Trump gets a lot of chances because as a person, he's a walking indictment of the cultural beliefs of most Americans. People genuinely believe that successful people have what they have because of creativity, foresight, or hard work. Trump has none of those things. He was born wealthy, and he's spent his entire life letting most of his wealth just sit and grow on easy investments which insulate him from all of his failures. If he were forced to earn his money from scratch, he'd be holed up in a shithole apartment dodging bill collectors within a month.
For a lot of people, the internal thought process about Trump is, "he can't possibly be this incompetent and terrible, because that would mean such awful people can get so far ahead of others. That can't be true, can it?"