He’s not an insurgent; he’s the standardbearer for a faction of the country’s political elite. I believe that, on balance, this particular faction happens to comprise many of the the smartest and most conscientious individuals from within that elite. So I’m supporting Obama and his train, people like Samantha Power and Robert Malley and Lawrence Lessig, just as a peasant might cheer for an aristocratic faction made up of reasonably decent individuals against other factions made up of out-and-out thugs. Not because the peasant doesn’t know the game is rigged, or doesn’t have the wit to imagine a better world. But because incremental change matters, and because the right incremental changes can lead, like water flowing downhill, to bigger and more profound ones.
Also, while I am a radical in analysis, I am an incrementalist in practice, because life is short.
(Though I disagree with the reason "because life is short". In genetic algorithms it's important for your fitness function to be reasonably discriminating even in the vast area of the space that's far from optimum. Recent elections brought home to me how much that principle applies to politics.)
ETA: Peter Norvig posted another, quite different endorsement worth reading.