John Tory has always been around: a friendly, avuncular man about town, forever popping up here and there.

I recall seeing him march in the 2003 Pride Parade a few years after I arrived in Toronto. He was running for mayor then, and it felt somewhat remarkable, as he was a prominent conservative at a time when a lot of conservatives didn’t do Pride.

Some still don’t. That’s what makes him a compelling civic and political figure: he showed up for things for a long time on the road to being mayor. Indeed, John Tory has mounted what has to be one of the longest sustained efforts to attain elected office, running a decades-long political marathon.

He worked in premier Bill Davis’s and mayor Mel Lastman’s backrooms. There were intermittent stints practicing law, serving as CEO of Rogers and running the CFL. He also ran Kim Campbell’s failed 1993 federal election campaign, one that wasn’t so friendly as it had the infamous attack ad that mocked Jean Chrétien’s facial paralysis, suggesting there’s a calculated political ruthlessness behind Tory’s friendliness.

In 2003, he ran for mayor, losing to David Miller. The next year, he became leader of the Ontario Progressive Conservatives, but the party lost the 2007 general election and Kathleen Wynne beat him in Don Valley West, the riding he chose to run in. He later lost a byelection and ultimately resigned as leader.

Still in the public eye, or ear rather, Tory became CFRB’s drive time radio host each weekday. He also chaired CivicAction, a municipal engagement organization that has also been a stepping-stone into political office for MPPs Mitzie Hunter and Rod Phillips.

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All of this requires showing up. Days. Evenings. Weekends. Endless events and speeches. It’s relentless. Such civic mindedness is to be admired. After years of it, he finally won high office in 2014: the Toronto mayoralty.

In so many ways, his trajectory tacks in the right (no pun intended) direction to be a great and memorable mayor, saying things big city mayors say and supporting bold ideas as he did during his time with CivicAction. Once in office though, there was little follow through.

On a number of issues, it has taken large groups of prominent Torontonians to get the mayor to act decisively and make the right decision, like on police carding and the shelter crisis last winter. Instead of leading the city away from multibillion dollar generational transit mistakes, he’s rebuilding the east Gardiner and keeping Rob Ford’s Scarborough subway alive. Closing pools after promising to keep them open, undermining measures to make Toronto’s deadly streets safer for pedestrians and cyclists, and shelving stormwater and flood mitigation efforts are all leadership failures.

When Doug Ford announced his attack on local democracy, the response Tory mounted was one of equivocation instead of the fierce defence so many Torontonians wanted and needed.

Over the last four years, I’ve wished Tory would pull out what I call an “inner Bloomberg,” a boldness like New York’s three-term mayor Michael Bloomberg had who, while a wealthy conservative cast in a similar mould as Tory, used his position to dramatically push through big changes in his city.

If not Bloomberg, I hoped an inner-Bill Davis might rise. Tory’s political mentor helped invent modern Ontario, expanding the school and university systems and founding TVO. He even cancelled the Spadina Expressway.

Instead, Tory exhibits a radical fidelity to the status quo in a city with big problems and lots of potential. He’s a true conservative perhaps, but even conservative big city mayors often demonstrate action and boldness because big cities, by their nature, demand it. The status quo is stagnation.

Keeping taxes low certainly wins votes, but with transit and housing files in crisis and worsening inequality, the city feels as if it’s sliding into decline, a slow chipping away, something that is easily ignored if you’re not touched by any of it.

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Why does John Tory want to be mayor? This is what’s most confounding about him: a lifetime of effort to attain such a position and, once in, squandering a meaningful legacy despite having incredible political capital. He certainly still wants to be mayor as he refused to part ways with his effective, but controversial adviser Nick Kouvalis, who has undermined the very values Tory says he stands for, another sign of that calculated ruthlessness behind the friendliness.

I can’t know what kind of pressure the scion of a wealthy family is under to make their own mark in the world. The urge towards public service is one honourable way to do it, but if the legacy is the status quo, what was all that effort for?

John Tory would make an excellent Governor General of Toronto, if such a position existed: a glad-handing, friendly figurehead who doesn’t have to deal with messiness of politics, where standing for things and boldly leading the way isn’t required.

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