And yet here we are.  
Perhaps it's reach not money.  
Trump also received m/billions worth of free advertizing for every foolish thing that he said or did and the violence at his rallies. Plenty of people found it foolish but many more found it "good common sense" free from "political correctness".

Maybe it's another game changer like Kennedy besting Nixon in a new medium - television.  By that I mean social media being a game changer, as well as or instead of the foreign Russian connection.