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For years, Bill and Joyce Cummings were undercover billionaires. They lived well, but not large, maintaining their relatively modest Winchester home (along with a smallish condo in Florida), driving decade-old cars, and flying economy class. When Bill, ever frugal, said hello to his neighbors, he would complain about the money he spent keeping his yard maintained.

People generally knew that Bill did well for himself as the founder, president, and eventual chairman of Cummings Properties, but most didn’t suspect that he was one of the wealthiest people in America. That all changed around a decade ago, when he and his wife signed onto The Giving Pledge, a campaign started by Bill and Melinda Gates and Warren Buffet that encourages the ultrarich to donate more than half of their wealth to charity.

Today, there’s simply no hiding, now that the couple has begun what Bill Cummings calls the “great fun” of giving away their fortune. “Rather than leaving it around for somebody else who gets to give all the money away, we thought, ‘Well, why not start now, when we can be a part of it?’” says Cummings. 

The Cummings Foundation was started in the 1980s, but for many years, it mostly accumulated assets—first accepting revenue, and then real estate assets, from Cummings Properties. Over the past decade, though, the foundation has become a philanthropic force in northeastern Massachusetts. In total, it has awarded more than 1,200 grants totaling $375 million, supporting more than 750 organizations. In July, the foundation announced that it would be increasing its annual grant program from $25 million to $30 million, and in August it announced a $10 million grant to Salem State University—the largest cash gift ever made to a state university in Massachusetts. 

While the Cummings Foundation does support some work abroad, in places like Rwanda, the bulk of its focus has remained local to Essex, Middlesex, and Suffolk counties, At first, the grants went exclusively to organizations in the 11 communities where Cummings Properties operates buildings (Cummings, 85, notes that he still bikes to all 11 cities and towns, “just to say I’m still doing it”). However, the foundation eventually started making gifts to organizations in Boston and other nearby cities with areas of great need, including Nativity Preparatory School in Boston, an accredited, tuition-free, Jesuit middle school serving boys of all faiths from low-income families.

Doing good across the North Shore

Gloucester-based Backyard Growers, which builds and operates community and school gardens, received a $250,000 Cummings Foundation grant this year, after receiving $100,000 in 2017. Executive director Alison Woitunski DiFiore says the latest grant represents a “defining moment” for the organization. “We’re relatively young, and this is a ten-year grant, so this is a recognition that we’ll still be here in ten years,” she says. “We really want to expand our impact, and this grant will be instrumental in our next stage as an organization.” 

In 2021, the foundation announced a $20 million gift to Endicott College to expand the School of Nursing, including a new School of Nursing and Health Sciences building that will open in the fall of 2023. “For a place like Endicott, a $20 million grant was transformative,” says Steven DiSalvo, Endicott’s president. “It was by far the largest gift this institution has ever received. These kinds of things get people very excited, and now I have other people who have stepped up with grants of $6 million and $2 million, in part because the Cummings Foundation stepped up first. These sorts of things have a way of inspiring others.” 

DiSalvo, who recently joined the foundation’s board, describes Bill and Joyce Cummings as “the most humble couple” that he’s met. “I’ve been around philanthropists who are driven by ego and name, and by how big the letters are on the building,” he says. “There’s none of that with Bill and Joyce Cummings.” 

Indeed, Cummings seems to see philanthropy as a group project of sorts. Talk to him for more than a few minutes, and he may offer you a spot on one of the foundation’s grant-making committees. Past recipients dot the organization’s board, and Cummings Properties gives its employees cash to dole out to charities of their choice during the holidays. Committee and board members fall in love with institutions that apply for grants, and then, if those organizations are not selected, some of those people end up donating their own money. 

“We call it democratizing philanthropy,” Cummings says. “I’ve got a relatively short runway left. The foundation, however, has no sort of sunset to it. I expect its runway will be a lot longer than mine. One way to do that is to start early and get people involved who aren’t part of the organization, but who really love doing that work.”