In Boston, an Approach to Housing That Avoids Eviction

Posted on August 7th, 2022.

Tenants’ rights attorney Jay Rose spent four-plus decades waging legal battles on behalf of poor folks. So taking a job as a legal consultant for the nation’s largest for-profit affordable housing landlord might seem an odd choice. But executives at Boston-based WinnCompanies—which manages approximately $14 billion worth of largely affordable and military housing in 550 developments across 22 states—recently learned an unpleasant fact and knew the organization needed help from someone like Rose.

In 2018, WinnCompanies and other large Boston-area property managers were invited to join a newly formed Eviction Prevention Task Force, run by the Office of Housing Stability within Boston’s Department of Neighborhood Development. The group used company-provided information from 2015 through 2017 and data from the local housing court system to determine which landlords were doing the most evicting.

WinnCompanies learned it was the largest landlord in the city of Boston, and “we were also responsible for a fairly high rate of evictions in the city, and that’s not something we expected,” says Trevor Samios, senior vice president of Connected Communities, WinnCompanies’ resident services department. “It wasn’t a list we wanted to be on.”

The company hadn’t previously tracked its own eviction rates or reasons for evicting, which is typical; most landlords don’t. Even at the government level, one-third of U.S. counties don’t publish yearly eviction information, and there’s no federal government tracking. Samios did provide Shelterforce with some information he called his “back-of-the-napkin” figures: WinnCompanies manages 7,304 affordable units in Boston. From 2015 to 2017, the company filed 1,178 eviction cases; 374 of those were executed.

The city of Boston wasn’t the only local government starting to ask questions around that time, Samios says; other jurisdictions were also searching for solutions to their own affordable housing crises and high eviction rates. So when Rose approached WinnCompanies with a plan in 2019, company executives decided to accept his offer to help them overhaul the company’s policies and processes.

Rose, who spent several years at Greater Boston Legal Services, poured his “pet peeves of the last 40 years” into the partnership, he says. The result, called the Housing Stability Program, “is me trying to get a major owner to be as tenant-friendly as possible,” Rose says, and it should save the company money.

The 9 Steps of Housing Stability

WinnCompanies wanted to cut its eviction rates by 50% within five years. Rose wanted to keep tenants from seeing the inside of a courthouse. To achieve both those goals, WinnCompanies has in-house housing-stability coordinators who help tenants access relief sources, sometimes introducing options they didn’t know they had. The program is built around upstream interventions that are far more proactive than typical eviction prevention programs—which often don’t intervene until the tenant is significantly behind on rent.

“Often with eviction cases, there’s no problem-solving that happens before the case gets filed,” says Esme Caramello, a clinical professor of law and faculty director of the Harvard Legal Aid Bureau. “The landlord has a lawyer; the tenant doesn’t have a lawyer. The landlord says, ‘You didn’t pay the rent.’ The tenant says, ‘Oh, sorry, I had to pay for a funeral.’ Then the tenant loses their house.”

WinnCompanies’ property management team members must follow nine steps with every family to reduce the likelihood any rent delinquency will end in an eviction and to make the rent-collection process more consistent and fair. Before new tenants sign a lease, on-site housing specialists explain the Housing Stability Program and provide details on it and other available tenant support options (step 1). Each year, the tenant and on-site manager review and sign a Housing Stability Notice as a refresher (step 2).

“If you’re signing a 17-page document and it’s 85 degrees and you’re thinking about getting your child’s bed set up, chances are you’re not looking at every piece of that document methodically,” Samios says. So the managers are trained to go out of their way to ensure every tenant really understands and remembers their options.

Tenants who fall behind on their rent first receive a reminder they’re late (step 3) and are offered help from on-staff housing stability coordinators (step 4). WinnCompanies removed any threatening or punitive language from its standard rent-collection letters to try to encourage tenants to reach out and ask for help.

Local managers help tenants recertify for any subsidies they already receive (step 5) and access emergency rent assistance (step 6). Samios says this is a “tremendous amount of work” totaling thousands of hours by WinnCompanies employees. Nonetheless, they have not hired more staff, instead redirecting the focus to prioritize housing stability. “Without housing stability, residents do not participate in other community-based programming or seek mobility programs we provide,” Samios says. And it’s helped the company collect about $30 million in emergency rent relief payments on behalf of its tenants during the pandemic.

