Insider knowledge plus large number of people VS Insider knowledge and a small cartel. Place your bets please.
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Here is my thinking:
Obama could run an effective shadow government, from the outside, because he had so many on the inside willing to carry out his orders. The FBI, DOJ, CIA, DEA, the entire entrenched Bureaucracy was working with/for him. In addition, Wall Street, K-Street, Big Bank, and BIG TECH, the Media all were with him.
Trump may not have the same level of cooperation inside the government, that would allow him to work as effectively outside of it, as Obama. This is a sad fact, I think.