On a sunny afternoon this September, city councillor Dianne Saxe and I walked through Greektown—across quiet residential neighbourhoods lined with neatly cut lawns and manicured gardens—while she explained why she was the best candidate to lead Ward 14 — Toronto-Danforth.

Just a few weeks earlier, Saxe had been registered to run in University-Rosedale, the ward on the other side of the Don River where she’d served as city councillor since 2022. Her decision to jump to Danforth came at the last minute—the final move in a frantic game of musical chairs that scrambled multiple council races across the city in the final days of the nomination period.

On Aug. 17, Mike Layton, the former city councillor who represented Trinity-Spadina and University-Rosedale from 2010 to 2022, decided he wanted his old stomping grounds back and entered the race there. Two days later, Toronto-Danforth councillor Paula Fletcher made the surprising decision not to run for re-election after representing the ward for over two decades. An open seat for city council is a rare opportunity in a city where incumbents have a huge advantage, and candidates immediately came flocking. Saxe was one of them. With just minutes to spare before registration closed at 2 p.m. on Aug. 21, she switched to the race for  Toronto-Danforth.

At the time of the switch, Saxe’s official election website still touted her unique connection to the ward she was now leaving behind. “University–Rosedale isn’t just where I serve – it’s where I’m from. Three generations of my family were born right here in our ward. I grew up attending local schools, and I’ve spent my life living, working, and volunteering across our neighbourhoods,” it read, on Aug. 21. “This community shaped who I am, and my love for our neighbourhoods drives everything I do at City Hall.”

After the switch, her biography became far less geographically specific: “Toronto has been my home my whole life – my family has deep roots here.”

Saxe knows that critics say she left the race in University-Rosedale because she was “ducking away” from a face-off against a well-known progressive champion. She says that, after years of building relationships and working alongside the community in University-Rosedale, the decision to switch wards wasn’t an easy one.

But, as we walked through the streets of the community she now hoped to lead, she told me she still wanted to be on the frontline of making change in the city. And she knew with Layton running, there was no longer an opening for her in University-Rosedale. Layton is the son of  the late federal NDP leader Jack Layton and stepson to Toronto’s current Mayor Olivia Chow. “There are celebrities, and there are outsiders,” said Saxe. “And I know which one I am.”

Now, in a crowded race of hopeful candidates that includes former councillor Mary Fragedakis and Sara Ehrhardt—the local trustee who seems to have much of the ward’s progressive machinery behind her—Saxe is in danger of seeming like more of an outsider than ever.

In Saxe’s telling, this isn’t the first time that an insider has forced her off course. In 2015, after four decades as a leading environmental and energy lawyer, Saxe was appointed to be the Environmental Commissioner of Ontario—an independent environment watchdog responsible for holding the government accountable.

After Saxe served in the role for three and a half years, Doug Ford abolished her office. “I did 17 of the best environmental reports that Ontario’s ever had, and all it did was get my office dissolved,” said Saxe. This became a pivotal moment in her career that would eventually lead her to running for municipal office in 2022. “Either I decided to walk away, or to keep fighting,” she said.

The decision to drop out of the race in University-Rosedale and run in the ward next door, Saxe said, was made out of the same desire to fight to make Toronto a better city.

Despite never having lived in Toronto-Danforth, Saxe believes that her background in environment, climate, and energy make her a qualified candidate to represent the area— which she said is one of the more environmentally conscious wards in the city.

Within the ward’s boundaries, one of Toronto’s most environmentally ambitious urban projects has been in the works for the past 13 years. The project aims to transform the Toronto Port Lands from an industrial region into a climate-positive, mixed-use community that includes green spaces, housing, businesses, and industrial infrastructure. The City anticipates that the full development of the Port Lands will take over 20 years.

In the event that Saxe wins the race for Toronto-Danforth, she said the possibility of helping move this project forward with her expertise is one of the things she is most looking forward to. “You only get that opportunity in a city like this once, if you’re lucky, every generation or two,” said Saxe.

Even though Sara Ehrhardt doesn’t live in Toronto-Danforth, few people would say that she doesn’t know the community. A public policy professional with a background in engineering, Ehrhardt got her start in local politics as a mother fighting the slated closure of the Duke of Connaught Junior and Senior School pool. After successfully advocating for the pool to remain open, she helped expand swimming programs in the east end, and fought to protect funding for childcare centres. After years of community advocacy, she was elected as the local Toronto District School Board trustee in 2022.

Ehrhardt’s entry into this ward race, however, raised some eyebrows. For some Toronto-Danforth residents, it seemed too coincidental that Ehrhardt announced her plan to enter the race just hours after her “mentor” Paul Fletcher’s last-minute decision to retire from her position after two decades—a decision announced just three days before candidate registration closed, leaving minimal time for others to enter the race. Along the campaign trail, Saxe said that she has heard a number of residents express frustration about what appeared to be “an attempt to just deliver Ward 14 to a new person without the public really having much say.”

In an interview with Ehrhardt, I asked her why she decided to enter the race when she did. Ehrhardt said that she never would have ran against her mentor. But when the opportunity to succeed Fletcher opened up, she jumped into the race with her “whole heart.”

“I’ve loved serving as the elected trustee. But I feel that I have more to give the community. I feel I’ve got a lot I could bring that’s useful as a city councilor with my background in engineering and public policy,” said Ehrhardt.

A few weeks after my interview with Saxe, I spent part of an afternoon shadowing Ehrhardt and her team while they knocked on doors in a residential neighborhood near Jones Avenue and Hunter Street. I was surprised by the number of people she and her team knew personally—some even by name—including details about their families and careers.

Ehrhardt told me that throughout her time volunteering across Toronto’s east end and her time as elected school trustee for the ward, she had probably already knocked on every single door at least once.

As we approached a red-brick house, Ehrhardt pointed to it and said she knew the family, before climbing the steps and ringing the doorbell.  A woman answered the door, a cellphone pressed to her ear.  Even though it was a work call, she took a few minutes to chat with Ehrhardt, who asked how her family was doing before even bringing up her campaign.