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So... do you think he has the objectivity to regret all of his actions yet? Not regret as in that he did anything morally wrong because he's far too much a narcissist to think that. But rather regret that he put himself in the crosshairs to be actually held to account for the first time when he's previously been able to mostly get away with criminal shit his whole life.
If he hadn't run for office, he could have continued to be just another sleazeball rich gangster wannabe in New York and probably lived out the rest of his life without any real consequences for being a piece of shit. He'd have been insulated by low expectations and mostly being a forgettable joke of a man. But now that he poses a real and ongoing danger to the public and democracy itself, people are motivated to hold him liable for his dozens of crimes in several major high profile cases.
Do you think he wishes he'd have just stayed in Manhattan and continued screwing people over in his property deals and business schemes? I bet it keeps him up at night, and it should.
Remember the look on his face when he won? He was horrified! Same when he first met with Obama and they had a joint press conference. His body language was like, "oh fuck, what am I even doing here."
I think regret is hard for him though, because to regret something means you have to feel, in some way, you could have done something better or differently. You have to take ownership of bad feelings and in your part of bad outcomes. I just don't think his brain will let that happen. Everything bad is always someone else's fault.
But yeah...maybe in some dark, cobweb encrusted corner of his mind, he wishes he was just a NY scam artist and fake "tycoon." It served him well enough, as you noted.