In early 2021, Wayland tapped Omar Easy, a former NFL player-turned-Everett schools administrator, to lead its school system. The town had announced a commitment to becoming antiracist. Easy, who would be the district’s first Black superintendent, intended to help the largely white, affluent district live up to that promise.
But in his first year and a half, a series of controversies erupted over his leadership, including accusations he’d bullied subordinates over the alleged mistreatment of a Black teacher by white colleagues. Last month, after Easy threatened to file a discrimination complaint about the racism he’d faced in Wayland — including, most overtly, someone spray-painting “OMAR = [racial slur]” in large, white letters next to the high school — the committee placed him on leave without public explanation.
“This has been devastating,” said Dovie King, a Wayland mother and a candidate for School Committee. “Residents are left to piece things together without having all the facts.”
Easy’s supporters say the town ultimately couldn’t handle his zero-tolerance approach to dealing with racism. His detractors say the problem was Easy’s top-down, abrasive leadership style. In either case, his story offers a window into today’s hyper-charged school politics, especially surrounding racial issues, and the intense scrutiny Black school leaders often face as they try to navigate them in majority-white communities.
“He was making change probably faster than what Wayland thought that he should be, and what Wayland was ready for,” said Shavon Drayton, of Boston, whose children attend Wayland High School through the Metco program.
Just a dozen of the state’s approximately 300 school districts had Black superintendents last year. And their number is shrinking, said Thomas Scott, executive director of the Massachusetts Association of School Superintendents. Over the past year, Black superintendents have left Boston, South Hadley, and Athol-Royalston, following rocky tenures.
“Everyone is aware there’s a problem here,” Scott said. “We are alarmed.”
Easy, 45, has filed a complaint against Wayland with the Massachusetts Commission Against Discrimination, detailing a litany of allegations. The commission is still investigating the complaint, which has been widely discussed in town since Patch first posted it on Feb. 12. It’s the second complaint he’s filed in three years with that agency, which in 2020 dismissed his allegation of racial discrimination against Everett after he was passed over for that city’s superintendent’s job. (MetroWest Daily News first reported Easy’s earlier complaint.) Everett told the commission that Easy — who, though a high school administrator for seven years, had only a single year’s teaching experience and had never been a superintendent or principal — lacked the experience they sought for the position.
Easy’s critics believe his Wayland complaint is also without merit.
“Wayland, like every town in the state, needs to work harder on racial issues,” said Catherine Radmer, a Wayland resident. But, she said, “this was not about race. It was about one man’s performance in a job.”
Easy, his lawyer, and the School Committee declined comment. The teachers union did not respond to a request for comment.
Easy’s troubles in Wayland began almost right away. His first leadership retreat soured after some top administrative leaders declined to participate in an icebreaker, and couldn’t agree on ground rules for the team, two people in attendance said. One, who spoke on condition of anonymity, said Easy’s leadership coach, John Pierce, who facilitated the retreat, tried to get the group to promise not to undermine Easy; he said that felt combative, like, “You’re going to be on board or not.” But Pierce said he suggested they agree not to undermine their collective decisions after reaching a strong consensus together.
As Easy set about trying to make Wayland more student-centered — his motto was “Every Child, Every Day!” — he sometimes clashed with teachers and principals. For example, an Easy-created committee recommended allowing students to take home most graded tests over the objection of teachers, who worried kids would share the tests and cheat, said Drayton, a member of the committee.
Easy also made a point of standing up for the district’s few Black students and teachers, responding to racist incidents in ways that sometimes generated controversy, according to Easy’s complaint and multiple interviews with families and staff.
In December 2021, after someone scrawled a racial slur, “BLACK PEOPLE DIE,” and “ALL BLACK PEOPLE NEED TO LEAVE THE DISTRICT NOW” in middle school bathrooms, Easy assigned staff to monitor bathrooms and proposed installing surveillance cameras in the halls, Easy’s complaint and parents said. That seemed like an overreaction to some teachers and parents, who felt children would be surveilled, said Chanel Daly, whose eighth-grader attends Wayland Middle School through Metco. But others, especially Black families whose kids were scared like Daly’s, appreciated his firm response.
“For once, it was a really strong stance that this type of behavior will not be tolerated,” Daly said.
Weeks later, after spectators in Westford yelled racist taunts at a Black player on the Wayland girls’ basketball team, Easy again made waves with some parents, Daly said, when he canceled all spring sports games with Westford.
When parents and students wrote a letter to Easy last May raising concerns that a new Black teacher, Courtland Ferreria-Douglas, was experiencing “bullying” by white colleagues who micromanaged and “rudely” reprimanded him in front of students, Easy ordered an internal civil-rights investigation, led by the assistant superintendent. An Aug. 22 report obtained by the Globe found no conclusive evidence of racial discrimination toward Ferreria-Douglas, but it did find he experienced a hostile work environment, which represented a “systemic failure to appropriately and successfully support a new staff member of color.” A final version of the report was completed some weeks later; school officials would not comment on whether there were any changes. Easy moved to terminate one of the white teachers, his complaint said; the teacher later resigned.
Ferreria-Douglas, who said he is one of just two Black subject matter teachers at Wayland High, said he believed his co-workers scrutinized him, didn’t speak to him, and cut off his access to shared course materials due to both racism and a difference in opinion about teaching practices.
Easy, he said, “stood up for me. . . . If I weren’t Black, they wouldn’t be treating me this way.”
