I could but wont go into a lenghty explanation of the underlying psychological for such a physiological phenomenon.
He was trained from youth to treat everything as a mere game..
It's one thing to say he is extremely competitive and a past master at gamesmanship. It's another thing to say he treats everything as a "mere" game. That's demonstrably false. If that were the case — no sense of proportion or priority — he would still be managing apartment complexes in Queens. Instead, he has developed massive buildings all over the nation and in several other nations, as well as 27 luxury resort properties that he has developed — privately, no shareholders — and his side businesses of merchandise and media properties. That's not just a game.
Close but not quite. He was trained from youth to believe everything is a negotiation/deal.
You don't build buildings and become a billionaire if you think everything is a game.
His military school added another dimension--teaching him life is a battleground.