| Name | Years |
|---|---|
| Ernest Barnard | 1903–1927 |
| Bob McRoy | 1916–1917 |
| Billy Evans | 1927–1935 |
| C.C. Slapnicka | 1935–1941 |
| Roger Peckinpaugh | 1941–1946 |
| Bill Veeck | 1946–1949 |
| Hank Greenberg | 1950–1957 |
| Frank Lane | 1957–1961 |
| Gabe Paul | 1961–1973 |
| Phil Seghi | 1973–1985 |
| Joe Klein | 1985–1987 |
| Hank Peters | 1987–1991 |
| John Hart | 1991–2001 |
| Mark Shapiro | 2001–2010 |
| Chris Antonetti | 2010–2015 |
| Mike Chernoff | 2015–present |
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| Name | Years |
|---|---|
| Charles W. Somers | 1900–1916 |
| Jim Dunn | 1916–1922 |
| Dunn estate | 1922–1927 |
| Alva Bradley | 1927–1946 |
| Bill Veeck | 1946–1949 |
| Ellis Ryan | 1949–1952 |
| Myron H. Wilson | 1953–1956 |
| William R. Daley | 1956–1962 |
| Gabe Paul | 1963–1966 |
| Vernon Stouffer | 1967–1972 |
| Nick Mileti | 1972–1976 |
| Ted Bonda | 1977–1978 |
| Steve O'Neill | 1978–1983 |
| O'Neill estate | 1983–1986 |
| Richard E. Jacobs | 1986–2000 |
| Larry J. Dolan | 2000–2025 |
| Paul J. Dolan | 2025–present |
| David Blitzer[a] | 2022–present |