A well-loved longtime high school history teacher announced her sudden retirement this week along with critical comments about the school administration, causing ripples in the Island community.

Principal Sara Dingledy acknowledged Mrs. Weintraub's contributions and said conversations about discipline continue.

Mark Lovewell

Principal Sara Dingledy acknowledged Mrs. Weintraub's contributions and said conversations about discipline continue.

Mark Lovewell

In a letter sent to the regional high school district committee Monday, Elaine Cawley Weintraub said she will retire effective June 30 of this year.

Mrs. Weintraub has taught for 25 years and has been history department chairman at the regional high school since 1995. Among other things she has taught African American, Irish and Brazilian history. She created the African American Heritage Trail history project, an annual academic competition, and the Brazilian American Friendship lunch. Through the years, she had led many history classes on spring break trips to Ireland.

In her retirement letter, Mrs. Weintraub took broad aim at the high school administration, criticizing what she described as an overarching emphasis on rules and discipline.

“My educational program has been undermined in numerous and ever increasing ways,” she wrote. The letter is published as a letter to the editor in the Gazette.

Superintendent Matt D'Andrea.

Mark Lovewell

Superintendent Matt D'Andrea.

Mark Lovewell

In a lengthy attachment to the letter, Ms. Weintraub outlined a time when she was not allowed to bring students out of the school building for a one-period school trip to see windows being prepared for a church in Germany that was previously a synagogue before Kristallnacht.

Mrs. Weintraub was not present at the school committee meeting Monday. Reached by phone, she said the decision to retire came slowly over the course of the year.

“It came in different stages,” she said. “Then . . . I realized . . . the system is very much keeping the students in the classroom, that seemed to be a very high priority and discipline seemed a high priority.”

She said she hopes her achievements continue without her, and she thanked students and parents who showed her support.

“I’m a student’s teacher,” she said. “I’m not politically correct. For me the students have always been it.”

In an email to the Gazette following the meeting, high school principal Sara Dingledy acknowledged Mrs. Weintraub and her many contributions to the school. Ms. Dingledy, who took the helm last August, declined to respond to the allegations about the field trip, saying it would be inappropriate to do so in the press. As for the concerns about disciplinary procedures in the high school, she acknowledged that there has been ongoing work this to address the internal culture at the high school, and that there have been many gains.

“For generations, her class has been welcome respite," senior Willa Vigneault said of Mrs. Weintraub.

Mark Lovewell

“For generations, her class has been welcome respite," senior Willa Vigneault said of Mrs. Weintraub.

Mark Lovewell

“In terms of the discipline conversation, I would say that there are a lot of things we are working on as a school to create a safe environment for all, and a set of expectations that raise the bar for all students and staff in the high school,” the principal wrote. “There is a fantastic staff and a fantastic student body that deserves a culture of reliability and responsiveness.”

She praised the school guidance department and the collaborative efforts of youth counselors at Martha’s Vineyard Community Services, pointedly refuting Mrs. Weintraub’s assertion in the attachment to her letter that students were being “sent across the street,” a reference to the Islandwide Youth Collaborative and Island Counseling Center that are part of the Community Services campus across the road from the high school.

“In terms of the claim that we ‘send kids across the street,’ I will say that we value our incredible partnership with ICC and IWYC,” Ms. Dingledy wrote. “That is a core of our ability to connect kids to therapeutic services that schools don’t provide. We have two great social workers/school adjustment counselors who do this work on site and address crises and check ins. We also have a strong guidance staff to tackle academic advisement issues. If the school committee wishes to expand the guidance department and add a counselor, I would wholeheartedly welcome that. You can never have enough student supports.”

School committee agreed to hold public hearing to address concerns about discipline.

Mark Lovewell

School committee agreed to hold public hearing to address concerns about discipline.

Mark Lovewell

Meanwhile the school committee meeting Monday night saw a large attendance of nearly 50 people, many who came to express disappointment mixed with anger that Mrs. Weintraub was leaving. There were also warm words of praise for the longtime teacher.

“For generations, her class has been welcome respite and a place where students could be themselves and truly honor their individuality,” said graduating senior Willa Vigneault.

“She has been a voice for many who were voiceless,” Vineyard schools superintendent Matthew D’Andrea agreed.

The comments sparked a wider discussion among school committee members about whether better communication is needed with the community on disciplinary issues. The committee agreed to devote a public meeting to the topic to listen to parent, student and community concerns. The hearing has yet to be scheduled.