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A Legacy of Protection


Justin Bell

Three generations of Knights of Columbus Insurance agents, including General Agent Joseph P. DiCalogero (front row, center) and his father, former General Agent Joseph B. DiCalogero (front right) are pictured. Also pictured are field agents Jeffrey Denehy (front left) and (back row, left to right) Joseph DiCalogero Jr., John DiCalogero, Matthew DiCalogero, Timothy Coskren and Robert DiCalogero. (Photo by Bryce Vickmark)

Early in his career as a Knights of Columbus Insurance field agent, Joseph P. DiCalogero visited with Pasquale and Lorraine Bruno, and strongly suggested that they start saving for the years ahead. Raising seven children in Melrose, Mass., the couple was focused on providing college expenses and had not really thought about their own financial future.

Now in their early 80s, the Brunos are thankful they heeded their agent’s advice.

“As far as we’re concerned, whatever he tells us to do, we do,” said Pasquale, who is now in a position financially where he only works because he want to — a few days a week at a food counter he used to own.

DiCalogero, 56, a member of Reading (Mass.) Council 1031, served the Knights of Columbus as a field agent for 15 years before working the past 20 years as a general agent. In helping numerous New England families like the Brunos make important financial decisions, DiCalogero knows he is walking in the footsteps of many other dedicated agents, including his father, Joseph B. DiCalogero. In fact, three of Joseph B.’s sons — Joseph P., John and Robert — as well as son-in-law Tim Coskren, have become Knights of Columbus agents. Similarly, Joseph P. has ushered in a third generation of agents: his sons, Joseph J. and Matthew, and nephew, Jeff Denehy.

For the DiCalogeros, Knights of Columbus Insurance is truly a family affair — and not only because so many of them are agents. The DiCalogeros are acutely aware that Venerable Michael McGivney established the Knights of Columbus in 1882 with an eye to the financial security of members’ families.

Father McGivney’s vision continues to inspire their work. For the DiCalogeros, “Insurance for brother Knights, by brother Knights, with brother Knights in mind” is not a corporate slogan; it’s a family motto and a proud legacy that continues to grow.


At 88, Joseph B. DiCalogero can still rattle off differences between two insurance policies from the 1950s and clearly explain why the Knights’ offering is better.

“The insurance was less expensive, and it had more value,” he said.

Born in 1926 to Sicilian immigrant parents, Joseph B. grew up in the North End, a Boston neighborhood that he describes as being 99 percent Italian at the time.

After serving in the U.S. Navy toward the end of World War II, he returned to Boston and went to business school. He joined the Knights of Columbus in 1949 and began working for the commercial insurance industry a year later.

Joseph B. soon became more involved with the Knights and at age 26 served as grand knight of Ausonia Council 1513 in Boston’s North End. In 1955, he married his wife, Marion, and two years later began a nearly four-decade career with the Knights of Columbus.

“The Knights of Columbus was not my first job, but I knew it would be my last,” said Joseph B.

Beginning as a field agent, he worked as the first regional supervisor at the Knights of Columbus headquarters in New Haven, Conn., and later returned to the field as a general agent, retiring in December 1994.

His son, Joseph P., recalls practically growing up with Knights of Columbus Insurance. Starting at age 8, he and his sisters would assist their father by stuffing 8,000-10,000 envelopes for summer mailings.

“We knew this was coming every summer, and we hated it,” Joseph P. said with a laugh.

From the family’s home in Norwood, a southern suburb of Boston, he often found himself traveling with his dad to council meetings and parishes lugging a projector for presentations. As a second-grade student, he attended the first Knights of Columbus Insurance conference to be held outside of New Haven.

As a general agent, the elder DiCalogero would often drive two hours each way to Springfield, in an old Buick with 200,000 miles. One month after the Buick’s axle broke on their street in Norwood, he bought a winning raffle ticket. The prize? A car.

“You tell me this is not Father McGivney looking over your shoulder,” Joseph P. said, recalling the incident.

Joseph P. also recounted one day when he was 18, when his dad told him to get in the car, but would not tell him where they were going. When they reached their destination, the teen took part in a First Degree exemplification with Norwood Council 252.

