On Monday, June 26, after two months of campaigning,102 hopefuls, countless debates and a death threat against candidates, the Toronto mayoral by-election came to a close with several top news outlets calling it in favour of frontrunner Olivia Chow. Former NDP MP and councillor Chow will be the third woman in Toronto’s history to hold the title of mayor, and the first Asian-Canadian woman to do so. While Chow is a political force in her own right, she is also the widow of successful NDP leader and former Toronto councillor, Jack Layton.

Running on a platform of making Toronto a ‘more affordable, safe and caring city’ with a focus on increasing affordable housing and support for renters, Chow established a clear lead early in the race and maintained it throughout weeks of public opinion polling.

With more than 100 candidates registered in the race, it was a crowded field — but top contenders quickly emerged. A group of seven candidates who consistently polled at five per cent and above held the majority of media attention throughout the campaign — former city councillor and ‘housing czar’ Ana Bailão, Beaches-East York Councillor Brad Bradford, Chow, former Toronto Sun columnist Anthony Furey, former MPP Mitzie Hunter, Toronto — St. Paul’s Councillor Josh Matlow, and former Toronto police chief Mark Saunders. Final results also saw policy analyst Chloe Brown perform surprisingly well, doubling Bradford’s support.

With Olivia Chow winning a plurality of votes, Ana Bailão came in a close second, outperforming her polls and leading through much of the evening’s early vote returns. This built on a strong surge in polls in the days leading up to the election following a high-profile endorsement from former mayor John Tory. Former police chief Mark Saunders came in a distant third despite an informal endorsement from Premier — and Torontonian — Doug Ford.

Turnout was also surprisingly high for a city by-election, with nearly 725,000 ballots cast — ahead of 2022’s general election and not far behind 2018.

Chow’s relationship with Premier Ford

A Toronto mayor’s relationship with the provincial government will be an important contributor to their success. Municipalities in Ontario are creatures of the province, allowing the provincial government to make laws and regulations applying to them — as we’ve seen with the reduction in the number of Toronto council seats in 2018 and the upcoming dissolution of Peel Region. The city relies on both provincial and federal governments for critical funding. Even recently-introduced “strong mayor” powers, giving Toronto’s mayor greater independence from council, can only be used to support prescribed provincial priorities.

Chow, historically progressive in her stints as an MP and councillor, has clashed with Premier Ford in the past — most notably in the 2014 mayoral race. Her approach this time around has been different. Although she disagrees with some provincial government decisions, such as opening parts of Ontario Place to private development, enacting strong-mayor powers and proposing to move the Ontario Science Centre, much of her campaign has been focused on her own vision for the city. And despite Premier Ford’s support for Mark Saunders, he maintained throughout the campaign that he would ‘work with anyone’ who was elected.

Working with a divided city council

It will be essential for Chow to work in unison with councillors to tackle the myriad of issues the city faces. Since she has explicitly stated she would not use Premier Ford’s strong-mayor powers to pass legislation without majority support, she will instead need to rely on her ability to build consensus and compromise on the important issue impacting Torontonians.

As for Brad Bradford and Josh Matlow, they will be returning to their positions as councillors, likely to face some alienation from their fellow councillors, as over half of Council endorsed Bailão for mayor.

While city councillors are technically non-partisan, they make their priorities known through voting records and involvement in community activities; many members of council (including Bradford) will likely disagree with Chow’s approach to property taxes, policing and homelessness.

Bradford will see himself as the de facto leader of the opposition despite no such role in city politics, a thorn in the side of Chow with eyes on running again for mayor in three years’ time. Expect his focus to shift to being a city-wide critic, not just a local councillor; after all, if he runs again it will likely be for the top job — not his local ward.

Candidates’ next moves

Ana Bailão will most likely return to the private sector — prior to resigning the position for her mayoral campaign, she joined development company Dreams Unlimited as Head of Affordable Housing. But with her surprisingly strong showing in tonight’s results, it might not be the last Toronto has seen of her.

Mark Saunders, the preferred candidate of Premier Doug Ford, often polled as the runner-up to Chow in the weeks leading up to election day. In the end, he wound up in third place, with opposition to Chow seemingly coalescing around Bailão in the final days of the campaign. He will likely step back from the public eye while considering a run in the 2026 provincial election as he did in the last election under the Ontario PC banner.

Mitzie Hunter, who gave up her seat as MPP for Scarborough-Guildwood to run for mayor, may also remain out of politics and return to the nonprofit sector where she has previously held executive positions.

After Anthony Furey gained momentum in the final weeks of the campaign, receiving some high-profile endorsements (including Jordan Peterson, Conrad Black, and John Baird), he will likely return to his fellowship at digital media platform True North while working to consolidate and build on the populist right-wing base he’s built up.

What now?

It has been close to a decade since Toronto has had a new mayor, and the city has changed radically since 2014. Chow has her work cut out for her, facing an acute housing crisis, rising cost of living, public safety concerns and demand for transit and infrastructure upgrades. Fixing these issues starts with mayor-elect Chow’s relationships with the Premier and federal government and strong advocacy for Toronto in provincial and federal budgets.

There is also opportunity for the city to gain or lose operation of services to the provincial government. The uploading strategy could further strain the relationship between Chow and Ford; for example, if the TTC was uploaded by the provincial government, it may impact the legitimacy of Chow’s proposed property tax increases, which she states are also needed to build critical affordable housing capacity in the city.

H+K will be watching in the coming weeks and months as mayor-elect Chow settles into the new role, establishes her priorities for the city and staffs her office. Our experts will be focused on making sense of the transition for Toronto’s municipal leadership to provide actionable advice and strategic insight.

Authored by Kiki Cekota, Will Stewart, Matt Boudreau, Shanice Scott and Patrick Rooney.