I would have to vote for Scheherezade.
In the first story of One Thousand and One Nights, a Sultan catches his wife sleeping with another man and he goes a bit crazy. He likes having a wife but he doesn’t like being cheated on so from then on he takes a different wife every night and has her killed the next morning. As you could imagine, pretty soon there aren’t too many women left in the kingdom. One of the last women left was named Scheherazade and she had a plan. If she told the king a different story every night and each one had a cliff-hanger ending, the Sultan would be desperate for the rest of the story and let her live another day. So far so good but Scheherezade was also exceptionally smart. A lot of the people in her stories were crazy with grief and decided that killing someone was the best way to deal with it. A lot of the time they were talked out of it by stories that the characters told. After about, oh, a thousand nights of the same thing, the Sultan started to get the picture. He realized that he’d lost his compassion and returned to his normal Sultanly self.
If you are coaching Andy Roddick, if you know that a match in the semifinals of a grand slam can turn on one or two points, if you know that mental skills are the difference between first and second place and confidence is a huge part of that, you keep your player as loose as possible by making tennis fun and you make it clear that you got his back. You even jump out of an airplane with him if he wants to.
Red Auerbach was a master at reading the personalities of his players, he treated them all differently. Some guys he coddled and some guys he rode mercilessly. Phil Jackson has similar skills though he does it differently, he appeals to his players’ intelligence. It says a lot about professional sports at the moment that Phil not only wanted to trade the best player in the league, Kobe Bryant, but that management refused and booted him instead. Entertainment has become more important than winning.
Of course, what does that make Roger Federer? Three grand slams in one year without a coach. That’s a successful player-coach if I ever saw one.