A former Portland Public Schools employee could receive anywhere from 15 to 30 years in federal prison when he is sentenced for sexually abusing a 6-year-old autistic student in his care.

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, 2021. Image from court video

Benjamin Conroy, 33, pleaded guilty in August to one count of sexually exploiting a child at Ocean Avenue Elementary School. He was originally scheduled to be sentenced Wednesday, but the hearing was postponed Tuesday night and will be scheduled for a later date.

Sentencing recommendations filed in the case reveal new details about Conroy’s life, including a history of addiction and struggles to treat his bipolar disorder.

Conroy’s attorney, David Beneman, is asking U.S. District Judge Nancy Torresen to consider an 18-year sentence followed by seven years of supervised release. The U.S. Attorney’s Office is calling for Conroy to serve 25 years and five years of supervision, arguing anything less would fail to take into account the age and vulnerability of the student, and the fact that Conroy had abused his position as a special education technician.

Conroy was arrested in October 2021 after a man he had been messaging on the dating app Grindr reported that he had received “several disturbing images and messages” from Conroy, who was only known to police at the time as “Str8 Vers Anon.”  The conversation included several images of a man abusing what appeared to be a child as well as exposing himself in a public park to women and girls.

Three days later, a woman reported she was assaulted by a man on a park bench at Portland’s Western Prom.


A group of witnesses helped detain the man until police arrived. They identified him as Conroy and later linked him to the Grindr Anon account. Conroy admitted to some of the images but initially disputed having been responsible for the pictures of a minor. Conroy was originally facing multiple charges in state court before federal charges were levied.

He is pleading not guilty to a second count of transporting child pornography tied to his use of Grindr to send at least one person screenshots from the video of Conroy abusing the child, now identified in court documents as a 6-year-old student.

In a sentencing recommendation filed this month, Beneman said that the abuse occurred during an untreated state of bipolar mania.


Conroy grew up in South Portland, one of four children who were all involved in sports. When he suffered a serious back injury playing soccer in his midteens, Conroy was prescribed opiates that later led to addiction, Beneman wrote. Conroy spent several years meeting with doctors who continued to misdiagnose and doubt his pain until he was 20, when a doctor identified the cause: a broken vertebra that could be repaired with surgery.

“The experience – five years of being told there was nothing wrong only to finally find he had a surgically repairable break – left Benjamin wary of the medical profession,” Beneman wrote. That led Conroy to be reluctant to share information with medical professionals, Beneman added, which likely was why he wasn’t diagnosed with bipolar disorder until later in adulthood.


Beneman also references childhood sexual abuse that traumatized Conroy when he was about 5 years old and an eight-year engagement to a woman that ended in 2018. That same year he got into a car crash and sustained a concussion.

Conroy was initially diagnosed with bipolar disorder in 2019. In May 2022, more than six months after Conroy’s arrest, Beneman said a psychiatrist who evaluated Conroy believed that he did not have “the most efficacious treatment” and “was likely symptomatic at the time he was accused of engaging in crimes,” the evaluation stated.

His mother, aunt and siblings wrote in court records that Conroy’s charges shocked them.

“I’ve had one reoccurring response: nothing about this makes sense,” wrote one aunt in response to Conroy’s charges. “Nothing about this is consistent with the young man I’ve known.”

Conroy’s personal history aside, Beneman also asked the judge to consider a sentence that’s “proportionate” to the type of abuse that occurred, pointing to the length of time and the nature of the inappropriate touching.

Prosecutors, meanwhile, said Conroy was using mental health and his previously unreported childhood abuse to downplay a very serious offense.



“For the defendant to brush off and minimize the uniquely vulnerable nature of his victim in this case is frankly offensive,” Assistant U.S. Attorney Sheila Sawyer said. If not for the citizen’s report to police, “there is simply no reason to believe that the defendant would have ever been caught, let alone prosecuted, for the abuse of his victim, because she simply could not tell anyone what he had done to her.”

Conroy’s conduct – abusing a non-verbal victim who was younger than 12, recording it on video and distributing it – was reprehensible, Sawyer argued.

“And still yet, that was not enough,” Sawyer said. “After he abused this child and videotaped the abuse, Conroy then distributed multiple screenshots of the abuse to a stranger he had just met on Grindr – and then bragged about what he had done to his victim.”

Conroy graduated from the University of Maine in Orono in 2012. He had been working in schools as an education technician since 2014 after obtaining his teaching certificate that year.

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