Interesting comments about Wilson and Roosevelt. I think Roosevelt's scheme to change the size of the Supreme Court in order to get around the supreme court's early opposition to much of his program was radical (and dictatorial), but when there was no appetite in Congress for changing the court, he backed down. He was maybe more of a wannabe dictator. His economic agenda was approved by the congress precisely because both chambers largely agreed with his Keynesian approach. Like Hitler, he never shook Jessie owens' hand, but that doesn't make him a dictator, does it?
Wilson is another matter. He had a deep and abiding love of power. I agree that you can call him a dictator, and a dictator was probably just what was needed at the time. (You must remember that in his day, and frankly in Roosevelt's day as well, the term "dictator" did not carry the negative connotation that it does now.)
I'm not sure that we need a dictator now, or whether Trump will be one, but if he is, he will not have been the first.
I think that is why he will be criticized for going that direction more. He seems to be a dictator for just wanting to be one.