20 years on, David Miller's 2003 win looms over Toronto mayoral race

The battle lines in Toronto's upcoming mayoral race may feel familiar to some: A conservative has left office and a wide open race to replace him has taken shape. Candidates lament a city in disrepair and spar over the future of the waterfront. 

It all resembles 2003, city hall watchers say, when Toronto elected its first — and only — centre-left mayor since amalgamation in 1998. 

Not since David Miller left office in 2010 has a progressive candidate stood a better chance of winning the mayor's seat, said Zack Taylor, political science professor at Western University. Progressives running this time can learn from Miller's first successful campaign, Taylor added. 

Miller told The Canadian Press that he hears the echoes too. 

"There was a feeling that the city wasn't investing in the priorities of the people," Miller said of his 2003 run. "And I think there's a parallel today. We do see a lot of services declining."

Miller's tenure interrupted 18 years of conservative mayoralties starting with his predecessor Mel Lastman, through to Rob Ford and John Tory.

Tory secured a third term, winning a landslide victory in the October 2022 election, before resigning in February after admitting to an affair with a staffer. 

There is evidence that Tory remains popular, with some polls ahead of the June 26 mayoral byelection putting him in first place – even though he's not running in the field that included a whopping 102 candidates when nominations closed on Friday. 

In the packed race, veteran politician Olivia Chow, a former federal lawmaker and a long-standing member of the left-wing New Democratic Party, is a leading candidate. Coun. Josh Matlow is also being championed by the progressive left. 

The list of others seen as vying for centre-left votes includes former deputy mayor Ana Bailão, former provincial education minister Mitzie Hunter and Coun. Anthony Perruzza.

Even though voters overwhelmingly backed the conservative Tory less than a year ago, Miller and Taylor argued that Toronto may be ready to turn the ideological page. 

For Miller, a successful progressive candidate needs to be "straightforward, clear and consistent," including by talking candidly about the need to hike taxes to boost services, as he did in 2003. 

Miller said progressives can also gain traction by running against what he described as a "raft of backroom dealing, particularly between the mayor and the premier." When Miller first ran, his predecessor Lastman's final term had been marred by a municipal finance scandal and a confession to an extramarital affair.

During Tory's administration, many criticized the so-called strong mayor powers granted by Premier Doug Ford, which allow the mayor to pass a budget with one-third council support.