The initial idea to transform the underside of the Gardiner Expressway into a public space came from Judy Matthews, a local Toronto urban planner and activist.

The donation represented one of the most significant gifts in Toronto's history, and it was hoped that it would inspire other Torontonians to make similar philanthropic contributions to city-building initiatives.

A panel of 12 artists, policy experts and community leaders took the suggestions and whittled them down to a shortlist of four names: "The Artery," "The Bentway," "The Canopy," and "Gathering Place."

[10] The Bentway spans six Toronto neighbourhoods with a total of 77,000 residents: Liberty Village, Niagara, Fort York, Fashion District, CityPlace, and Harbourfront.

[13] Designed by Agency—Agency (New York City) and SHEEEP (Toronto),[14] Bentway Staging Grounds collects and leverages runoff water from the highway into oversized planters in the space below.