For J. Barry Driscoll, insurance man, perseverance is a trump card in life

J. Barry DriscollJ. Barry Driscoll

Barry Driscoll has taken good notes on life for 82 years now and the sketchpad of his character lays out both a standard for success in a business set up to serve others and a lesson in what a gut will to persevere can make happen, the cornerstones of the insurance business he founded more than a half century ago at a rented desk in a downtown Boston high rise: the J. Barry Driscoll Insurance Agency.

The young man of 1960 took an industry known for its tedium and core densities, and made success in it personal. So personal, in fact, that today four of his children own and operate The Driscoll Agency, one of New England’s leading insurance firms, while still learning from a role model of a father who comes to work every day, yet still finds time for his second love—a round of golf.

In an interview with the Boston Irish Reporter, Driscoll tells the archetypal story of a lunch conversation decades ago with a lawyer representing a large Boston construction firm who was sifting through local insurance companies for the right match. After the meal, Driscoll, an academic of sorts—a “Double Eagle” out of BC High and Boston College— asked the attorney how he had fared in the interview. “Well, you’re not smarter than the others; you just work harder,” the attorney said.

Driscoll got the business, and he and his family have been building on that experience ever since, their goal always being to work harder and smarter and offer the finest in service to hundreds of businesses and thousands of individuals across the region.
When Driscoll set out on his own at the age of 30 with little more than change in his pocket to rub together, he was determined to treat individuals the way he wanted to be regarded. “I’ve done that all my working life,” he says.

J. Barry Driscoll, with heritage ties to Cork, is old school in ways that the rest of us need to return to the classroom to learn about. All of the technologies available to business today, he says, all of the social media and techniques for completing a transaction are fallow without “heart” —a collective commitment to serve others. Always. It is a commitment reflected through the lives of his five children and his wife, Kathryn (Cauley), originally from Dorchester.

Such resolve was instilled in childhood. Barry, one of five siblings, was born in Milton. His father, Daniel, who grew up in Roxbury, ran a Boston insurance agency, the Associated Mutual. His mother, Edith, who was raised in Dorchester, died when he was four. Early on, the young Driscoll learned the rudiments of multi-tasking, precision, and organization. His dad, until he remarried, juggled family and work, keeping all the precious balls in the air. Family dinners were an example.

“Like clockwork, we ate family dinners from Sunday through Friday at precisely 6 p.m.,” recalls Driscoll. “Then on Saturdays, we ate at 7 p.m. None of us as kids could figure it out. We finally realized that Dad had to work Saturday mornings, then he played golf at Wollaston, his only break of the week. He was that dedicated to family and work. It was a work ethic instilled in all of us.”

That work ethic was amplified through extended family. His wife’s father, a renowned physician, was Health Commissioner of the City of Boston and the personal physician of the legendary Mayor James Michael Curley. It was no surprise that many years ago, Dr. Cauley purchased a summer home in the Minot section of Scituate on the “Irish Riviera,” just down the street from the mayor’s retreat. It was at the nearby Cliff Hotel in Scituate that Barry met Kathryn.

Driscoll’s paternal grandfather, Daniel, was secretary of the powerful state branch of the American Federation of Labor (AFL), and worked hard to secure fair pay and benefits for AFL members and redemptions where deserved. A gripping story marks the family memory of this grandfather:

While sitting in the State House anteroom of Gov. Curtis Guild’s office in 1907, seeking a pardon for an AFL member, Daniel encountered a man with a handgun entering the room aiming to shoot the governor. Instead, he shot AFL president Edward Cohen twice in the head at close range, mistaking him for the governor, then bullets hit Daniel Driscoll once in the head, and injured a third man. Cohen died from his wounds.

State House aides, along with Gov. Guild, overpowered the gunman, and the governor assisted in caring for the wounded. “It was simply the deed of a maniac running amuck,” Guild was quoted in a New York Times report on the shootings. As he was being dragged from the executive wing, the gunman, who had just been released from the Danvers Asylum, declared, “I meant to shoot the governor!” Daniel Driscoll was taken by horse-drawn carriage to Massachusetts General Hospital for treatment and recovery.

