"Dr." Fred

The most charitable explanation for "Dr." Fred is that he's degenerated into the professional equivalent of those pathetic aging former chess masters who try to eek out a subsistence living by charging five bucks a game. People often play with them out of sympathy, or for the novelty of having lost to a past great. It's part of the chess culture, and it's basically harmless and sort of quaint. The difference, of course, is that its almost impossible to have sympathy for Dr. Fred. His hustle is for a hell of a lot more than subsistence. He was also never actually a master of his field, a fact that becomes increasingly obvious as our exposure to him goes on. Now he's reduced himself to trying to collect someone else's winnings.