I agree. He has always aspired to be accepted by the 'real' rich and smart crowd but they never accepted him. He finally just bought his way into their circles. Didnt work. He wasnt raised like they were. He couldnt fake elite. Wasnt interested in higher things. He was too gauche. So he always said he felt more comfortable on the construction sites and talking to taxi drivers (and the occasional model or stripper too!)
Makes perfect sense.
Good intentions but no sense of class on how to make things work smoothly in those circles. Gets the everyman votes, but not the academic supporters or people who enjoy cute kittens.
He is a dilettante politician always coming up a bit short.
Occasionally (ok, maybe more than that depending on the issue!) incompetent, but not a devious crook.
Really good at getting debts refinanced!
That is my take.