Glad to hear you working on holding your boundaries and self-esteem. Folks like that often try to make themselves look better by downing others. He seems to be caught in the co-dependency cycle. I've been in similar relationships in the past. They are often hard and unpleasant to break out of as once the people around them start holding their boundaries the "perps" get upset and angry...
One of the best books I found enlightening was "The Human Magnet Syndrome: Why We Love People Who Hurt Us" by Ross Rosenberg. Certainly was eye opening. Maybe as an anonymous gift to him?
Ha that's a good one... Might be worth dropping in his letterbox.