Full disclosure: Trump is not my first, second, third, or fourth choice.
Having said that, there are three ways the establishment crushes opponents, in no particular order. The first is by taking away their sources of revenue. The second is by tying them up in the courts. The third is by finding dirt, and either blackmailing the opponent or dishing the dirt to the media.
Why Trump angers the establishment is because for him, none of these work. First, he already has all the money he needs, so no one can fire him. Second, he will tie up in the courts any group that attempts to tie him up in the courts, and his pockets are deeper. Third, his life is already an open book, and he wears his scandals like a tailor-made suit, so he cannot be shamed into compliance.
At best, he is like a commando, beating the establishment on its own territory. At worst, he is like a suicide bomber, and when he blows up, he will take the establishment with him.
I wish Trump would expose what Obama has on Boehner, McConnell and Graham and others. I really want it out now- before elections. Take away the ability to black-mail the big wigs in the GOPE.