His father was more libertarian than him. The trend is now going the other way. You can bet that if he's elected he's going to become even LESS libertarian once in office (gotta get that second term). Once the message and rhetoric becomes watered down, the policies are doomed. And then the unlibertarian policies become the new definition of libertarianism in the eyes of everyone else (see Reagan). Gradualism in theory is perpetuity in practice. I can't think of one politician whose actions were more libertarian than his rhetoric.
It has happened in plenty of countries, but you need the people to move. You can't sneak libertarian policies through the legislative process in the middle of the night.
The people can be lead there, or they can do the leading, but they have to show up with you.
This is why Rand will need us more than ever.