Stacy Wolff, a kindergarten teacher from Boston’s historically Black Roxbury community, learned this year that Harvard University could owe her reparations. Wolff could see herself in the stories of her ancestors, especially her eight-generations-removed grandfather, Darby Vassall, a freedman who, as a boy, had been enslaved by a family of Harvard founding donors. A teacher, he helped found the first school for Black children in Boston.
Wolff, now working in Silver Spring, Maryland, remembers teaching classes in her Roxbury school that had only kids of color, too little funding, and worn textbooks and broken toys. Centuries have passed, segregation overturned, yet Wolff’s classroom faced the same challenges as Vassall’s.
More than 200 years after Vassall helped establish the first school for African American students in Boston, public schools in the area remain implicitly segregated, with increased resources doing little to affect student outcomes by race. These students now, and generations of Black students who needed the U.S. Supreme Court to access an equal and desegregated education in 1954, share an unseen linkage to Harvard’s history.
Before Brown, there was Sarah Roberts, age 5
About 100 years before Brown v. Board of Education, the landmark opinion that desegregated public schools 68 years ago. Sarah Roberts, a 5-year-old Black girl, walked into the kindergarten of her local public school and was quickly forced out by a Boston police officer. The ensuing legal case, Roberts v. City of Boston (1850), set the first precedent for legally enforcing segregated classrooms in the country and was cited in almost every school segregation case across America. Behind Sarah’s story is a deeper, forgotten history of Harvard University’s role in informing school segregation and of the people who fought back.
Wolff’s ancestor believed education created freedom. Vassall helped found Boston’s first Black school — the Abiel Smith School. He hoped his children would learn to read and write in classrooms free from racism and abuse, characterized by a style of discipline designed to demoralize. During that period, teachers used to send misbehaving Black children and send them to the “n— seat,” where they were laughed at by other students and teachers.
In 1812, Boston’s African American community rallied around Vassall’s attempt to create a new school. Black sailors raised over $200, and several residents in the predominantly Black area of Beacon Hill chipped. Soon, the new classroom had desks and places for students to study. While the new school served as a source of hope for the Black community, the Boston School Committee mocked the effort. In an attempt to assert control, the committee forced parents to hire an unqualified White headmaster, Abner Forbes. Parents watched Forbes whip the Black children, force them to remain in complete silence during recess, and yell racial slurs at them. Soon, parents began withdrawing their children, the classroom abandoned.
Sarah was one of the children who would have attended the Abiel Smith School. Her father, Benjamin Roberts, often worked with Vassall and his son-in-law Jonas Clark on improving education. They had written petitions together and led meetings discussing integration. Clark collected 200 signatures for a petition to ensure equal access to education — Roberts was one of the co-authors.
Roberts hoped to test the constitutionality of segregated schools. Other towns near Boston — Salem, New Bedford, Nantucket Island, Lowell — had gradually integrated their classrooms. In 1848, he tried to sign his daughter up for five Boston schools. Each time, Sarah was forcibly removed or denied entrance. Roberts sued the City of Boston, hoping the courts would ensure integration.
How elite views fed school segregation
On a bitterly cold December morning, Roberts and other Black Boston parents lined up to watch the legal proceedings. At the center of the courtroom, Massachusetts Supreme Court Chief Justice Lemuel Shaw sat before the 5-year-old Black girl and the three lawyers who argued her case. Her dad remained hopeful because Shaw had once searched for loopholes in the Fugitive Slave Act of 1793. But Shaw also served in other roles beyond the court — as Harvard overseer and Harvard fellow — which shaped his view of education and who deserved it.
Between 1800 and 1850, the university, which profited from enslaved Black people like Vasall’s family, had transformed into an institution of wealth and privilege. Throughout Vassall’s adult life, Harvard’s total assets increased five-fold from $250,000 to $1,250,000. By 1850, Harvard’s total assets had grown a lot more than those of other elite universities at that time.
The composition of Harvard students had also changed. The university turned from a religious school into a national university for the wealthy across America, increasingly attracting the sons of prosperous Southern families. Six men — Israel Thorndike, James and Thomas Perkins, Peter Brooks, Benjamin Bussey, Abbot Lawrence — whose businesses profited from slavery in the South made combined personal contributions of $497,400 between 1800 and 1850, amounting to 50% of total major donations at the time.
Harvard’s decision to focus on attracting wealthier students also reshaped public education in Boston. Institutions like the Boston Latin School transformed into feeders for the university, creating a separate caste of secondary schools within the Boston Public School system.
Shaw embraced the Harvard ideology of education at the time — that quality schooling could be denied to students who didn’t meet admissions criteria. In his majority opinion, Shaw implied that the existence of unequal secondary schools like the Boston Latin School justified any schools’ right to deny students admission — even on the basis of race. Because schools in Boston could admit different students based on the “qualifications of the scholars,” Black kids could be denied an education.
Shaw’s opinion in Roberts v. City of Boston would spark a wave of court cases that upheld public school segregation. A footnote (No. 6) in Brown v. Board of Education noted that the “separate but equal” doctrine in Plessy v. Ferguson could be traced back to Shaw’s opinion. Not until 1954 would Brown v. Board of Education allow public schools to desegregate, and it would take many years for that to be the reality in practice. And as we well know, the U.S. District Court for the District of Massachusetts 1974 order to desegregate Boston schools sparked massive outrage, making this city iconic for the resistance of White parents to integrate.
The legacy of “selective” secondary schools that Harvard helped establish continues to the present day. The oldest public school in the country, Boston Latin School, is still a feeder school for Harvard, according to The Harvard Crimson, and sent 26 students to the university’s Class of 2020.
Today, most Massachusetts residents still falsely believe the issue of school segregation has been resolved. A 2020 poll found that while a majority believe school segregation is a “big” or “somewhat big” problem in the United States, less than half think classroom segregation is still an issue in Massachusetts. At the same time, the number of segregated classrooms in Boston has only increased over the past 50 years.
Investing in children’s potential to thrive
Last month, Harvard released its report detailing the university’s ties to slavery. It also announced the creation of a $100 million fund dedicated to grappling with its legacy, and some of the money will go toward partnerships with disadvantaged schools. Stacy Wolff says she hopes disenfranchised Boston schools can be a part of this effort.
Last year, her family members visited Harvard Square. They searched for their ancestors in the Old Burying Ground, where soft slabs of mud swallowed the soles of their shoes. They took a picture beside the plaque that commemorates their ancestors and other Black people enslaved by Harvard’s founding donors. In the basement of Christ Church, between cobwebs and abandoned files, the family finally found a mound with a small piece of paper framed before it: “When finally sealed in 1865, the tomb contained ten coffins, those of its owner [Henry Vassall], his wife [Penelope Royall]... and Darby, son of Henry Vassall’s negro coachman ‘Tony.’”
Two hundred years ago, in the basement of a Boston church, Darby Vassall prayed for freedom — with education as a cornerstone. Now, in this basement, his descendants had a prayer of their own: “Thank you for bringing us, through all these generations, to freedom.”
Wolff is still hoping and praying for Boston’s students — that they achieve their highest potential and the kind of freedom a richly resourced education provides.
Carissa Chen is a Harvard College graduate currently pursuing a master’s degree under the Rhodes Scholarship at University of Oxford. As a Harvard undergraduate, she was studying the university’s role in slavery when she met Darby Vassall’s descendants, who learned more about their family’s history through her work.