‘Speak your truth’: How one student leader’s confrontational approach reflects generational shift in fighting injustice

Outspoken and relentless in his quest for answers, the teenager’s direct approach at times contrasted starkly with the more cautious, guarded takes of his School Committee elders, all of them political appointees who serve at the pleasure of the mayor.

“You know that expression, ‘defies the laws of physics’? I defy the laws of politics,” James said. “I answered to the students, and not to anyone else.”

The passion James brought to his public service began with his own turbulent personal history, the traumatic losses he rarely mentioned, even to close friends. It also reflects a generational shift, according to experts. Across the country, younger leaders are moving toward more confrontational approaches, forged in an era of historic social upheaval and destined to clash with an older, more conservative brand of leadership.

“This generation of young people is no longer satisfied with incremental change,” said Chris Buttimer, a researcher at the MIT Teaching Systems Lab who has studied student activism. “They want to fundamentally change structures.”

Known for his scathing critiques of Boston’s schools, James is also a sterling example of the system’s potential: A young Black man raised by a single, immigrant mother in a South Boston housing development, nurtured by teachers who recognized his potential, accepted by one of the city’s best public high schools, and then by a prestigious Ivy League college, Columbia University.

He attributes his lack of fear to his upbringing by a Jamaican mother of uncommon strength, who taught him to reject societal “rules” put in place to oppress the powerless. But tragedy and trauma made James fearless, too: When, at 12 years old, he lost his mother and his world collapsed, it felt like he had nothing left to lose.

Until then, it had been the two of them against the world, their feisty natures so closely entwined, James thought of them as two halves of the same person.

“Colors looked different after she was gone,” he said. “The sky looked darker.”

After his mother’s sudden death at age 31, James shuttled between relatives and family friends, enduring episodes of emotional abuse and struggles with his mental health, he said. Just beginning to identify as gay, he encountered intolerance in his own family.

After a relative abruptly kicked him out of their home on Easter morning in 2016 — in part for identifying as gay, James said — he recalls walking to a nearby T stop, carrying his few belongings in a garbage bag and wondering where to go next. He was still just 12.

“I felt so disappointed in the human race,” he said. “I remember just thinking how adults misuse their power over children.”

Anjali Nirmalan, his sixth-grade English teacher, remembers James as a gifted child who struggled with authority, frequently serving detentions for talking too much or too loudly.

“He wasn’t raised to ignore things, or to tell a teacher [about a problem], but to take care of it himself,” said Nirmalan, who now teaches in Mexico. “He had a lot of qualities you want in a leader.”

His close friend Charlene Adames-Pimentel recalls rampant homophobia in their middle school, where James was a target who constantly fought back. (“How’s your GPA?” was one of his favorite comebacks.)

“He was that person that everyone wanted to break, and you can’t break him,” Adames-Pimentel said. “He was intimidating in the sense that he was always right, and always himself.”

Nirmalan recalls talking with James about “working the system” to find more socially acceptable methods of fighting injustice. His seventh-grade math teacher, Kwame Adams, now a BPS administrator, also coached him, said James: “He would pull me aside and say, ‘Next time, how can you say this in a more respectful way and still make your point?’ ”

Accepted to Boston Latin Academy, a highly ranked, selective public high school, James enrolled there one year after Donald Trump’s election, as racist speech increased around the country.

The teenager felt his fighting instincts kick in. He vowed to become a lawyer one day, to protect vulnerable minorities and immigrants. Later, James resolved to become a legislator, after a court internship helped him see the links between policy, laws, poverty, homelessness, and other problems that harm underrepresented communities.

But as he began to step up as a student leader, advocating for his peers in Boston schools, James encountered an eye-opening contradiction: Good teachers strive to empower their students. But when students then demand change of their own schools, they may find adults inclined to silence them.

Nirmalan, the teacher who was one of James’s first mentors, often feels conflicted about how to guide young leaders.

“Do you train them to keep their heads down and keep going,” she said, “or to speak truth to power?”

