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.
