To Mayor John Tory’s trusted advisers, it seemed an incongruous end to months of internal debate and strategizing on how to address Toronto’s financial challenges, build transit — and not hurt his shot at re-election.

Jet-lagged and still wearing the Christmas-themed, Don-Cherry-style jacket from his appearance at the Santa Claus parade, Tory delivered an impassioned speech on his willingness to back road tolls, even if it meant putting his political career at risk.

“This is the right way forward. This is the right time and it’s the right thing to do,” Tory told his relieved staffers gathered in the boardroom of his second-floor office at city hall, four days before announcing the proposal publicly in a speech to the Toronto Region Board of Trade.

The road to that watershed moment — and raising Tory’s comfort level to make the boldest, most significant decision of his mayoralty — took months of preparation of all those assembled: chief of staff Chris Eby; principal secretary Vic Gupta; Siri Agrell, director of strategic initiatives; Amanda Galbraith, director of communications, and Luke Robertson, director of council and stakeholder relations.

They began laying the groundwork with Tory’s call for 2.6 per cent reductions from city departments and agencies. But that narrative of the right — cutting waste and finding efficiencies will solve all fiscal challenges — doesn’t build subway lines.

Then there were the forceful urgings of Peter Wallace, the respected city manager: Toronto council must take a hard look at how it is going to pay for urgently needed, already approved, capital costs, including transit expansion.

A KPMG report provided a list of politically unpalatable ways to pay the tab. Council could impose new taxes or levies on commercial parking spaces, hotel rooms, and alcohol, gasoline or road tolls. Other tax measures included a municipal income or sales tax.

What Tory refused to do, despite appeals from left-wing councillors, was retreat from his 2014 campaign promise to keep property tax increases at or below the rate of inflation.

Over the summer, Tory concluded he had no choice. The city has $33 billion in unfunded projects. It fell to his staff to narrow the choices.

A hotel tax was a no brainer. There would be little political fallout by making visitors pay.

But reinstating a vehicle registration tax was a non-starter. This was favoured by Wallace, and recommended by KPMG, but Tory could never get council support for it after his predecessor, Rob Ford (now deceased), made it toxic.

Tory also gleaned from his monthly meetings with Premier Kathleen Wynne there would be other no-goes. These included a sales tax and an alcohol tax. Wynne didn’t want to get blamed for these.

A parking levy came with major implementation issues, possible legal challenges and too many councillors seeking exemptions.

There was also vigourous lobbying by a coalition of commercial real estate associations and representatives of some of the city’s wealthiest landowners. “Parking levy is my ‘don’t go there,’ ” Michael Brooks, CEO of Real Property of Canada, told Tory’s executive committee.

In a September speech to the Toronto Region Board of Trade, Tory argued the city had to look at “unlocking the value” of Toronto Hydro. Translation: sell a piece of the city-owned asset.

But reports of a behind-the-scenes privatization push involving Hydro executives and the utility’s board of directors scuttled that idea, sources say.

Tory was not eager to become the face of privatization the way Wynne has, to her detriment, with Hydro One.

So that proposal, too, came off the table.

With the list of options whittled down, road tolls started to look pretty good to Tory’s inner circle.

But they also knew that backing tolls on the Don Valley Parkway and Gardiner Expressway was a steep political hill to climb for Tory.

Would the move open the door to anti-tax-crusader Doug Ford attempting a return to city politics in, perhaps, the 2018 mayoral campaign?

In 2003, in his losing run for mayor, Tory attacked David Miller for musing about road tolls, suggesting his rival’s support for such a measure made him a “highway robber.”

Tory also rejected road tolls in the 2014 mayoral race.

In October, when Tory was heading out of town with his wife, Barb Hackett, staff tucked a Pembina Institute report, titled Fare Driving, into his binder. It endorses tolling as a fair way for the city to generate badly needed cash.

When Tory arrived back at city hall, he jokingly asked his staff if they were “trying to propagandize” him on tolls? But he also told them he was “more open to it than you think,” despite his lingering doubts on how to square it with his previous position in 2003.

On Oct. 28, Agrell and Gupta met with a group of city-building stakeholders to discuss Tory’s willingness to embrace new revenue sources. Those present, including Richard Joy, executive director of the non-profit education and research Urban Land Institute, were encouraged.

“This is a step in the right direction, a big step, and we can’t, in the name of getting it perfect, not let this go forward,” Joy says.

Back at city hall, Tory’s team agreed: they could sell road tolls and get it through council, particularly if the funds were dedicated to transit expansion.

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Tolls were attractive on the political spectrum. To conservatives, they are a form of tax in which the user pays. Progressives like them because they reduce congestion and fund transit.

Tolling the Gardiner and DVP also worked because it also hit all those 905ers using the city-owned and maintained highways.

The tolls could raise a significant amount of money.

And finally, Tory’s high approval rating, still hovering around 70 per cent, gave him the political capital to do bold things.

But the insiders also knew it was a political gamble. The car is still king in Toronto, and tolls of this kind would be a first in Canada.

Staff worked to raise Tory’s comfort level, reaching out to councillors for feedback. They sensed views had evolved. Research and polling data showed a softening of public attitudes, especially if toll money is used to ease congestion.

Last month, while Tory and Eby were in Israel with a business delegation, the mayor’s staff in Toronto sent over a package of material, including a draft of his speech “Time to Build,” speech breaking the tolling news, for the mayor to read on the flight home.

And so they braced for the Sunday afternoon meeting at city hall, the day Santa Claus came to town. Staff was confident their boss was tracking in the toll direction — even with the Ford factor.

If Tory’s 2014 mayoral rival surfaced, Tory would push back and demand to know how Ford planned to pay for Toronto’s needs. Galbraith assured Tory the flip-flop-focus in media coverage would be a one-day wonder.

His boardroom speech green-lighting tolls — while channelling Don Cherry — made his staff feel proud to work for him, says Galbraith.

“He did not have to step up and lead this discussion,” she says. “Being a leader to him meant being honest with the people of this city, that, to build the transit and infrastructure we need, we have to step up and pay for it. Transit isn’t free.”

Four days later, on the eve of Tory’s “Time-to-Build” speech to the Toronto Region Board of Trade, the mayor’s staff invited a small group of civic leaders to city hall for a briefing.

Richard Joy couldn’t believe his ears.

“It was amazing to think that the mayor was advancing road tolls. Road tolls for many, many people was probably the third rail, but, at the same time, the brass ring, both a policy tool and a revenue tool.”

Joy had a front row seat to the 2003 Toronto mayoral race as director of operations for Barbara Hall’s campaign, when Tory attacked David Miller on road tolls. But he also heard Tory many times, as head of CivicAction, admit he regretted that. Still, that was before he was an elected official.

“It was a really surprisingly great step . . . a kind of Nixon-to-China moment . . . (and) seems to be landing relatively well at this early stage.”

(U.S. Republican president Richard Nixon surprised the world by opening diplomatic dialogue with communist China in the early 1970s.)

With files from David Rider

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