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Kenn Harvey, principal at Riverdale Collegiate Institute, is interviewed by a reporter, in Toronto, on Dec. 12, 2019. The school received $2.26-million from the estate of George Trimble, a former student.Christopher Katsarov/The Globe and Mail

When the mountain of unexpected paperwork landed on his desk, Toronto high-school principal Kenn Harvey cast a leery eye and called the bank in Kansas City with one question: “Is this worth my while?”

His school, Riverdale Collegiate Institute in the city’s east end, was a beneficiary in a former student’s will. As Mr. Harvey soon learned, it was indeed worth his while.

The former student, George Trimble, had died at the age of 100, after amassing a $23-million fortune. The physician, who practised medicine in Kansas City, Mo., had left his estate to 10 institutions that affected his life.

Now, three years later, two of those institutions – Mr. Harvey’s school and Morse Street Junior Public School, also in Toronto – have the enviable task of figuring out how to spend $2.26-million each. Dr. Trimble’s gift to the two schools he attended is the largest donation received by the Toronto District School Board (TDSB), Canada’s biggest public school board.

“It’s a really great problem to have,” Mr. Harvey said in an interview.

Soon after the donation was announced to the school community, suggestions came in on how to use it. However, the options for public schools are limited: In Ontario, ministry of education guidelines prevent schools from spending fundraising money and donations on items the province covers, such as textbooks and capital projects. Such funds are typically spent on playground structures, field trips, guest speakers and technology such as iPads and laptops.

Mr. Harvey said he is mindful of that fact. “I think one of the great things about public education is that it is equitable. It’s really important the funds can’t be used for things that should be funded through provincial grants,” he said.

So how will the schools spend their windfall?

Both have formed committees made up of their principals, parents, teachers, school staff and students.

Morse Street has spent some of Dr. Trimble’s donation, along with money it previously raised, to revamp the elementary school’s playground with multiple play areas and a climbing structure.

Mr. Harvey said the Riverdale committee is considering using some of the money to financially support students who can’t afford trips or to enter contests, and perhaps help with programs or initiatives in the community.

The larger portion – about $2-million – is being invested, and the committee is looking at how the interest could pay for bursaries for graduating students going to university or college. Mr. Harvey acknowledged that his school has some advantaged students, but many new Canadians and residents of social housing also attend.

The diploma of George Trembelzky is photographed at Riverdale Collegiate Institute. Both schools have formed committees made up of their principals, parents, teachers, school staff and students, to decide how to use the money.Christopher Katsarov/The Globe and Mail

In October, the school tried out the idea. At its commencement ceremony for last year’s graduating class, 10 students received $2,500 each in bursaries from Dr. Trimble’s donation, based on their academic marks, community involvement and financial need. “It was a really nice surprise for the kids," Mr. Harvey recalled.

He added: “We can do a ton with it. But there’s a responsibility to use it properly and that … causes a little bit of trepidation.”

Dr. Trimble’s niece, Lisa Hamilton, said her Uncle George would appreciate that the school was trying to help students who may face barriers pursuing postsecondary education.

“I think he was trying to support the people who supported him all those years he was studying and working,” she said in a phone interview from her home in Willow Springs, Mo., a four-hour drive from Kansas City.

Dr. Trimble was born and raised in Toronto. His parents left Poland in the early 1900s, getting off a boat in New York and heading straight for Toronto. They owned a dry goods store not far from the schools Dr. Trimble attended, and lived in the apartment above.

The graduating class photograph of George Trimble at Riverdale Collegiate Institute, in Toronto, on Dec. 12, 2019.Christopher Katsarov/The Globe and Mail

Ms. Hamilton said the family faced anti-Semitism and changed their last name from Trembetzky to Trimble before her uncle and her father, David, entered medical school at the University of Toronto.

David Trimble moved to Los Angeles to practise internal medicine and his brother followed, working at a hospital in Long Beach before transferring to Kansas City. He specialized in infectious diseases, Ms. Hamilton said.

She remembered her uncle, who died in June, 2016, as a simple, quiet and kind man. He never married and had no children.

“He didn’t spend money on cars or houses or anything like that. I think he liked his work more than anything. But I also think he enjoyed investing just to see the returns,” Ms. Hamilton said.

Ryan Bird, a spokesman for the TDSB, said the board was grateful that “Dr. Trimble felt so strongly about his experience at both schools that he wanted to ensure he supported them after he passed.

“This extremely generous donation, the largest ever at the TDSB, will ensure his legacy lives on in the community and schools he loved,” he said.

Added Mr. Harvey: “The blessing of Dr. Trimble’s donation is we’re allowed to do whatever we want with it [within the guidelines]. It’s an unbelievable thing for him to do.”