Sadly, I think what you’re calling stupidity is at the core of his narcissism, selfishness, and immaturity. He’s smart, but he’s not sane or emotionally stable. I don’t think he’s developed his intelligence into anything useful. His worldview is so warped, he can’t fathom how helping people he doesn’t like could possibly benefit him. I also think we’d agree that if Trump hadn’t been born into a rich family, nobody would’ve ever heard of it. He might’ve lurched his way up the corporate ladder somewhere…

As for Woodward, etc, I think Trump is doing what psychopaths and sociopaths often do. They can’t help but flirt with the danger of getting caught. Trump is betting that he can outsmart Woodward. If Trump wins in November (which I really hope doesn’t happen), that book will be like a serial killer trophy for him.