Presented by Mr. Joseph B. Baker in 1951. The Board of Trustees, at the unanimous request of the Fishing Bay Penguin Fleet, to whom this trophy was initially entrusted, adopted requirements for competition and for perpetuation of the award identical to those prescribed by the deed of gift for the Henry E. Hutcheson, Jr. Memorial Trophy. In 1967, when the award class failed to have the required number of eligible yachts for two successive seasons, the award was changed by the Board to the Jet 14 Class. Windmill became the award class in 1971. Mobjack became the award class in 1975. Flying Scot became the award class in 2010.
| 1951 | J. Marshall Moseley | |
| 1952 | J. Marshall Moseley | |
| 1953 | J. Marshall Moseley | |
| 1954 | Mary Reid Dunn | |
| 1955 | J. Marshall Moseley | |
| 1956 | Anthony Dunn | |
| 1957 | Anthony Dunn | |
| 1958 | John Moseley, III | |
| 1959 | John Moseley, III | |
| 1960 | John Moseley, III | |
| 1961 | Howard M. McCue, Jr. | |
| 1964 | William M. Harris | |
| 1967 | W. Harry Schwarzchild, III | |
| 1968 | O. Van Pelt Sessoms | |
| 1972 | John Ogden, III | |
| 1973 | John Ogden, III | |
| 1976 | A. Owen Davidson, Jr. | |
| 1977 | William B. Pierce | |
| 1978 | Wesley D. Jones | |
| 1979 | George A. Barrows | |
| 1980 | George A. Barrows | |
| 1981 | Denton C. Roberts | |
| 1982 | Denton C. Roberts | |
| 1983 | F. Case Whittemore | |
| 1984 | F. Case Whittemore | |
| 1985 | F. Case Whittemore | |
| 1986 | F. Case Whittemore | |
| 1987 | James T. Poindexter, III | |
| 1988 | Anthony D. Sakowski | |
| 1989 | James T. Poindexter, III | |
| 1990 | Edgar E. Roberts | |
| 1991 | Edgar E. Roberts | |
| 1992 | Edgar E. Roberts | |
| 1993 | F. Case Whittemore | |
| 1994 | F. Case Whittemore | |
| 1995 | F. Case Whittemore | |
| 1996 | Thomas J. Roberts | |
| 1997 | Jerry Desvernine | |
| 1998 | F. Case Whittemore | |
| 1999 | Rob Whittemore | |
| 2000 | F. Case Whittemore | |
| 2001 | Meg Roberts | |
| 2002 | Meg Roberts | |
| 2003 | Not Awarded | |
| 2004 | Not Awarded | |
| 2005 | Cheryl Desvernine | |
| 2006 | Not Awarded | |
| 2007 | Not Awarded | |
| 2008 | Not Awarded | |
| 2009 | Not Awarded | |
| 2010 | John B. Wake, Jr. | |
| 2011 | Len Guenther Jr. | |
| 2012 | Robert P. Whittemore | |
| 2013 | Robert P. Whittemore | |
| 2014 | Sharon S. Wake | |
| 2015 | John B. Wake, Jr. | |
| 2016 | John B. Wake, Jr. |