Isn't everybody in media and business making "position statements" and being angry at you, the best way to show that you are "against the establishment"?
That is kind of a false statement, though. If he were to say that Freedom of the Press is no longer protected, the press would be very angry with you -- but I don't think it would improve your image of being against the establishment.
"The best" way to show you are against the establishment is to either a) prove the media's criticisms wrong, or b) have several actions that would stand against whatever "the establishment" is in our example.
What Trump has done is very seldom given examples of what is wrong, he has just unilaterally declared that the MSM is crooked. He has not eroded trust in an article or statement, or in most cases proving the left-leaning or progressive media wrong, he has made declarations that reach far further than his original aim. This is very in line with his character, which has been largely reactionary and often quick to pass judgments without truly "aiming" them first.
The parallels, for example, between his declarations of the media being wrong having much broader effects than intended, and his immigration bill which ultimately affected masses of people it shouldn't have, are difficult to ignore. Both were made in haste, both were aimed at a specific goal, and both had broad implications that were not originally intended.
