Skip Flanagan spent his formative years in Maryland where he attended and graduated from St. Paul's School. While at St. Paul's, he was a Kinsolving Scholar and earned All-Maryland honors while participating in football and lacrosse. In 2009, the school presented the Alumnus of the Year Award to the 1963 graduate.
Flanagan's undergraduate and graduate degrees were garnered at Rutgers, Harvard, and Michigan respectively. His areas of study include English, history, adolescent psychology, and education. He has done postdoctoral work at Johns Hopkins.
Serving as a faculty master and then the Dean of Students at Avon Old Farms from 1972 to 1982, Skip departed Connecticut to become the headmaster at Western Reserve Academy. He held this post for 26 years. During that same time he was the Chairman of The National Association of Boarding Schools and The English Speaking Union's Secondary School
Exchange Program. Recently he was recognized by the United States Congress for his contribution to education at the national level.
Presently, his duties as Dean at Avon span the areas of admissions, college placement, and development. He is also the varsity lacrosse coach. Flanagan is in the Lacrosse Hall of Fame (a regional selectee) and is a member of Avon's Athletic Hall of Fame as well. Further, he was accorded the honor of being named to the Under Armour All-America Squad as Head Coach in 2008. In 2010, he will be on the coaching staff of Team England as they participate in the World Lacrosse Championships to be held in Manchester, England. Lastly, he continues his service in the United States Coast Guard and is a Flotilla Commander, reporting on a monthly basis.
Skip and his wife, Britt, also a professional educator, have two daughters and five grandchildren, all of whom reside in Connecticut.