Tony La Russa played professional baseball for 16 seasons, mostly in the minor leagues, and started law school while he was still playing. But his first job after graduating law school was as a manager of a Double-A team, and he never looked back. La Russa went on to win three pennants and one World Series title with the Oakland A’s, and three pennants and two World Series with the St. Louis Cardinals. He won the MLB manager of the year award four times.