Only when these options have been exhausted are tenants served with an eviction notice, which gives them a specific deadline for contacting the property manager (step 7) and offers the option to set up an affordable, often long-term payment plan (step 8)—all before the courts get involved at step 9.

Samios says 75,000 residents would have faced near-certain evictions pre-COVID but are now stable because of WinnCompanies’ program.

Changing How Things Are Done

Tenants fighting to remain in their homes are often railroaded into repayment agreements they can’t stick to. Caramello describes how these plans usually come about: “The landlord, the landlord’s lawyer, and the tenant stand in the hallway [outside the courtroom]. The lawyer says, ‘Here’s a payment plan. Sign it or you’ll get evicted.’ So the tenant signs, and then they’re on a payment plan that they, in many cases, cannot do.”

WinnCompanies avoids the bully-in-the-hallway treatment, Rose says, by giving on-site managers the ability to enter into repayment agreements, hopefully avoiding court altogether. Property managers are empowered to offer longer-term, individualized repayment plans with smaller installments, giving tenants a much better chance of sticking with the plan. Tenants who agree to some repayment plan and remain in contact with management won’t be evicted. If the repayment plan needs adjusting to better accommodate the tenant’s ability to repay, on-site management can do that too.

Another simple change Rose advocated for when crafting the program is applying, on behalf of tenants, for a retroactive increase in benefits following an income change. Tenants often take a long time to report a job loss or hours reduction, and Rose says tenants or landlords typically file the recertification when they learn of the tenant’s change in income. But a reduction in the tenant’s share of the rent can and should be retroactive to the time of the income loss. Filing it that way benefits tenants and WinnCompanies and can clear up significant amounts of rent arrearages.

Rose also convinced WinnCompanies’ attorneys to agree to a six-month probationary period following a settlement over back rent; most are at least one year. Many landlords include rules in settlement agreements that allow them to kick tenants out for violating any provision of the lease during a probationary period—even one unrelated to rent payment. Rose convinced the company to remove that correlation, which he says “will save some tenancies down the road.”

The Final Chance

Rose got creative with his knowledge of the system to add an extra layer of tenant protection at the end of the process when the court is finally involved. Despite housing stability coordinators’ best outreach efforts, Rose says about half of tenants who fall behind on rent just don’t engage with management. He calls it the “ostrich impact.”

“There are just people who aren’t responding. For those people, it’s not real until they’re in court. Then they show up and ask for a payment plan,” says Rose. “The management says, ‘Jay, we can’t just ignore the people who won’t engage.’ Because it’s maybe half the people who don’t engage until the shit hits the fan.”

So he came up with a work-around. In Massachusetts, the eviction process happens in two steps. First, the landlord must provide a tenant with a Notice to Quit, which lists the amount owed and the date by which the late amount must be paid for the tenant to avoid eviction. If the tenant fails to pay or leave by the date on the Notice to Quit, the landlord can serve the tenant with an eviction summons. The date the tenant is served the eviction summons is known as the “service date.” But at this point, the eviction itself does not yet exist in court records.

“This is all still within our ecosystem, not in the court system, and not on their permanent record,” Samios says. “When people get [the eviction summons] from us on their door, typically that’s when a lot of people come in and say, ‘OK, I will pay now,’ or, ‘I want to work something out now.’”

The eviction summons the tenant receives contains an entry date, which is the day the tenant must appear in court. It’s also the date the eviction is filed and becomes part of the tenant’s rental record. By law, the entry date may not fall on a Monday and must be at least seven days but not more than 30 days after the service date. Under the Housing Stability Program, WinnCompanies employees are now trained to set the entry date as far out as legally possible, whereas “before, everyone would always pick the eighth day,” according to Rose.

“So now the tenant gets served. It’s real to them. And then there’s this two- to three-week period where they’re engaged, and that’s when we offer them everything in the program,” he says. “If that person engages, the management doesn’t file [the eviction]. As long as they sign some sort of payment plan within the 20 to 30 days, they don’t file.”

That creates a chunk of time in which the tenant can apply for rental assistance, pay the arrearage, or work out a payment agreement. Rose says this makes the eviction feel “real” to the tenant without it being “real” to the court—thereby avoiding a permanent scar on the tenant’s rental records.

