Dean Conway
August 25, 1947–March 9, 2025
Dean Joseph Conway of Jamaica Plain was a teacher, soccer coach, mentor and friend who affected us with his vibrant curiosity, generous spirit and humble commitment to a kinder and more just world. He died peacefully at home from complications of Dementia with Lewy bodies on March 9 at the age of 77.
Born to Elizabeth and Joseph Conway, Dean lived in New York and Connecticut with siblings Jay and Jill before the family settled in Greenfield, Massachusetts. Always a hard worker, he studied rigorously at Deerfield Academy and then Georgetown University, where he was captain of the soccer team and graduated in 1970 with a bachelor’s degree in English.
An intuitive and gifted teacher for more than 40 years, Dean had a particular connection with and fondness for students at the seventh through ninth grade levels. He taught with a characteristic balance of humor, play and serious study. As a faculty member at Park School in Brookline from 1979 to 1997, he taught English, Latin and social studies, coached soccer and hockey, and served as Head of the Upper School from 1985 to 1991. Dean always highly regarded the community of teachers and staff at Park, and the friendships he developed there lasted through the end of his life.
Dean was the founding English teacher at Beacon Academy, a school for promising students with few resources, from 2005 to 2010. Many Beacon students have written moving letters of thanks to Mr. Conway, especially for his famed vocabulary lessons. Dean found the years at Beacon, before retirement, special and gratifying.
Engaged with the game of soccer and especially youth coaching throughout his life, Dean began working with Mass Youth Soccer in 1992 and was Head State Coach and Director of Coaching from 1997 to 2002. He genuinely enjoyed his long involvement in Jamaica Plain Youth Soccer, maintained reciprocal relationships with a community of European coaches and friends, and participated in several other organizations, including New England Scores and the Boston Breakers. Dean also coached and played hockey, and was a lifelong bike rider. He wrote the book Soccer Calling: A Handbook for Youth Soccer Coaches, , which was published in 2005. In 2006 Dean was the second-ever recipient of US Youth Soccer’s Fleck Award for Excellence in Youth Coaching Education, a national recognition for educating coaches with “integrity, honor, humor, and humility.” In 2024 Mass Youth Soccer announced the Dean Conway Coach Education Grant, honoring Dean’s passion for youth development in underserved communities.
Dean was involved with various organizations and schools, including Roxbury Community College, Fenway High School, Mother Caroline Academy, Nativity Prep, Squash Busters, the Haitian Multi-Service Center in Dorchester, and Sakala Youth Community Center in Haiti. He volunteered seemingly inexhaustible time to these organizations and others.
Dean was married to his wife, Cindy, for 47 years. Their two daughters, Sarah and Megan, were a great source of joy for Dean. Dean lit up when he talked about his family; he and Cindy took a sincere interest in the girls’ activities and whole-heartedly encouraged them to pursue what mattered to them. Much of what was important to Dean became vital to his daughters’ lives and work, such as music and writing for Megan, and sports and conservation for Sarah.
Many who knew Dean express an inability to convey their full appreciation for him. He was well loved and his achievements were significant, yet humility was central to his way. Always with a positive beat and light touch, he shared his eclectic interests and enthusiasm for learning with nearly everyone he met.
Dean is survived by his wife, Cindy; his daughters, Sarah and Megan; his brother, Jay; his sister, Jill Villatoro; Jay’s wife, Jean; Sarah’s wife, Camille Palumbo; his granddaughter, Mara Conway Palumbo; his aunt Marilyn Eade and her four children and many dear friends.
The family gives thanks and holds gratitude for this remarkable man and the extraordinary impact he had on so many people. Peace and love.
A remembrance celebration will take place April 6 at Mann Rodgers & Commonwealth Funeral Home in Jamaica Plain, with visitation from 12 noon to 2 p.m. and a service, which will be livestreamed, at 2 p.m. A reception will follow.
In lieu of flowers, memorial donations may be made to Sakala Youth Community Center in Haiti (sakala-haiti.org/donate) or to Mass Youth Soccer (512 Old Union Turnpike, Lancaster MA, 01523) by check with “Dean Conway” in the memo.