| Players | Years played with Pirates |
|---|---|
| Jake Beckley | 1888-1889, 1891-1896 |
| Bert Blyleven | 1978-1980 |
| Jim Bunning | 1968-1969 |
| *Max Carey | 1910-1926 |
| Jack Chesbro | 1899-1902 |
| *Fred Clarke | 1900-1911, 1913-1915 |
| *Roberto Clemente | 1955-1972 |
| Joe Cronin | 1926-1927 |
| Kiki Cuyler | 1921-1927 |
| Barney Dreyfuss | 1900-1932 |
| Pud Galvin | 1887-1889, 1891-1892 |
| Rich Gossage | 1977 |
| Hank Greenberg | 1947 |
| Burleigh Grimes | 1916-1917, 1928-1929, 1934 |
| Ned Hanlon | 1889, 1891 |
| Billy Herman | 1947 |
| Waite Hoyt | 1933-1937 |
| Joe Kelley | 1892 |
| George Kelly | 1917 |
| *Ralph Kiner | 1946-1953 |
| Chuck Klein | 1939 |
| Freddy Lindstrom | 1933-1934 |
| Al Lopez | 1940-1946 |
| Connie Mack | 1891-1896 |
| Heinie Manush | 1938-1939 |
| Rabbit Maranville | 1921-1924 |
| *Bill Mazeroski | 1956-1972 |
| *Willie Stargell | 1962-1982 |
| Casey Stengel | 1918-1919 |
| *Pie Traynor | 1920-1937 |
| Dazzy Vance | 1915 |
| *Arky Vaughan | 1932-1941 |
| Rube Waddell | 1900-1901 |
| *Honus Wagner | 1900-1907 |
| *Lloyd Waner | 1927-1941, 1944-1945 |
| *Paul Waner | 1926-1940 |
| Vic Willis | 1906-1909 |
| * Played more games with Pittsburgh than any other team. Bold Face indicates a Hall of Famer elected as a player, others were elected as managers or executives. |
|
| Managers | Years with Pirates |
|---|---|
| Fred Clarke | 1900-1915 |
| Frankie Frisch | 1940-1946 |
| Ned Hanlon | 1889, 1891 |
| Billy Herman | 1947 |
| Connie Mack | 1894-1896 |
| Bill McKechnie | 1922-1926 |
| Billy Southworth | 1918-1920 |
| Pie Traynor | 1934-1939 |
| Honus Wagner | 1917 |
| Bold Face indicates a Hall of Famer elected as a manager, others were elected as players or executives. | |
