Why is Donald Trump a jerk? Sounds like you have capitalist envy.
APPRENTICE PING
If you've watched the show, or followed Trump regularly, you'll know that the key words in his life are "bigger and better" -- whether it be wives (better, not bigger), buildings, investments or whatever, the thing Trump strives for is to live up to his namesake and trump the competition, whoever they might be.
Simply put, this is why some will look at him and admire him, while others will look at him with disdain.
Self-made? Not exactly, but then again, I bet nearly all of us feel we had an "average" upbringing--though I'll be willing to wager that that "average" upbringing varies greatly among us. Trump has increased his position in life through a combination of skill, talent, guts, luck, and opportunism.