Robert O'Brien Obituary, Robert (Bob) K. O'Brien Died In Jupiter, Florida At The Age Of 88

Robert O’Brien Obituary, Robert (Bob) K. O’Brien Died In Jupiter, Florida At The Age Of 88

Robert O’Brien Obituary, Death – At the age of 88, Robert (Bob) K. O’Brien died on June 2, 2023 in Jupiter, Florida. His wife of 57 years, Barbara Hickey O’Brien, son Kevin R. O’Brien, and parents Arlene M. Lanois O’Brien Knight and Robert Ivor O’Brien before him in death. Brendan R. O’Brien, daughter-in-law Julie Grasso, and grandsons Samuel and Gianna of Portsmouth, NH; lady friend Donna M. Cohen of Jupiter, FL; sister Janet A. Martin of Leicester, MA and her four children; and loyal friend and colleague Laurie Weil survive him.

Bob was born in Worcester, Massachusetts on December 8, 1934, and attended Worcester public schools until graduating from what is now Worcester State University in 1958. Bob and Barbara were longtime Worcester State supporters who established a variety of scholarships and activities at the university. The Barbara (Hickey) O’Brien ’57 Education Department at Worcester State University was designated in 2015, and Bob got an honorary Ph.D. from the university in 2018. More than 150 Worcester State students have benefited from Bob and Barbara’s scholarships.

Bob began his career as an Actuarial Trainee with State Mutual Life Insurance Company, eventually advancing to the position of Vice President of Group Reinsurance. Bob started Health Reinsurance Management after leaving State Mutual in 1989, and company later merged with Cologne Life Re to become Health Reinsurance Management Partnership (HRMP). HRMP developed into a global corporation that is still in operation today, headquartered in Danvers, Massachusetts. Bob retired after selling his stake in HRMP in 2003.

Bob was a licensed pilot with an Instrument Rating who owned a number of single-engine planes and frequently flew himself on business trips. Bob loved golf and was a member of the Georgetown Golf Club in Massachusetts, the Abenaqui Country Club in Rye, New Hampshire, and Jonathan’s Landing in Jupiter, Florida. Bob has lived in Worcester, Westboro, Revere, Hyannis, and Newburyport, Massachusetts; Portsmouth, New Hampshire; and Jupiter, Florida.

Bob and his wife Barbara traveled throughout the world, visiting all seven continents. Bob was renowned across his communities as a nice and compassionate man who did several favors for others. His friends and neighbors remembered him as someone who always had a smile and a handshake, a container of homemade pasta sauce, and even a doggie treat on hand when a crisis arose. Celebrations of Bob’s life will take place later this summer in Worcester, MA, and in the fall in Jupiter, FL. Please send an email to for further information.