Toronto's waterfront has long been a place where big dreams go to die. From John Graves Simcoe's "Walks and Gardens lands" to the powerhouse port of the 1950s – and beyond – one scheme after another has been imagined, half-built and abandoned.

Will Fleissig

That may be changing. Will Fleissig is betting that it is. The 66-year-old, after a distinguished career as a planner and real estate developer in the United States, answered the call last year to take over as chief executive of Waterfront Toronto, the government agency charged with remaking 2,000 acres of public and private land on the doorstep of downtown.

The plans involve the biggest infrastructure project, and the most valuable real estate play, in the city's history. The overall waterfront plan could one day house 40,000 residents and 40,000 jobs. And they might just transform how the GTA thinks of itself.

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"When a headhunter called me," Mr. Fleissig says, "he said: 'One of the tasks is to redefine cities in Canada.' I asked: 'Do you really mean that?' And the answer was yes. That's pretty hard to resist."

What Waterfront does – or fails to do – will have a massive impact on the city. Perched on the edge of his office couch on a Friday afternoon, Mr. Fleissig sounds entirely alert to that reality. "If you ask what I do, I'm a city-builder and this is an enormous opportunity."

Waterfront under Mr. Fleissig is making no little plans. This week, it opened a call for an "innovation and funding partner" to plan Quayside, a new, 12-acre neighbourhood near Queens Quay and Parliament. There are a lot of goals: energy efficiency, resiliency to climate change, creating affordable housing, building a tech jobs hub, making the waterfront a regional destination and raising the bar for architecture, landscape and urban design. All while making money for Waterfront Toronto.

These will also be the agency's goals as it proceeds to plan a 750-acre swath in and around the port lands. "It's not just a stack of spinning plates," Fleissig argues. "It all comes together into city-building. Our goal is to use the waterfront as a test bed for how we construct the future city."

When Waterfront Toronto was formed in 2001 as a partnership of the city, province and federal governments with $1.5-billion in funding, it was something of a flyer. "The world is urbanizing, and we need models for the 21st-century city," says Mark Wilson, until recently the chair of Waterfront's board. "We had room, because of the scale of what we're doing on the waterfront, to explore that."

The agency has proved itself. It started the Canary District neighbourhood, opened for the Pan Am Games, and built an excellent park, Corktown Common, whose berms will also keep the Don River from flooding the downtown core. It has added the landmark Sugar Beach, where thousands of people attended the Sugar Shack TO festival last weekend; and rebuilt Queens Quay and the Central Waterfront, giving a much-needed lift to Harbourfront's public spaces. It has begun planning an exciting new Toronto Island ferry terminal.

Waterfront has lured about $10-billion in private investment for condo, apartment and office construction, largely maintaining strong architecture, and brought in a presence from George Brown College and, soon, OCADU. It's also contributed indirectly to the boom in the South Core district of downtown.

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Despite some sniping during the Rob Ford era – Doug Ford almost derailed the agency's careful plans by freelancing a plan for an amusement park – there have been no real scandals or screw-ups. Under former CEO John Campbell, the agency managed to keep three levels of government largely happy. "I think people see the vision, feel it, believe it," Fleissig says. "The model works. And the question is, now that we have that commitment, how do we leverage it and move on to the next stage?"

Waterfront's approach so far has been largely to build parks and infrastructure, and then make deals with real estate developers for particular blocks. The resulting buildings, particularly at the River City complex, are very good.

The Quayside project suggests what's next. Waterfront isn't looking for real estate developers yet; it's looking for "innovation and technology partners, equity investors and infrastructure-oriented funds" to help figure out what the business model for the area should be. It will include housing, but it will also include tech jobs; it could use new "clean technology" to achieve building performance and to test new systems and techniques. As Fleissig sees it, a new alliance of pension funds, tech companies, educational institutions and philanthropic groups can set an example here.

Wilson puts it this way: "We're moving into a more project-by-project approach, which requires a more entrepreneurial sensibility … that's one of the reasons we picked Will. He has built multiple companies. He has operated independently as a developer. But he's also worked in city hall."

Fleissig moved from San Francisco to Toronto's Summerhill neighbourhood a year ago, along with his wife, architect Wendy Kohn, and their two teenage daughters. After a career as an urban designer, he became a planner in Denver – running a transformation of the city's downtown in the 1980s, becoming chief planner – and then a private developer. As a businessman, he hired Toronto-based KPMB Architects to design a mixed-use building in downtown Denver. "He was an amazing client," recalls KPMB partner Bruce Kuwabara, who has served on the Waterfront Toronto design review panel. "His skills are incredibly broad – design, city-building, economics, and engagement. He really covers the territory for urban development."

Later in San Francisco, Fleissig was a partner in the development company Communitas, which focuses specifically on partnerships with public organizations. "That's what I'm most known for, building that sort of relationship," he says.

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Fleissig admits that he's learned a few things in his first year about getting things done in Canada – "you need to have more people at the table than you do in the U.S." – and that's especially true for the organization's signature project, the Don Mouth Naturalization.

The overall waterfront plan could one day house 40,000 residents and 40,000 jobs. Fred Lum/The Globe and Mail

That is a $1.25-billion flood-protection project that would reorient the mouth of Don River, creating wetlands that moderate the river's swells. The design, by leading landscape architects Michael Van Valkenburgh Associates, would allow more than 600 acres of the port lands and surrounding area to become viable for development. The payoff – much of that is public land – would be in the tens of billions. This includes public land in the Keating Channel neighbourhood, some of which would be opened up when the eastern Gardiner Expressway is rebuilt slightly to the north of its current location.

Private development includes the project dubbed East Harbour on the east side of the Don; the owner, First Gulf, has been pursuing approvals for that large mixed-use project over the past few years, but the site is in the Don's flood plain. "East Harbour doesn't happen unless the Port Lands happens," Wilson says. "You have a developer who says, we're prepared to make an enormous investment in the economy of Toronto and of Canada, but governments have to do their thing."

The big question now: Will they? The three-government structure has allowed Waterfront to move quickly, but in order to keep moving it needs the city, Ontario and Canada to line up agendas and funding. That three-way match, a slot-machine jackpot, is plausible right now. The city is on board. "We have alignment around the Prime Minister and the Premier and the mayor around affordable housing," Fleissig says, and Waterfront officials "are in deep discussions" with the province. As for the federal government, "all I can say is that we are in very good shape."

If the flood-protection project goes forward, Quayside should set the tone for the next major project stage: the development of Villiers Island in the 2020s. This area, which is already in planning, would combine open space and some sort of cultural venue with a new neighbourhood of offices, retail and housing.

The shape of that should be an opportunity to pursue sustainable building, and the best in walkable, fine-grained urban design and contemporary architecture. Kuwabara (who has various connections with the waterfront) argues the result ought to look to examples like Hamburg's Hafen City. "I think the lessons here, in terms of a sustainable mixed-use waterfront, should come from Europe," he says. "If it's just more Toronto, that's an absolute failure."

Fleissig says Villiers Island "will show how to make a 21st-century sustainable city." Will it get built? "I think it will," he says. We've been raising the bar, and we'll keep raising the bar."

If there's room anywhere in Toronto for such big dreams, it's on the waterfront.