Danny Murtaugh was probably the most successful manager in the Pirates franchise history. His career record was 1,115-950, an astounding .540 winning percentage. He won four division titles with the Pirates in four different stints of managing. He also won two National League Championships and two World Series Championships with the Pirates. His number 40 was retired by the Pirates in 1977.

Chuck Tanner managed the Pirates from 1977 to 1985. He went 711-685, which amounts to a .509 winning percentage. 1979 may have been his best and most successful managerial seasons. That year, his Pirates won the Eastern Division, the National League Championship, and the World Series Championship. He was a wonderful manager.  

Fred Clarke was one of the few people that could have made it to the Hall of Fame as a player or a manager. In fifteen seasons as a player with the Pirates, he batted .315 with 2,703 hits. As the Pirates manager, he won 1,422 games while only losing 969 for an amazing percentage of .595. He won National League Championships in 1901, 1902, 1903, and 1909. He won the World Series in 1909 as well. He was inducted into the Hall of Fame in 1945.

Bill McKechnie managed from 1922 to 1926, compiling a managerial record of 409 and 293. He won the National League Championship in 1925 and then went on to win the World Series. He is the only manager ever to win a pennant with three different teams. He was elected to the Hall of Fame in 1962.

Although Jim Leyland went only 851 and 863 in his ten year managerial stint with the Pirates, most players who played for him will tell you that he was their favorite manager to play for. He won Eastern Division titles in 1990, 1991, and 1992 with the Pirates. After his tenure with the Pirates, he went on to win the World Series with the Florida Marlins in 1997. he is currently manager of the Detroit Tigers.