There are a number of people who are just incompetent in life.
Or he was involved in his radical life.
What did Obama really do after college?
There are many of his generation that are victims of the "participation trophy" philosophy.
They were taught as children that no matter how little effort they put in to a task, they deserve success.
Just from that brief history and having raised kids in that period, I read the pattern.
And naturally these forever teens have to blame others for their failure. Might as well blame someone successful, rich and the guy trying to eliminate the Department of Education.