Sailing Professional ~ Brand Ambassador  ~ World Champion

Skip Dieball’s sailing career has evolved from regional champion to world-wide sailing icon, as evidenced by his nomination for the ROLEX YACHTSMAN OF THE YEAR (2004 & 2015), nomination for US SAILINGS Sportsman of the year (2010), US SAILING Champion of Champions (2009) and World Champion (2015 & 2022).

In his sailing career, Dieball has earned 40 Major One Design Titles (World, Continental, National & Midwinter).  In addition to these achievements, he actively pursued an opportunity to represent the United States in both the 2000 and 2004 Olympic Games.  In August 2019, Dieball and his teammates will represent the USA in the Pan American Games in Lima, Peru.  In February 2022, Dieball won the Renegade Iceboat World Championship.

Dieball continues to build on his success on and off the water. He is the Managing Director of Sheridan Shore Sailing School in Wilmette, Illinois.  There, he and his team inspire new sailors to learn the beauty of sailing.  

Born and raised in Toledo, Ohio, Dieball graduated from Eastern Michigan University.  He lives in Chicago’s North Shore community, with his wife Laurie and their daughter Meghan, daughter Mallory and son Max.  They are members of the US SAILING, Inter-Lake Yachting Association, North Cape Yacht Club, Four Lakes Ice Yacht Club, Wilmette Harbor Club and various class associations.

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