Joe McCarthy managed from 1926 to 1950, winning one pennant with the Chicago Cubs and eight with the New York Yankees. Under his direction, the Bronx Bombers won seven World Series in the 1930s and early 1940s. Among the men on our Top 5 list, McCarthy had the best overall winning percentage, .615. Longtime New York Giants manager John McGraw also steered nine of his clubs to the post-season, but his teams only won three World Series.