I think he does. He has radical leftist leanings, and surrounds himself with radical leftists. IMO, he believes that since America was asleep enough to elect him, then they’re asleep enough to allow a guy like Van Jones to work for him. He thinks to himself “hey, my past is shady, suspect, full of malignant mentors and ideas, and they still elected me, so why not hire a fellow traveler like Van? No one will care. They elected ME POTUS, after all, and no one is more radical that I am, and Van will just be a mere “czar...”
Obama must have had a career path in mind for his protege. Allow Jones time to "grow in the job" and get some creds so he can be moved up the ladder to more senior positions. Before you know it, Jones is a cabinet secretary.