Mary Skipper is one of two final candidates for superintendent of the Boston Public Schools. The School Committee is expected to make its choice on Wednesday. Read a profile of the other candidate, Tommy Welch, here.
It has been decades since Boston chose a superintendent with local roots as deep as Mary Skipper’s: an Arlington kid who grew up bowling at Sacco’s in Somerville and picking up shifts at Johnnie’s Foodmaster; a Tufts classics major who taught Latin at Boston Latin Academy before working her way up in Boston Public Schools, from principal to district administrator overseeing three dozen high schools.
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Some see Skipper, the superintendent in Somerville since 2015, as the antidote to what ails Boston’s schools, a vivid, homegrown contrast to the parade of outsider school chiefs who have tried to solve the district’s longstanding problems. On Wednesday night, they will learn if the School Committee agrees, as it chooses between Skipper and another local finalist, Tommy Welch, to lead BPS through one of the tensest, most consequential chapters in its history.
In the past when the Boston job came open, and she was asked about her interest, Skipper never felt compelled to change her mission. This time, she said in an interview Friday, it struck her as a calling she could not ignore.
“We’re at a point where we need everyone to come off the sidelines,” said Skipper, 55. “So to say that everyone else should do something, and not do something myself . . . I need to at least not be a bystander.”
The longtime Dorchester resident is direct and down-to-earth, a former softball shortstop, a breast cancer survivor, and now a doting grandmother. Married to a retired Boston College High School religion teacher, with three adult children who attended BPS, she calls herself a “prayerful” person; her colleagues describe her as a visionary leader who gets the best out of those around her. Enduring a grueling, nine-hour day of public interviews over Zoom last week, she answered a barrage of sometimes repetitive questions with an occasional Boston accent and no sign of impatience.
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Doubters question if her experience running a 5,000-student district has prepared her for the job in Boston, with 10 times as many students and far more complex challenges. Following years of state and federal oversight of BPS’s persistent service gaps for English learners and students with disabilities, state Education Commissioner Jeffrey Riley recommended Friday that the district officially be declared underperforming before reaching an eleventh-hour agreement with Mayor Michelle Wu on Monday that avoided the designation and aims to improve the district.
Like Welch, who built his career in Los Angeles and came to Boston in 2015, Skipper won acclaim for creating an innovative high school, TechBoston Academy, in 2002, then adding a new middle school onto that foundation. Both Welch and Skipper advanced to jobs overseeing BPS high schools; Welch now serves as a regional BPS administrator.
Skipper’s ascent may seem unlikely. The daughter of a single mother who worked in her elementary school cafeteria, she grew up with her aunt and uncle’s family, sharing a small house and one car, and started working at a grocery store at age 14. She kept that job for 15 years — long after becoming a teacher — and credits it with giving her vital people skills.
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She knows unlikely things can happen, as they did in 2011, when President Barack Obama chose to hold up TechBoston Academy as a national model during a visit to Boston. “What’s happening here is working,” Obama said, standing in the school gym. “We know what works. . . . And that means there can’t be any more excuses.”
A photo taken that day still hangs on her refrigerator at home, she said, prized a decade later because it captured the “awe and joy” on her students’ faces.
Nora Vernazza, who worked beside Skipper to expand TechBoston, said her former boss has a rare gift for building teams, finding strengths even in imperfect colleagues, and inspiring hard work.
“She develops relationships, and she knows how to develop people,” said Vernazza, who succeeded Skipper as TechBoston’s head of school.
Under Skipper’s tenure, Somerville students have achieved better graduation rates, attendance, and performance on the state MCAS exams. Some of those trends began before her arrival, but not all. Dropout rates, for example, fell dramatically after she took charge.
Skipper has credited close analysis of dropouts’ history: After examining their school records to see what was missing, the district made changes to address unmet needs. The approach echoes the model she used at TechBoston, where educators studied students’ individual records to craft schedules and teacher assignments for their specific needs.
Other gains during her tenure have benefited teachers and staff, whose new contract includes groundbreaking pay increases for paraprofessionals, caps on special education caseloads, and a boost in paid parental leave.
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Like any district leader, Skipper has weathered her share of controversy. Public outcry erupted last year after a Somerville parent went public with her complaint about school leaders, who notified police about a 6-year-old first-grader accused of inappropriately touching a classmate in 2019. Somerville officials said they were following state and federal rules.
Other parents criticized her for keeping schools closed longer than some other places during the pandemic, and one sued, claiming Somerville failed to follow special education laws while learning was remote.
Somerville mother Consuelo Perez said her daughter’s special needs were not met during the pandemic, a problem she said was compounded by a lack of clarity about the program requirements. In frustration, Perez said, she hired a lawyer and e-mailed Skipper in December, but never heard back from the superintendent.
“I know it’s not Mary Skipper’s responsibility, but then at the same time, it is,” Perez said. “Step in and say, ‘What is going on?’ or ‘This crazy parent is asking for the curriculum, why don’t you just give her the curriculum?’ ”
A district spokeswoman said the superintendent and district have been responsive to the family’s concerns, by engaging appropriate team members.
Among her top concerns in Boston, Skipper said, is the frayed trust between families and administrators. She said she would repair it with honest conversations, and by explaining her decisions.
Observers say Skipper listens closely, training her intense gaze on others, and often acts on what she learns. When high school students in Somerville asked for schools to stay open late, to give them safe spaces after school, Skipper pursued the idea within days, said Jessica Boston Davis, the district’s director for equity and excellence.
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Antwain Sheffield still remembers a conversation he had with Skipper 15 years ago, when he was a struggling sophomore at TechBoston. She urged the teenager to seize control of his own future and offered him a chance to mentor younger students, an experience that put him on a path to a career. Sheffield later earned two college degrees and now works as a counselor at TechBoston.
“She’s one of those people who sees things in you that you can’t see in yourself,” he said. “That was a turning point for me, when I saw a future, not just a diploma.”
Skipper acknowledges her “deficit” in a diverse district, as a white woman who does not speak a second language. (Welch is biracial and bilingual.) She has also been upfront about a recent family crisis — her husband, Peter, 74, suffered a heart attack six weeks ago — and about her commitment to stay on the job in Somerville until the fall, if she is hired by Boston.
“You owe that to the people who put their trust in you,” she said. “I don’t believe in weakening one thing to strengthen something else.”
Adria Watson, Christopher Huffaker, and James Vaznis of the Globe staff contributed to this report.
The Great Divide is an investigative team that explores educational inequality in Boston and statewide. Sign up to receive our newsletter, and send ideas and tips to thegreatdivide@globe.com.
Jenna Russell can be reached at jenna.russell@globe.com. Follow her on Twitter @jrussglobe.