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Boston’s homeless doc Jim O’Connell says recent crisis among ‘the toughest’ he faced

Dr. Jim O’Connell hardly ever saw people living in tents, let alone encampments of people sleeping on the streets, during the first three decades of his 40-year career treating Boston’s homeless.

The nature of homelessness and the health threats the population faces is ever-shifting, O’Connell said during a recent interview. And as it shifted once more in the last decade, O’Connell saw something new.

A confluence of factors led to the encampment by the intersection of Massachusetts Avenue and Melnea Cass Boulevard that was rife with drug dealing, substance use and sex trafficking: the closure of the Long Island campus in Boston Harbor where hundreds of people had sought shelter and social services, the contraction of other city shelter space, the explosive scourge of opioids and the proximity to methadone clinics.

Mass and Cass represented a small fraction of the total homeless population of Boston, O’Connell said. Yet it presented new challenges for the city, among the toughest he has encountered.

“Boston has always been a caring city,” O’Connell said. But he worries that as people drove by Mass and Cass or other areas with public drug use and homelessness, their sympathy toward homeless people steadily faded. Compassion fatigue set in, and then anger.

“I understand the anger, but it’s still people that have been devastated by something beyond their control, who are desperately in need of care,” he said. “And so how to manage that, I think, has been one of the toughest things I’ve seen.”

O’Connell, president of Boston Health Care for the Homeless, is one of the nation’s most prominent practitioners of homeless medicine and the subject of a 2023 book, “Rough Sleepers,” by the acclaimed author Tracy Kidder.

Since he joined the fledgling organization as its founding physician in 1985, O’Connell has been on the front lines fighting some of the last half-century’s most disastrous public health threats, from HIV/AIDS and tuberculosis to COVID-19 and opioid addiction.

People experiencing homelessness “are so susceptible to whatever the next infectious communicable disease is, whatever the change in policy will be, whatever the attitude of the populace is,” he said.

The city has since cleared the tents at Mass and Cass and dispersed the encampments. Police officers cruise the area, preventing them from reforming. But the challenges presented by congregate drug use have not disappeared.

Boston residents grumble that the people who previously populated the encampment have been dispersed across the city, into the South End, Downtown Crossing, Boston Common and other areas. Some residents of the South End say the area “remains an open-air drug market,” teeming with public drug use, discarded needles and drug deals occurring in plain sight.

Mass and Cass
The tents of a homeless camp line the sidewalk in the area commonly known as Mass and Cass in Boston on Oct. 23, 2021.(AP Photo/Michael Dwyer, File)

As homelessness problem worsens, no easy solutions

Sitting in his office at the Boston Health Care for the Homeless headquarters, on the block between Boston Medical Center and Mass and Cass, O’Connell can hear police officers on a loudspeaker outside, ordering people lingering in the area to disperse.

O’Connell, in his 40 years caring for people living on the street, has watched a succession of city leaders take varying approaches to tackle a homelessness issue he says has only worsened since his career began.

He doesn’t think the strategy to address Mass and Cass was a failure. But it showed officials that the solution to homelessness and drug use needed to be bigger than clearing tents and finding people shelter.

“We needed more for people than just a place to go at nighttime,” he said.

Finding a solution to the city’s homelessness and public substance use issue has become another hotly debated piece of an already contentious mayoral election.

Boston mayoral candidate Josh Kraft, the leading challenger to Mayor Michelle Wu, has proposed a multifaceted plan to tackle homelessness, addiction, drug dealing and mental illness among people living on the street.

It includes increasing law enforcement of quality of life crimes, public drug use and indefinite street living. Kraft says prosecutions should be handled in specialty courts that can steer people toward treatment and recovery services rather than prison.

Mass. and Cass
A person sits on the street beside a wheelchair outside the Boston Health Care for the Homeless program on Albany Street in Boston’s South End on July 2, 2025.(Will Katcher/MassLive)

Some of those strategies are already in the works. Under Wu, the city removed the tent encampment at Mass and Cass, helped move people off the street and into recovery and permanent housing, and “deployed a coordinated response team for the first time” to provide social services citywide, Wu’s campaign said in a response to Kraft’s plan.

