It's not unattractive to those who have achieved success. Birds of a feather.
SOME of us know it, but not everyone knows it. This is why politicians repeat themselves ad nauseum while on the campaign trail. You need to repeat yourself with every new crowd you come across to increase your base. An analogy might be when a popular singer shows up to perform a concert. The fans may have already have heard the performer's most popular songs hundreds of times, but when it's performed in person, it's like you've heard it for the first time and you'll remember where you heard it in person. Personalize your message for EVERY new crowd.
Those who have achieved great success and have a bit of class don't brag about it at every turn. The guy comes off as a typical rich spoiled blowhard brat from Long Island. If he wants to win anything instead of being a spoiler who will hand the election over to Hillary, he needs to sharpen his message and tone down the gas bag bore act. I like what he is saying about restructuring our trade deals, but I'd like to hear more specifics. He just seems to blurt out general statements, many which are patently false with no real data to back them up. He has time to get it together and he definitely has a chance to win vs the lackluster field he's up against. If he's so damn smart, he'll figure this out, if he keeps up the hollow circus act, he'll be out before Super Tuesday. The GOP better hope that he doesn't get offended and feel that the Republican establishment has treated him unfairly and decide to run as a third party candidate. That will make Clinton an easy winner.