From his early days in education, Mass. commissioner sought to level playing field

That disconnect, stubborn and systemic, between potential and opportunity has driven him and defined his career, people who know him said, as he made his way from one struggling urban school to the next. And it has led him now to an awkward, unprecedented, and, for him, seemingly inevitable reckoning, as he tries to force Boston to address longstanding school deficiencies, using the threat of state takeover as leverage.

Critics say his approach has been heavy-handed, intrusive, and unfair, placing too much of the burden on a new mayor and not enough on his own department, while demanding quick fixes and unrealistic timelines for problems decades in the making.

His words, at times, can sound patronizing, implying that Wu has failed to grasp the gravity of the situation. In an interview, he said he wants the mayor to “take personal responsibility and realize how critical the issue is”; in the first plan he proposed, in May, he asked Wu to sign a pledge to “always put the interests of students first, ahead of adults.”

Wu’s office declined to comment for this article. But the mayor has shown restraint in her public response, though she made a point last week to say that students are already her priority. She also described the city’s counterproposal to Riley’s plan as, “collaborative … and not patronizing.”

Some observers say the optics make them squeamish: a white, male bureaucrat, appointed to his post in 2018 over two highly qualified finalists, both women of color, now stepping in to tell two other accomplished women of color, Wu and outgoing Superintendent Brenda Cassellius, how to run their own school district.

Riley, reticent and reserved in an interview, said such critiques should be secondary. The focus, he said, shouldn’t be on who he is but what Boston’s underserved students need.

“I don’t think [the optics] should get in the way of 40,000 children who need a better experience,” the commissioner, 50, said in an interview Wednesday, “and I think the mayor and I agree on that.”

Nor is he bothered by rumors that his tough scrutiny of Boston is fueled by a desire to lead the state’s largest district, via a state takeover, or as its superintendent, with Cassellius due to leave after the school year ends. “I have an important job that I love, and no interest in running BPS,” said Riley, who earns a salary of $257,000. “I only have an interest in improving the education for the students there.”

How to achieve that improvement — by negotiating an uneasy partnership with Wu, 37, and a new superintendent yet to be named, or by wrestling authority away from them — is the question looming still unanswered. Riley and Wu have been trying to negotiate a pact since May 20, just before another state report again assailed the district for its lack of progress.

Now cast as an outsider meddling in city affairs, the commissioner nonetheless has deep Boston roots. He lives in the city, and sent his own children to school there, and built his reputation and career in BPS.

A product of suburban Belmont High School, where he was a soccer standout, and Pomona College, a small liberal arts school in southern California, Riley spent three years teaching in Baltimore after college, where he also earned a master’s degree in counseling at Johns Hopkins University. He saw students arrested, shot, and killed, but he also gained new confidence. “After that, everything seemed easy,” he told the Lawrence Eagle-Tribune in 2012.

Riley worked as a counselor in a Brockton alternative school after returning to Massachusetts, then sought a second master’s degree at Harvard’s Graduate School of Education. He also served an internship at Edwards Middle School in Charlestown, where he convinced powerhouse principal Charles McAfee to mentor him in how to lead, and improve, a school.

“I was intrigued by his confidence,” recalls McAfee, a school turnaround specialist now retired from BPS. “I had two candidates, and he came in and said, ‘I’m the one you want’ … I said, ‘Excuse me? You think you’re pretty good. You better be.’”

The two men developed a close and lasting bond as McAfee tutored his protégé in the complex duties of an urban principal, from managing angry parents and defusing racial tensions to navigating diverse cultures and shrugging off unconstructive criticism.

It was his work with McAfee at the Edwards school, said Riley, that convinced him to stick with education, when he saw how strong leadership could drive transformation in the face of poverty. “He was running an amazing school,” said Riley. “It made me believe we can get this done.”

Riley left Boston to run a new middle school in Tyngsborough, where he was known as a good-natured leader willing to be dunked in tanks and “pied” in the face by students. Then, McAfee enticed him back to the city in 2005. The pair teamed up again to try to stabilize Madison Park Technical Vocational High School in Roxbury, one attempt among many that did not yield lasting changes at the troubled school.

McAfee said he saw a passion in Riley for doing right by kids, and for moving forward, toward the newest, best ideas that might engage them.

“When you have that love of education and all kids, and then you see the data [on BPS], how could that be acceptable?” McAfee said. “It’s not out of anger; it’s a passion. There are people with egos who want to put their stamp on things. … He will never be that person, no matter what they say.”

Riley next served as principal at Edwards Middle School from 2007 to 2009, following in his mentor’s footsteps. The school had declined after McAfee’s departure, and was on the brink of closing. But Riley revived it, extending the school day, adding extracurricular options to engage students and weeklong academic boot camps, an effort he later replicated widely as a BPS district administrator.

