Before making a last-minute decision to face incumbent Mayor John Tory in an election, Keesmaat was the City of Toronto's chief planner from 2012 to 2017. She was instrumental in shepherding a number of urban improvements through a skeptical city council. Wikimedia Commons/Taxiarchos228

After conservative Doug Ford, the newly elected Premier of Ontario, announced that Toronto will lose 18 city council seats, Jennifer Keesmaat decided to run for office.

On the last Friday of July, less than six hours before the registration deadline to run for Mayor of Toronto, the city's former chief planner Jennifer Keesmaat, was at her office and checking Twitter.

The night before, the Toronto Star had broken news that the recently elected Premier of Ontario, Doug Ford, planned to dynamite Toronto's upcoming municipal election, slashing the number of available council seats from 47 to 25, effective immediately.

After years of study and public consultation, the city had just finished redrawing its ward boundaries to ensure more equal representation. Under Ford's plan, announced with no warning, some councillors elected this fall could end up representing more than 100,000 people—more than the population of some Canadian territories. “I heard the story break… on Thursday evening and saw it unfold on the Friday morning,” said Keesmaat. “I had been in an early-morning meeting and it was when I came out of that meeting that everything became crystal clear.”

“It was very much the last straw,” she said. “All of those concerns that have been building and building over many months... culminated in that moment.” Keesmaat cycled to city hall, joined the line at the city clerk's office, and put her name on the ballot for the October 7 election.

“We're spinning our wheels on transit, we're not advancing transit even close to as aggressively as we should be to be keeping up with the pace of growth in the city,” she said that Friday. “The affordable housing crisis is absolutely a top priority for the city… and public safety, in terms of the violence we've seen on our streets, and road safety.”

Before making a last-minute decision to face incumbent Mayor John Tory in an election, Keesmaat was the City of Toronto's chief planner from 2012 to 2017. She was instrumental in shepherding a number of urban improvements through a skeptical city council. The King Street transit pilot, which currently limits auto traffic on the city's busiest streetcar route, was approved during her tenure. So were some the city's most popular bike lanes, along Richmond and Adelaide streets.

However, she was also in charge of planning when council decided to spend more than a billion dollars rebuilding a lightly-used section of elevated waterfront expressway. The titanically expensive one-stop subway extension into Scarborough was also approved while she was at city hall.

Mayor John Tory criticized Keesmaat for speaking out publicly against those decisions, but she was unapologetic, earning a reputation for expressing her opinion even when politicians preferred she did not.

“You’re not appointed the chief planner to sit on the fence,” she said at the time in 2015. “You’re supposed to give your best professional advice on all of these issues large and small.”

However, asked last week she would not say whether she would revisit those issues if she were to be elected, saying only that she would be releasing “a full and comprehensive policy platform” shortly.

At the time of writing, Keesmaat has offered very few specifics about her campaign other than promising “bold” ideas on transit, affordability, and public safety at a later date.

The new mayor, whoever it is, will be forced to reckon with a growing financial problem at city hall. The city manager has repeatedly warned council about the city’s financial position—simply not enough revenue to match expenses--and it has been told to find ways to generate more money.

John Tory and previous mayor Rob Ford have avoided raising property taxes (the city’s main source of revenue) above inflation and have generally been shy about creating new taxes. But the city's transit and community housing systems are facing repair backlogs in the billions of dollars and city services are perennially underfunded.

One of the ways Keesmaat thinks the city could raise more money is by asking developers to pay more. Over the last eight years, Toronto has been the center of one of the largest building booms in North America, sprouting hundreds of new condominiums and office buildings.

“When I was chief planner … we raised the planning fee,” she said. “That was win-win. Everyone was very happy with that outcome and that’s a perfect example of the kind of innovate ways we can deliver city services.”

Another challenge for the new mayor will be Premier Doug Ford, the older brother of the controversial and now-deceased former mayor, Rob Ford. Doug was a city councillor during Rob Ford's tempestuous, drug-scandalized term as mayor from 2010 to 2014, but, until being elected Premier June 7, had not held any other political office.

Like his brother, he’s brash, has little regard for convention, and appears to have a particular distaste for Toronto's left-leaning city councillors and progressive city-building agendas.

Keesmaat says liberal and conservative politicians like Ford actually have a good deal of shared interests. There’s a financial argument to be made for good public transit, she mentions as an example. “That’s one of the things that I’ve done in my professional life is I’ve worked across the political spectrum and with players of all stripes and colours and at all levels of government.”

“I can truly work with a whole variety of different people, and I can absolutely work with Doug Ford,” she said. If elected, she’ll have no choice. Ontario has considerable power over its municipalities, even ones as large as City of Toronto that has more than 2.8 million residents and an $11-billion operating budget.

Ford has the ability to blow up an active Toronto election on a whim, as he already made clear last month. If he gets his way, city council may be much more suburban and conservative than it already is. What’s more, it's likely Doug Ford will find other ways to hobble Canada’s largest city and Ontario’s economic heart in the years to come. “Someone said to me a few days ago: ‘It always feels like Toronto is an underachiever of a city, Toronto is never quite meeting its full potential,’” Keesmaat said. “And that's very much what I'm seeking to address in this campaign, to present a vision that's bolder, that’s about Toronto really reaching for its full potential.”

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