Wait.... so..... you're admitting that Trump is naive about people? How does that square with his decades of experience in dealing with people throughout his real estate mogul career? (hint - it doesn't)
Bureaucrats/Politicians and Business people are completely different animals. Business people are motivated by success and profit. Bureaucrats are motivated by status quo stagnation, and entrenched corruption for personal gain. It is two different worlds.
Trump was naive in that he assumed that everyone was working for the good of the people and the good of the country. We were all shocked at how deep the swamp was. Nobody knew how deep and tentacled the corruption nepotism in D.C., and in the media, went until Trump exposed it. Who knew?
When Trump had to deal with the mafia, at least the mafia had some sense of honor. And they were working for what was best for the organization. There is no honor in D.C. and people there are willing to work against what is in their own self interests, the interests of their family, their children, and their neighbors, and the interests of America and the American people, to achieve some political goal. This is counterintuitive.
Washington D.C. makes the mafia look like Boy Scouts.