Personal
- Bachelor of Arts Degree in Management, Sonoma State University, California
- Commodore St. Thomas Yacht Club 1989 & 2002
- President Caribbean Sailing Association 2012 – 2015
- Member Advisory Council, Sailing Yacht Research Foundation 2016
- St. Thomas-St. John Chamber of Commerce – Bill LaMotta Community Service Award 2003
- Rotary Club of St. Thomas Paul Harris Fellow Award
- Virgin Islands Medal of Honor 2008
- Inducted into the National Sailing Hall of Fame 2023
Olympic Classes
- 1984 Olympic Games, Los Angeles; Finn Class, 11th Place
- 1986 Central American and Caribbean Games, Santa Domingo; Laser Class, Silver Medal
- 1988 Olympic Games, Pusan, Korea; Finn Class, Silver Medal
- 1990 Goodwill Games, Seattle, USA; Finn Class, Bronze Medal
- 1995 Pan Am Games, Argentina; Match Racing, Silver Medal
America’s Cup
- 2000 Louis Vuitton Cup; Team Dennis Conner, 3rd Place Challenger
- 2003 Louis Vuitton Cup; Oracle-BMW Racing, 2nd Place Challenger
- 2007 America’s Cup; Alinghi, Winner
Match Racing
- 1997, 1998 Trofeo Challenge; 1st
- 1998, 1999, 2001, 2002 Congressional Cup; 1st
- 2001 Bermuda Gold Cup; 1st
- 2002 Stienlager Cup; 1st
- 2002 Match Racing World Tour; 1st
- 2005 Portugal Match Cup; 1st
- 2006 Monsoon Cup; 1st
- 2009, 2010 Budget Marine Match Race; 1st
- 2009 Carlos Aguilar Match Race; 1st
- 2011 Pete Sheilds Match Race; 1st
- 2011 Gill BVI Match Race; 1st
Caribbean
- Heineken Regatta; 1st (4x)
- International Rolex Regatta; 1st (8x)
- BVI Spring Regatta; 1st (8x)
- Antigua Sailing Week; 1st Overall (3x)
Grand Prix and Super Yacht
- 1989 50’ World Cup; Carat, 1st
- 1990 Maxi World Championships; Matador2, 1st
- 2011 Maxi Yacht Rolex Cup; 1st
- 2012 Loro Piana Superyacht Cup; 1st
- 2013 Newport Bucket; P2; 1st
- 2014 Maxi Yacht Rolex Cup; Highland Fling 82, 1st
- 2015 Loro Piana Superyacht Cup; P2; 1st
- 2015 Block Island Race; Comanche; 1st
- 2016 St. Barths Bucket; 1st
- 2017 52 Super Series Porto Portals; 1st
- 2018 Maxi Yacht Rolex Cup; 1st
- 2019 Palma Superyacht Cup; 1st
- 2020 TP52 Super Series Capetown; 2nd
- 2021 Voilles de St. Tropez; 1st
- 2022 Palma Superyacht Cup; 2nd
- 2023 St. Barths Bucket; 1st
- 2024 St. Barths Bucket; 2nd