Do you have any hints at what would make you consider him not stupid, historically? Being confident and narcissistic, and even talented at bullshit doesn’t make you smart. And recognizing weaknesses in the system isn’t really smart, even if it is perceptive, when those weaknesses are really just strong arm tactics that happen to be available to him through brazenness, inheritance, litigation, cruelty and others recognizing him as a convenient money laundering option.