I have found that "The man" is the guy who dominates whatever consideration is at hand. If you work in a company that is owned by one and employs three, "the man" is the owner. I imagine that most people view the man as the guy that keeps them from getting what they want.
You may not have noticed that all politicians win for exactly the reason you cite. Most adapt their presentation to effect that image. Trump is pretty much what he is.
Regarding your view of his leadership style, you seem to be confusing his public communications with his leadership style.
The feeling that he tapped in to has been a vague presence for several years. The Movie "Network" came out in 1976 and contained the Howard Beal character who identified the same sentiment that Trump did by calling on people to yell, "I'm as mad as Hell and i'm not going to take it anymore!"
https://en.wikipedia.org/wiki/Network_(film)
Beal gave a lengthy description of what "IT" is and it hasn't changed. People who just strive to live day to day have a vague feeling of what is right track and what is wrong track and right now, we linger at about 60% who feel that our country is on the wrong track year after year after year.
Beal's main thrust was that he didn't know exactly what to do, but that everyone needed to grasp one idea: "I'm a human being, God Damn it!" and that we, as a people, needed to get mad. Well, the people got mad and Trump is there to "shake things up".
I don't know if what he does will be enlightened or tragic, but, like he said, "What have you got to lose?"
Right now, the world is in flames, the US debt is riding a rocket straight up, the hate filled and fearful of our country and the world are segmented and led by those who are filled with greater hate and greater fear and there needs to be someone who will challenge the insanity.
All of this negativity came to the surface over the last 16 years under the corrosive leadership of the two worst presidents to ever serve back to back in the history of our Republic augmented by the worst the world has to offer world wide.
As Americans, both individually and as a group, we might not be geniuses, but we can smell the stink of failure and it's all around us.
RealClearPolitics - Election Other - Direction of Country
https://www.youtube.com/watch?v=ZwMVMbmQBug