Because Reagan understood the electorate better than any of his peers. Clinton partially did. No one has since. Not either Bush, and not Kerry.
The key to winning is not to sell an ideology or to convince people. It is to understand where the electorate is at any given moment and to respond to that. Sometimes that means explaining where the electorate is wrong and convincing them. But the key is to address the concerns of the people.
"The most successful politician is he who says what everybody is thinking in the loudest voice" TR
