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Your first job at the Pine Street Inn was working the front desk. How did this experience at the men’s shelter shape your understanding of the homelessness issue and the operations of the Pine Street Inn?
My first job was actually working with volunteers and clothing donors, helping coordinate our food groups. Every day at three o’clock, I had to go down and cover the front desk from three to six. So I did administrative stuff during the day and then went downstairs. And I have to say, downstairs was a lot more fun. You got to spend time with the men and really get to know them because many of the same fellows would come back. You got to hear their stories and have a nice banter with them. It didn’t take long for me to realize that they were all unique but all struggling with a lot of different things.
Over your 24 years as president and executive director, what have been some of the most significant changes you’ve seen in the homelessness sector?
“When I first came to Pine Street, shelter was really just about all we did. We started doing a little bit of housing, but it wasn’t enough to impact shelter numbers and move the right people out of shelter.”
Well, I think the shift to housing is significant. When I first came to Pine Street, shelter was really just about all we did. We started doing a little bit of housing, but it wasn’t enough to impact shelter numbers and move the right people out of shelter. Now, we have a lot of data that we didn’t have before. We know how long people stay, why they come, and what support they need. This better data and improved systems have made a big difference. The movement to supportive housing has been nothing but positive.
How has the Pine Street Inn adapted to the challenges posed by such things as the opioid crisis and the high cost of living in the region?
The opioid crisis is probably one of the most difficult challenges we’ve faced, not just at Pine Street but as a city and across the country. On the positive side, we now have medicated-assisted treatment that targets receptors in the brain to help with opioid cravings. This is a major pharmaceutical change from years ago. We’ve also shifted our Shattuck Shelter to be a low-barrier shelter where people can come and work with us on next steps, whether that’s getting clean, finding work, or securing housing. While “Mass and Cass” still has its struggles, things have improved somewhat. The housing crisis is another major challenge. We’ve responded by building supportive housing and helping people find ways to afford rent, like getting a second job or finding a roommate. Despite our efforts, the high housing prices and low vacancy rates remain enormous struggles for us.
Can you elaborate on the Pine Street Inn’s role as a housing developer and the significance of reaching the milestone of 1200 permanent housing units coming next year?
We’ve been developers for many years, probably 30 to 40 years. Initially, we did what I would call affordable housing with minimal support. We then realized that some people in shelters and on the street needed intensive support and lower-barrier housing. Now, we try to get those with no other housing options into homes. We aim to hit 1100 units this fall and 1200 within a year. We’ve worked hard to build a substantial supply of housing in a city like Boston. We’ve started doing 50 to 100 unit buildings and found great partners. For instance, the Community Builders is our development partner on two current projects, and we will provide the support services.
How has the organization’s approach to homelessness changed with increased focus on permanent housing solutions from the moment someone enters the shelter?
When I first came to Pine Street, finding housing was largely an individual’s responsibility. Now, we have a team focused on housing placement and prevention from the moment someone seeks help. We ask if there’s an alternative to shelter, like transportation or temporary financial support. About 20% of those we triage avoid shelter or stay briefly. Unfortunately, the rest end up in shelter due to a lack of alternatives.
Correct me if I’m wrong, but Boston has a relatively low percentage of unsheltered homeless people compared to other parts of the country. What strategies have been key to this success, and how does the Pine Street Inn contribute?
About 3% of Boston’s homeless population stays outside, compared to 55% in San Francisco. Boston’s success is due to long-standing street outreach programs, low-barrier shelters, and continuous development of housing and support services. Although our street numbers rose slightly last year, our overall strategy has kept them relatively low, making Boston one of the top cities with the lowest street count.
You mentioned this before regarding data. How has the use of data transformed the way the Pine Street Inn operates and addresses homelessness?
Data helps us categorize people by length of stay and needs, allowing us to provide better support. About 20% of our guests are chronically homeless and need housing with support services. Another group needs short-term rental assistance. Our triage team works on short-term solutions for those who need immediate help, whether it’s transportation or temporary financial support. This data-driven approach has improved system flow and kept street numbers low.
In 2021, the Pine Street Inn received a $15 million pledge from the Yawkey Foundation to build 400 new apartments over five years. Where does this stand, and how significant was this for the Inn?
