The Gold Medal has been granted every year since 1930 (except during World War II) “in recognition of outstanding contributions to the City of New York.”
The prestigious list of honorees includes civil servants like Robert Moses, E. Virgil Conway and Ray Kelly; Mayors Fiorello LaGuardia, Robert Wagner and Rudy Giuliani; entertainers Oscar Hammerstein, Richard Rodgers and Tony Randall; corporate stalwarts like the Rockefellers; and city icons such as Carnegie Hall, the Museum of the City of New York and the New York Post.
In 2007, the award was named after long-time Association Chairman, Richard A. Cook.
| 1930 | The Honorable Julius Miller |
| 1931 | Mr. Harvey Dow Gibson |
| 1932 | The Honorable Samuel Seabury |
| 1933 | The Honorable Grover A. Whalen |
| 1934 | The Honorable Robert Moses |
| 1935 | Mr. John D. Rockefeller, Jr. |
| 1936 | The Honorable Thomas E. Dewey |
| 1937 | Mr. James Speyer |
| 1938 | Mrs. August Belmont |
| 1939 | Mr. Cleveland E. Dodge |
| 1940 | The Honorable Fiorello H. LaGuardia |
| 1946 | His Eminence Francis Cardinal Spellma, Mrs. Ogden Reid |
| 1947 | Mr. Frederick H. Ecker |
| 1948 | The Honorable William O‘Dwyer |
| 1949 | Dr. Millicent C. McIntosh |
| 1950 | Mr. Oscar Hammerstien I, Mr. Richard Rodgers |
| 1951 | Mr. Alfred P. Sloan, Jr. |
| 1952 | The Honorable Howard S. Cullman |
| 1953 | The Honorable John Hay Whitney |
| 1954 | Mr. Arthur Hays Sulzberger |
| 1955 | Brigadier General David Sarnoff |
| 1956 | The Honorable Robert J. Wagner |
| 1957 | Mr. Keith S. McHugh |
| 1958 | Mr. Samuel D. Leidesdorf |
| 1959 | Mr. John D. Rockefeller III |
| 1960 | Dr. Howard A. Rusk |
| 1961 | Mrs. Charles S. Guggenheimer |
| 1962 | The Honorable James A. Farley |
| 1963 | The Honorable Paul R. Screvane |
| 1964 | Mr. Edmund F. Wagner |
| 1965 | Mr. David Rockefeller |
| 1966 | Mr. Austin J. Tobin |
| 1967 | Mr. John A. Coleman |
| 1968 | Mr. Gustave L. Levy |
| 1969 | Mr. J. Victor Herd |
| 1970 | Mr. Jack I. Straus |
| 1971 | Mr. William S. Renchard |
| 1972 | Mr. Robert S. Curtiss |
| 1973 | Mr. Gilbert W. Fitzhugh |
| 1974 | Mr. Leonard H. Goldenson |
| 1975 | Mr. George Champion |
| 1976 | Mr. William M. Ellinghaus |
| 1977 | Mr. Ellmore C. Patterson |
| 1978 | Mr. J. Henry Smith |
| 1979 | Mr. Charles F. Luce |
| 1980 | Mr. Harry B. Helmsley |
| 1981 | Mr. Richard R. Shinn |
| 1982 | Museum of the City of New York |
| 1983 | Dr. Edward J. Mortola |
| 1984 | Mr. J. Peter Grace |
| 1985 | Mr. Gene F. Jankowski |
| 1986 | Mr. E. Virgil Conway |
| 1987 | Mr. Edmund T. Pratt, Jr. |
| 1988 | Mr. Delbert C. Staley |
| 1989 | Mr. John J. Phelan, Jr. |
| 1990 | Mr. Felix G. Rohatyn |
| 1991 | Carnegie Hall |
| 1992 | Mr. William R. Chaney |
| 1993 | Mr. Tony Randall |
| 1994 | Mr. John F. McGillicuddy |
| 1995 | Mr. David A. Olsen |
| 1996 | Mr. Kenneth J. Gorman |
| 1997 | Mr. Simon J. Critchell |
| 1998 | The Honorable Rudolph W. Giuliani |
| 1999 | Mr. Robert R. Douglass |
| 2000 | Mr. Robert M. Johnson |
| 2001 | Mr. Robert B. Catell |
| 2001 | Mr. Charles J. Hamm |
| 2002 | Mr. Charles J. Urstadt |
| 2003 | The Right Reverend Mark S. Sisk |
| 2004 | The New York Post |
| 2005 | The Honorable Robert M. Morgenthau |
| 2006 | The Honorable Raymond W. Kelly |
| 2007 | John C. Cushman, III |
| 2008 | The Honorable Michael R. Bloomberg |
| 2009 | The Guardian Life Insurance Company of America |
| 2010 | Mr. Ralph K. Smith |
| 2011 | The Crew of US Airways Flight 1549 |
| 2012 | Dominick M. Servedio |
| 2013 | The Hotel Association of New York and President Joseph Spinnato |
| 2014 | The Actors Fund |
| 2015 | Jaros Baum & Bolles and the Fire Department of the City of New York |
| 2016 | Richmond County Savings Bank |
| 2017 | Fordham University |
| 2018 | Joel Dolci |
| 2019 | New York Society of Association Executives (NYSAE) |
