Leo was a good provider for his family. Smart with his money, a hard worker. These are good things. He made sure his kids went to good schools and had every opportunity they could. They seem to be a great family. But I think coming from a place like that, somewhat counterintuitively, is a barrier to achieving at the highest level. They have and use all the tools for success, but when they come up against a person who has learned these things as well, and who knows they'll be on the streets if they don't perform, the incentive for that little extra something comes out.
I can't say it isn't just a cognitive bias of mine. My mind just jumps to Chris Simms vs Michael Irvin. Not rational, not fair. But adversity in youth makes better players.