| Year | Name | Team | League |
| 1936 | Rickey, BranchBranch Rickey (1) | St. Louis Cardinals | National |
| 1937 | Barrow, EdEd Barrow (1) | New York Yankees | American |
| 1938 | Giles, WarrenWarren Giles | Cincinnati Reds | National |
| 1939 | MacPhail, LarryLarry MacPhail | Brooklyn Dodgers | National |
| 1940 | Briggs, Sr., WalterWalter Briggs, Sr. | Detroit Tigers | American |
| 1941 | Barrow, EdEd Barrow (2) | New York Yankees | American |
| 1942 | Rickey, BranchBranch Rickey (2) | St. Louis Cardinals | National |
| 1943 | Griffith, ClarkClark Griffith | Washington Senators | American |
| 1944 | DeWitt, BillBill DeWitt | St. Louis Browns | American |
| 1945 | Wrigley, PhilPhil Wrigley | Chicago Cubs | National |
| 1946 | Yawkey, TomTom Yawkey | Boston Red Sox | American |
| 1947 | Rickey, BranchBranch Rickey (3) | Brooklyn Dodgers | National |
| 1948 | Veeck, BillBill Veeck (1) | Cleveland Indians | American |
| 1949 | Carpenter, BobBob Carpenter | Philadelphia Phillies | National |
| 1950 | Weiss, GeorgeGeorge Weiss (1) | New York Yankees | American |
| 1951 | Weiss, GeorgeGeorge Weiss (2) | New York Yankees | American |
| 1952 | Weiss, GeorgeGeorge Weiss (3) | New York Yankees | American |
| 1953 | Perini, LouLou Perini | Milwaukee Braves | National |
| 1954 | Stoneham, HoraceHorace Stoneham | New York Giants | National |
| 1955 | O'Malley, WalterWalter O'Malley | Brooklyn Dodgers | National |
| 1956 | Paul, GabeGabe Paul (1) | Cincinnati Redlegs | National |
| 1957 | Lane, FrankFrank Lane | St. Louis Cardinals | National |
| 1958 | Brown, Joe L.Joe L. Brown | Pittsburgh Pirates | National |
| 1959 | Bavasi, BuzzieBuzzie Bavasi | Los Angeles Dodgers | National |
| 1960 | Weiss, GeorgeGeorge Weiss (4) | New York Yankees | American |
| 1961 | Topping, DanDan Topping | New York Yankees | American |
| 1962 | Haney, FredFred Haney | Los Angeles Angels | American |
| 1963 | Devine, BingBing Devine (1) | St. Louis Cardinals | National |
| 1964 | Devine, BingBing Devine (2) | St. Louis Cardinals | National |
| 1965 | Griffith, CalvinCalvin Griffith | Minnesota Twins | American |
| 1966 | MacPhail, LeeLee MacPhail | MLB Chief Assistant | zzza !– |
| 1967 | O'Connell, DickDick O'Connell (1) | Boston Red Sox | American |
| 1968 | Campbell, JimJim Campbell | Detroit Tigers | American |
| 1969 | Murphy, JohnnyJohnny Murphy | New York Mets | National |
| 1970 | Dalton, HarryHarry Dalton (1) | Baltimore Orioles | American |
| 1971 | Tallis, CedricCedric Tallis | Kansas City Royals | American |
| 1972 | Hemond, RolandRoland Hemond (1) | Chicago White Sox | American |
| 1973 | Howsam, BobBob Howsam | Cincinnati Reds | National |
| 1974 | Paul, GabeGabe Paul (2) | New York Yankees | American |
| 1975 | O'Connell, DickDick O'Connell (2) | Boston Red Sox | American |
| 1976 | Burke, JoeJoe Burke | Kansas City Royals | American |
| 1977 | Veeck, BillBill Veeck (2) | Chicago White Sox | American |
| 1978 | Richardson, SpecSpec Richardson | San Francisco Giants | National |
| 1979 | Peters, HankHank Peters (1) | Baltimore Orioles | American |
| 1980 | Smith, TalTal Smith | Houston Astros | National |
| 1981 | McHale, JohnJohn McHale | Montreal Expos | National |
| 1982 | Dalton, HarryHarry Dalton (2) | Milwaukee Brewers | National |
| 1983 | Peters, HankHank Peters (2) | Baltimore Orioles | American |
| 1984 | Green, DallasDallas Green | Chicago Cubs | National |
| 1985 | Schuerholz, JohnJohn Schuerholz | Kansas City Royals | American |
| 1986 | Cashen, FrankFrank Cashen | New York Mets | National |
| 1987 | Rosen, AlAl Rosen | San Francisco Giants | National |
| 1988 | Claire, FredFred Claire | Los Angeles Dodgers | National |
| 1989 | Hemond, RolandRoland Hemond (2) | Baltimore Orioles | American |
| 1990 | Quinn, BobBob Quinn | Cincinnati Reds | National |
| 1991 | MacPhail, AndyAndy MacPhail | Minnesota Twins | American |
| 1992 | Duquette, DanDan Duquette (1) | Montreal Expos | National |
| 1993 | Thomas, LeeLee Thomas | Philadelphia Phillies | National |
| 1994 | Hart, JohnJohn Hart (1) | Cleveland Indians | American |
| 1995 | Hart, JohnJohn Hart (2) | Cleveland Indians | American |
| 1996 | Melvin, DougDoug Melvin | Texas Rangers | American |
| 1997 | Bonifay, CamCam Bonifay | Pittsburgh Pirates | National |
| 1998 | Hunsicker, GerryGerry Hunsicker | Houston Astros | National |
| 1999 | Beane, BillyBilly Beane (1) | Oakland Athletics | American |
| 2000 | Jocketty, WaltWalt Jocketty (1) | St. Louis Cardinals | National |
| 2001 | Gillick, PatPat Gillick | Seattle Mariners | American |
| 2002 | Ryan, TerryTerry Ryan (1) | Minnesota Twins | American |
| 2003 | Sabean, BrianBrian Sabean | San Francisco Giants | National |
| 2004 | Jocketty, WaltWalt Jocketty (2) | St. Louis Cardinals | National |
| 2005 | Shapiro, MarkMark Shapiro (1) | Cleveland Indians | American |
| 2006 | Ryan, TerryTerry Ryan (2) | Minnesota Twins | American |
| 2007 | Shapiro, MarkMark Shapiro (2) | Cleveland Indians | American |
| 2008 | Friedman, AndrewAndrew Friedman | Tampa Bay Rays | American |
| 2009 | O'Dowd, DanDan O'Dowd | Colorado Rockies | National |
| 2010 | Jocketty, WaltWalt Jocketty (3) | Cincinnati Reds | National |
| 2011 | Dave Dombrowski
Doug Melvin (2) | Detroit Tigers
Milwaukee Brewers | American
National |
| 2012 | Beane, BillyBilly Beane (2) | Oakland Athletics | American |
| 2013 | Cherington, BenBen Cherington | Boston Red Sox | American |
| 2014 | Duquette, DanDan Duquette (2) | Baltimore Orioles | American |
| 2015 | Anthopoulos, AlexAlex Anthopoulos | Toronto Blue Jays | American |
| 2016 | Epstein, TheoTheo Epstein | Chicago Cubs | National |