Local Difference Makers

On a Friday morning in 2016, Richard Roller found himself holding hands in a circle of middle schoolers in downtown New Bedford. The young men clasping Roller’s hands at the center of their school’s gymnasium were students from economically disadvantaged families living in the once booming industrial city. The circle is how they started each day in a school that acknowledges the challenges they face and promises them a top-tier, independent education. 

Nativity Preparatory School New Bedford is an all-boys middle school that opened in 2000. It is a tuition-free school for boys in grades five through eight whose family incomes fall below certain benchmarks. While it was founded in the Jesuit tradition with an emphasis on education, character, and service, there is no religious affiliation and its 50 students share a variety of cultural backgrounds.

As Roller and his wife, Joan, prepared to retire from Tabor after 46 years of service, he received a call from John Martin, a former Tabor colleague who was the Head of School at Nativity Prep. Martin was calling to gauge Roller’s interest in joining the board of trustees. “I didn’t know much about Nativity, but I knew John and I respected the work he did,” Roller says. “I decided to give it some thought.”

To help make the case, Martin invited Roller to attend a Friday morning all-school meeting. After announcements, the students and faculty formed their traditional circle. “If you’re in the room, you’re in the circle,” Roller says. “So I’m there observing and all of a sudden I’m in the circle holding hands with these two little kids.” The principal proceeded to express his gratitude to two different teachers, and then he asked everyone to go around and share something they were thankful for from the past week.

Roller was moved as the students spoke with confidence and candor. “When I was in the fifth grade, I didn’t want to be seen, let alone have to speak in front of fifty other students and adults,” he says. One sixth grader pointed to two of his classmates and shared how they helped him through a particularly difficult family situation. If it weren’t for those boys and their families, he said, he didn’t know where he would have slept that week.

“I was blown away by this,” Roller says. “Not by what the young man said, although I was blown away by that, but I was so impressed by what it said to me about the trust that he must have in the people in that room––to feel safe enough to make himself that vulnerable, and to share something that was that private. By the time it got to me, I was thinking two things. One, I better have something to say. And secondly, I want to be a part of this place.”

Roller is currently in his sixth year on Nativity’s Board of Trustees and his second year as the board’s chair. In this capacity, he has gained an even deeper appreciation for the school’s life-changing potential. One striking statistic is that 98% of its students go on to graduate from high school. “That’s 27% higher than the average high school graduation rate of a young man in New Bedford,” Roller notes with sober appreciation.

At Tabor, Roller wore many hats over the course of his nearly half-century tenure. Among the titles he held were Director of Advancement, Director of College Counseling, Athletic Director, Dean of Faculty, and Assistant Head of School. He has relied on this vast experience in his work leading Nativity’s board.

“While the scale is entirely different at Nativity, we’re one twelfth the size of Tabor, the themes are still the same,” says Roller. “Tabor has an Admissions program, and so does Nativity. Tabor looks to place kids in college, Nativity looks to place kids in secondary schools. Tabor raises money every year through the annual fund [Fund for Tabor], and Nativity has to raise our entire operating budget.”

With no tuition revenue, Nativity Prep is funded entirely by donations. Roller is quick to praise the philanthropic spirit of the local businesses, foundations, and individuals who help keep the lights on. “We get a lot of loyal support from the New Bedford community,” he says, adding that this generosity is fortified when donors see the value of a Nativity education.

Perhaps no example illuminates this value more than how the school supported its students during the dark, early days of the pandemic. “The pandemic pointed out to me, more rapidly than anything else, the difference between kids from advantaged and disadvantaged backgrounds,” says Roller. “When you say we’re going remote, it sounds simple. Until you discover a bunch of your kids don’t have devices and some of them don’t have any access to the Internet.”

After Massachusetts required schools to switch to remote learning, Nativity’s Board of Trustees purchased tablets for every student and faculty member and procured internet access for the families of students who lacked it. These resources supported the work of Nativity’s dedicated teachers and insulated students from the learning losses that afflicted schools across the country.

“In the first set of standardized testing we did after the pandemic, the average scores were only one point below the last pre-pandemic tests we administered,” says Roller, “Nationally, post-pandemic testing scores dropped dramatically.”

Among the school’s achievements Roller is most proud of are its pandemic response and its recently approved strategic plan. “We went through an entire year’s exercise in looking at ourselves,” says Roller. “What do we do well? Where are some of our challenges? How do we address these things and what new directions might we want to go in?”

One outcome is that the school plans to reinvigorate Nativity for Life, a unique program that supports alumni after they graduate by offering academic assistance and other resources as they move through high school and beyond. Another discussion that emerged during the planning process was whether Nativity should become co-educational.

After considerable discussion, the board reaffirmed Nativity’s commitment to remaining single sex and providing the best middle school education available for young men in the Greater New Bedford area. The decision was reached with nearly unanimous input from several of the school’s strongest constituencies and a close consideration of the latest work of Richard Reeves, author of Of Boys and Men.

