TORONTO - For John Tory, the road to political hell was paved with good intentions.
Anointed as the second coming of longtime premier Bill Davis and the Big Blue Machine that ruled Ontario for 42 years, Tory seemed to have everything going for him when he took the Progressive Conservative crown in 2004.
Wealthy and well-educated, affable and outgoing, Tory was a Conservative dream: a former business executive with a strong social conscience who had lived and breathed the party's principles practically from birth.
To his colleagues and former staff, Tory is the consummate gentleman. A "class act" who "oozes integrity," said his predecessor, Ernie Eves.
When he lost his bid to be Toronto mayor in 2003, Tory threw a fundraiser to help rival Barbara Hall clear her campaign debts.
Even after conceding defeat in Thursday's career-ending byelection, Tory took the humbling step of walking into a boisterous Liberal victory party to personally congratulate winner Rick Johnson - putting him straight in the path of reporters and their pointed questions about whether he would resign.
"The thing that is so truly amazing about John is that he is universally liked and universally respected, and there's hardly another politician that you can say that about," said Diana Arajs, who worked on his 2007 campaign.
But it was Tory's stubborn desire to do what he thought was right - even when the political timing was off - that ended up doing him in, many say.
Tory, who broke down several times during an emotional session with reporters Friday, suggested that perhaps he was too honest for the "show business" side of politics.
"There's certainly far more temptations and far more opportunities and far more days when it seems necessary to do that than there should be," he said.
"I just tried to resist that every single day with every ounce of determination I had ... because I always felt that if you didn't have your integrity intact when you left this business, you had nothing. And that's not just this business, it's life generally."
Tory's political career - which spanned all three levels of government - is littered with examples of good intentions gone awry.
In orchestrating former prime minister Kim Campbell's unsuccessful 1993 federal election campaign, Tory was criticized for attack ads that appeared to mock Jean Chretien's facial deformity.
That fateful election marked the beginning of the end of the federal Progressive Conservative party, which ended up with only two seats.
During the 2007 Ontario election, Tory left his safe Conservative seat in Orangeville to run in the Toronto neighbourhood where he grew up and now lived - even though it meant going head-to-head with Education Minister Kathleen Wynne.
He lost, forcing him to wander in the political desert for the next 17 months.
Tory could have taken the easy way out and stayed put, but he made the promise and intended to keep it, said one source.
The same went for his doomed campaign proposal to extend public funding to faith-based schools, which tanked with voters and led to one of the party's worst showings ever.
Tory refused to back off the promise until the dying days of his campaign, despite opposition from some of his own caucus members.
Tory listened to those who said he was going in the wrong direction, but he didn't always hear what they were trying to tell him, said one former staffer, who spoke on condition of anonymity.
"He's very dogged, and once he takes his position, he is wedded to it," the source said.
"He really is a man of his word, which is a bit of an irony, really, because everyone wants politicians to be honest."
Even after the loss and a tepid 66.9 per cent approval rating at a leadership vote last year, Tory was reluctant to reach out to a vocal neo-conservative faction whose ideas clashed with his own centrist "Red Tory" views, some say.
Resentment grew in the months that followed, weakening Tory's grip on the leadership as critics lashed out at his indecision and failure to find a path back into the legislature.
Experts say Tory just didn't have the right political instincts for the job.
"He worked best when he had really strong leaders to work for, whether that was Bill Davis or Brian Mulroney," said David Docherty, a politics professor at Wilfrid Laurier University.
"But when he was on his own or working with people who weren't strong, such as Kim Campbell, it's clear his political instincts aren't that great."
Tory, 54, said it's too early to say what he will do now that he's stepping down as leader. But he vowed to stay involved with the provincial party that's been such a large part of his life for 40 years.
He urged politicians of all stripes to do better for the people they represent, many of whom are hurting as the province tumbles into recession.
"The ideology that one has in any party, including our own, is such that it should never blind you to the realities of the fact that you are in this business to help people," he said.
After taking a long-overdue rest, Tory said he wants to find a job where he could make a difference.
Those who know him predict he might head up a charity or go back into the media business - even broadcast radio, one of his first loves.
For his part, Tory seems to be leaving with few regrets.
He admits it was a bad idea to mix religion, politics and education in the 2007 campaign, but wouldn't shrink from that controversial promise Friday, insisting it was about "fairness" in the Ontario school system.
His biggest regret seemed to that he had disappointed so many others, including Davis, his mentor.
Tory struggled to fight back tears as spoke about Davis, who took the byelection defeat harder than he did.
Davis wanted to be at his press conference, but Tory told the former premier that it would be better if he stayed away.
"You couldn't ask for a better friend and a better mentor and a better example," Tory added.
"He's not perfect and nor am I and nor is anyone. But he was an outstanding public servant and a humane, compassionate person that really, to me, epitomized what a Progressive Conservative is all about."
In the eyes of another former premier, John Tory is leaving politics a winner, not a loser.
"If he made any mistakes, and we all make mistakes no matter what we're doing in life, I don't think he was necessarily prepared for the brutalist game that politics can sometimes be," said Eves.
"He's leaving with his principles intact and his integrity intact, and that's a big win for him."
