Borrowing a tactic from the business world, the Star performed 鈥360 performance reviews鈥 of the leading contenders in the mayoral race. We talked to people all around the candidates 鈥 those who have worked above them, next to them and under them 鈥 to understand their strengths and weaknesses as voters prepare to decide who will be Toronto鈥檚 next leader.
Early in Ana Bail茫o鈥檚 first term as councillor, then-mayor Rob Ford, an unpredictable leader whose proposed service cuts shocked the city, brought a plan to council to sell off 675 海角社区官网Community Housing properties to private investors.
With 86,000 families on the wait-list for public housing, the unloading of these properties 鈥 a collection of single-family homes scattered across the city 鈥 was an unpopular pitch.
Bail茫o, a rookie councillor, had recently become chair of the city鈥檚 affordable housing committee. Then considered a low-profile portfolio, housing would become, over the course of her 12-year council career, one of Toronto鈥檚 most urgent challenges.
Bail茫o consulted with experts, then met with Ford and negotiated a compromise: they would sell 56 unoccupied homes now, while establishing a task force to explore options for the rest.
Ford, elected on a promise to stop the 鈥済ravy train鈥 of wasteful spending at city hall, agreed.
That deal, which saved more than 600 community housing properties, was among the first brokered by Bail茫o in a move that would shape her reputation as a consensus builder who works effectively across ideological lines and a strong advocate for affordable housing.
A centrist with a progressive bent, Bail茫o has built a political career on collaboration and consensus. At city hall, where she was both a councillor and deputy mayor until 2022, people who worked with or for her say she was known for the kind of behind-the-scenes political grunt work that is often not visible to the public: shopping proposals around to councillors, getting ideas costed with staff and grinding out deals.
Some view consensus seeking as a weakness in politics. Critics have questioned whether, , Bail茫o could go to battle with provincial and federal leaders, or if her would leave 海角社区官网in a weak position.
The times we鈥檙e in require a mayor who cannot only govern effectively, but inspire, lead public opinion and make bold visionary moves. Even some who respect and support Bail茫o wonder whether she can be that person.
Supporters acknowledge that her collaborative leadership style may not get the attention that some grandstanding and bombastic members of councils past have received for loudly opposing certain proposals, but say her strategic approach gets the work done.
鈥淪he has never been a person who鈥檚 focused on grabbing the spotlight,鈥 but 鈥渟he has been a key player on many issues,鈥 said former 海角社区官网mayor Barbara Hall, who has endorsed Bail茫o.
Those who believe she鈥檚 the best candidate say voters need only look at her background to see evidence of the tenacity and life experience that make her well-suited for the job.
Bail茫o, 47, came to 海角社区官网from Portugal as a teen in the early 90s with her 6-year-old sister. They joined their father, a construction worker, and mother, a seamstress, in a multi-family flat near College and Lansdowne, where she learned first-hand how access to affordable housing is critical to building a life here as a newcomer.
She arrived speaking little English, but learned the language quickly and became her family鈥檚 leader, attending her sister鈥檚 parent-teacher interviews and accompanying her parents to meetings with bankers and lawyers. 鈥淚 had to grow up very fast,鈥 she said.
After school each day, Bail茫o delivered her little sister home to their father, then met her mother downtown where together they worked cleaning office buildings from 5:30 to 9:30 p.m. She still remembers her first pay cheque: $237.
After graduating from the University of Toronto, Bail茫o worked as a morning news reader for CHIN Radio, as a political assistant for a 海角社区官网city councillor and as a banking executive.
She lost her first run for 海角社区官网city council in 2003, but tried again in 2010 and was elected to represent her ward, Davenport, in the city鈥檚 west end.
Today, she worries that as 海角社区官网becomes increasingly unaffordable newcomers no longer feel the sense of possibility she did when she arrived in Canada. 鈥淭he identity of Toronto, and the soul of the city is tied to that feeling of opportunity,鈥 Bail茫o said, and that鈥檚 what drives her focus on affordable housing.
Complicating Bail茫o鈥檚 record on that issue is the Housing Now program, launched in 2019 when she was deputy mayor. Meant to rapidly produce thousands of affordable housing units, the program has struggled amid numerous challenges, and has yet to produce a single unit, leading some opponents to call it 鈥淗ousing Never.鈥
As a politician, Bail茫o is known for her strong work ethic and due diligence. She needs to know her files deeply and insists on having all the details before making a decision, former staffers and colleagues said.
鈥淪he won鈥檛 get outworked by many people,鈥 said former council colleague Josh Colle, who with Bail茫o and Mary Margaret McMahon, another former councillor, made up an informal voting bloc they called the Mighty Middle. (To others, they were the Mushy Middle.)
鈥淪he鈥檚 calm, but she鈥檚 not afraid of putting people in their place either,鈥 McMahon said. 鈥淚鈥檝e seen it firsthand.鈥
Facing challenging times, 海角社区官网needs a leader with integrity, someone who 鈥渆ven if you disagree with her position, she still has a way of commanding that respect,鈥 said Braden Root-McCaig, her former chief of staff, who is currently working on her election campaign.
That integrity has earned Bail茫o strong professional relationships with collegueges across the political spectrum, so much so that when she was charged in 2012 with impaired driving, councillors from left and right stood by her. Today, Bail茫o calls the DUI 鈥渢he biggest mistake of my life.鈥
Bail茫o has earned the support of numerous sitting councillors, major labour unions, MPs and former mayors Barbara Hall and Art Eggleton, and she is well-liked in her Davenport riding, where she was re-elected in 2018. (She did not seek re-election in 2022.)
But she is not well known to the public outside Davenport, perhaps in part because the passion seen in Bail茫o at community barbecues and events doesn鈥檛 always shine through at city hall, where her manners and restraint can read as corporate or stilted, some who worked closely with her have noted.
鈥淚 can be loud,鈥 Bail茫o said over coffee on a park bench near her downtown campaign office one morning in late May. When former mayor Rob Ford first proposed selling the community housing properties, 鈥淚 took buses of tenants out to Parliament Hill to protest,鈥 she said.
鈥淚 can be very loud,鈥 she said again, eyes flashing as though she was preparing, at that moment, to prove the claim. 鈥淏ut,鈥 she said, returning to her default calm, 鈥測ou need to be strategic at certain points in time as well.鈥
And that, she believes, is a strength: knowing when to fight, and when to be strategic.
Amy Dempsey is senior writer for the Star, based in Ottawa. Follow her on Twitter:
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