Kennedy was an elitist. If you doubt me, just look at his friends, his father, and his brothers. He would probably be a middle-of-the-road Republican today, but he was definitely a part of the "in" crowd.
If you really want someone who rubs the elitists the wrong way, you really wanted someone like Rand Paul or Ted Cruz.
Is Trump really "outside the reins of the power elite?" Maybe, but not so much as people think. When it comes to the issues, Trump and Hillary are really remarkably alike. Neither will cut check the growth of government, neither will promote liberty and, when it comes right down to it, neither will really respect your 2nd Amendment rights. Even if he is not an "elitist," a Trump win will be a pretty hollow victory.
No matter which one wins, keep your powder dry.
Onward and upward,
airforce