A Portland school employee who was arrested this month and charged with sex crimes against a student is now facing charges in federal court, and an affidavit says the state is investigating a separate report that he previously abused two other children at another elementary school.

The charges against Benjamin Conroy are all related to the same student from the classroom where he recently worked as an education technician at Ocean Avenue Elementary School. It is not yet clear if he will face additional charges related to other children.

Jackie Farwell, spokeswoman for the Department of Health and Human Services, said Tuesday she could not comment about the other allegations.

Portland police arrested Conroy on Oct. 13 and charged him with sexually exploiting the child from his classroom. That case is still pending in Cumberland County Superior Court, and Conroy is in custody at the York County Jail.

On Monday, the U.S. Attorney’s Office in Maine also charged him with sexual exploitation of a minor and transportation of child pornography. Both crimes are felonies, and the first carries a mandatory minimum sentence of 15 years in prison.

An affidavit filed in the U.S. District Court of Maine says the Department of Health and Human Services recently received the new allegation of abuse regarding two children who were previously students of Conroy when he was working at another elementary school in Maine. The affidavit does not identify the school or provide any further details. Assistant U.S. Attorney Sheila Sawyer said she could not share any additional information.

Benjamin Conroy in a Zoom court appearance Oct. 15

Benjamin Conroy, an education technician who worked at Ocean Avenue Elementary School in Portland, appeared in court via Zoom on Oct. 15. Image from court video

The federal court docket did not list an attorney for Conroy as of Tuesday. An attorney who briefly represented him in a state court hearing earlier this month did not respond to an email Tuesday afternoon.

The affidavit says Conroy has worked with children on the autism spectrum for more than eight years, both in homes and in schools.

Portland Public Schools hired Conroy this summer, and he worked in a classroom for students on the autism spectrum. The district said he previously worked for Casa, which provides  behavioral health support to schools, and before that for Regional School Unit 22 in Hampden and Regional School Unit 2 in Hallowell.

Conroy worked at the Leroy H. Smith School in RSU 22 from 2014-16, and at Hall-Dale Elementary School in RSU 2 from 2016-19, according to information from the Maine Department of Education and those districts. Officials in both districts said they were not aware of any recent complaints with DHHS.

“No complaints or concerns have come to my attention,” RSU 2 Superintendent Tonya Arnold wrote in an email. “If information is provided to us that is relevant, we would immediately involve our legal counsel and follow all steps necessary to ensure we do the right thing for kids.”

Arnold has previously said Conroy was employed as an education technician by the district from Sept. 2016 to April 2019, and that there was no other information she could share in response to questions about whether the district was aware of any misconduct on his part, involving students or otherwise, during his time there.

Conroy has past convictions for operating under the influence in October 2018 and again in December 2018 as well as for criminal trespassing in September 2018, though the Department of Education has said his record would not have been reason for him to have failed a background check or been denied credentials to be in a classroom.

He previously held a state education technician credential that was valid through Feb. 1, 2024, but it was revoked on Oct. 15, according to Kelli Deveaux, a spokeswoman for the Department of Education.

Deveaux said that while she could not disclose any investigation materials in Conroy’s certification file, the credential was revoked in accordance with state statute, which says evidence a person has injured the health or welfare of a child can be grounds for revocation or suspension of a certification. The state can also suspend or revoke a certification based on its rules regarding criminal offenses, fraud or gross incompetence.

In RSU 22, Conroy completed all necessary screening and background checks prior to his start date in the fall of 2014 and there were “no red flags,” according to Assistant Superintendent Christine Boone. Boone said Conroy left the district of his own accord and the district had no record of any complaints. She also said she was not aware of any recent complaint to DHHS.

Farwell said DHHS investigates reports of abuse or neglect by a parent or custodian, and refers other reports to the appropriate district attorney. District Attorney Meaghan Maloney, whose office covers Kennebec County, where Hall-Dale Elementary School is located, said she does not have any open cases against Conroy and could not comment about any investigations. District Attorney Natasha Irving, whose office includes Waldo County, where Leroy H. Smith School is located, did not respond to an email Tuesday evening.

Special Agent David Pawson of Homeland Security Investigations wrote the affidavit filed in federal court. It recounts the investigation by the Portland Police Department, including details already known in state court, and the more recent findings of a search of Conroy’s electronic devices.

Pawson wrote that Portland police received a citizen’s report on Oct. 5 about alleged unlawful sexual acts revealed on the Grindr dating app. The citizen reported a conversation with someone who used the screen name “Str8 Vers Anon” and who sent several digital photographs depicting an adult man exposing his genitals in public.

The affidavit says another set of photographs showed what appeared to be the arm of a young child performing a sexual act. The citizen took screenshots of the photos during the conversation and attempted to solicit more information from the user, but was unable to ascertain the user’s actual identity or location.

On Oct. 8, Portland police responded to a call about a man on the Western Promenade who shoved his genitals in a woman’s face and pushed her. Police identified him as Conroy and issued a summons for unlawful sexual contact. The affidavit says the officer investigating the photos saw similarities between Conroy and the reported behavior of the Grindr user “Str8 Vers Anon.” During an interview with the officer, Conroy confirmed he was the man depicted in some of the photos taken in public, but denied any knowledge when shown one of the photos of the child, the affidavit says.

Following the incident Oct. 8, Conroy was placed on administrative leave from his job with Portland Public Schools. He was ordered not to come to any schools or have contact with any students or their families. Portland Superintendent Xavier Botana and communications officials in the district did not respond Tuesday to inquiries about the status of an internal investigation into the case.

According to court records, the Portland police officer who had been investigating the Grindr complaint learned that Conroy worked at Ocean Avenue and later spoke to the principal and the lead teacher in Conroy’s classroom. The principal recognized the floor and chair in the photos from the school, and the lead teacher was able to narrow down the possible victims. The officer spoke to a parent on Oct. 12 who said she was sure the photo depicted her daughter’s hand and clothes.

Conroy was charged with sexual exploitation of a minor, dissemination of sexually explicit material and possession of sexually explicit material. Portland police executed a search warrant the same day he was arrested, seizing a tablet and two cell phones. Pawson wrote that investigators found a short video that appeared to be the source of the explicit photographs of the child.

Note: This story was updated Oct. 29 to correct the name of Casa, a private non-profit that provides behavioral health support to schools.

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