Joseph M. Sullivan

Joseph Michael Sullivan, age 81, beloved educator, mentor and role model who positively impacted many lives throughout his storied careers in education and the United States Army Reserves, passed away peacefully with his family by his side on October 25, 2024, at Massachusetts General Hospital in Boston.

Born in Medford, Mass., on April 19, 1943, he was the son of the late Lillian Angela (Brennan) Sullivan and William Joseph Sullivan. He was raised in the Edgeworth section of Malden and attended the Immaculate Conception Elementary School and Malden Catholic High School.

He graduated from Providence College with a bachelor’s degree in English in 1965. Some of his best memories at Providence are when he proudly played on the Friars men’s ice hockey team, where the team made its first appearance in the NCAA Frozen Four and won the 1964 ECAC Championship. He earned a master’s degree in Adult Basic Education from the University of Maine in 1967, a master’s degree in teaching American studies from Salem State College in 1969, a Certificate of Advanced Graduate Studies from Boston University in 1977 and a Doctorate degree in Leadership in Schooling from the University of Massachusetts-Lowell in 2001, where he was awarded the Best Dissertation Award. He is also a 1985 Graduate of the United States Command and General Staff College.

Dr. Sullivan taught at the Massachusetts Correctional Institution at Norfolk from 1966 to 1968, before transferring to the Correctional Institution at Concord as the Principal of Schools from 1968 to 1974. He was appointed Supervising Principal of the Massachusetts Department of Corrections from 1975 to 1977, where he extended the prison schools into the community throughout the state. 

In 1977, he was thrilled to be selected as the Vice Principal at Wakefield Memorial High School and remained in this role until 1995. It was at WHS where he developed his legendary nickname “The Warden” and earned a reputation for his tough but fair discipline, kindness, and dedication to preparing his students for life. He also served as acting Principal at WHS from 1992 to 1995. He was Principal of Carver High/Middle School from 1995 to 1998 before being selected as Principal of Gloucester High School in 1998. He retired from the Principalship at Gloucester schools in 2008 and became the Principal of Saint Joseph’s School in Wakefield, where he has served for the last 16 years. He often said his time at Saint Joseph’s School brought him some of the happiest and most fulfilling moments of his career.

Dr. Sullivan enlisted in the Army Reserves in 1965 as a Private and rose to the rank of Colonel, where he served as the Commander of the 399th Combat Support Hospital, Executive Officer for the 351st General Hospital and selected as Deputy Chief of Staff-Logistics for the 94th Regional Support Command before retiring in 2003.

Dr. Sullivan received many awards throughout his life including a Legion of Merit, three Meritorious Service Medals, several Army Commendation Medals, the Paul Harris Fellow award by the Gloucester Rotary Club, the 2004 Gloucester Entrepreneur of the Year Award, and The Harvard University Alumni Association-Harvard Book Award for Leadership in 2008. He was also elected to the Principal’s Cabinet of the Catholic Schools of the Archdiocese of Boston in 2021.

As a loving husband, father, grandfather, brother and devoted friend, Dr. Sullivan touched the hearts of everyone who knew him. His family was his greatest joy, and he dedicated his life to loving, supporting, and guiding them, right up until the very end of his life. He was a quietly faithful person and took great comfort from time spent at St. Joseph Parish where he attended Mass regularly, found quiet reflection in the chapel and participated in the men’s bible study group. He could often be found in the stands cheering on his grandchildren at sporting events, plays and award ceremonies, fly fishing at Spot Pond, eating orange candy slices and perfecting his amateur photography skills, never letting a hurricane or Nor’easter deter him from getting the perfect picture.

Dr. Sullivan is survived by his wife Maureen Sullivan, with whom he shared 56 wonderful years of marriage. He was the loving father of Erin Squeglia and her husband Peter of Reading, Mark Sullivan and his wife Denise of Oakland, Florida, and Brian Sullivan and his wife Kelly of Wakefield. He was the adoring Grampy to Peter, Brynn, Mae, Lily, Patrick, Dylan, Morgan, and Mason. He is predeceased by his brother William M. Sullivan. 

Visitation for relatives and friends will be held at the McDonald Funeral Home, 19 Yale Ave., Wakefield, on Sunday, November 3 from 1 - 5 pm. His Funeral Mass will be celebrated in St. Joseph Church, 173 Albion Street, Wakefield, on Monday, November 4 at 10:00 am. Interment, Forest Glade Cemetery, Wakefield.

In lieu of flowers, donations to support scholarships for students in need may be made to Saint Joseph School, 15 Gould Street, Wakefield, MA, 01880.