You are right , except:
‘circumstances always break for him, from the passage of Obamacare to Roberts’ betrayal of the Constitution’ -
circumstances always break for him only because he plays dirty and abuses his power to manipulate, control, threaten the players to go his way...
I think it's a case of both. The 'tell' for me is that he wins by a hair, time after time, by unpredictable breaks, like Roberts' sell-out and despite Scott Brown's senate seat win.