Given in 1977 in memory of Wesley Van Winkle, great grandson of Past Commodores:
Charles A. Van Winkle and H. Schuyler Horn, and grandson of Arthur D. Van Winkle,
and son of current MIYC members: Past Commodore Daniel Van Winkle and Betsy Van
Winkle. Awarded to the junior sailor who has been designated by the Trustees to have had
the most impact on the junior sailing program during the summer, customarily judged by the
highest cumulative race results for the season.
| 1977 | William Scott Parry | 2000 | Kaitlyn Parry |
| 1978 | David Guthrie Phillips | 2001 | Peter Smith |
| 1979 | William P. Conley, Jr. | 2002 | Martha Canning |
| 1980 | Michael Repko | 2003 | Robbie Christian |
| 1981 | Laura Van Winkle | 2004 | Peter Augusciak |
| 1982 | Frank Conley | 2005 | John Canning |
| 1983 | Chris Taber | 2006 | Nathaniel Humphrey |
| 1984 | Barney Hodges, Matt Taber | 2007-08 | Max Plummer |
| 1986 | Hunter Townsend | 2009 | Cassidy Walsh |
| 1987-88 | Bobby Schock | 2010 | Owen Sullivan |
| 1990 | Whit Townsend | 2011-12 | Annie Longo |
| 1991-92 | Grant Stuart | 2013 | Sasha Oaks |
| 1993 | Will Canning | 2014 | Libby Stuart |
| 1994 | Kate Canning | 2015 – 16 | Austin Halsey |
| 1995 | Will Canning | 2017 | James Castle |
| 1996 | Jeremy Collins | 2018 | Austin Halsey |
| 1997 | Kate Canning | 2019 | Vincent Maupin |
| 1998-99 | Jessica Wood |