I think Trump is a transformative type leader. He wants his hires to expand the perimeters of the organization by individual, innovative thinking. Ric Grenell is a great example of someone who excels in this type of setting. He found his own way to success in the administration, excelling at any post he was given. Dan and Stephen Miller are like this, as well, I think.
Lot of the old government fixtures, and military, can only function in a transactional setting. That is, they expect to toe the company line for recognition and to be punished if they don't. They are not people people who can function successfully outside that box.
So Trump hires who were looking for a line to toe in order to be praised didn't find one. Afraid to hew their own course for recognition, they accused Trump of being unorganized. Milley and Bolton are the poster boys for this type. Incapable of creating their own success in an environment they are not constantly being praised or punished in.
Milley, if the China shit is true, was perhaps just looking for recognition and praise from anyone who would give it. A low format individual, IMO. If he wasn't being praised by Trump, then Trump must be wrong/bad. That just could be the limit of his intellectual capacity.
Hoping, (yeah, I know) Trump was culling out the useless candidates in his first term so he can hit the ground running the next time around.