James began his School Committee term last fall at a moment of unprecedented turmoil. School buildings remained shut down by the pandemic, as criticism mounted. Committee meetings took place on Zoom, making public input difficult. In October, board chairman Michael Loconto resigned after he was caught mocking Asian speakers’ names at a public hearing on exam school admissions. (Two other members, Alexandra Oliver-Dávila and Lorna Rivera, also resigned under fire, in June, for their private texts about white families, exchanged during the heated debate that night.)

Keenly observant and unafraid of conflict, James called out hypocrisy where he saw it: in budget cuts that threatened his teachers and mentors; in school reopening plans that failed to address aging ventilation systems; in leaders who claimed to value student voices, but failed to give the School Committee’s lone student representative, elected by their peers, equal standing as a voting member.

His blunt-spoken Twitter feed attracted 1,500 followers, in a city where disillusioned parents, teachers, and observers crave real talk about the system’s failings. But he also irritated some adult decision-makers. James said Superintendent Brenda Cassellius and the board’s then-chairwoman, Oliver-Dávila, both asked him to tone down his message.

Cassellius said she admired James’s passion and tireless preparation for meetings, and believed deeply in his potential, as she wrote in a glowing recommendation to Columbia. But she said she worried that the traumas of his past, and of the pandemic, were affecting him as his tone grew harsher.

“It takes compromise, a lot of listening to others, and treating others with respect,” Cassellius said in an interview. “I’m always graceful; I don’t raise my voice; I’m never going to ‘go there’ . . . At School Committee or in Congress, there are rules, and that piece was new [to James].”

James said he was fully aware of committee conventions, and ultimately made a conscious choice to reject them. “I chose not to practice respectability politics because it wasn’t getting anyone anywhere,” he said.

Even then, observers including Sharon Hinton, president of Black Teachers Matter Inc., said she marveled at the restraint James displayed when committee members brushed aside his probing questions with a cursory “Thank you, Mr. James.”

By late winter, tensions between student leaders and adults erupted. In March, James and a half-dozen other students resigned from the district’s student advisory council, citing their frustration with adults who pushed them to soften their tone and water down their agenda. Closing the loop on his move outside the system, James also resigned from the School Committee.

The students’ resignations also protested the district’s use of unlicensed and unorthodox student counseling practices, brought to light with help from James’s public following and Twitter platform, and by press conferences he led.

It was not the patient, collaborative approach some adults might have preferred. But it was effective: the counseling, described by some students as an abusive cult, ended, its leader removed from her role. An investigation began.

“Speak your truth,” James urged his following on Twitter, but he took little satisfaction in the outcome. It underscored another troubling contradiction: only by rejecting the formal roles designed to amplify their voices had the students seized real influence.

James did not disappear after giving up his seat on the School Committee. He continued to push for equity and accountability in BPS — and to generate controversy.

After a June 16 School Committee meeting where James used inflammatory language to defend Oliver-Davila and Rivera, the two former board members accused of antiwhite racism, one Twitter user posted a video of his comments and tagged Columbia, suggesting that the school reconsider James’s admission. “Is this the type of student you want at your school?” the tweet asked.

James said he knew people would be upset by his use of the phrase “I too hate white people,” but his purpose was to make a point, about the unfairness of punishing people of color for voicing frustration with racism.

It remains to be seen what lessons James’s successors will take from recent upheaval. Dorion Levy, 15, a sophomore at Boston Community Leadership Academy who is working to rebuild the district’s student advisory council, said the shake-up showed that students can force change. But Ajanee Igharo, 17, a senior at Boston Latin Academy, acknowledged it will not be easy to find a student leader as bold as James.

“He showed us a different way, and I think it’s important,” she said. “If it wasn’t, it wouldn’t have bothered people so much.”

An energetic mentor of his younger peers, James is teaching a college-level civic engagement class for middle and high school students this summer, part of a city youth development program.

And as he prepares to leave Boston for college, he is reflecting on the lessons of the past year, and pondering his future. Once certain he would study political science and run for public office one day, he has lately considered other majors — even as some of Boston’s mayoral candidates continue to seek his counsel on engaging young voters.

“I’m never going to stop being honest, and I don’t know if I’m going to survive that way in politics,” he said. “But nothing is going to change unless people are brutally honest.”

Jenna Russell can be reached at jenna.russell@globe.com. Follow her on Twitter @jrussglobe.