Boston Superintendent Interviews: Santos Speaks From Insider Perspective

Boston school leaders and community members interview three finalists under consideration for Boston Public Schools superintendent this week. Read highlights from the interviews with Marie Izquierdo and Brenda Cassellius.

In the race to become the next superintendent of Boston Public Schools, no finalist knows Boston better than Oscar Santos.

Santos is the only BPS alumnus among the three finalists (he graduated from Boston Latin School) and the only former Boston teacher and principal. (He’s certainly the only one whose photograph appeared on the front of the Boston Herald, alongside an open letter.)

But Santos’s most recent work has been as principal of Cathedral High, a small Catholic school in Boston’s South End, and as superintendent of Randolph Public Schools — with approximately 2,800 students. Unlike Izquierdo or Cassellius, he has never held a comparable state or big-city post.

In that sense, though he’s a known quantity for many here, it may be hardest to predict how Santos would lead BPS.

Here are four takeaways from his public interviews Wednesday.

1. He’s ready to tout his local knowledge.

Santos didn’t lean inordinately much on his familiarity with greater Boston and — in particular — BPS. But it did come up in questioning — most prominently in Santos’s repeated invocation of the city’s texture: its neighborhood-to-neighborhood diversity and its racial wealth gap.

He repeatedly cited the 2015 finding by the Federal Reserve Bank of Boston that the median net worth of white households in the city was nearly $250,000, while it was just $8 at the median black household.

Santos said that BPS policy must be designed so as to respond to that “heartbreaking” gap, and said as superintendent, he’d act to make sure all BPS staff  “meet [students] where they are.”

Santos also pushed back on school committee member Michael O’Neill’s contention — based on federal metrics — that poverty is declining in Boston, asking how that could be possible as “the cost of living is through the roof.” Santos also said that many “prized Bostonians” are moving away.

2. He takes the ‘school-to-prison pipeline’ personally.

The student member of the school committee asked Santos about how he’d prevent the so-called “school-to-prison pipeline.”

Santos said he knows it all too well, from his childhood in Uphams Corner: “I know friends who, unfortunately, ended up in jail — friends who did not finish school because they got into a fight, or something happened.” He rattled off statistics regarding how people with a history of suspensions or expulsions from school have higher rates of incarceration down the road. And he said he’s fought against that “pipeline” all his career.

In 2012 as Randolph’s superintendent, Santos fought to withhold security footage from the town’s police department after an incident, citing student privacy. (Ultimately, he was overruled by the school committee.)

On Wednesday, he said he stands by the decision:  “If there’s a weapon, or a substance, yes, you call the police. If not, you don’t,” he said.

3. He can be tough — and make mistakes.

Santos has prompted pushback in his two latest posts.

At Cathedral High in 2018, students protested Santos’s firing of a popular African-American basketball coach over an alleged conduct violation, and for the lack of staff diversity at a school made up predominantly of students of color.

And the situation may have only been rougher during his time in Randolph.

Former Randolph school committee member Larry Azer said, “Oscar had his challenges” as superintendent there. Azer said Santos came into the job in 2010 with “big ideas — a number of which had merit.” But Azer thought Santos sometimes failed to get other groups in town to join his efforts, then “moved ahead anyway.” He added, “That didn’t sit well with people.”

In an afternoon interview, Santos conceded that he has made “a lot of mistakes,” including misjudging the extent to which he had won over colleagues in Randolph. Afterward, he said that he had learned a lot on the job, including about what he called “operational excellence”—clearing out any obstacles that can impede learning.

Santos got a fierce defense from Andrew Azer, Larry’s brother, who served as the school committee’s chair. He said he found Santos to be “open and honest,” innovative, and determined to bring about needed change. (The district had faced the threat of state takeover not long before Santos arrived.)

But Andrew Azer, too, conceded that superintendent’s approach “could definitely rub [some people] the wrong way.”

4. Santos argues his resume prepares him for this job better than you might think.

The core of Santos’s pitch — from the Herald letter to his final interview — is that he may not have as much top-level experience as the other two finalists, but he knows Boston Public Schools inside and out. He added that he’s had to manage political dysfunction and tough decisions, albeit on a smaller scale.

By now, Santos said, he’s ready to take the heat for “right-sizing” the physical plant of Boston Public Schools or for controversial reconfigurations of grades in the districts. He even parted ways with other candidates by calling for the racial reintegration of Boston’s public schools — a policy that prompted riots and years of turmoil in the city.

Santos didn’t detail what form that would take. But he said: "I know Boston… and it has not been an equitable city, in many ways. And I think that the schools — the public schools — are the grounds to be able to bridge those divides."

So while many of Santos’s comments were technical, he made a comment Wednesday afternoon that might have tantalized onlookers who are concerned about recent turnover at the top of BPS.

“I understand how important this job is. I understand the hard work that lies ahead. And I want you to know, I am 100% committed to doing this work,” Santos said. “I don’t view this as a stepping-stone; I don’t view this as something I’ll do for a couple years… Our city deserves it.” In other words, if chosen, he’d be here to stay.