It almost seemed he looked at these positions like a continuation of The Apprentice. Might work in business but here the potential for great damage is too great. Of course he had no portfolios of experienced applicants to choose from and his dealings with govt while extensive were with gaming commissions, zoning boards, community planning districts, not the kind of background a POTUS usually has. Even his overseas ventures brought him into limited contact with national govt. All in all his successes can be chalkedvup more to his audacity and determination than to his appointments, save of course the federal judiciary.
And then, there are people like Carl Icahn, whom he trusted and who would have been GREAT in his Cabinet, who declined to be a part of this administration, because they knew what kind of a hassle they would have been put through, had they accepted any position at all.