In Memoriam: Robert J. Dowling – A Lifelong Commitment to Insurance and Community

Robert J Dowling

Robert J. Dowling, affectionately known as “Bob,” passed away peacefully in Canton on May 18, 2023. Born in Newton, Bob was a loving husband, father, brother, and grandfather who touched many lives with his kindness and thoughtfulness.

Bob is survived by his beloved wife, Elizabeth A. “Betty” Dowling; children Kathleen Dowling of Canton, Robert Dowling of Foxboro, Michael J. Dowling of Walpole, and Paul R. Dowling of Quincy, Ft Lauderdale, and Bangkok, Thailand; brother Milo John Dowling of Newport, RI, and N.C; and predeceased by siblings William H. Dowling and Claire Whynot. Bob was a proud and loving grandfather to Shannon, Nicholas, Jessica, Brooke, Jonathan, and Zachary.

Bob’s educational journey began at St. Charles School in Waltham, followed by Northeastern University, where he built a strong foundation for his career. After graduating, he joined Kemper Insurance and dedicated 29 years of his life to the company, working his way up to New England Branch Manager. In 1983, Bob left Kemper to pursue his entrepreneurial dreams, purchasing an insurance agency in Braintree. Starting with just two part-time employees, Bob’s hard work and dedication led to the growth of Dowling Insurance into one of the most respected insurance agencies on the South Shore, employing 21 people.

A man of many interests, Bob was an avid golfer and a member of Wampatuck Golf Club in Canton, Norfolk Country Club, Glastonbury Golf Club, Weatherford Country Club in CT, and the Leo Martin Golf Club. His passion for the sport was evident in his numerous accomplishments, including winning five Club Championships and the prestigious title of NE Left-handed Champion.

Bob’s involvement in his community extended far beyond his professional life. As a member of the Knights of Columbus Council 2095 in Canton, he actively contributed to the betterment of the community. He was also an active member of St. Gerard Majella Church in Canton, where he dedicated his time and energy to various initiatives. His commitment to the insurance industry was exemplified by his role as Vice President of the South Shore Insurance Agents Association and his membership on the Arbella Insurance Board of Directors since 1988.

In every aspect of his life, Bob was a loving, kind, and thoughtful individual who always put the needs of others before his own. His warm personality and unwavering dedication to his family, friends, and community will forever be remembered and cherished by all who knew him.

As we mourn the loss of John “Bob” Dowling, we also celebrate a life well-lived, filled with love, kindness, and thoughtfulness. His memory will live on in the hearts and minds of those fortunate enough to know him. May he rest in peace.

Relatives and friends are invited to attend a Funeral Mass at St. Oscar Romero Church, Canton Tuesday, May 23, at 11:00 am. Visiting hours omitted burial private. Donations may be made in Bob’s memory to Boston Med Flight 150 Hanscom Dr. Bedford, MA 01730 in lieu of flowers.

A memory or condolences can be left for the Dowling family here: Dockray & Thomas Funeral Home, Canton, MA

Agency Checklists’ interview with Bob Dowling about his growing and perpetuating Dowling Insurance

In June 2011, Agency Checklists published an interview with Bob Dowling. His commonsense observations about agency perpetuation and development ring as true today as they did then. We recommend this short interview to our readers as it is the voice of a master. The link to the interview is below:

Listening And Learning From A Master – Agency Checklists Talks With Bob Dowling, The Dowling Insurance Agency

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