Barrie Sketchley, TDSB’s longest-serving principal, remembered for his kindness, inclusion

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Barrie Sketchley, the Toronto District School Board’s longest-serving principal who helped shape generations of students at Rosedale Heights School of the Arts, has died at 85.

Sketchley spent 42 years working for the TDSB, including 34 years leading Rosedale Heights as its founding principal. His death was announced Wednesday by the school, which remembered him as much more than an administrator.

“We will miss Barrie’s leadership, his smiles, his love, his wonderful stories of the amazing life he led,” Rosedale Heights’ current principal Joseph Ghassibe wrote in a letter to the school community, according to Global News.

Those stories included his first commercial flight to the United Kingdom in 1957, ski trips and the road trips he loved taking.

‘I love working with young people’

For Sketchley, working with young people was never just a job. During a May 2023 interview with CTV News, he recalled walking into a classroom in 1965 and said he “never wanted to look back and I’ve loved all of those years in between.”

“I love working with young people, seeing them mature, watching where they’re going, helping them get there,” he said.

His connection to Rosedale Heights was clear when the school board tried to transfer him to Harbord Collegiate for the fall of 2025. Students and parents pushed back, and Sketchley was allowed to stay until his planned retirement at the end of that school year, CP24 reported.

“With over 30 years of dedicated service to Rosedale Heights, Principal Sketchley’s deep connection to students, families, and staff has shaped the identity of the school,” Superintendent Jennifer Chan wrote at the time, according to Global News.

Cancer diagnosis

But Sketchley left the school last May after being diagnosed with cancer.

Tasha Kheiriddin, co-chair of the school’s Parent Council, told CP24 that the community sent him boxes of get-well and farewell cards after he became ill and left suddenly.

“He was a principal like no other,” she said Wednesday. “Mr. Sketchley was someone who created this culture of kindness, inclusivity, acceptance, and a love of learning. He inspired everyone to do their best.”

Champion of the arts

Kheiriddin, who is running for TDSB trustee in Ward 7, also called Sketchley a champion of the arts, adding that the entire school board benefitted from his work.

“The whole TDSB owes him a great debt,” she said.

For Ghassibe, Sketchley’s legacy comes down to empowerment and a belief in what young people can achieve.

“Barrie truly believed (and knew) that children are our future. Thousands of students (as well as families and staff) have benefitted from his leadership, support, and love,” he wrote.

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