Given in 1971 in honor of John McLeod, former Counselor at MIYC.
John was a beloved swimming counselor who was civic minded and enthusiastic,
and inspired MIYC to create this award.
| 1971 Polly Attwood | 1989-90 Jr. Yacht Club |
| 1972 Susan Dana | 1991 Will Canning, Tim Sheffield |
| 1973 Amy Dana | 1992 Whit Townsend |
| 1974 Ted Parker | 1993 Meg Keiley |
| 1975 Sadie Ashton | 1994 Kate Canning |
| 1976 Betsy Trimble | 1995 Jordi St. John |
| 1977 John H. Hellier | 1996 Andrew Halsey |
| 1978 Cora Trimble | 1997 Martha Canning |
| 1979 Mark Liebig | 1998 Bailey Briggs |
| 1980 Katy Hodges | 1999 Kaitlin Parry |
| 1981 Tina Havlik | 2000 Anthony Parry |
| 1982 Laura Van Winkle | 2001 Jessica Wood |
| 1983 Barney Hodges | 2002 Dana McGuire |
| 1984 Bobby Schock | 2003 Olivia Parry |
| 1985 Peter Fickeisen | 2004 John Secor |
| 1986 Laura Taber | 2005 Thad Pryor |
| 1987 Will Canning | 2006 Eleanor Parry |
| 1988 Nathaniel Roundy | Trophy Retired |