Westmoreland

Wilkinsburg educator tapped for Penn-Trafford High School assistant principal role


Megan Flaherty’s experience as assistant principal, special education background, student-first mentality made her the ideal candidate
Quincey Reese
By Quincey Reese
4 Min Read Dec. 19, 2025 | 4 hours Ago
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Penn-Trafford’s newest administrator is in for more than a career change.

Megan Flaherty, a former administrator and special education teacher from Wilkinsburg School District, was hired last month as Penn-Trafford High School’s next assistant principal.

She will replace Jim Simpson — who has been a transitionary principal at the high school since the spring, after 17 years leading the district’s Penn Middle School.

The new job also marks a transition for Flaherty’s family. She plans to move into the area so her twins, Tegan and Tre Hall, can attend Penn-Trafford when they start kindergarten next year.

Flaherty, 41, of West Mifflin was drawn to the district for its strong academics.

“I went to West Mifflin, and that was middle-of-the-road, average size,” she said, “but I feel like Penn-Trafford has a lot more to offer my kids. When looking to embrace everything, Penn-Trafford had a lot of good qualities for me as a mom, as well as an administrator.”

Flaherty started at the high school Nov. 17, with a starting salary of $91,500. She has been shadowing Simpson, who is set to retire Jan. 30.

“I can see all the pearls of what he is doing,” she said. “I can implement my own style in a way, but I get to see the perspective of a veteran — especially just joining the district as somebody new and newer to administration.”

Principal: Flaherty takes ‘student first’ approach

Flaherty was selected from a pool of about 40 applicants, high school Principal Tony Aquilio said.

Her previous experience as an assistant principal, special education background and student-first mentality made her the ideal candidate for the job, Aquilio said.

“One of our questions in the interview process was about dealing with a hungry child or identifying some child neglect issues from a legal standpoint,” he said. “When she answered the question, before she even got into the legal part of the question, she made it very clear that she’d make sure that student had food first and a meal first, which, to me, stood out.

“Yeah, she knows the law. She knows the process of what to do and identifying students, but she was there for the student first.”

Flaherty will manage the school students in grades 10 and 11, Aquilio said. Assistant Principal Luke Healey, who was hired in August 2024, will manage the students in grades nine and 12.

Having two assistant principals helps the high school’s administrators better support the 1,200 students enrolled this year, he said.

“They learn about the students. They get a chance to learn about them individually, academically, what they like outside of school,” Aquilio said. “It helps builds those relationships.”

‘Learning what the students need’

Flaherty worked about two years as an assistant principal at Wilkinsburg, a school district for pre-K to sixth grade students, in the district’s Kelly Primary and Turner Intermediate before shifting to a special education teacher position in September.

Prior to Wilkinsburg, Flaherty worked nearly a decade as a program coordinator at Pressley Ridge Day School in Pittsburgh’s North Side. She worked with k-12 students who had individualized education plans or behavioral issues and helped school districts manage their own special education programs.

“I really enjoyed the aspects of being the program coordinator and making sure everything ran smoothly — supporting the teachers, the behavior specialists and, ultimately, the students,” she said.

After becoming pregnant with her twins during the covid-19 pandemic, Flaherty knew she wanted to work at a public school. She began pursuing a doctorate degree in administration leadership from Point Park University, which she is slated to receive in April.

“I want to start by building relationships, getting to know the kids and the building,” she said. “Learning what the students need is really important to me — making sure that they feel safe coming to school everyday and parents feel safe sending their kids to school every day.”

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About the Writers

Quincey Reese is a TribLive reporter covering the Greensburg and Hempfield areas. She also does reporting for the Penn-Trafford Star. A Penn Township native, she joined the Trib in 2023 after working as a Jim Borden Scholarship intern at the company for two summers. She can be reached at qreese@triblive.com.

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