gets. It's right up there with the Superbowl and the Summer Olympics, except its in 3rd place.