Robert M. Jennings

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

Bob was born and raised in Dorchester. As a graduate from Boston College High School in 1952 and later from Boston College in 1956, Bob was a proud “Double Eagle”. He attended Boston University where he earned his master’s degree. He married his wife, Pauline, in 1958 and began their family in Dorchester before settling in Weymouth in 1968. While attending college, Bob served in the Navy Reserve at the South Weymouth Naval Air Station.

Bob devoted his career to education. His first teaching assignment was in the Westwood Public Schools, followed by more than 40 years with the Milton Public Schools, where he taught high school history and ran the driver's education program. After retiring, he remained active in R.E.A.M. (Retired Educators Association of Massachusetts), serving two terms as president.

Bob had a lifelong passion for teaching as well as learning. Later in life he developed a love for photography and was always taking pictures and was often the backup photographer at the many weddings he attended. Although he held many roles and titles throughout his life, Bob always said his greatest and most important job was being a husband, father, and grandfather.

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

He 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.

Bob was the proudest grandfather to Patrick, Colin, and Caroline Buckley; David and Julia Jennings; Alexandra and Christopher Leaverton; Andrew and Katherine Ng and Matthew and Meghan Jennings. Great grandfather of Wyatt Buckley.

Relatives and friends are respectfully invited to the visiting hours for Bob on Thursday, March 12, 2026, from 4:00 to 7:00 PM in the CC Shepherd Funeral Home, 134 Pleasant Street (Columbian Square), South Weymouth.

Relatives and friends will gather at the funeral home Friday morning for a celebration of life at 9:30 AM prior to the Funeral Mass in the Immaculate Conception Church, Broad Street, East Weymouth, at 10:30 AM.

Burial will immediately follow at St. Francis Xavier Cemetery on the corner of Washington Street and Middle Street in East Weymouth.

In lieu of flowers, the family would appreciate donations to Cranberry Hospice & Palliative Care.  https://giving.bilh.org/bethisraeldeaconesshospitalplymouth/cranberry-hospice-annual-fund/