After studying business at Salem State University, joining his father in the K of C insurance trade was not a complicated decision for Joseph P. He saw the success his father had enjoyed and figured he would try it out while he was young and still unmarried.

Thirty-five years later, the Knights of Columbus has been the only career that Joseph P. has ever known.

It wasn’t long before Joseph P. married his high school sweetheart, Lauren. She had long been familiar with the Order, since her father was also a member, and she had even shared envelope stuffing duties.

As a field agent, Joseph P. could work out of his home, eating dinner with his wife, Lauren, and children before heading out to evening appointments. As an agent under contract and working on commissions, he could dictate his own schedule, allowing time for extracurricular activities, such as coaching youth sports.

“That’s why I think a field agent has the greatest job in the world, if you can handle it,” he said.

Lauren DiCalogero has also appreciated the community built between the families of agents.

“It’s more than just a company you work for. You become good friends with people, you support each other,” she said, citing trips and families taking care of each other’s kids.


The DiCalogero family’s contributions to Knights of Columbus Insurance and its mission has continued to grow.

Joseph P. currently directs 22 field agents who serve Knights in Vermont, New Hampshire and a third of Massachusetts — an area that comprises 170 councils and approximately 23,000 members.

When Joseph P.’s sons first showed interest in becoming K of C agents for him, however, he directed them to get other jobs first.

“I wanted them to see what it was like outside the Knights of Columbus,” he said.

Joseph P. also wanted to make sure the initiative to work for the Knights came from his sons, not the other way around. He knew that Knights of Columbus insurance agents are paid according to how hard they work, and they need to be self-motivated and disciplined in order to succeed.

Joseph J., 26, a member of Valencia Council 80 in Milford, Mass., said his father wanted him to get phone experience with inside sales and “build up courage to sit in front of people” in outside sales. He did both in the credit card field before eventually coming on board with the Knights.

Likewise, older brother Matthew, 29, a member of Methuen (Mass.) Council 4027, described his move to sell insurance for the Knights as a “gravitational pull” after graduating from business school and working in the banking industry. Shortly after starting with the Knights in 2013, he married his wife, Morgan, and appreciates that his career will provide for a family.

Although Joseph B. DiCalogero has been officially retired from Knights of Columbus Insurance for nearly 20 years, he and his wife, Marion, continue to stay involved. For instance, they assisted their agent grandsons with stuffing 23 trays — more than 3,000 — of envelopes for their August mailing.

“It’s come full circle,” said Joseph P.

In protecting the financial future of Knights of Columbus families, the DiCalogeros know that they and other K of C insurance agents are participating in a larger legacy.

It began simply, when Father McGivney, a young parish priest at St. Mary’s Church in New Haven, conceived of a fraternity grounded in charity to protect the vulnerable.

“I think it’s phenomenal how his vision is our vision,” Joseph P. said.

Father McGivney probably could not imagine how expansive the fraternal benefit society would become, Joseph P. said. Now a Fortune 1000 company, the Order is on target to surpass $100 billion of insurance in force in 2015, and there is no higher rated insurer in North America.

“I think it’s amazing, and it’s just going to continue to grow and grow,” Joseph P. said.

“Still, we’re the best kept secret in the industry,” he added. “People should know more about the Knights of Columbus and what we do. Forget the insurance for a second. We donated $170 million just last year to charities, and we had 130 million volunteer man-hours. That’s unbelievable.”

The Order has “a great story to tell,” Joseph P. said. “But we have to get in to see more people, to tell that story.”

Longtime client, Rich O’Connell, obtained his first K of C insurance policy when his dad bought one from Joseph B. in the early 1960s. O’Connell has since acquired a handful more policies over the years through the DiCalogeros, a crucial time being when he started his own civil engineering business.

Shopping around, he met with an insurance agent from another company. When the agent asked what insurance he carried currently, O’Connell replied that it was with the Knights of Columbus. The meeting was then cut short as the agent started putting away his materials.

“I can’t do any better than those guys,” the agent said, according to O’Connell.

It is hard to imagine Father McGivney not smiling at that.

JUSTIN BELL works for St. Mary of the Annunciation Parish in Danvers, Mass., and in Boston Public Schools and is a correspondent for the National Catholic Register. He is a member of Denver (Colo.) Council 539.