Optimist Skipper Trophy (Sherin Skipper of the Year)
Donated in 1994 by the Jim Phillip family in honor of Michael H. Sherin, who was a major force in launching the Optimist fleet on Geneva Lake, this silver tray is awarded annually to the Optimist skipper of the year. GLSS racing coaches and the director select the winner based on the skipper’s leadership on and off the water as demonstrated by work ethic, sportsmanship, attitude, sailing performance, teamwork, and determination to improve. Mike Sherin, who is a long-time member of the LGYC race committee and a frequent principal race officer, served as president of the Geneva Lake Sailing School in 1989 and 1990 and as commodore of Lake Geneva Yacht Club in 2000 and 2001.
- 1994 Vincent Porter
- 1995 Vincent Porter
- 1996 Bill McCloy
- 1997 Matt Bollero
- 1998 David Lyon
- 1999 Patrick Doran
- 2000 Patrick Doran
- 2001 Jake Jacobs
- 2002 Charlie Morris
- 2003 Veronica Doran
- 2004 Charlie Morris
- 2005 Joe Rolander
- 2006 Leslie Poole
- 2007 Griffin Rolander
- 2008 Mitchell Lee
- 2009 Griffin Rolander
- 2010 Stuart Henry
- 2011 Mark Davies
- 2012 Mark Davies
- 2013 Chapman Petersen
- 2014 Chapman Petersen
- 2015 Chapman Petersen
- 2016 Aran Freytag
- 2017 Joseph Plummer
- 2018 Jacob Zils
- 2019 Connor Pecht
- 2020 Annie Samis
- 2021 Sophie Niemann
- 2022 Sophie Niemann
- 2023 Tilly Niemann