Dr. Carol Johnson, then Boston’s superintendent, made Riley the district’s innovation chief after watching him revitalize the Edwards school, where he also created new incentive structures to engage the best teachers for more hours, and drew families close.

“Students and families were visible to him. He knew them by name, and his enthusiasm was contagious,” Johnson said. “He has innovation in his DNA, and he can be impatient if people aren’t moving quickly enough to change things.”

His talent for rebuilding struggling schools won Riley attention, and led him, in 2012, to his first high-profile statewide role, when the state appointed him receiver of the underperforming Lawrence Public Schools. An outsider placed in charge of rehabilitating the 13,000-student system, Riley said the most important thing he did was to assemble a group of parent advisers from each school, which he called “an incredible guiding force.”

Former Lawrence Mayor Dan Rivera said Riley was collaborative, accessible, and innovative, a partner instead of an enforcer, whose restraint won him respect and loyalty. “He came in as receiver and quickly became our superintendent,” he said. “It really was about the kids with him. I felt that every day.”

Riley’s legacy in Lawrence is still being debated, a decade later. Gains made in his first few years proved hard to sustain, and many in the city are now demanding an end to the prolonged takeover.

But his impact there convinced state leaders to tap him again, six years later, for the job of state commissioner of education. His selection, in 2018, disappointed those who hoped the state would choose a woman for the job, for the first time ever, and those who backed two other finalists, Angelica Infante-Green, a deputy commissioner in New York and rising star later named commissioner in Rhode Island, and Penny Schwinn, who became commissioner in Tennessee.

Parent activist Keri Rodrigues, a leader and founder of Massachusetts Parents United and the National Parents Union, was one of those who saw a missed opportunity. “I thought we needed fresh eyes,” she said in an interview. “I wanted someone from outside.”

But in the four years since, Rodrigues said, Riley has won her over with his willingness to listen and to hear tough criticism. During the pandemic, she asked him to join a Zoom meeting with hundreds of parents — many of them upset and worried about the consequences of school closures on children with special needs. She said he spent hours answering questions and addressing their fears.

Tom Scott, executive director of the Massachusetts Association of School Superintendents, said Riley was similarly accessible to school district leaders across the state at the height of the pandemic, handing out his cellphone number and responding to every text message.

“He had to create a playbook from scratch, from square one, and figure it out,” Scott said. “It was a very trying, very tense time, and if he was sweating, I didn’t see it.”

Current and former colleagues say Riley can be boisterous and wickedly funny in private, swapping stories about the unexpected twists and turns of school administration. That part of his persona has remained mostly hidden from public view, especially during the disruption of the past two years, as his leadership during the pandemic drew waves of controversy, criticism, even threats from some who disagreed with his directives on masking and closing and opening schools.

Unlike Wu, widely known as the mother of two BPS students, Riley, who is divorced, rarely makes public mention of his own two children, one a recent BPS graduate and the other still in high school in the district. Friends say he wants to protect their privacy. Behind the scenes, though, his experience as a parent has sharpened his grasp of families’ needs and expectations — and of the frustrations they can face, he said.

He recalled one conference with educators at his child’s school where he was “told things that weren’t true, and I knew it, but the average parent wouldn’t know.” The experience underscored for him the importance of honesty, he said, and sharing information, so parents can make the best decisions for their children.

Rodrigues said Riley has talked with her about his experiences as a parent, and it changed the way she saw him.

“That fact that he has also walked that road, and that he was willing to share it, revealed his humanity as a dad,” she said. “Instead of trying to talk us out of being mad, he said, ‘I get it; I’d be mad too. Now how can we figure it out together?’”

Margaret McKenna, longtime president of Lesley University and former chairwoman of the state Board of Elementary and Secondary Education, also cited Riley’s humanity, his “salt of the earth” quality, and real concern for kids, and she pointed out the complexities of his position, bound as it is to the governor’s education agenda, which stresses accountability. But she too has found it painful to watch the state’s tactics with BPS, she said, with its punitive, enforcing tone and patriarchal undercurrents.

“The approach should be, ‘You guys are having trouble; how can we help you?’” said McKenna, who voted for Infante-Green for commissioner in 2018 instead of Riley, citing her diverse experience. “DESE’s job is to help them be better, to be a place you go for help, and I don’t think it is that now.”

Johnson, the former BPS superintendent, sees cause for optimism, given Riley’s knowledge of the district, if the plan gives Wu a chance to lead, and accounts for lingering impact from the pandemic.

Riley jokes that his history as a middle school principal makes him impervious to rumors and insults, but some who know him see another reason for his sometimes blunt approach.

“He’s so focused on kids, he doesn’t care about politics,” said Rivera, the former Lawrence mayor, who occasionally tried to advise Riley on political strategy. “He would tell me ’No, that’s not why we’re here.’”

Jenna Russell can be reached at [email protected] Follow her on Twitter @jrussglobe.