About The Campaign

Meet the Leadership

photo of the Kennedys

“We feel so blessed to have watched our daughter’s progression as a leader in her community in academics and sports…[through] the opportunities that Winsor provides.”

Sam Kennedy P‘23

Amanda and Sam Kennedy P’23

Amanda and Sam Kennedy are proud to support Winsor’s investments in everything that keeps the institution strong and moving forward: our faculty, students, staff, and facilities. Sam is president and CEO of the Boston Red Sox as well as Fenway Sports Management. Now in his 19th year there, Sam originally joined the organization as vice president of corporate partnerships and rose to the role of executive vice president and COO, overseeing ticketing, sales, sponsorships, and marketing. Sam and Amanda both graduated from Trinity College, where he now serves on the Board of Fellows. He also serves on the Beth Israel Deaconess Medical Center Trustee/Advisory Board and Marketing Committee; the Trinity College Board of Fellows; Winsor School Board of Trustees; Dana-Farber’s Visiting Committee for Institute Initiatives; The BASE’s Advisory Committee; and Camp Harbor View Board of Directors. Sam has served as a Trustee at Winsor since 2018. Amanda is a chartered financial analyst (CFA) and member of the CFA Boston Society. She has served on the Trinity College Alumni Association Executive Committee and is currently engaged with REACH Beyond Domestic Violence, as well as the Wellesley Free Library Foundation.  Amanda is a Winsor corporator and longtime member of the Parents Association, serving as both a class rep and co-chair. They live in Boston with their two children, Jimmy and Allison ’23. 

Our goal is ambitious. Our success is guaranteed, with your support.