A bus outside the Leroy H. Smith School in Winterport is pictured Aug. 4, 2020. Credit: Natalie Williams / BDN

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An educational technician who was arrested on multiple sex crime charges last week in Cumberland County worked for a public school in Winterport for about two years before landing at Portland Public Schools. 

Benjamin Conroy, 32, was employed in Regional School Unit 22 at the Leroy H. Smith School in Winterport as an ed tech from fall 2014 to August 2016, according to Assistant Superintendent Christine Boone. The Smith School serves pre-kindergarten through 4th grades. 

Conroy is accused of sharing disturbing photos of school-aged children on a dating app, including sexually explicit pictures of a young girl with special needs who is a student at Ocean Avenue School in Portland, where he is now employed. 

Conroy passed all background screenings as required by state law and resigned from RSU 22 of his own accord, Boone said. No complaints were made against him during his time there and no investigations were conducted. RSU 22 also conducts reference checks to ensure that potential employees “demonstrate integrity and are reliable,” she said, and Conroy passed that check. 

After leaving RSU 22, Conroy worked for Regional School Unit 2 at Hall-Dale Elementary School in Hallowell from September 2016 until sometime in 2019, Maine Department of Education records show. 

Before joining Portland Public Schools, he worked for Casa, a Portland-based organization whose work brought him into contact with children with special needs, both at their homes and at school. Conroy served as a behavioral health professional for that organization, said Tess Nacelewicz, a Portland Public Schools spokesperson. 

As an employee of Casa, he worked with students from Portland’s Longfellow Elementary and Lyman Moore Middle schools during the 2020-21 school year, Nacelewicz said. 

“We have identified the small number of students Mr. Conroy worked with last year, and we have already been in direct communication with those families about the ongoing police investigation of Mr. Conroy, as well as about ways that we can provide support for them,” Nacelewicz said. 

Conroy was then hired on June 28 for the school district’s summer program, and then hired as an ed tech on Aug. 23, Nacelewicz said. 

Conroy has been arrested twice since the beginning of October. On Oct. 8, Conroy was arrested for allegedly exposing himself and pushing up against a woman on Portland’s Western Promenade. He was then arrested last Wednesday night after someone to whom Conroy had sent sexually explicit photos of children reported him on Oct. 5, according to Portland police.

Conroy is now on administrative leave and not allowed to access school grounds or contact any students or their families, Portland Superintendent Xavier Botana said. His criminal record includes three convictions stemming from arrests in 2018, according to Conroy’s state criminal history — two for OUI and one for criminal trespassing.

Conroy is charged with sexually exploiting a child, a Class A crime; dissemination of sexually explicit material, a Class B crime; and possession of sexually explicit material, a Class C crime. He is being held at York County jail on $50,000 cash bail. 

Conroy has also been charged with unlawful sexual contact, a Class D crime, for the Oct. 8 incident, according to police. 

He faces up to 30 years in prison and a $50,000 fine on the most serious charge, sexually exploiting a child.

A Cumberland County court clerk said Monday that court documents in Conroy’s case were unavailable due to a court order from Justice MaryGay Kennedy, which the clerk said was “unusual.” 

BDN writer Nick Schroeder contributed to this report.

Lia Russell

Lia Russell is a reporter on the city desk for the Bangor Daily News. Send tips to LRussell@bangordailynews.com.