Right now, the only possible logical implication of the message on the hat is that he must think it's not so great. What, if anything, does he propose to do about it? Andrew Shepherd (yes, a character in an Aaron Sorkin liberal fantasy, but dude still has a point), has guys like Trump nailed:
For the record, yes, I am a card-carrying member of the ACLU, but the more important question is "Why aren't you, [Donald]?" Now this is an organization whose sole purpose is to defend the Bill of Rights, so it naturally begs the question, why would a senator, his party's most powerful spokesman and a candidate for President, choose to reject upholding the constitution? Now if you can answer that question, folks, then you're smarter than I am, because I didn't understand it until a few hours ago.
America isn't easy. America is advanced citizenship. You've gotta want it bad, 'cause it's gonna put up a fight. It's gonna say, "You want free speech? Let's see you acknowledge a man whose words make your blood boil, who's standing center stage and advocating at the top of his lungs that which you would spend a lifetime opposing at the top of yours." You want to claim this land as the land of the free? Then the symbol of your country cannot just be a flag. The symbol also has to be one of its citizens exercising his right to burn that flag in protest. Now show me that, defend that, celebrate that in your classrooms.
Then you can stand up and sing about the land of the free.
I've known [Donald Trump] for years. And I've been operating under the assumption that the reason [he] devotes so much time and energy to shouting at the rain was that he simply didn't get it. Well, I was wrong. [Trump]'s problem isn't that he doesn't get it. [Trump]'s problem is that he can't sell it!
We have serious problems to solve, and we need serious people to solve them. And whatever your particular problem is, I promise you [Trump] is not the least bit interested in solving it. He is interested in two things, and two things only: making you afraid of it, and telling you who's to blame for it. That, ladies and gentlemen, is how you win elections. You gather a group of middle age, middle class, middle income voters who remember with longing an easier time, and you talk to them about family, and American values and character, and you wave an old photo of the President's girlfriend and you scream about patriotism. You tell them she's to blame for their lot in life. And you go on television and you call her a whore.
Instead of the president's girlfriend, this time it's immigrants and Muslims. But the principle is rock-solid and unvarying.