And yet ...
Think about his behavior. Most recently, responding to an annoyingly effective rhetorical salvo against him, he derided and vilified the Khans, parents of a U.S. military officer killed in Iraq. As anyone but he could have predicted, his heartless remarks blew up in his face.
Why did a man who claims to be smarter than everybody else in the room behave so stupidly, and why has he committed such unforced errors so often during his campaign?
One answer is that he has found that his comments go over like gangbusters with his supporters. But another is that, contrary to his own pronouncements, he's not that smart. He actually doesn't know any better.
Trump has gone his entire adult life without knowing how to be an adult. He has never had to be one: first his father's money, then his own, has served to smooth his path. Physically he's seventy but emotionally, he's somewhere around four. Really.
What about his family, especially his children? (Best to tread lightly regarding his wives.) Well, I didn't watch the convention speeches so I don't know what his relationship with his kids is like. I assume it's at least okay or they wouldn't be campaigning for him. I conclude he's at least somewhat capable of warm feelings for others.
Yet we don't hear longtime friends and acquaintances gushing about what a great guy he is. Trump is the only one who gushes about Trump. By way of compensation, perhaps, he does so unceasingly.
In my experience, the more you praise yourself, the more desperate you are for others' esteem (understandably, if you never get it) and the worse you take any criticism. Throughout his adult life, Trump has sought to aggrandize himself. Throughout his adult life, he has overreacted to criticism or mockery. (He's still very publicly pissed about that "short-fingered vulgarian" epithet from more than a quarter-century ago, for heaven's sake.) He loves the spotlight, but only on his terms.
He's the presidential nominee of one of the two major political parties, in spite of that party's leaders' best efforts to deny him that prize. He's also the leader of a mass movement. Even his fiercest critics, and I'm one, have to admit that he has come farther than anyone thought he would. Yet even if he wins in November — even if he captures the country's ultimate political prize — it won't be enough. Becoming president won't garner him the respect and admiration he craves. Becoming president won't fill the void in his heart.
Whatever happens in November, Trump will try to spin it to his best advantage. That alone would make pitying him a tall order. Remembering that he has cheerfully flouted all sorts of rhetorical taboos, inciting (or rather, reinforcing and legitimizing) bigotry and violence among his supporters, makes it almost impossible to imagine feeling sorry for him. (I'm trying not to envision the damage he could do as president, lest I undo my whole argument.)
And yet ... his lifelong, very public quest for respect from anyone and everyone attests to how badly damaged he is. If his reckless, divisive campaign for the presidency (or, heaven forbid, his capture of the office) doesn't wreck the country, you might spare him just a bit of compassion. However much money he has, he's a most pitiable person.