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Oscar Santos has taken on difficult challenges as an educator

David L. Ryan/Globe Staff/Globe Staff

Oscar Santos aggressively pushed for change as superintendent of Randolph schools nearly a decade ago, as he attempted to ward off a state takeover of the then-underperforming district.

His mission was difficult and far reaching: extending the school day, overhauling teacher evaluations, increasing principal accountability, introducing new curriculums, revamping instruction for students with language barriers, integrating students with disabilities into traditional classrooms, and moving the sixth grades from four elementary schools to the middle school.

Along the way, he gained plenty of cheerleaders but also detractors, including a majority of the School Committee. In November 2012, little more than two years into the job and after receiving a lackluster evaluation, he announced he would leave when his contract expired the following June.


“It was a sad day for those of us who knew change needed to take place,” said Ida Gordon, a School Committee member at the time who is now the chair.

Others interviewed for this story disagreed, characterizing Santos as autocratic. They said he pushed change through so quickly, it was difficult to implement.

“He did terrible damage to a system that was slowly beginning to recover” when he arrived, said Ann Barysh, who worked with Santos as Randolph’s director of history and social studies, noting a number of hard-working administrators left. “There are no quick fixes in education. ... It requires people who are united and committed.”

Santos’s three years as superintendent in Randolph, a diverse system of 3,000 students south of Boston, is receiving renewed attention as he makes a bid for Boston’s top job. The 46-year-old has the most extensive superintendent experience among the three Boston finalists, and the Boston School Committee is using his time in Randolph as a lens to determine whether he can lead the state’s largest school system, with 55,500 students and 125 schools.


Santos, who currently is president of Cathedral 7-12 High School in Boston, would bring a distinctively local perspective to the helm of the city’s school system, which for decades has gone to out-of-staters. He grew up in Dorchester — the son of a single mother from the Dominican Republic — went through the school system, and graduated from its crown jewel, Boston Latin School.

He also worked for 14 years in the system as a teacher and a headmaster, transforming Boston International High School from a small transition program for new immigrants to a full-fledged high school.

John Drew, who recruited Santos to Cathedral when he was trustee chairman, said, “It was only a question of time before people came in and pulled him away.”

“I don’t want to lose him,” he said.

He credited Santos for recruiting young teachers, expanding academic offerings, and overseeing the construction of an “applied learning center” that focuses on the sciences and the arts.

In an interview, Santos, a married father of two teenaged children who lives in Canton, said he is driven to do his work so students can achieve throughout their lives.

“It’s important to be a champion and advocate for young people,” he said. “The quality of education is the difference between success and having a really tough life ahead of you.”

Santos’s days in Randolph can dazzle but also raise potential red flags, a Globe review found.

His arrival in Randolph in 2010 came 2½ years after state officials declared the school system underperforming, the culmination of years of acrimony between town and school officials as well as financial problems that shuttered two elementary schools and eliminated nearly all busing, 68 classroom teachers, and about half of the academic offerings at the high school.


The state had a hand in picking Santos as superintendent and — although the system had started to experience gains in MCAS scores and an infusion of more local funding — the state still wanted more dramatic improvement. Santos quickly assessed the situation and took action, said David Murphy, town manager at the time.

“Oscar had a sense of urgency for change that the School Committee didn’t have,” Murphy said. “I think he saw the school system through the eyes of the young people he served.”

Toward the end of his first year on the job, Santos earned praise from then-state Education Commissioner Mitchell Chester. In a March 2011 memo, Chester wrote that “Randolph’s current conditions show tremendous promise,” noting continued gains in MCAS scores and a collaborative environment between school and town officials.

But Chester added that more work remained to bolster classroom instruction, teacher support, and programs for students with disabilities and language barriers.

During Santos’s three years, student enrollment increased. High school graduation rates rose by double digits to nearly 80 percent, while suspension rates decreased.

But MCAS results were mixed, according to a Globe review. Performance in the elementary schools went up in some grades and subjects and down in others between 2010 and 2013; middle school scores declined, while high school scores mostly climbed.


Randolph’s high school went from one of the best high schools in the state to the bottom 20 percent, and the middle school slid into the bottom 20 percent, according to state rankings. Its four elementary schools were in the bottom 20 percent when Santos arrived and when he left.

The principals of the high school and the middle school left during Santos’s tenure as did other administrators.

Santos attributed some of the drop in accountability levels to changes in the way the state assessed school performance. He defended his record in Randolph, including increasing the diversity of administrators.

“By the time I left Randolph, we had a good central office and we had a focus on instructional core, and we were doing the work and making the progress that needed to be made,” Santos said.

He added, “If anyone tells you a superintendency is easy, grab your bag and run.”

Andrew Azer, who served on the School Committee during Santos’s tenure, said Santos came into a difficult situation — but laid the foundation that eventually enabled the school system to shed its “underperforming” designation in 2017.

His only criticism was that Santos “sometimes lacked communication.”

“It’s hard for a lot of people to have someone new come in and refocus the district,” Azer said. “He challenged people and held people accountable. ... He was driving the bus and knew the buck stopped with him.”


James Vaznis can be reached at james.vaznis@globe.com.