It’s not a matter of naivete. Rather, President Trump believes very strongly in his own powers of persuasion. And why shouldn’t he since his entire life’s experience reinforces his confidence. But the whole Mueller thing is about setting him up for impeachment, and I don’t think the President fully appreciates the danger. He is not naive or ignorant, just naturally inclined. The very fact that his attorneys are negotiating with Mueller indicates so.
I think you paint an unflattering picture of Trump's ability to read people. It's a bit insulting, IMHO, almost like some of the arguments the left proposes. Like Trump is full of himself, etc. I prefer to think of him as just an outright winner - knows how to win, knows how to adjust when he needs to - I think he's masterful at it.