It's a curse, I know. I'm looking for a 12 step program to try and cure me.
He was a poor litigator for the President re: elections. Very poor.
One of the more baffling aspects of Trump's time as president is how such a bright man could surround himself with such terrible talent. And it's not just the Giuliani's and Powell's and Wood's of the world. Time and time againt throughout his entire administration he has been horribly served by the people he appointed.
People who are personally highly engaged and “control freaks” also tend to have a problem with delegation, particularly in areas that either personally affect them or are of pronounced professional interest to them. Jimmy Carter had this problem in spades. They tend to direct everything in an extreme hands-on manner. Thus, their staff become ciphers, more or less.
Those who are capable are generally not attracted to an extremely hands-on manager or CEO...or president.
Beyond this, Trump had very few capable types to choose among to begin with. Most of the capable had already been sucked up by the elite establishment, were dedicated to that establishment, or didn’t want to cross the establishment and make their lives significantly more difficult and less profitable. This was exceedingly pronounced within the legal profession.