Current
The Pickett Trophy is named in honour of Commodore Lew Pickett.
It is presented to the Best Boy overall for the Learn to Sail program
| 1957 | Rob Ball |
| 1958 | Rob Ball |
| 1959 | Doug Hazelton |
| 1960 | Doug Hazelton |
| 1961 | Bob Ross |
| 1962 | Rick Clark |
| 1963 | Peter Theirs |
| 1964 | B. Misener |
| 1965 | Jim Schoenhardt |
| 1966 | Billy Acri |
| 1967 | Paul Walker |
| 1969 | John Irwin |
| 1970 | Kim Husebye |
| 1972 | M. Quinsey |
| 1973 | R. Jenkins |
| 1973 | I. MacLaren |
| 1974 | Phil Prendergast |
| 1974 | Andrew Cameron |
| 1975 | Phil Prendergast |
| 1975 | Mark Newman |
| 1976 | Paul Flewwelling |
| 1976 | Don Clark |
| 1977 | Leigh Davidson |
| 1977 | Tom Rieckelman |
| 1978 | Bill Waldie |
| 1978 | Eric Neate |
| 1979 | Ron Statler |
| 1979 | Lawrence Brooks |
| 1980 | Jim Hamilton |
| 1980 | Jim Raymond |
| 1980 | Ron Statler |
| 1980 | Paul Lucki |
| 1981 | Randy McMeekin |
| 1981 | Stewart Hendeerson |
| 1981 | Eric Hickland |
| 1982 | John Thompson |
| 1982 | Alex Lynch |
| 1983 | Glen Benoy |
| 1983 | Patrick Fitzgerald |
| 1984-1997 | Unknown |
| 1998 | Conrad Stang |
| 1999 | Chris Jackobson |
| 2000 | Matt Searle |
| 2001 | Thomas Rannelli |
| 2001 | Cameron Lymburner |
| 2002 | Matthew Romaschin |
| 2003 | Ron Phillips |
| 2004 | Dave Jenkins |
| 2005 | Chris Ball |
| 2006 | Chris Ball |
| 2007 | Tristan Bourelle |
| 2008 | ? |
| 2009 | Ben Taylor |
| 2010 | Liam Tiernay |