Robert M. Jennings

Robert M. Jennings, age 91, of Weymouth, passed away on March 5, 2026.

Born and raised in Dorchester, Bob graduated from Boston College High School in 1952 and from Boston College in 1956, earning the distinction of being a proud “Double Eagle.” He later received a master’s degree from Boston University. In 1958 he married Pauline Houlihan, and together they raised their family first in Dorchester before settling in Weymouth in 1968. While attending college, he served in the Navy Reserve at the South Weymouth Naval Air Station.

Bob devoted his career to education, first teaching in the Westwood Public Schools and then spending more than forty years with the Milton Public Schools, where he taught high school history and directed the driver’s education program. After retirement, he remained active in the Retired Educators Association of Massachusetts and served two terms as its president. He maintained a lifelong passion for both teaching and learning. In later years he developed a deep love for photography, capturing moments at countless family gatherings and frequently serving as the backup photographer at weddings he attended. Though he held many roles throughout his life, Bob always considered his most important work to be that of husband, father, and grandfather.

He was predeceased by his beloved wife, Pauline Jennings (Houlihan), and by his parents, Henry and Margaret (Mantle) Jennings.

Bob is survived by his loving children: Mary-Elizabeth Jennings of Grafton; Elaine M. Buckley and her husband Kevin of Duxbury; Michael R. Jennings and his wife Kathleen of Kingston; Paula M. Leaverton and her husband Gary of Plymouth; Annemarie Ng and her husband Kai of Halifax; Stephen M. Jennings and his wife Kristina of Colorado Springs, Colorado; and Christine G. Jennings of East Falmouth. He was the proud grandfather of Patrick, Colin, and Caroline Buckley; David and Julia Jennings; Alexandra and Christopher Leaverton; Andrew and Katherine Ng; and Matthew and Meghan Jennings, and the great-grandfather of Wyatt Buckley.