He doesn’t know of any other landlord or property management company who’s used that window as a time to allow tenants to pay their back rent or set up a payment plan. He notes that achieving similar results in other states would require aligning the process with that state’s eviction filing rules, which would differ from Boston’s. Company leadership has asked legal counsel to “look for nuances in filing timelines to support both our program and objective to systematically lower evictions,” according to Samios.


Because tenant retention isn’t usually property managers’ focus, educating office staff on the long-term negative effects evictions have on renters, especially low-income renters, has been key to successfully implementing the program.

Retraining local housing court attorneys the company works with at its 500-plus developments was also key. Landlords seeking evictions typically want the tenants gone as soon as possible, so it was a big change for WinnCompanies’ attorneys to be told they’re expected to find a way to preserve tenancy as often as they can, Samios says. “We expected some pushback but were surprised to find that, at the end of the day, we are their clients, and they’re going to bill their hours in the same way, so they were amenable to making those changes.”

Michael Kane, executive director of Mass Alliance of HUD Tenants, says WinnCompanies’ approach with its retained attorneys is unique.

“Most companies turn evictions over to their lawyer and just let the lawyer run rampant. They retain law firms that make money on the evictions,” Kane says, “costing them a lot of money as well as reputational damage.”


Gilbert Winn, WinnCompanies’ CEO, considers the shift to focusing on tenant retention a “natural evolution” for the company as it’s grown. Eviction rates climbed as the company grew beyond a size where they had personal relationships with each attorney, Winn says.

The company started to calculate eviction costs—lost rent, legal fees, and unit turnover expenses—compared with how much back rent the company could collect using internal resources, such as providing rent assistance or offering them a payment plan.

“We started to realize that there were many cases where we would actually not lose money by preserving tenancy,” says Winn.

Pre-pandemic, it cost the company anywhere from $4,500 to $8,000 to kick one household out. Winn says “there’s not enough of a baseline to do an economic analysis” to determine whether WinnCompanies is saving or losing money since implementing the program, especially considering the unique job and housing markets—and unusually high availability of assistance—brought on by the pandemic. Nonetheless, it’s promising.

“On its surface, we have served roughly 16,000 households with two or more services in the Housing Stability Program,” says Samios. “Even at the low end of $4,500 per eviction in a smaller [metropolitan service area], this is significant operating savings.”

WinnCompanies stopped evicting tenants before the federal eviction moratorium began in early 2020 and hasn’t evicted a single tenant for nonpayment of rent since the pandemic began.

In Good Company

WinnCompanies isn’t the only housing organization in the Boston area looking for ways to realize the economic benefits of keeping tenants instead of kicking them out. Matt Pritchard, executive director of HomeStart, a Boston-area housing advocacy nonprofit, has been arguing for years that booting renters costs more than keeping them—over 500% more, in fact, according to research conducted during a pilot eviction prevention program that Pritchard’s team conducted in 2010 in collaboration with the Boston Housing Authority. BHA was the largest housing provider in the city; it was also the most prolific evictor.

“We worked with the finance team and the resident services team at BHA for about a year, and they showed us it was costing them over $10,000 to evict a family, but it was only costing HomeStart about $2,000 to prevent the eviction from happening,” Pritchard says. “The [Boston] Housing Authority acknowledged that HomeStart’s intervention was saving them an obscene amount of money every year.”

HomeStart, BHA, and other funding partners created a pilot program called the Renew Collaborative, in which a HomeStart representative would meet an evicted tenant in court, make a small payment to the landlord to delay the eviction proceedings, and then work with the family to identify the financial drivers that caused the nonpayment issue and eviction. The HomeStart representative would then create a blueprint to help the family mitigate the risk of ending up in arrears again, working with them for as long as 12 months. Over that period, the HomeStart representative would also help identify opportunities for the family to earn or save money moving forward.

Following the pilot program’s success, BHA agreed to expand and continue the program on a per-intervention reimbursement model. Upon engagement with an evicted family, BHA pays HomeStart a fee. If, after 12 months of HomeStart intervention, the family has fulfilled all its obligations associated with the original negotiation agreement, BHA pays HomeStart an additional sum.

