I've had the chance to watch a number of Trump speeches and interviews. He's been campaigning against his Republican opponents in the primaries, the establishment (which includes the GOPe) and already Clinton and Obama.
I see Clinton as a very flawed candidate. While conceding the media will campaign against Trump in their attempt to defend her, I just don't think their level of success will be enough, not against this candidate.
The best real time example I can think of is Trump's temporary ban on Muslims coming to the US. Clinton has been using this for a while, ridiculing Trump in her stump speeches. The media started ridiculing Trump over this immediately. Yet, Trump has stuck to his guns, circumventing the media, using it in most of his speeches. You do realize that polling indicates the public now agrees with Trump.
I disagree with your analysis. Trump's statement was "Ban Muslims from entering the US until we figure out what the hell is going on." That's hardly a coherent policy statement. It was the press, who from the start, used the words "temporary ban", words that Trump didn't use. Over time Trump has moderated his position to be consistent with "prohibit entry of people from terrorist regions until they are properly vetted". This has been the position of most of the Republican candidates since long before Trump's outburst.