“Hundreds of people who had been living on the streets are now in recovery and permanent housing, and fatal overdoses have dropped,” the mayor’s campaign said. “Boston police and public health officials are working seven days a week to stop outdoor substance use and address the real quality of life issues that residents face.”

Wu also announced $200,000 in new grant funding this month to expand the city’s coordinated response team, aiming to end outdoor substance use in city neighborhoods.

Mass. and Cass
A Boston Public Health Commission police cruiser parked on Atkinson Street, near the intersection of Massachusetts Avenue with Melnea Cass Boulevard, an area known as Mass and Cass, on July 14, 2025. A green sign now warns people to keep the sidewalks clear of tents.(Will Katcher/MassLive)

Last year saw a 38% decrease in overdose mortality among Bostonians, according to city officials. The city permanently housed 94 people who were previously homeless and established “low-threshold housing” that more than 450 people sought last year.

Kraft has also proposed a new recovery campus, with housing and social services available, that could partially fill the gap left by the closure of the Long Island facility more than a decade ago. He said earlier this month that the leader of a neighboring city — which one, he left unclear — had suggested a possible location for such a facility.

With so much of the conversation around homelessness tied to substance use disorder, a recovery campus is probably necessary, O’Connell said. But he hopes for a facility that can offer more than just recovery services, like the Long Island campus, where the city could provide shelter and a range of services, all removed from the urban bustle.

It was “a little village dedicated to the many needs of homeless people,” O’Connell said.

To recreate it on the mainland, particularly in a neighborhood with permanent residents, would be a lengthy process, he cautioned.

City officials are working with Health Care for the Homeless and other partners to address “the needs of people living with substance use disorder while working to improve quality of life within all communities,” Dr. Bisola Ojikutu, the city’s public health commissioner, said in a statement.

“Addiction is a chronic disorder, and nationwide there are significant gaps in the system of care and treatment for people who are living with substance use disorder,” she said, “particularly for those who are also struggling with homelessness and mental health issues.”

Thoughts of retirement after 40 years in the field

O’Connell never intended to end up in this line of work.

His story is well reported: after completing a residency at Massachusetts General Hospital, he was headed for an oncology fellowship at Memorial Sloan Kettering Cancer Center in Manhattan. His mentor asked if he might first spend a year helping kickstart a brand new program treating Boston’s homeless population. The rest is history.

O’Connell learned volumes during his days and nights riding around Boston, in search of people on the margins in need of medical attention.

Dr. Jim O'Connell
Dr. Jim O’Connell, the president of the Boston Health Care for the Homeless Program, pictured at the organization’s headquarters on Albany Street in Boston’s South End on July 2, 2025.(Will Katcher/MassLive)

When he began this work in the 1980s, O’Connell imagined that homelessness was a temporary phenomenon of the times. He learned the hard way that he could provide health care for homeless people, but he could not end homelessness.

“So much to my chagrin, 40 years later, I have to look back and say homelessness is arguably much worse now than it was when we started,” he said. “We had to let go of that dream that we were really contributing to the end of homelessness.”

He learned that caring for people living without permanent shelter requires unique creativity. For example, it can be difficult to assess an elderly homeless person’s mental state using the traditional tests for memory if they don’t know the day of the week or the current president.

For another, delivering tuberculosis medications to homeless patients in some cases meant sending them to a bar or coffeehouse where they were regulars.

Now 77, O’Connell no longer works the 100-plus hour weeks he once did.

But those memories are never far away. Lining the hallway outside O’Connell’s office are portraits of former patients, people who “opened up their lives” to their doctors, all of them now dead of various causes.

“It’s a reminder of how harsh homelessness is,” he said.

People who are homeless die at four times the rate of their counterparts who are housed. Those living on the street die at 12 times the rate of people their same age with roofs over their heads, he said.

“These people died all close to really good care,” he said. “I thought we were doing really good care for them. We could ease their suffering a lot, but we don’t always change the mortality projection. That’s the toughest thing to deal with. What could we have done?”

O’Connell has thought about retiring and ushering in the next generation of caregivers. He’d like to have time to travel while he is able. He has no immediate plans to step away, though he doesn’t think he would work past 80.

“But there’s something about when work gets into your bloodstream or something, and then it’s hard to let it go,” he said.

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