Compared to governing, winning elections is easy. And while Olivia Chow and her team might not describe their victory in Toronto’s mayoral by-election as a cakewalk, the challenges they now face are considerable. As mayor, Chow must navigate a chronically underfunded Toronto while navigating relationships with a divided city council, a Progressive Conservative government in Ontario fond of bullying the province’s cities, a Liberal federal government facing its own challenges, and a progressive community that has big expectations of her.

If you followed the results on election night, you saw a neck-and-neck race, with Ana Bailão leading for part of the night. By the time counting was over, Chow had pressed ahead with 269,372 votes to Bailão’s 235,175: a margin of victory just under 5 percent—comfortable, but hardly a blowout. A former city councillor and deputy mayor, Bailão was endorsed by John Tory, whose scandal-induced resignation from the mayoralty launched the by-election in the first place. Bailão has been labelled “a pragmatic centrist,” which describes a heap of Canadian politicians across levels of government. Her campaign made her look like an establishment candidate offering more of the same. And “same,” for skeptics, meant underinvestment in the city and de-prioritization of public space—hallmarks of the Tory years. Chow wasn’t an establishment candidate; her campaign was premised on a break with that past, arguing in favour of raising revenue, of community engagement, and of a city in which everyone might find themselves at home.

That difference could matter. Indeed, it could end up serving the new mayor well. If investments in public infrastructure backed by community buy-in pay off, the city might see results. Better, safer, more frequent transit. Or more affordable homes and people off the street. Accessible and clean public parks and spaces. Trash cans with room for, you know, trash. Saman Tabasinejad, acting executive director of Progress Toronto, a progressive advocacy organization, says Chow has set a high baseline. “With John Tory we had to fight for basic things like opening up the washrooms in parks,” she says. “Whereas now we’re in a different scenario. Advocates have someone who has shown that she listens and meets with activists.”

That different scenario became official on Wednesday, July 12, when Chow rode to City Hall on a bicycle to be sworn in as mayor in a ceremony emceed by actor Jean Yoon. Two days before, Chow called for a review of Ontario’s property assessment system in the wake of a Toronto Star investigation that found inequities between the richest and poorest owners, with the former not paying their share compared to the latter.

Chow’s win represents a chance to run Toronto differently. She also represents a racialized community that has been shut out of the city’s top office despite making up a sizable portion of its population. She was born to a middle-class family in Hong Kong in 1957 and came to Canada with them in 1970. By 1985, she had entered politics as a school trustee. Later, she became a Toronto city councillor and, after that, a member of Parliament. She ran for mayor of Toronto in 2014 and lost. In 2015, she tried to return to federal politics but lost the election to Liberal Adam Vaughan. The losses did not stop her. But now she faces a bigger challenge than those elections: changing the course of a city that has long been travelling, stubbornly, in the same direction.

Building a different city means adopting a different way of thinking about cities. It also means a new way of doing business. Tabasinejad believes Chow’s approach of relying on social movements to bolster her mandate while standing up, in plain sight, to other levels of government will work. “One thing that sets Olivia apart from her predecessors is the fact that she’s going to be negotiating in public,” she says. Tory and Bailão were cast as master negotiators with connections, who could work the backrooms and across all levels of government, but Tabasinejad doesn’t buy it. “That’s hogwash,” she argues. “That hasn’t worked.” Backroom deals and backslapping buddy politics will only get you so far. Cozy relationships with elites are one thing, but without public pressure and support from core communities, politicians are all too likely to shy away from making difficult or controversial decisions—like shifting resources away from police and to community-led, non-policing programs. Moreover, it’s all too easy for politicians in the backroom to accept that what their well-to-do, suited buddies are telling them is the gospel truth.

But to be successful, there’s another key part of her mayoralty that Chow will have to unlock: convincing non-progressives that her break with the Toronto of the past is better for the city’s future. You might look at overflowing garbage cans and transit delays and think the argument is self-evident, but convincing Torontonians to invest in their city—yes, taxes—after years of austerity conditioning is a project. Chow faces an entrenched political establishment, and not a few members of that establishment seem convinced her election will bring a Marxist revolution. The Canadian Taxpayers Federation called her a “threat to Toronto taxpayers.” During the race, Ontario premier Doug Ford opposed Chow as a “lefty” mayor, saying her win would be an “unmitigated disaster” and warning her tenure would drive business away from the city. Tabasinejad says progressives “have to talk to people on the ground” and “create a groundswell movement and dispel people’s fears.” That entails selling Chow’s agenda across the city and putting pressure on city councillors, Premier Ford, and Prime Minister Trudeau to get on board.

Within days of winning the election, Chow faced her first skirmish with the province over the Ford government’s Ontario Place project. The redevelopment, which will span twelve acres, includes an upscale spa, an expanded entertainment facility, and a massive parking garage to go with it. Toronto city officials said some of the design “overwhelms the public realm” and “prioritizes private uses” by limiting access to the waterfront to those willing to pay. Chow is fighting for that public realm, but the Ford government has played what it likely thinks is a checkmate. “If an agreement to transfer the City of Toronto-owned water or lands to the Government of Ontario is not reached, expropriation will be required,” says a report prepared for the government’s environmental assessment of the project. In short, the Ford government needs the space to redevelop, and it will get it, one way or another—even if it has to force the city to give it up.

The Ontario Place redevelopment seems an ideal issue for Chow to take a stand on. She ran on a promise to “keep Ontario Place public,” and she’s sticking to that promise. She must. Her vision for the city is premised on inclusion, which means maximum public space, accessible and open to everyone.

Asked about the environmental assessment report, she said she’d take the Ford government to court if they try to seize city land. “Hopefully we don’t get to a stage where we have two levels of government seeing each other in court,” she said, noting that the option was “available.”

Will that work? We’ll see. The struggle over Ontario Place may serve as a study of how Chow will balance movement building, conciliation, and fighting. There’s no way she can please everyone. Such is the nature of governing. The question is whether she can choose her battles wisely over the next three years, capitalize on social movement support, and deliver structural change on the city’s political priorities. But struggle is something left-wing progressives are used to. What they’re less used to is winning.

David Moscrop
David Moscrop is a political theorist, a contributing columnist for the Washington Post, and the author of Too Dumb for Democracy?