Trump is just a really weird dude. I don't think he lives in the same reality as most people. Most of his lies and exaggerations don't even help or hurt him in any way. They're just random things that come out of this weirdo's mouth.
"My inauguration had the biggest crowd ever."
"Mr. Trump. Nobody was asking..."
"My dick isn't as small as my hands."
"We never..."
"This hair is real. Somebody come up on stage, and pull on it."
"Why..."
Well, I don't think that is completely off the wall.
It is just sort of eccentric, trying to connect with an entire popular mainstream, in a way that is awkward.
I think folks from his generation can understand where he is coming from. You have to remember, he is in his seventies. His whole life he has been used to trying to stay relevant. At that age, it probably gets to be a bit of a chore and a bit difficult.
My parents seem out of touch sometimes, and I know there are quite a few boomers on this forum that are in that age bracket.
SO, when you make light of his eccentricities, you are really making fun of that entire generation.