Game Changer: Kathy Masterson Reflects on Decades of Coaching, Leading and Winning

As a teacher, high school coach and athletic director, Kathy Masterson has shepherded a lot of student-athletes through high school sports programs over the years, beginning with her own alma mater, Southampton High School, in the mid-1990s. From there, positions followed at Shelter Island and Westhampton Beach — where she worked as a physical education teacher for several years before being named AD in 2006. In 2022, Masterson became the AD for the East Hampton School District. Earlier this month, Masterson announced that she will retire from her East Hampton position at the end of this school year. This week, Masterson joins editors Annette Hinkle and Drew Budd as well as news reporter (and sports lover) Cailin Riley to talk about the legacy of championship high school teams on the East End, her dedication to local athletes and her passion for building the best athletic program that she can.