When every other word is a superlative, superlatives lose their effect
Perhaps Trump missed out on Beginning Writing class in 5th grade, where most of us learned that superlatives have the greatest impact if they are used sparingly and reserved to describe that which is truly superlative.
With Trump, everything is the greatest, the best, the biggest, the smartest, the worst, the stupidest etc. Where Giuliani was the "a noun, a verb and 9/11" candidate, Trump is the "a noun and a superlative adverb/adjective" candidate.
I won't speculate on why the media lets him get away with such blather, but anybody with an ounce of sense realizes that Trump disrespects our collective intelligence every time he unthinkingly tosses out one of his ineffective bromides. It's little more than word salad placeholding for a lazy mind that can't be bothered to do better.
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With his strange hand gestures that don't accord with anything he's saying.
And his vocabulary is probably smaller than his hands 
Yeah, like that. 
