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:
Theory #2 : He is a master troll. This is an older interview with Scott Adams (Dilbert) that supports that premise :
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Trump is actually very serious....His hair shows that (irony intended).
He is a textbook example of a demagogue: https://en.wikipedia.org/wiki/Demagogue
It's like reading his campaign manual...
Trump is actually the classic example of a spoiled brat that has never been held accountable for anything. He doesn't speak plain, nor does he "tell it like it is." He actually just reacts and speaks stream of consciousness.
If I said "blue", Trump would blurt out the first thing that came to his feeble brain. He might say "we have to nuke suede shoes."
The thing is that the uneducated sector of the American populace is prone to follow and agree with Trump's narsacistic demagoguery, out of false indignation. Many uneducated workers have been disaffected by the growth in this nation, and instead of blaming people that are responsible they blame minorities, women, muslims, immigrants and refugees.
People's wages have stagnated while the rich have reaped all the profits in the last 40 years. That has fueled the anger. Ordinary people struggle to make ends meet. They see no future for their children and fear what will happen to them if anything major happens to them.
Ironically, This unrest has also fueled the Bernie political revolution. The Bernie people actually have it right. They are angry at Wall Street, at banks, at pharmaceuticals, at medical expenses, at outrageous education bills and student loan interest, at low stagnate wages, at cuts in benefits, and over taxation of the middle class and poor, at unnecessary wars.
Trump is trying to tap into this anger and misdirect it to his advantage. He fuels hate and division. He demonizes innocent people for atrocities that others have caused.
Trump is a typical adolescent that is out of control.