This was our biggest gift ever. We have had a long relationship with the foundation. Mrs. Yawkey was a donor when she was alive, and the foundation has been funding us on an annual basis. We have had a long relationship with some of the trustees, particularly with Maureen Bleday and Alicia Verity, who were on the staff there. We were in regular contact with them about what was happening. The pandemic was extraordinarily difficult for us. We did not know what we were up against, and we knew the shelters were overcrowded. The pandemic really hit in the winter when we had probably 150 people across all of our shelters sleeping on the floor or in hallways. We knew we had to find a way to get people out of shelters, especially older people and those who were medically vulnerable. When we approached the foundation and explained that we needed to ramp up housing, the foundation responded by asking how they could help. They are now helping us fund the support in supportive housing. We are more than halfway to our goal of 400 units, which is a 40% increase from where we were before we received the Yawkey gift. We have over 300 of those units either completed or in the pipeline, with about another 100 units to go.
What best practices have you adopted from other cities or organizations that have positively impacted Pine Street Inn’s operations?
We work very closely with the City of Boston. Every city that receives HUD money is required to have a plan related to homelessness and a set of goals and targets that we are expected to meet. One of the things that Boston has done well is that the city, the Mayor’s Office of Housing, and Sheila Dillon—her team and her staff—coordinate all of us who do street outreach, shelter work, and permanent housing work. We use a by-name list where we look at every single long-term homeless person, I think it’s now twice a month. We literally go through it and ask, where are they? Where is there a housing option for them? Who’s showing them the apartment? Who’s ensuring they get leased up? Or why did this person say no to something, or we can’t find this person. And it’s a by-name list. In a city like Boston, where the numbers are reasonable, you can do that. It has been really effective. I think our use of data and our efforts to figure out the global need and how we can meet it have been commendable. The city has been particularly willing to move in the direction of housing with support, even when it’s really difficult, and I give the city a lot of credit for that. These are not easy programs to get zoning relief for. Nothing is easy to get zoning relief for in Boston, but these are particularly difficult, and I give the city a lot of credit for that.
You’ve been doing this for 40 years. Reflecting on your time with the Pine Street Inn, what has been the most rewarding experience, and what keeps you motivated in your work?
I think the most motivating thing has been seeing people move out and into housing, especially those who have been on the streets for a long time. We had a guy named Sam, who is now deceased, but he slept on the floor of our lobby for probably 10 years. He had schizophrenia. We tried and tried to house him, tried to do anything, and he just said no to everything. Then we bought this small apartment building, which was going to be very low-barrier housing for men with mental illness who slept outside. Sam used to sleep outside and then come and sleep in the lobby at around 2:00 AM. When we bought the building, fixed it up, and got some funding from the Department of Mental Health to create this very low-barrier housing, one of our staff mentioned it to Sam.
On a Sunday night, I got a call at home saying, “Hey, Sam wants to see that new building.” I said, “Take him over and show it to him.” Sam saw it and said, “Oh, I really like it. I’ll take it.” He had no staff and the paint was still drying. Sam took the top room on the top floor, which was four stories up, and said, “I’ll take it.” He moved in and lived out his life there.
One morning, when we went in to check on him, they knocked on the door but got no answer. Everyone panicked. It turned out that his stuff was on the bed, and he was sleeping on the floor on newspaper, just like he did in the lobby. When they finally got the door open, they asked, “Sam, what’s up? Why didn’t you answer?” He replied, “I’m exhausted. I haven’t had a good night’s sleep in 25 years. I’ve been sleeping out or sleeping on the floor at Pine Street, and I’ve been terrified. But here, I can lock the door. I’m up on the fourth floor and can look down to see who’s coming in.” Sam, with his schizophrenia and paranoia, moved in with literally everything he had, all his bags and belongings, and he lived out his life there with a very different quality of life. He loved it and became kind of the grandfather of the house.
Stories like that really motivate me. The staff are amazing. It has been the biggest privilege of my life to be able to work with them. They are amazing.
Please visit the Pine Street Inn website to learn more about how you can help with Boston’s homeless!
The Pine Street Inn is located at 444 Harrison Ave, Boston, MA 02108 617-892-9100




One Response
Abusive staff behavior began once guests are housed, I am one of their victims, but i caught them on time stamped security camera. They filed court papers full of wild claims and accusations that i said loads of racist things.
My cameras prove i said nothing racist ever.
It was supposed to be supportive housing but what they did was attack me and any possibility of attaining housing again in Boston with libel to housing authorities and police.
HateCrimeHoax.org
PineStreetInn.co
plus Bay Cove Human Services,
baycovehumanservices.com
is also my site.
Pine Street created an activist out of me.
I’m working with Cambridge mayor Simmons staffers about similar abuse claims at bay cove managed sites in Cambridge.
For some odd reason, not one news outlet has snapped this scandalous story up.
I wonder why that is?!?
~Jeramy Dalpe