Trump and his team are smart in that they understand the concept of means to an end very well. He was a Democrat not too long ago, but then when he decided to enter the political arena, he saw the easiest/most untapped demographic to go after. All of the Spurtacular and MellenialMessiah types. White people on edge about their perceived loss of clout to the "liberal cucks" and the "snowflakes."
Combine that with Hillary's historical unlikability and you had a recipe for success. The problem is that this time the Democrats picked a more likeable, less polarizing candidate. Meanwhile some of Trump's supporters are having a crisis of conscience in the face is his undeniable evil and jumping ship. It's been fun to watch.