our legal system is not a sunday school. you are not punished for doing wrong. rather, you are required to compensate those whom you do financial harm to. there's no moral question, here. it's dollars and cents.
the actual problem here is the character limit that twitter pushes down, which is forcing trump to truncate his arguments in such a way that they can be misinterpreted essentially at will. one of the best things he can do for himself at this point is to move to a platform that doesn't have character limits. this should be a lesson for future candidates, as well. it's practically an algorithm to be taken out of context.
had trump said "It is not ‘freedom of the press’ when newspapers and others are allowed to say and write whatever they want with the intent to harm me, in contempt of the truth !"
...then he would be right. which is of course what he means to say. nobody thinks the media is neutral.
the bottom line is that i've seen quite a few stories that he would be right to launch legal action against, and would probably win compensation regarding if he did. this is not in the realm of discourse, and does not provide a reason to vote for him. but, he is raising a very valid concern about the level of discourse and the role that an incompetent media can play in the election cycle.
http://www.theatlantic.com/politics/archive/2016/08/does-the-first-amendment-protect-deliberate-lies/496004/
fwiw, this is the exact, precise reason that i have refused to use twitter from day one. this is the only twitter profile i've ever created.
https://twitter.com/dgkfgjklgjkgjka