Nobody can beat around the bush better than John Tory. I’m sitting with the recently deposed head of the Ontario Progressive Conservatives in the glossy Bloor Street apartment he shares with his wife, the real estate developer Barbara Hackett, and he’s trying to nail down what went wrong in his four and a half years as party leader. In conversation, he revolves restlessly around the issue of his resignation, shaping his answers with long, discursive defences of the many mistakes, real or imagined, that rendered him ineffective.

What Tory lacks in succinctness he makes up for in sincerity. It seems he is too honourable for the dirty business of modern politics. He genuinely yearns for “honest discussions” about pressing issues, from potholes to health care, social housing to, yes, religious school funding. This last concern, which became the defining issue of his losing campaign in the 2007 provincial election, is frequently cited as the beginning of the end of his leadership. But the truth is, Tory never stood a chance. The man who hoped to revive urban conservatism was assassinated by forces within his own party before his work could even begin. Tory’s opponents destroyed not only his political career, but with it, the Conservatives’ last, best hope for a return to power.

Tory was groomed for a life in politics. The son of John Sr., the former consigliere to Ken Thomson, and Liz, a force among the social elite, John Jr. began his career at the family law firm, Tory Tory Deslauriers and Binnington, before making his first foray into politics as Premier Bill Davis’s principal secretary in the early ’80s. Davis, the great Conservative unifier whose inclusive Big Blue Machine dominated Ontario politics from 1971 to 1985, became something of a political godfather and mentor to Tory.

After a spell in backroom federal politics, running campaigns for Brian Mulroney and Kim Campbell, Tory went to work for Ted Rogers, overseeing Rogers’ media and cable divisions in the late ’90s. But his desire to be of public service persisted, and he returned to politics in 2003, running against David Miller in a closely fought mayoral campaign that many Torontonians now wish Tory had won.

By the time he took over the PC leadership from Ernie Eves in 2004, the party was deeply divided between Mike Harris’s old Common Sense Revolutionaries and the more moderate Conservatives led by Eves. Tory’s corporate manner and principled stands didn’t ingratiate him to the party’s ultra-right-wing faction.

In the 2007 general election, for example, he made the kamikaze decision to contest Don Valley West against the popular Liberal education minister, Kathleen Wynne. Tory had already won a safe rural seat (the one vacated by Eves), but after having promised to broaden his party’s support in Toronto, which hadn’t elected a single Conservative MPP since 1999, he chose to lead by example.

Though polls showed that the next-door riding of Willowdale was a safer bet, the leader was set on Don Valley West. “That’s the riding where I spent 48 years of my life,” he says. An honourable decision—and consummately stupid. While it’s true that he was raised in Lawrence Park, along with his three siblings, and later raised his own four kids in the same neighbourhood, Tory would have broken no vow by running in Willowdale instead.

Tory’s antagonists inside the PC party, none of whom will speak on the record, say the 2007 election disaster was the predictable result of an ill-advised experiment in fuzzy, non-ideological politics. They say their former leader’s notorious school-funding promise destroyed his “brand” forever. Ontario taxpayers have been funding Catholic schools since the mid-’80s, to the exclusion of all other faith-based schools; every other province in the country either funds all religion-based schools or none. Tory’s initiative—essentially a review of the provincial funding policy—wasn’t wrong-headed. It was an attempt to right a long-standing inequity. But it proved highly unpopular with voters. Although tolerant Ontario would never openly admit such a thing, it panicked at the prospect of state-supported Muslim schools, and nothing could have saved the man who was advocating for them.