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Trump's biggest failing was directly related to personnel choices. Some of it is understandable. As the first real political outsider to be president since Washington (the subsequent generals who were elected were de facto politicians because that's the nature of being a flag officer), Trump didn't have a close cadre of confidents he could rely on. Nor did he really have an appreciation for the depth of and breadth of The Swamp and the tenacity, ferocity of its most dangerous creatures. He also didn't understand that the Republicans in DC wanted him to fail just as much as Democrats, arguably even more.

Reagan faced similar headwinds when he came to DC, but he had the benefit of being governor of a huge state and building reasonably loyal political staff from that experience, staff he brought with him, much to the chagrin of establishment DC.

But, even excepting Trump's lack of political experience, he has some history of surrounding himself with rent-seeking morons; see: Omarosa and his LONGTIME personal lawyer, Michael Cohen. Trump was one of the richest men in Manhattan for decades yet he settled on a guy who graduated from literally one of the worst law schools in the country to be his personal lawyer? That's weird.

Trump had no realistic choices. Mitch pretty much boxed him in with severe limits on who he would confirm and who he wouldn’t. This was enforced by his refusal to let the Senate go into recess for a single day for the entire four years to prevent his OWN PRESIDENT from making any recess appointments.

Next, the pussyhats and the restaurant terrorists and the universities made life an absolute hell for anyone who thought they might work for the Trump administration. So the “killers” he wanted to bring in vanished. Remember all those members of his business advisory council who quit within weeks? It was because of threats and boycotts.

Trump had almost no ability to appoint who he wanted to.
Realistically, he had about 40% of the normal power a President has and look at all he accomplished. The White House was utterly infested with spies like Vindman.

He was alone, under attack from all points of the compass.