Robert Joseph (Bob) Cunniff (May 24, 1938 - November 14, 2023)

In loving memory of
Robert Joseph (Bob) Cunniff
  • May 24, 1938
  • -
  • November 14, 2023

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Surrounded by family, Robert Joseph (Bob) Cunniff passed away on November 14, 2023 at Gulf Coast Medical Center in Fort Myers after a long battle with Pulmonary Fibrosis. Bob was 85.

Born and raised in South Boston, MA, he was proud to be both a “Gatey” and a “Chippie,” which in South Boston meant he was a graduate of Gate of Heaven schools and played for the renowned Chippewa Boston Park League Football Team.

Bob was the husband to Elaine Cunniff and the late Lynda Cunniff, the mother of his four children. He leaves his family, daughters Karen Johnson and her husband Ray of Braintree, MA and Kelly Kennedy and her husband Mark of Quincy, MA; Bob’s sons Rob Cunniff and his wife Susan of Colorado Springs, CO and Sean Cunniff and his wife Tracy of Plymouth, MA.

Bob was the proud “Papa” to 6 grandchildren, Chris, Joshua, Ashley, Noah, and Grace Cunniff and Ben Johnson. He had one great grandson, Michael Brady.

He had two brothers. He is survived by Edward “Teddy” Cunniff of North Quincy, MA and is preceded in death by John Cunniff of Albany, New York. He also leaves two sisters-in-law Mary Claire and Marie Cunniff, several nieces and nephews, many friends and former colleagues.

Bob led a life of service. At the age of 21, he enlisted in the United States Army and was trained for Special Forces (“Green Beret”) and recruited and trained South Vietnam Montagnard fighters. Upon return to the States, he used the GI Bill to put himself through college and earned degrees in Education and School Administration at Boston State College (now UMASS Boston). He married Lynda and raised their family in Kingston, MA.

He taught Junior High science in Hingham for several years and then transitioned to the Silver Lake Regional School District in Kingston. He had a 25 year career there and filled many positions including Assistant Principal, Head Master, Director of Secondary Education and Assistant to the Superintendent. He retired in 2000.

Bob married Elaine in 1996. In 2015, they relocated to Fort Myers where he enjoyed golf, Red Sox and Minnesota Twins Spring Training, warm weather and life at the Hideaway Country Club. He was active in the Augusta community of the Hideaway serving on the Board as Director, Vice President and Secretary.

Bob was a dedicated member of the Lee County Sheriff’s Office Civilian Support Unit and V.O.I.C.E. program for several years. He was affectionately known as “Mr. Bob” to the students at the Villas Elementary School, which was his most recent assignment. He could be found routinely teaching students to read in addition to his duties as an assistant to the School Resource Officer. Although 85 years of age, he continued to serve, remained active and young in spirit.

Burial will be in the Massachusetts National Cemetery in Bourne on Cape Cod at a future date.

Baldwin Brothers Funeral & Cremation Society, Fort Myers is entrusted with final care.

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  1. Kathleen Mogayzel says:
    27 Nov 2023
    After reading his obituary, I have a renewed admiration for all his talents and contributions to any group he joined...a Renaissance man. He was generous with time and treasure to Coastal Printmakers which he and Elaine founded. The artistic side of him might not be known to some. Bob liked to tease and could hold his own amongst our group of mainly women printmakers. We miss you, and now it's forever.

  2. Mike Murray says:
    22 Nov 2023
    Bob was a great man and one of the reasons I’ve been a teacher for the past 29 years. I could not have become the teacher I am without his encouragement, guidance and support.

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