“We knew our 12-month outcomes were great, but I’m a little bit of a skeptic and wasn’t certain we weren’t just kicking the can down the street and these families were getting evicted a year and a day later,” Pritchard says. “So we asked them to pull data from households we had served 24 and 36 months prior, which was a data set of about 300 households, and they showed us that 36 months after the intervention, only 5% of our families had been evicted for nonpayment.”

Pritchard supports WinnCompanies’ Housing Stability Program but points out that size and scale allow BHA and WinnCompanies to delay collecting rent and absorb immediate financial losses in exchange for the long-term benefits. Small landlords nationwide claim they’ve shouldered a serious financial burden from pandemic-related job losses suffered by tenants; their mortgages are due even if the rent hasn’t been paid (though a recent study from JPMorgan Chase found that landlords profited more in 2020 than in 2019). This inability to absorb financial losses is a barrier for smaller landlords participating in programs like this, Caramello says.

“Obviously, the owner of what we call in Boston a ‘triple-decker’—who lives in the first floor and rents out the other two floors to people—is not going to have a stability coordinator on staff,” she says. “So there is going to be a role for the nonprofit sector or the government sector to provide that type of infrastructure that Winn[Companies] can provide for its own development.”

HomeStart’s program is available on a case-by-case basis for a fee, which has been attractive to smaller, cash-strapped housing authorities in rural parts of Massachusetts. Pritchard calls it the nation’s first “economically sustainable, market-driven eviction prevention program” but says the community of individual landlords, like those Caramello described, are “so disparate that we haven’t peeled back the economics of an eviction for mom and pops like we have institutional property owners and housing authorities.”

Convincing small, rural Massachusetts housing authorities that eviction prevention was worth the mission required far less proof of concept than Pritchard expected.

“We’d go into a housing authority where they’ve got Fox News playing in the lobby, everybody’s wearing a red hat, and the housing administrator would say, ‘I have no interest in this program, because these people had their shot, and we have four people lined up to rent for every one unit of housing,’” he says.

And yet, even without a warm welcome from the housing authority, a Renew Collaborative partner attorney started showing up at the local housing court every week, telling the housing authority representative they’d be providing eviction prevention services, and stepping in uninvited to defend tenants with cases on that day’s docket.

“Within three months, we’d prevented 35 evictions in that housing authority, with the red hats, right before the holidays,” he says. “A month and a half later, in mid-January, that same housing authority approached our partner and said they were already preparing their budget for next fiscal year and were going to start paying for the service.”

HomeStart’s cost-benefit analysis found that it costs private landlords just more than $6,000 to execute an eviction, whereas the per-intervention cost is just $2,000. With a per-intervention payment structure, the hope is small landlords who may not have access to WinnCompanies-sized infrastructure can choose a WinnCompanies-type approach to their rent-collection efforts.

“If you’re threatening and punitive, tenants may go into defense mode and ignore you or move out without knowing what their rights are. So it makes sense to cut people some slack,” says Kane of Mass Alliance of HUD Tenants. “Small landlords don’t have the same resources and may not be able to access government programs as readily as corporate landlords, but I think the principle of treating tenants decently and with respect is preferable to just taking them to court at the drop of a hat.”

Setting a Precedent

Though it hasn’t been tested outside of pandemic times, WinnCompanies’ Housing Stability Program is getting national attention. The White House invited WinnCompanies’ CEO to present the program at its Eviction Prevention Summit in June 2021.

Locally, the city of Boston has begun requiring developers to include an eviction prevention plan that’s modeled on WinnCompanies’ in their requests for city financing, according to Katie Forde, operations manager for Boston’s Office of Housing Stability. In fact, Forde says the city has returned proposals to one developer “over and over,” telling the developer to adjust the plan to more closely resemble WinnCompanies’ program.

“They don’t get any city money until we approve their eviction prevention plan,” she says. “It’s an easy way to inspire, if you will, the [property] owners. They know they’re not going to get funded without having a really stellar eviction prevention plan.”

Landlords tend to treat evictions for nonpayment as formulaic, taking steps to remove tenants without first trying to work out a plan that allows them to stay. Forde says getting local housing providers to rethink that process with tenant retention as a priority is an ongoing struggle—which is why the Office of Housing Stability has adopted a carrot-and-stick approach with its developers.

“We really want to change the culture in the city of Boston and hopefully be a model for the nation in that respect,” she says.


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