Morton Starr Cressy, Jr. was a 1927 graduate of the United States Naval Academy and an avid sailor. The Cressy Trophy was presented to the Naval Academy by his wife in his memory. The Cressy Trophy Regatta was originally a multi-division invitational high school regatta sailed in 420s and Lasers, hosted by USNA since 1979, sometimes in conjunction with the ISSA Mallory Trophy Regatta. The Deed of Gift was changed in 1985 to rededicate the Cressy Trophy as the National High School Singlehanded Championship trophy, sailed in Lasers. Since 1990, it has been recognized by the Interscholastic Yacht Racing Association, now the Interscholastic Sailing Association (ISSA), as the ISSA National Singlehanded Championship. Competition now rotates annually among the several ISSA districts, in the Fall of the preceding calendar year.

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