Jennifer Keesmaat fought hard to topple Tory, but none of it mattered

On Monday night, John Tory officially won a second term as mayor, handily beating his main rival Jennifer Keesmaat by more than 300,000 votes.

But weeks earlier, he'd already, unofficially, triumphed.

It was the afternoon of Sept. 22. Keesmaat, the chief city planner turned last-minute mayoral candidate, faced Tory, Sarah Climenhaga and Saron Gebresellasi at a live debate hosted by Global News.

A beacon of hope for many Toronto progressives — particularly those fuming after Premier Doug Ford's council-slashing legislation — Keesmaat seemed intent on distancing herself from Tory and his track record. And so she opened hard, skewering SmartTrack, Tory's shape-shifting campaign promise from 2014. The diluted transit plan, she proclaimed, was "dead in the water."

SmartTrack? Dead?

Not to the mayor.

"It's so hilarious you say that," Tory fired back, before holding up a piece of paper showing just-in provincial approval for the six new stations.

It didn't matter that there's much to criticize about Tory's signature proposal. That the 22 stops promised by Tory four years ago have been whittled down to six. That the system is seen by many as a branding exercise with so-called SmartTrack stations popping up on existing GO train lines. That it's merely one contribution — and a controversial one at that — toward fixing the city's laundry-list of transit needs.

None of it mattered. Because, in that moment, Tory proved he'd already won.

Tory's track record resonated with 63 per cent of voters

However furiously Keesmaat fought to shatter his every-man veneer, to highlight what she called his "dithering" leadership style and the right-wing leanings keeping him cozy with Ontario's polarizing new premier, Tory brushed aside her concerns with one piece of paper.

It highlighted the advantage — the momentum — Tory always had from the get-go. In September, he could flash his SmartTrack approval; by late October, he held up another provincial paper featuring a green light for the long-awaited downtown relief line's environmental assessment.

For every issue, be it transit or housing or crime, he could always say some form of the same refrain: I've met with the right people, I've taken action, I've secured some funding or government backing or outside support.

Many argue there's truth to that. There have been improvements on the transit file, on the economic front, and even when it comes to affordable housing, with Toronto hitting its annual approved affordable housing target of 1,000 units for the first time last year under Tory's watch.

That progress was enough to resonate with roughly 63 per cent of voters.

Tory's critics see it differently. Some claim his incendiary language around gun violence (he called the suspects involved in a high-profile shooting at a Scarborough playground "sewer rats") is stoking racial tensions and division, while others have questioned his commitment to funding programs for at-risk youth.

Meanwhile, gun violence is becoming routine, with hundreds of shootings so far this year, and more than two dozen people killed.

And two years into the city's plan to reduce the number of road-related deaths to zero, dozens of people have lost their lives in 2018, including more than 30 pedestrians.

Keesmaat remained in second place throughout the race

Amid that backdrop came Ford's council cuts, a sweeping change midway through an election that sparked court challenges, protests, and one judge's scathing — albeit later overturned — ruling that the province had "crossed the line."

The stunning move from Ford prompted harsh words from Tory, along with a criticized admission he knew from the premier himself that something was in the works, though the mayor didn't take the musings seriously.

That was the final push Keesmaat needed to sign up, and the rallying cry for her supporters.

But again: None of it mattered.

Friends and fans of the powerhouse planner kept her in second place through the race. But quietly, many questioned her tactics and debate performances.

Throughout much of the campaign, journalists asking questions about her policies were met with non-answers that were often assessments of Tory's failure in whatever topic was at hand. Ask Keesmaat about transit, for instance, and she'd quickly spout her well-worn phrase about his ideas being written on the "back of a napkin."

Even the press conference revealing her detailed, city-wide transit plan kicked off not with the map itself, but with criticism of her rival. So did her final appearance on Metro Morning, the Friday before election day: When asked why voters ought to trust her over a more experienced politician, Keesmaat spent 38-seconds of precious airtime naming and shaming Tory before explaining why having a planner at the helm could be a positive change.

Why, some wondered in hushed conversations after debates, and more loudly online, did she not just talk about herself and her ideas?

Even so, as the campaign progressed, what seemed like the real Keesmaat emerged: A thoughtful city-builder capable of dreaming up ideas like a rent-to-own program financed by a luxury home tax and a plan to transform city-owned golf courses into public spaces.

Ideas, like them or not, which set her apart from the mayor.

But none of that mattered, either.

For Keesmaat, running against a largely inoffensive leader with broad public support was surely a daunting task, and one underpinned by a lingering sense of inevitability: Tory, like the first two incumbent mayors seeking re-election after amalgamation, would come out on top.

And indeed, weeks before election night, Tory secured his second victory — with a wave of provincial paper.