Philly private school teacher sentenced to nearly 39 years for catfishing students, sharing their explicit photos

By day, Andrew Wolf enjoyed a reputation as one of the most popular teachers at the elite Springside Chestnut Hill Academy — a coach to players on the middle-school baseball team, a decorated educator, and a mentor to the dozens of boys who passed through his eighth-grade classroom each year.

But each night, he spent countless hours online plotting with others to exploit them.

The 42-year-old former math teacher was sentenced to nearly 39 years in federal prison Thursday for devising an elaborate catfishing scheme to trick dozens of his current and former students into sending him sexually explicit photos of themselves.

And while Wolf told a federal judge he hadn’t considered at the time the harm he was inflicting on them, he was confronted in court by the mother of one victim insistent that he reckon with the damage he had done.

The woman — who did not give her full name to protect her child’s identity — said her son, a once affable and popular teen, fell into a well of shame after discovering that nude photos he’d thought he’d sent to a teenage girl were instead in the possession of his math teacher, who’d shared them with other pedophiles over the internet.

“He spiraled into depression and self-harm,” the mother said of her then 13-year-old. “He began cutting his arms to deal with the emotions he’d never experienced before.”

Numerous stints in hospitals followed, she said. Attempts at suicide came and went.

She said her son finally seemed to be on the road to recovery. But in court, she held up a photo of his forearm, scarred to this day with the jagged strokes of nine letters from a particularly dark night when he’d carved the word worthless into his skin.

“I want [Wolf] to see what that looks like,” the woman said Thursday, turning to address the teacher at the defendant’s table. “I want to replace the pictures that you have in your head that you stole from our children and for you to see what you did actually looks like.”

When it came time for Wolf to address the judge, he turned to the boy’s mother instead.

“Hearing what [you] shared today just broke me,” he said through tears. “I thought I’d already come to understand … the consequences of my actions. I never dreamed they would have this impact. But I’ll think about this every single day.”

The emotional scene starkly demonstrated the devastation Wolf had wreaked on just one life during his 18 years teaching at the school. But prosecutors said that damage had been multiplied many times over by the breadth — and the callousness — of his crimes.

Evidence uncovered by FBI agents showed that Wolf’s interest had emerged years before he began teaching in 2004 at Chestnut Hill — a private K-12 campus in Northwest Philadelphia where annual tuition ranges from $32,000 to $43,000.

He spent hours communicating over encrypted messaging apps like Telegram, collecting a trove of explicit photos and videos of young boys and writing short stories detailing horrific sexual assaults of children that he posted on internet forums.

That activity only intensified after he landed his job as a teacher. Wolf quickly began expressing a sexual interest in his students — who ranged in age from 13 to 15 — in online conversations with several other men interested in child pornography, including one who went by the screen name “Mr. Pickles” and claimed to be a teacher.

Wolf shared photos of what he described as third and fourth graders at the school, appending a message to the group: “Worth raping.”

In other chats, he boasted of chaperoning a school camping trip in which he had stolen the underwear of one boy while he was sleeping and masturbated into clothes of another before replacing them in the child’s pack.

But it was one relationship in particular, Assistant U.S. Attorney Kelly M. Harrell said Thursday, that helped Wolf escalate his crimes.

In 2020, Kray Strange, a 19-year-old from Carthage, N.Y., reached out to Wolf over the internet after becoming a fan of his sexually violent fiction. Over 4,200 pages of online chat transcripts in the following 16 months they perfected their catfishing plan.

Strange, a college student, bragged about his ability to trick younger boys with online social media profiles he had created posing as a teenage girl named Alex. Within weeks, Wolf had compiled a spreadsheet with the names and social media handles of 78 of his current, former, and future students at Chestnut Hill.

Posing as Alex or as other fake internet personas, they would send explicit photos of young girls they found on the internet to encourage Wolf’s male students to send nudes of their own.

“Frankly, I don’t know when the man slept because he was engaging night after night after night, picture after picture after picture, chat after chat after chat with Mr. Strange,” the prosecutor said.

Success only fueled their brazenness.

On one occasion, they sought to persuade a student, while he was in class, to head to the bathroom to film himself masturbating. Wolf met with the boy’s parents just a few days later for a routine conference to discuss his grades.

Wolf and Strange tried to persuade another boy to sexually abuse his 10-year-old brother in his sleep and film it.

When students who had previously sent photos to their fake accounts began to grow suspicious or reticent, Wolf encouraged Strange to extort them by threatening to leak the images if they didn’t continue to send more.

“He decided to take the risk,” Wolf told Strange of one hesitant student, according to transcripts of their chats. “I guess wait until you are out of options and then make the leap.”

Not even the onset of the coronavirus pandemic in 2020, which shut down in-person learning at Chestnut Hill, deterred Wolf and Strange from their scheme.

Wolf bragged to Strange and the others in his Telegram group that he was aroused by Zoom teaching because it allowed him to watch his students in their bedrooms. He boasted of masturbating during online class sessions.

But even before the shutdowns, prosecutors said, Wolf’s behavior showed dangerous signs of escalating.

In early 2020, Wolf told his Telegram group of his attempts to groom a 10-year-old student at the school under the guise of teaching him about fitness.

He told the others he’d lured the child into the bathroom, lifted his shirt, and stuck his hands under the boy’s waistband, saying he wanted to examine his muscles.

“He just trusts me, which is exactly why it’s illegal,” Wolf recounted to his online pedophile group. “Too easy to manipulate a kid.”

In court Thursday, prosecutors said that had the school not shut down due to the pandemic weeks later, something far more serious might have occurred.

Wolf’s defense lawyers, Arthur Donato Jr. and Heather J. Mattes, maintained that the incident — like many of those detailed in his chats — never actually happened.

“There’s a certain level of trash talk that these people engage in,” Mattes said. “They talk about their fantasies and as real as you can make it the better it is for everyone involved.”

She noted that the FBI had not uncovered any evidence that Wolf had physically abused any of the children he interacted with.

But as the parents who filled the courtroom gallery, many clutching tissues to eyes wet with tears, attested, the damage Wolf had unleashed on their tight-knit school community was nearly as bad.

Several students have since transferred out of Chestnut Hill, finding it too difficult to return to a campus where their classmates know what happened to them, several parents said. School administrators said in a statement they were still offering psychological counseling to anyone who needed support.

But as U.S. District Judge Mark A. Kearney prepared to announce Wolf’s sentence, he insisted that Thursday’s court hearing could never bring the families or their children the closure they were seeking.

“Every one of these boys has been subject to severe trauma,” he said. “Stop thinking of vengeance and start thinking of your boys and the treatment they need.”

In addition to his prison term, Wolf was ordered to pay $200,000 in restitution and fines and to serve five years’ probation upon his release.

Strange, who pleaded guilty to child-pornography charges last year, is scheduled for sentencing in March.