Presented in 1980 by former Commodore Brenton S. Halsey as a perpetual award to recognize the skipper of the outstanding Cruising Class (renamed Offshore Division) yacht as determined by an objective standard applied over the Regular Racing Season. The award shall be made to the skipper, who is a member of Fishing Bay Yacht Club, of an enrolled Offshore Division yacht as determined by the CBYRA High Point scoring formula in FBYC sponsored races. Only Offshore events that offer starts in all offshore classes will be used in awarding this trophy.
| 1980 | William C. Spencer, II | |
| 1981 | Brenton S. Halsey | |
| 1982 | Strother Scott | |
| 1983 | Eugene Sydnor, Jr. | |
| 1984 | John R. Hawksworth | |
| 1985 | Chip Brierre | |
| 1986 | Donald Landau | |
| 1987 | William C. Spencer II | |
| 1988 | David Lee/John Adair | |
| 1989 | W. Garret/R. Whittet | |
| 1990 | William C. Spencer II | |
| 1991 | R. Strother Scott | |
| 1992 | R. Strother Scott | |
| 1993 | William C. Spencer II | |
| 1994 | James E. Rogers | |
| 1995 | James E. Rogers | |
| 1996 | James E. Rogers | |
| 1997 | James E. Rogers | |
| 1998 | Michael W. Karn | |
| 1999 | Michael W. Karn | |
| 2000 | F. Case Whittemore | |
| 2001 | Robert M. Whittet, III | |
| 2002 | F. Case Whittemore | |
| 2003 | Samuel W. Marshall | |
| 2004 | T. Leroi Lissenden | |
| 2005 | David S. Hinckle | |
| 2006 | Allan M. Heyward Jr. | |
| 2007 | J. Bradley Davis | |
| 2008 | Jerry Latell | |
| 2009 | Allan M. Heyward Jr. | |
| 2010 | Cyane Crump | |
| 2011 | J. Samuel Mitchener III | |
| 2012 | Craig R. Wright | |
| 2013 | Robert J. and Lisa Fleck | |
| 2014 | Craig R. Wright | |
| 2015 | Robert J. and Lisa Fleck | |
| 2016 | Robert J. and Lisa Fleck | |
| 2017 | Craig Wright | |
| 2018 | Craig Wright | |
| 2019 | Bob Fleck | |
| 2020 | Bob Fleck | |
| 2021 | Robert J. and Lisa Fleck | |
| 2022 | Robert J. and Lisa Fleck |