“Seeing the positive impact the Nativity experience has on boys from the local community has underscored for the board the correctness of this decision,” Roller says. “I’m struck by the educational challenges faced by young men today, particularly in early grades when they come from an economically disadvantaged background. I’m more committed to Nativity’s mission every day because I see it meeting a really significant need and changing for the better the trajectory of young lives.”

Two miles down the road, Our Sisters’ School (OSS) is meeting a similar need for young women. Founded in 2008, OSS is named for “Sister Sailors,” the daring women who contributed to New Bedford’s vibrant whaling industry. “So yes,” Head of School Sarah Herman writes on the website, “we’re brave.”

Margaret McSweeny ’02 learned about OSS shortly after she graduated from the University of Puget Sound, where she studied religion and social ethics. McSweeny had just moved back east from Montana for what she thought was a temporary stay in her hometown of Marion when she heard about the plan to open an all-girls school dedicated to creating opportunities for underserved students. JoAnn Tschaen—founder of Trips for Kids, a New Bedford nonprofit, and mother of Ryan Costello ’97—was working with other dedicated community leaders to open the school. McSweeny went to speak with them to learn more about the project. “Sign me up,” she said at the end of the meeting.

She joined AmeriCorps and became part of the inaugural OSS faculty, a dynamic group made up mostly of other AmeriCorps teachers. It wasn’t long before she was hooked. Staying local may not have been part of McSweeny’s plan, but she wasn’t surprised to discover her passion and aptitude for the work.

“I’ve always loved learning and I’ve always had an innate ability to work with children,” says McSweeny. “I wanted a job with purpose and something that contributed to the good of society. I found that in the humble job of teaching.” She notes the presence of strong influences in her life such as her mother Kelli McSweeny, a venerated Tabor faculty member who retired in 2019, and her sister, Cathy, who is a Head of School in Hong Kong.

McSweeny is currently on her third chapter with OSS. When her AmeriCorp term ended in 2010, she left to earn her teaching license while working at Friends Academy and Tabor. She returned as the Head of the Humanities Department in 2012 before leaving two years later to pursue her master’s degree in education. She then taught in the Fairhaven, MA public school system for three years. “That was an eye-opening experience,” McSweeny says. “I saw first-hand how the systemic way we approach education is undervaluing many of our educators and failing many of our kids.”

She returned to OSS in 2017, but she was determined to stay involved with the public education system. In 2020, she ran for and won a seat on the Old Rochester Regional School Committee. She was re-elected to a second term last spring. Among the most pressing issues McSweeny has sought to address are student social and emotional welfare, teacher retention and a commitment to meaningful professional development, and opposition to teaching to standardized testing and book banning. She has high praise for the district’s central office, but she acknowledges that committee work in today’s culture-war climate can be trying. Still, she believes it is vital to have contentious conversations without malice.

“I’m a huge proponent of sitting down and talking with people who don’t see eye to eye with you,” says McSweeny. “In fact, I think it’s where most growth happens for most individuals. I try to lead with love in everything I do, so finding where people are coming from and meeting them there, and then seeing what the long term goal is, I think that’s important, no more so than when we are speaking about our kids and our collective future.”

In her current role at OSS, McSweeny serves as the Advancement and Volunteer Coordinator. It’s critical work for an institution that relies on steadfast donor support to operate as a private, tuition-free school that is not eligible for state funding as a single-sex school. She also oversees the community service program, a pillar of the OSS education, and co-teaches a Community Connections class for seventh and eighth graders that fosters active civic engagement. The course empowers students to identify ways in which to engage in meaningful action while developing their own passions and interests. “We do a lot with student voice and choice here,” McSweeny says.

Last fall, she brought several students to testify at a public hearing of the Massachusetts Commission on the Status of Women. Two students spoke about bodily autonomy, and another addressed STEM education for girls and BIPOC students. Attending events like this is not uncommon for OSS students. “I’ve always felt that if you want to change things, you have to be an active participant in that change,” says McSweeny. “A compassionate society comes from us all being active in our citizenship, and serving others helps you to grow, as well. So I really push kids to do that.”

When she isn’t busy working at OSS, serving on the school committee, or raising her own three children, McSweeny devotes her energy to a number of organizations that ignite her passion. She sits on the committee for the Women’s Alliance of Southeastern Massachusetts and serves as the Vice Chair of the Tri-Town Education Foundation Fund.

“I kind of stick with what I know and do as much work there as I can,” says McSweeny of her advocacy efforts. “It’s not like I don’t care about climate change or animal welfare, but I’ve kind of found my niche with feminism and education.”

When others remark on her tireless involvement in these issues, McSweeny shrugs it off. “I don’t feel like I’m doing that much. The thing is, I’m surrounded by people, especially women, who are extraordinary,” she says, rattling off a list of the inspiring people she has worked with throughout her career. “When I’m with these people, I feel like the least accomplished person there. But I’m very happy to just have a seat at the table and continue to learn and grow through my interactions with them. I find great joy and meaning in those relationships and in this work.”