The Dowd story begins in 1865, when hard times fell in County Kerry, Ireland, causing James J. Dowd, his wife and 14 children, to leave their native soil to make a better life in America. The immigrant family settled in Holyoke, Massachusetts where Mr. Dowd took a job in a local textile mill. The Dowds soon became United States citizens, renouncing their Irish citizenship, but not their heritage.

One of the children, named James J. Dowd after his father and grandfather, went on to found The Dowd Insurance Agency in 1898, creating a legacy that now spans five generations, making it the oldest insurance agency in Massachusetts under continuous family ownership.


Mr. Dowd adapted the agency’s name to James J. Dowd & Son in anticipation of his son entering the business following his graduation from Holy Cross College. That son, also named James J. Dowd, joined the firm in 1916 following his father’s death. He gave up a promising career as a professional baseball pitcher with the Cincinnati Reds, and a contract for a “lucrative” $2,200 salary, to return to Holyoke and his father’s business.


Business prospered, and the agency outgrew its space in the former Ball Building. Mr. Dowd and his father-in-law Edward A. Sheehan constructed the Lincoln Building on Suffolk Street. That October, the agency moved to new quarters at 96 Suffolk Street, Holyoke.


On September 15, 1947, after serving as a French interpreter in the US Army Signal Corps and participating in the Normandy D-Day invasion of France, James J. Dowd Jr. joined the firm founded by his grandfather and now led by his father.


Another son, John E. Dowd, who was also a veteran of World War II, entered the business in December 1951 following his graduation from Holy Cross College. Shortly after, the business was incorporated under the name James J. Dowd & Sons Insurance Agency, Inc. By this time, the sons were thoroughly indoctrinated into the concept of the agency’s primary responsibility––its customers.


The agency continued to grow and prosper, moving to 136 Suffolk Street due to the need for additional office space and customer parking.


In March 1974, the sudden death of John E. Dowd brought about the entry of the fourth generation of the family into the business. James J. Dowd III joined agency in August, leaving his position as a commercial casualty underwriter with Fireman’s Fund American in Hartford. He had also previously spent a year with Equitable Life Assurance Society.


The following year, Robert W. Gilbert Jr. arrived on the scene. He had been a senior marketing representative for Aetna Casualty & Surety, and The Dowd Agencies had been one of his regular accounts. Recognizing Bob’s exceptional talents and integrity, James J. Dowd Jr. offered him a partnership in the firm.


After graduating from Saint Michael’s College and completion of a two-year training program with Fireman’s Fund Insurance Company in Parsippany, New Jersey, John E. Dowd Jr. joined the fourth generation of Dowds at the agency.


Now one of the largest insurance agencies in the region, the firm moved to its newest facility at 14 Bobala Road at Ingleside/West Holyoke with branch offices in Amherst and Southampton, becoming a regional presence in the insurance industry.


Having joined the agency in 1994, David W. Griffin Sr., became a partner at The Dowd Agencies.


After graduating from Bentley College and working as a commercial accounts underwriter at Liberty Mutual Business markets in Charlotte, NC, David W. Griffin Jr., son of partner David W. Griffin Sr., joined The Dowd Agencies as an account manager, marking the second generation of Griffins at the agency.


The Dowd Agencies acquired the Frank Moskal Insurance Agency, founded in 1930, expanding into Indian Orchard. This began several years of expansion and acquisitions during which The Dowd Agencies acquired The Orchard Insurance Agency and Collins Insurance Agency, further expanding its footprint into Springfield and Ludlow.


The Dowd Agencies joined the Alliance Main Street Insurance Group, LLC, a new entity comprised of 12 independent insurance agencies throughout Massachusetts, to provide greater leverage when negotiating with major insurance carriers on behalf of customers.


Quincy Perpetuation Partners (QPP) became a minority partner with The Dowd Agencies, LLC. QPP was developed to assist Quincy Mutual Insurance Company in Boston achieve strategic objectives relating to the future growth and operational success of their business.

Also in 2016, John E. Dowd III (Jack), son of John E. Dowd Jr., joined The Dowd Agencies, marking the fifth generation of Dowds employed at the oldest insurance agency in Massachusetts under continuous family ownership. After graduating from Saint Michael’s College, Jack spent three years working in the insurance industry in Boston, and then participated in the 18-month Agents Sons & Daughters Training Program for underwriting at Quincy Mutual Insurance prior to joining the family business.


The Dowd Agencies drops the former partner names of Cray in Hadley, Moskal in Indian Orchard and Collins in Ludlow.


Former partner and Chairman of the Board Robert W. Gilbert retires after 43 years of dedicated service to The Dowd Agencies. After being promoted to vice president in 2017, David W. Griffin Jr. became the new third partner at The Dowd Agencies in 2018.


Evan Dowd joins the fifth generation of Dowds at the agency and The Dowd Agencies Southampton office moves to new location at 124 College Highway.


The Dowd Agencies acquired Wilcox Insurance Agency, founded in 1923, adding two more branch offices in Westfield and Feeding Hills.


Having joined The Dowd Agencies in 2016, John E. Dowd III (Jack), son of John E. Dowd Jr., became vice president. Also in 2022, The Dowd Agencies acquired Ideal Insurance, founded in 1989, expanding the agency’s footprint with offices in Chicopee and Ludlow.


Today, the Dowd story continues as the three partners and the dedicated team working with them continue the time-honored commitment to “The Agency’s Primary Responsibility: Its Customers.” They carry on a long tradition built on trust over a century ago by a man who forged ahead with new ideas that would result in lasting service to his community.