Chris Pitts was ready to find a home for himself and his mother. After struggling with addiction, serving time in jail, and eventually becoming homeless, he had been sober for three years. He and his mother, Gloria, had spent time living in a park before finding shelter through the Somerville Homeless Coalition.
As they began applying for apartments, however, Chris learned that an old warrant on a drug charge was still hanging over him. He had not even known it existed, but it was enough to stop their housing application from moving forward. In April 2025, Chris appeared before Judge Kathleen Coffey at Pine Street Inn’s Homeless Court, where the case was dismissed.
A few months later, Chris and Gloria signed a lease for an apartment in Cambridge. Standing in their new home, Gloria summed up the moment simply: “We did it. This is home.”
Their experience captures what Homeless Court has sought to do for more than a decade: resolve legal issues that can continue to shape someone’s life long after the circumstances behind them have changed.
Bringing the Court to Pine Street
Massachusetts’ Homeless Court was modeled after a program launched in San Diego in 1989 to address legal issues facing homeless veterans. Similar courts later developed in Phoenix, Tucson, New Orleans, and Houston. Here, the initiative grew out of a collaboration among attorneys from the Committee for Public Counsel Services, the Suffolk County District Attorney’s Office, representatives from the Lemuel Shattuck Shelter, and court leaders.
As the program developed, Pine Street Inn and other Boston shelters, including Woods Mullen Shelter and St. Francis House, became part of the effort. Today, once a month, a community room at Pine Street becomes a courtroom where eligible individuals can resolve outstanding warrants and certain misdemeanor and nonviolent felony cases. Those appearing before the court are homeless or at risk of homelessness and are already working with a case manager or receiving services.
“I am proud to have served as founding and presiding judge of Homeless Court for over 14 years and am grateful that Judge Jack Garland is carrying this work forward,” said retired Judge Kathleen Coffey, former Chief Justice of West Roxbury District Court. “It has been an extraordinary honor to be in the position to help people move forward and rebuild their lives. I have been amazed and heartened by the resilience and hope I’ve seen over the years, as well as by the commitment from Pine Street and everyone involved,” she added.
By the time a case reaches Homeless Court, much of the difficult work has often already happened outside the courtroom. Someone may have entered recovery, begun working toward housing, reconnected with services, or taken other meaningful steps to change the direction of their life. The court gives those efforts context when considering an old charge or warrant that might otherwise continue to follow them.
Judge Coffey has described Homeless Court as the “court of second chances.” The phrase reflects an approach rooted not in ignoring accountability, but in recognizing when someone has done the work to move beyond the circumstances that first brought them into the legal system.
When a Legal Problem Becomes a Barrier
For someone without stable housing, even a relatively minor unresolved case can have consequences far beyond the courthouse. A warrant can complicate a housing application or job search at the very moment someone is trying to regain their footing. At the same time, the realities of homelessness can make court obligations much harder to manage.
Elizabeth Condron, Pine Street Inn’s Homeless Court coordinator, has described how quickly that can undo progress. Someone may finally reach the top of a housing list only to discover that an unresolved legal issue prevents them from moving ahead, sending them back to the beginning of a process that may already have taken months or years.
Homeless Court offers another way through that problem. Eligible cases may be dismissed or otherwise resolved, default warrants can be removed, and fines and court costs may be remitted. More than 1,100 people had been served by the program as of 2025.
The setting also matters. Holding court at Pine Street brings the legal process into a place where many appearing before the judge already know the staff and are connected to support. Case managers can speak to the progress they have witnessed, while attorneys and service providers work within a shared understanding of what is at stake beyond the disposition of a case.
Part of a Larger Path to Housing
Pine Street Inn’s involvement in Homeless Court fits within its broader focus on moving people out of homelessness and into housing with support services. Its services range from street outreach and emergency shelter to job training and supportive housing, with more of the organization’s work increasingly centered on helping people find and remain in a home.
Legal issues can complicate that process in ways that are not always obvious. An old warrant may look small compared with the challenges of finding affordable housing, recovering from addiction, or rebuilding after years of homelessness. But when that warrant prevents an application from moving forward, resolving it can become an essential part of the path home.
“Judge Coffey and everyone connected with Homeless Court have made it possible for hundreds of people to reclaim their lives,” said Lyndia Downie, president and executive director of Pine Street Inn. “We have been very lucky to have had Judge Coffey’s support all these years and are grateful we are able to continue the Homeless Court Program with Judge Garland,” she added.
That connection between legal assistance and housing is what made Chris’s case so consequential. Homeless Court did not find his apartment for him or do the difficult work that came before his appearance. It removed an old legal issue that no longer needed to stand between Chris, his mother, and the next chapter of their lives.
More than a decade after the first Homeless Court session in Massachusetts, that remains the idea at the center of the program: people who have worked to change their circumstances should have a meaningful opportunity to move forward. For helping make that possible, the Boston Bar Association will recognize Pine Street Inn’s Homeless Court with the 2026 John G. Brooks Legal Services Award at Spirit of the Bar on September 24.
