Charlie O. Finley won three World Series with the Oakland Athletics in 1972, 1973, and 1974. But he was crazy. He made a mule the team mascot, hired a 59 year old pitcher and sued MLB.
This story includes Joe DiMaggio, Sandy Koufax, Reggie Jackson, Rollie Fingers, Marvin Miller and the MLBPA, Curt Flood, and M. C. Hammer for some reason.