Ken Rideout, who was chair of the department where the conflict occurred, told the Globe that he and his staff were blindsided by the civil-rights investigation, stressing the probe found no evidence of race-based discrimination.
“Everybody that was investigated in that report was basically on the interview committee and was excited to work with this man,” he said of Ferreria-Douglas.
An allegation of racism was also at issue last school year, when Easy initiated the process to fire an administrator after learning that a Black colleague accused him of racially discriminating against her, Easy said in his MCAD complaint. The School Committee did not support the move, Easy’s complaint said, and, in an unusual step, Easy hired his own lawyer to represent him in that matter.
That administrator, however, said in an interview he was never accused of, or investigated for, racial discrimination and was shocked to see the accusation in Easy’s discrimination complaint — 16 months after the fact. He said he ultimately resigned.
Six months into Easy’s tenure, his relationship with the teachers union was deteriorating rapidly, a perilous situation for a new superintendent. The union organized a letter-writing campaign in January 2022 in which more than 100 educators and parents sent a total of more than 600 letters to the School Committee with a litany of concerns, including a top-heavy budget, secretive hiring, curriculum changes without teacher input, district interference in testing and grading practices, and a “hostile climate” where teachers feared retaliation for voicing opinions.
“Wayland educators have become increasingly concerned that the current changes are undermining our education system,” the letter said.
The union later criticized Easy for not meeting with the union as frequently as his predecessor, and for scheduling an emergency evacuation drill at Wayland High School without notifying the principal first, which the union decried as “reckless.” Easy canceled the drill at the last minute.
As tensions escalated, the School Committee largely stood by the new superintendent, issuing a statement disputing many of the union’s accusations, which it called “unjust and certainly not designed to be collaborative.” In June, the School Committee gave Easy a strong performance review, rating him “proficient” and calling him “data driven” and “action oriented.”
“He has taken our anti-racist resolution from paper to practice,” the evaluation said.
But it also urged him to spend more time in schools and improve his relationship with administrators.
A turning point came last fall, when the School Committee heard allegations that Easy had berated some administrators during an October meeting, committee Chairman Chris Ryan said. At that meeting, Easy had given a presentation about teacher-on-teacher harassment, citing the case at the high school, and implored administrators to live up to Wayland’s antiracism pledge, according to his MCAD complaint. Tensions also rose in a discussion of academic issues at the elementary schools, according to several attendees who spoke on condition of anonymity.
Ryan said in a November School Committee meeting that he received complaints from six or seven attendees who’d described Easy’s behavior as “berating, shaming, bullying.” Easy denied bullying anyone.
Two administrators in attendance told the School Committee — and several additional administrators told the Globe — they did not find Easy’s behavior problematic.
“He was direct and to the point and didn’t sugarcoat things,” La Toya Rivers, Wayland’s Metco director, said in an interview. “There were people who disagreed with things he said. Some people were digging their heels in.”
In November, the School Committee voted to keep Easy in his job while an outside investigator looked into the Oct. 13 meeting. Since then, Wayland has spent $28,700 on the investigation into Easy, records show, yet says it has no report on what happened. The committee has refused to say whether the investigation has ended, and if so, what it found. But Easy, in his discrimination complaint, said the probe concluded in January and exonerated him of any wrongdoing.
In December, Easy filed a demand for arbitration, records show, alleging the district’s handling of the complaints amounted to a breach of contract.
Around the same time, teachers union representatives stood at a School Committee meeting and accused Easy of driving out “far too many well-respected, established, and excellent teachers.”
“Our district has eroded to the point where our teachers need to leave their forever jobs in order to escape,” said John Berry, the union’s high school representative.
On the morning of Dec. 21, the graffiti calling Easy a racial slur was discovered on a community pool’s fence by Wayland High.
The town reacted with horror. Students and parents organized demonstrations. The School Committee pledged to support Easy. They listened to Black families’ suggestions on how to become more antiracist.
On Jan. 19, Easy’s lawyer sent the School Committee a draft version of the MCAD complaint he later filed.
“My name across the street here in white bold letters equals to one of the most diminishing, marginalizing, hateful, brutally un-humane words you can associate with any human being,” Easy told the School Committee at a Jan. 25 meeting.
“I don’t feel safe,” he added.
In early February, three administrators announced departures. On Feb. 8, the School Committee met behind closed doors to discuss Easy’s demand for arbitration and his draft discrimination complaint. They agreed to put Easy on paid administrative leave as part of their litigation strategy, Ryan, the chair, said in a March 16 letter to the attorney general responding to a resident’s complaint that the School Committee had violated open meeting laws.
Easy’s supporters, including some lawyers, viewed Ryan’s statement as an admission of retaliation. But Boston University law professor Michael Harper said placing Easy on paid leave made sense legally, as the situation had grown “adversarial and polarized,” and he wouldn’t be financially harmed.
Six weeks later, a cloud of uncertainty hovers. Easy still has 15 months left in his contract. His discrimination complaint is pending. And the police haven’t arrested anyone for the graffiti at the high school.
The Great Divide team explores educational inequality in Boston and statewide. Sign up to receive our newsletter, and send ideas and tips to firstname.lastname@example.org.
A previous version of this story gave an incorrect figure for the number of individuals who sent letters to the Wayland School Committee as part of a union-organized letter writing campaign detailing concerns about Superintendent Omar Easy. More than 100 people sent a total of more than 600 letters.
Naomi Martin can be reached at email@example.com. James Vaznis can be reached at firstname.lastname@example.org. Follow him on Twitter @globevaznis.