Most cities debate their troubled infrastructure to a standstill. Toronto has been arguing about the Gardiner Expressway for decades. Ilana Altman didn't wait for that debate to resolve. As CEO of The Bentway — a public space and cultural platform built underneath Toronto's elevated waterfront highway — she's been proving that you don't have to tear something down, or wait for it to die, to embed new values in it.

In this conversation, Ilana and Iain cover the full arc: how the Bentway went from idea to open in under three years, what it actually takes to run a 24/7 public space underneath a working highway, and why the conservancy model it pioneered is still largely foreign to Canadian cities. They get into the practical constraints — maintenance access, lighting limits, the challenge of food and beverage on a linear site — and what those constraints have forced the team to do creatively. Including turning highway maintenance equipment into community mascots.

But the deeper conversation is about civic joy as a strategy. The Bentway's Dominoes project — 2.7 kilometres of oversized dominoes run through Toronto streets by 300 volunteers — became one of the city's most shared moments in recent memory. Ilana traces what that kind of project actually does: not just entertain, but rebuild the connective tissue of a city that's been losing its volunteers, its optimism, and its willingness to celebrate what it's accomplished.

With FIFA FanFest coming to the Bentway this summer and the full seven-kilometre Under Gardiner Public Realm Plan now approved by council, the window to get the rest of the corridor right is open. Ilana is clear-eyed about how short that window is.

In this episode:

• How the Bentway went from philanthropic idea to open public space in under three years
• What makes it genuinely different from the High Line and other post-industrial urban renewal projects
• The conservancy model and why it's still novel in Canada
• Shade as a climate virtue — and how the Bentway reframed it
• The Boom Buddies: turning maintenance constraints into public education
• Why volunteerism in Toronto is down 30% and what Dominoes did about it
• The urgency of the eastern Gardiner corridor and the window that's closing
• Toronto's self-confidence problem — and what it would take to fall back in love with the city