At high noon on November 3, which happened to be his 1,001st day as Canada’s minister of finance, Jim Flaherty took the podium at Pearson airport’s Sheraton Gateway Hotel and announced that Ontario, once the economic engine of Canada, had become a welfare case. Beginning in 2009, the province would receive $347 million from the federal equalization program, which pools money from rich provinces and gives it to poor ones. He never smiled, but as always, his weary-eyed, pursed-lip poker face seemed to be stifling a smirk.

The media started firing questions: Was Ontario being shortchanged? Why the paltry $347 million, compared with Quebec’s $8-billion windfall? The suspicion was that Flaherty had shafted his home province—again. This is the man who called Ontario the “last place” to invest in Canada, so presumably he would be reluctant to throw good money after bad. But there was more to it than that. The wildly opinionated Liberal strategist Warren Kinsella once said that most people in Ontario believe Conservatives have “tiny black hearts,” and every time Flaherty—the most prominent survivor of the Harris era—meets the press, that’s the story they look for.

On this day, Flaherty beat the rap by means of a simple redirection: the real story wasn’t whether or not Ontario was receiving enough money, but the fact that it was on the dole. “Ontario is entitled to enter the program and will be receiving substantial funds,” Flaherty said, wearing rimless glasses and a dollar-green tie tucked neatly inside a dark single-breasted suit. “Regrettably, I expect that Ontario will be in the equalization program for some time to come.” Though he delivered the lines with all the sincerity he could muster, they nonetheless poisoned the microphone for the next speaker, the Ontario Finance Minister, Dwight Duncan, who used up most of his air time digging his way out from under the prediction that his province was about to become a perpetual mooch. He spoke with his hands in his pockets and a squeak in his voice, his fully exposed, bright red tie narrowing from his gut up to his chin like political heartburn.

It was a clever move by Flaherty, but it didn’t put to rest the original question. Was he screwing Ontario? No one could say for sure. The equalization formula is the kabbalah of Canadian politics, indecipherable to all but a small group of bureaucratic mystics. Any reporter who tried to sort through the sefirot of nominal GDP, resource price volatility and fiscal capacity would miss deadline. In any event, the answer lay not in the formula, but in Jim Flaherty’s heart, and in whether or not it’s as tiny as 416ers seem to believe.

Jim Flaherty lives in Whitby, amid miles of residential culs-de-sac lined with detached homes featuring big garages out front and swimming pools out back—the kind of place that, photographed from above, perpetuates the suburban stereotype of conformity and soul-sucking meaninglessness. Flaherty, however, doesn’t live in one of those ticky-tacky little boxes. He lives in the one home that doesn’t fit the mould: an original farmhouse, its name and date of birth—Mayfield, 1845—engraved in a boulder at the driveway’s edge. Set on two hec­tares behind a fortress-like hedge, it’s the house you might fail to notice as you drive through the area. But once you do notice it, you’ll wonder, “Who lives in that place?” It is the alpha house, occupied by the alpha family: Flaherty, the local MP; his wife, Christine Elliott, the local MPP; and their 17-year-old triplet sons, John, Galen and Quinn.

Two things are key to understanding Flaherty and his perceived indifference to Toronto. The first is that he’s not from these parts. He was born and raised in Montreal’s West Island, the sixth of eight children in an Irish Catholic family. The second is that the story of his upbringing is one of self-reliance and an almost puritanical belief in the principles of discipline and hard work. His father was the sole breadwinner, an entrepreneur with a science degree who made chemicals for the pulp and paper industry. Young Jimmy’s first job was the same as his brothers’: a paper route for the now-defunct Montreal Star. “We all earned our money,” says Flaherty, “which my children find rather remarkable—that they should go and make money for themselves rather than ask their parents for it.” He attended Loyola High, a private school run by Jesuits, renowned for its intellectually and physically rigorous curriculum. “We were all rough and tough growing up,” he adds. “With the Jesuits, too. There was no mamby-pamby type of thing. Boys were boys, and boys were expected to bang into each other. And that was fine.” He played varsity hockey, and his skills and grades were good enough to earn him a ticket to Princeton, which he entered at age 16.

After Princeton, he came to Toronto to study law at Osgoode, graduating in 1973. He then co-founded a law firm, Flaherty Dow Elliott & McCarthy, where he spent more than 20 years as a civil litigator. Jaime Watt, who helped organize both of Flaherty’s unsuccessful bids for the leader­ship of the Ontario Tories, thinks his years in court have influenced his political style. “Litigation is a zero-sum game,” he says. “One side wins, one loses. Jim is competitive. He likes to win.” He also likes to frame an issue and put his opponents on the defensive, leaving them squirming like witnes­ses on the stand.