Swampscott School Committee Chair Amy OConnor’s resignation has sparked warnings from town education leaders about misinformation, persistent public criticism and a growing divide over school finances. At Thursday’s School Committee meeting, Vice Chair Glenn Paster called OConnor’s resignation “a moment of reckoning for our community,” saying she was driven out by an environment that had become “untenable.”
“Amy deserved better,” Paster said. “The resignation of Amy OConnor, based on the reasons she outlined, is not a reflection on her, nor on the School Committee, nor on the staff of Swampscott Public Schools. It is, however, a moment of reckoning for our community,” he added.
OConnor, who has served 12 years on the committee and currently chairs it, announced on Monday that she was stepping down, citing a “small but vocal group” that she says has “mischaracterized” the district’s fiscal management and cast doubt on the work of school professionals.
“I no longer have the fortitude to continue pushing back against misinformation, mistrust and the persistent negative commentary on social media,” she wrote in her resignation letter.
OConnor’s resignation will be reported to the town clerk, who will notify the School Committee and Select Board, according to Paster. Those boards will then meet jointly to decide whether to appoint someone to serve until the next local election, when candidates could run for the remaining two years of OConnor’s term.
Paster said OConnor felt forced out by “an environment that had become untenable,” marked by “an us-versus-them mindset that pits town and school interests against one another.”
Quoting from her letter, he repeated her warning that painting the schools as irresponsible or overspending is “an easy trope that is inaccurate and harmful, to our town, to our reputation, and most of all, to our kids.”
He strongly defended the district’s financial leadership, calling Director of Finance and Operations Cheryl Herrick-Stella “one of, if not the best director of finance in the entire Commonwealth,” and describing newly appointed Superintendent Jason Calichman as “eager, willing to learn, ready to step up.”
“My call to Swampscott residents is simple,” Paster said. “Let this moment move us toward a healthier, more informed, and more united approach to supporting our schools. Our children, our educators, and our community deserve nothing less.”
OConnor moved to Swampscott in 2008 and joined the School Committee in 2013 after serving as PTO vice president and director of after-school programs. She has two children in the district and works as an associate partner at J.Hilburn, according to her LinkedIn profile.
In her resignation letter, she called the district “an important inflection point” and said she is “confident” Calichman will lead it “to even greater success.” She also praised Herrick-Stella as “among the most talented professionals in the state,” and credited Swampscott Education Association President Rebecca Bucklin with building a collaborative relationship between teachers and administrators that is “uncommon among our peer communities.”
OConnor pushed back on criticism of the school district’s budget practices. She noted in her resignation letter that last year the district closed with 1.3% of its annual budget unspent, a result she called “disciplined planning, constant monitoring and the expertise of our finance team” and argued that much of the backlash stems from “a lack of understanding of modern educational finance.”
“Massachusetts law intentionally separates school finance from municipal finance because the work requires specific licensure, deep expertise and constant adaptation,” she wrote. “Our professionals have that expertise. Unfortunately, some in positions in town leadership persist in insisting they know better.”
In a two-page statement posted on social media, the Swampscott Education Association echoed OConnor’s concerns and defended her record. The union said OConnor’s leadership helped ensure schools had the resources and stability they needed and created a climate where problems were faced “together rather than alone.” Her resignation, the association wrote, is “profoundly disappointing, and frankly heartbreaking.”
“To Amy, we say thank you,” the letter concluded. “Our schools are better because of you. Our community is stronger because of you.”
