Robert Kenneth O'Brien

He was predeceased by 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.

He is survived by his son, Brendan R. O’Brien and daughter in law, Julie Grasso and grandchildren, Samuel and Gianna of Portsmouth, NH; his lady friend, Donna M. Cohen of Jupiter, FL; a sister Janet A. Martin of Leicester, MA and her four children; and trusted friend and colleague Laurie Weil.

Bob was born December 8, 1934 in Worcester, MA and attended Worcester public schools, then graduated from what is now Worcester State University in 1958. Bob and Barbara were longtime supporters of Worcester State and created a number of scholarships and programs at the university. The department of education at Worcester State was renamed The Barbara (Hickey) O’Brien ’57 Education Department in 2015 and Bob received an honorary Ph.D from the university in 2018. Bob and Barbara’s scholarships have helped more than 150 Worcester State students.

Bob joined State Mutual Life Insurance Company as an Actuarial Trainee, later becoming an underwriter and eventually rising to Vice President of Group Reinsurance. After retiring from State Mutual in 1989, Bob founded Health Reinsurance Management, which later partnered with Cologne Life Re to become Health Reinsurance Management Partnership (HRMP.) HRMP grew into a worldwide company and remains in business to this day, based in Danvers, MA. Bob sold his interest in HRMP in 2003 and retired.

Bob was an active pilot with an Instrument Rating, owned a succession of single-engine airplanes, and often flew himself on business trips.

Bob enjoyed golf and was at different times a member of the Georgetown Golf Club in Massachusetts, Abenaqui Country Club in Rye, NH, and Jonathan’s Landing in Jupiter, Florida.

At different times, Bob resided in Worcester, Westboro, Revere, Hyannis and Newburyport, Massachusetts; Portsmouth, NH, and Jupiter, Florida.

Bob and his wife Barbara traveled the world and visited all seven continents.

Bob was known in all of his communities as a kind and thoughtful man who performed countless favors for others. His friends and neighbors knew him as someone who always had a smile and a handshake, a container of homemade pasta sauce, and even a doggie treat available when the situation arose.

Celebrations of Bob’s Life will be held later this summer in the Worcester, MA area, and in the fall in the Jupiter, FL area.