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Pine Street Inn to expand operation with new $1 million grant from Cummings Foundation

Pine Street Inn’s outreach team has run an overnight van on Boston’s streets since 1986.Dina Rudick

Pine Street Inn, New England’s largest provider of homelessness services, will expand its outreach operation and mission to find permanent housing solutions for unhoused people in Boston after it was selected to receive a $1 million grant over 10 years from Cummings Foundation.

Pine Street Inn’s largest grant from Cummings Foundation to date will go toward move-in costs that people often struggle to cover on their own, including furniture, first and last months’ rent, and security deposits, “opening a lot of doors to people,” said Lyndia Downie, president and executive director of Pine Street Inn.

The grant, a part of the foundation’s annual Cummings $30 Million Grant Program, will also help fund Pine Street’s outreach team, which has run an overnight van on Boston’s streets since 1986 to provide services and resources to individuals across the city who are experiencing homelessness. The outreach team works to move chronically homeless people directly into permanent housing.

“It’s hard. There’s no question it’s hard,” Downie said of working to find stable housing for people in Boston, citing a new report that Boston is the third most expensive rental market in the country. “On the other hand, we have a really resourceful staff, and this kind of money just allows them to be more creative, more resourceful, and just think creatively about what else we can do.”


Cummings Foundation, established by Joyce and Bill Cummings in 1986, awards $30 million to Boston-area nonprofits annually. This year, Pine Street Inn was among 150 grant winners from a pool of 630 applicants.

A broad swath of more than 90 community members volunteer to review grant applications and select recipients, a result of Joyce and Bill Cummings’ desire to “democratize the foundation,” said Andrew Bishop, grants manager for the foundation. Volunteers range from university presidents to local nurses to postal carriers, according to Bishop.


“We, in many ways, reject that more traditional model of philanthropy where you have a large staff and then you make a recommendation to a really small group of decision makers,” Bishop said.

During the application and selection process, volunteers toured Pine Street Inn’s facilities and spoke directly with staff who work on the outreach team.

It was during a second site visit from a volunteer at the foundation when, halfway through what Pine Street staff thought was another pitch presentation, they were surprised with the news that they had already been selected.

“Before we finished, he said, ‘I want to tell you that this is not a final. You’re in the final and we’re awarding you the grant.’ And none of us expected it. It was just amazing,” Downie said. “There was just so much joy in [the volunteer] telling us and, on our end, we were just over the moon.”

The grant awards Pine Street $100,000 in “nimble, flexible dollars” each year for a decade, according to Bishop, allowing Pine Street officials more discretion over how and when to spend the funds compared to public money.

“Much of Pine Street’s budget comes from restrictive governmental grants,” Bishop said, which the grants panel immediately recognized as an opportunity to provide Pine Street with the tools to ”be adaptive and to meet the challenges and the opportunities that their clients have where they are, and not on some formula that’s prescribed in the government grant.”


Downie called the freedom of the grant “enormous,” adding that it will allow the organization to overcome many roadblocks presented by public funding when they work to get an unhoused person off the street.

“It’s very intimidating for someone who’s been on the street a long time sometimes to engage on the public side — fill out applications, figure out how to get an ID, when they’re trying to survive and deal with mental health,” Downie said. “In many ways, this funding cuts a lot of that out.”

In total, the Cummings Foundation has given Pine Street Inn $1.8 million since they began their first formal philanthropic campaign, “100k for 100 organizations,” about a decade ago.

The current grant “completely lines up with our hope to keep trying to move the street numbers down as much as we can in Boston,” Downie said. “It’s a tough market to do it in, but we keep working at it.”

Sonel Cutler can be reached at Follow her @cutler_sonel.