Theory #1 : Trump speaks like regular folks because he has never read a book of any substance. Certainly not Dostoevsky or Walt Whitman. Tony Schwarz - ghostwriter for Trump's "Art of the Deal" says that is the case:
https://www.minnpost.com/eric-black-ink/2016/07/ghostwriter-art-deal-say...
Theory #2 : He is a master troll. This is an older interview with Scott Adams (Dilbert) that supports that premise :
http://reason.com/reasontv/2015/10/06/donald-trump-is-a-master-wizard
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