Growing up in Milton was far less intense for Barry Driscoll, more atypical of the day, plenty of pickup basketball, football, and baseball while attending grammar school and junior high school. He and his family were members of St. Mary of the Hills parish in Milton.

“A neighborhood priest used to come down to Milton sandlots, roll up his cassock, and play baseball with us,” Driscoll recalls. “He told us that we should be going to Catholic high school. Few did in those days, but my brother Dick and I carefully considered the appeal, and went to BC High, then on to Boston College.”

It wasn’t an easy ride. “In those days, there were no school buses and we had to take a trolley from Milton to Dorchester where we hopped a subway and another trolley car to the South End where BC High was located then. Since the school had no gym or playing fields in those days, we had to commute to the City of Boston gym for basketball and Franklin Field for football.”

Driscoll played basketball in high school and his brother, a former chairman of the board of Bank of New England, played basketball and football. “It was a long ride home, then dinner, then two to three hours of homework.”

Commuting, however, wasn’t a game- changer for Driscoll. After BC High, he was off to Boston College, pursuing a degree in economics and working summers at the Kemper Insurance Company at the urging of his dad. The direction was symbiotic.
The Korean War was brewing in those days, and after graduating from BC, Driscoll enlisted in Officers Candidate School (OCS) in Newport, Rhode Island, and was assigned duty for 36 months on a Navy destroyer. After his tour, Driscoll worked fulltime at Kemper Insurance for three years as a marketing representative, then joined his dad’s firm. When his father died, a doleful moment that still resonated with him, he decided to start his own firm in 1960.

“I had four children and no money,” he says. “But it was the only path that made sense to me.”

A man of intense vision, he endured, building a successful insurance business with a focus on the construction industry. The Driscoll Agency (, located on Longwater Circle in Norwell, now offers a full range of commercial and personal policies, surety bonds, group benefits and claims. Much of the recent growth has come via the hardworking hands of Driscoll’s children: Dennis, Jay, Jane, and Sally. Son Brian works for a Boston insurance company.

Reflecting on the second generation, Driscoll says, “I never forced or encouraged my children to join the firm. They had to ask. I told them early on that if they enjoyed coming to work at their other jobs, they should stay there.”

The children made individual decisions to join their father at work and expand the firm as they followed their father’s path in close involvement with industry organizations and charitable work. Over the years, the Driscoll Agency has donated more than $1 million to organizations like Boston College, BC High, Fontbonne Academy in Milton, Make A Wish Foundation, Rosie’s Place, The Jimmy Fund, National Ovarian Cancer Coalition, Massachusetts Melanoma Foundation, Friendship Home and The Foundation for Marisol’s Journey and Habitat for Humanity, among others.

Like their father, the Driscoll family takes its business personally. Not the most technically savvy person on the planet, Barry Driscoll is pleased his children have an age-appropriate grasp on high tech and social media, essential in these times to growing any business.

“Insurance is not a sexy industry,” Driscoll says, “but my children have found state-of-the-art ways of communicating the vision here. As far as Facebook goes, it’s a little too tricky for me.”

In his ninth decade, Driscoll is sanguine about the present and the future in his patriarch’s role, coming to work regularly, loving and guiding his children, and getting in some, chasing that five handicap he once owned.

“I’ve been blessed throughout,” says Driscoll, who regularly attends St. Elizabeth’s Church in Milton. He has taken good notes all along, and is grateful for a long life: “I have no regrets, only praise for the many gifts bestowed on me.”

Greg O’Brien is president of Stony Brook Group, a publishing and political/communications strategy company based in Brewster on Cape Cod. A regular contributor to the Boston Irish Reporter, he is the author/editor of several books and contributes to various regional and national publications.