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When most people pass underneath Toronto's Gardiner Expressway, they see nothing but a grim, grey mass of concrete. Judy Matthews saw something different. When urban-design consultant Ken Greenberg took her down for a look, "It was, like, wow. The monumentality. The beauty. It was like a cathedral. You could see the potential."

Before long, Ms. Matthews and her husband Wil, leading Toronto philanthropists, were approaching Mayor John Tory with a bold plan and a pledge of $25-million to make it happen. Why not transform the forbidding no-go zone under the expressway into a creative new public space complete with playgrounds, trails, markets, performance venues, bike paths – even a skating rink? The mayor jumped at the offer and project Under Gardiner was born. Ms. Matthews wants to "turn things on their head" and make the gritty underside of the expressway into "a vibrant new kind of place that is going to be warm and welcoming for thousands of people."

It's a great idea that would do all sorts of good things for the city: Create new public space in booming downtown high-rise neighbourhoods that have too little of it; break through the Gardiner to connect the city to its developing new waterfront; go beyond grass and park benches to change the way people think about parks and public spaces.

But what's most exciting is the precedent it sets for private philanthropy. Wealthy Canadians tend to give their millions to medical research, hospitals, museums or universities. Ms. Matthews is challenging them to think differently and consider donating to superior public-space projects that enhance the quality of city life. In these days of tight money and slow growth, she argues, we can't expect governments to do it all.

"The city is struggling. They have so many needs to meet. If you recognize a need in the city and you have a capacity to fill that need, that's part of the true meaning of being a citizen."

In the United States, it's already commonplace for private donors to fund public spaces. Piles of private money went into Millennium Park in Chicago, Bryant Park and the High Line in Manhattan, and Prospect Park in Brooklyn, among many others. One New Yorker gave $100-million to the Central Park Conservancy, the group that oversees New York's oasis. Billionaire Barry Diller has offered more than that to build a "floating park" on a pier in the Hudson River off Manhattan that would include lush landscaping and an outdoor performance space.

Canada is way behind in this kind of giving. Ms. Matthews, who went back to school to study urban planning after raising four children, was behind the 1990s revitalization of St. George Street at the University of Toronto. The Matthews were also among the donors who helped create the Toronto Music Garden at the west end of the harbourfront. Otherwise, Canadians giving to creative public spaces has been thin.

The Canadian way is to leave that sort of thing to governments. The trouble is that they often don't do it very well. Cutting the grass and emptying the trash in a traditional public park is something city hall can do. Ask it to build or, worse, maintain, a 21st-century public space and the results can be disappointing.

Something as innovative and sophisticated as Under Gardiner would be tough for city hall alone to tackle. As Mr. Greenberg puts it: "It is hard to do the extraordinary through government."

Ms. Matthews sees the project as a public-private collaboration. It isn't a matter of rich people coming in to build a park on their own. It isn't a matter of leaving it all to government either. The space will remain publicly owned. Waterfront Toronto, the government agency that handles waterfront development, will play a big organizing role. But private citizens and groups will join in. She wants to see a new model for maintenance and programming and she has already travelled to New York to see how the Central Park Conservancy works.

What she has proposed is hugely ambitious: to transform the underside of the Gardiner from scratch. But if she and her collaborators succeed, they will do more than build a brilliant public space in an unlikely spot and create a new model for public-private partnership. She will set an example for other people of wealth who want to do something out of the ordinary with their money.

Asked what she would say to other philanthropists, she smiles: "I'd say come and join us. There's lots to do."