A Portland Public Schools educational technician was arrested in 2021 for sexually abusing an elementary school student with special needs.

The ed tech, Benjamin Conroy, pleaded guilty to one count of sexual exploitation of a minor and was sentenced to 22 years in federal prison. He died in a New Jersey correctional facility in 2024, two years into that sentence.

Now, that student and her mother have filed a lawsuit against the school district and its then-superintendent, Xavier Botana, claiming that both are responsible for violations of human rights, civil rights and negligent infliction of emotional distress because they hired Conroy to a student-facing position and failed to notice warning signs that he might harm a child.

“This case really focuses on the school district and the superintendent themselves for allowing the perpetrator to be in the position that he was in,” said John Flynn, the attorney who filed the case. “The school district was negligent in the hiring of this individual, was negligent in not enforcing the policies that they have in place to protect these individuals who are highly vulnerable in these populations.”

Flynn filed the suit on behalf of the student, who was 7 at the time, and her mother, who is appearing as both a legally competent adult for the child, and as a plaintiff herself; the suit argues the ordeal left her with severe emotional anguish. The Press Herald is not naming either of them.

The student has autism and is non-verbal. She was part of a program for students with special needs at Ocean Avenue Elementary, and school administrators told her mother that only female ed techs would be assigned to work with her.

In the summer of 2021, the lawsuit says, that program was understaffed and the district hired Conroy as an ed tech without a meaningful screening of his application, a background check or contacting his references. Conroy had a criminal background that included two operating under the influence convictions, but the state said that wouldn’t have disqualified him from being hired.

According to the lawsuit, colleagues noticed that Conroy exhibited odd behavior, but did not report it to supervisors.

In October, Conroy used a cell phone to record a video of him sexually exploiting a student, which he posted online. He was arrested after a man walked into the Portland Police Department and told officers he had received disturbing images from an unknown man on an online dating app, and said he thought the man may have sexually abused a young child. Conroy, who was 32 at the time, was arrested and charged with multiple sex crimes later that month.

The lawsuit argues Conroy’s use of a personal cell phone, the fact that he was in a one-on-one situation with the student as a male staff member, and the fact that he was alone with the student at all, are all violations of the district’s own policies. And it argues the district ignored warnings about Conroy, including a time when he allegedly told a coworker, “I’m going to do
something really bad.”

The lawsuit is seeking “punitive damages from Defendants in such amount as will appropriately discourage any future instances of similar conduct by Defendants or other public school institutions.”

A spokesperson for Portland Public Schools said the district does not comment on pending litigation, and an attorney for the district and Botana declined to comment.

Flynn said the family retained an attorney back in 2021 immediately after the incident, but that lawyer stopped contacting the family, and Flynn took over their claim in 2025.

He said Monday that it’s among the most egregious incidents he’s seen in his law career. He said the child, now 11, has exhibited concerning behaviors since the assault, has not received recommended clinical services, and has been forced to relocate to a different school district.

“The child continues to, as she grows, experience consequences of this emotionally, as one would expect,” Flynn said. “So that’s why I’m very committed to making sure that this young girl gets the support that she needs.”

Flynn originally filed in state court on June 12, but an attorney for Portland schools moved last week to have the case heard in the U.S. District Court for the District of Maine. Flynn said he is still evaluating whether he will seek to get the suit moved back to state court, and said some of the claims pertain to state law, while some pertain to federal law.

The case has been assigned to Judge Stacey Neumann. The district and Botana have until Wednesday to file a response.