Obituary: Leonard Francis D’Orlando, 89, Former RMHS Principal

South Yarmouth – Leonard Francis D’Orlando, “Len”, 89, of South Yarmouth, MA, passed away on January 6 in Hyannis, MA.

Len was born in Revere, MA to the late Anne and Leonard D’Orlando on May 4th, 1932. He graduated from Winthrop High School in 1949. He went on to earn an AB degree from Northeastern University in 1954, and his MAT degree from Harvard Graduate School of Education in 1955. Following graduation, Len enlisted in the United States Marine Corps and was honorably discharged in 1958. That same year, he began his teaching career at Reading Memorial High School, serving as classroom teacher, department chairman, and vice principal until he was named principal in 1978. He remained in that role until his retirement in 1986, at which point, he and wife Lillian built and moved into their dream home in South Yarmouth, MA where they spent the remainder of their days loving and caring for one another.

Len is survived by his two sons, Leonard Jr. of South Yarmouth, MA, his wife Maria (Ciccoria), and their three daughters, Nina and her husband Luke Martin of Minneapolis, MN, Kristina and her fiancé, Daniel Kliment of Harwich, MA, and Adrian of Dover, NH. Also, his son William (Bill), his wife Kimberly (Rotondi), and their two daughters, Allison and Abigail, all of North Reading, MA. Len is also survived by his sister Elaine O’Brien and her late husband Charles of Cherry Hill, NJ, nephews Christopher and Thomas, and niece Cathy, brother Dr. John D’Orlando, his wife Bonnie of Nahant, MA, and brother Richard D’Orlando and his lifelong partner, Gretchen Benkert, also of Nahant, MA. Len is predeceased by his adoring wife of 62 years, Lillian(Hopkins).

In recent years, Len spent all of his time caring for Lillian as her physical being became victim to a degenerative condition which eventually took her from us on May 17, 2020. Len longed for the day he would reunite with Lillian to enjoy eternal life.

Arrangements under the direction of Chapman Funerals & Cremations, Yarmouth.

Services to be private for immediate family only.

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