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The weirdest mayoralty ever—the inside story of Rob Ford’s city hall

Rob Ford | The Incredible Shrinking Mayor

Other politicians might savour the chance to boast of such an intimate strategic summit, but Ford prefers to play good ol’ boy. “I don’t want to get into it,” he says with an aw-shucks shrug. “We just had a private day together and I caught some big fish. In fact, I think I actually caught the second biggest fish ever in his lake.”

Despite reports that Harper never baited a hook, he too seems to have felt he had a big one on the line. A month later, when the Fords hosted an invitation-only tribute to Flaherty in their mother’s backyard, the prime minister dropped by to cast further goodwill upon the waters. Lauding Diane Ford for nurturing a political dynasty, he urged Ford’s faithful to get back out on the hustings and work for what he termed a “trifecta”: a Conservative victory in the October provincial elections that would put every level of the region’s government in the party’s hands. At the time, that prospect still seemed like a distinct possibility, and it is a measure of how swiftly Ford’s approval ratings sank last fall that, only weeks later, Conservative leader Tim Hudak scrupulously avoided any association with the suddenly problematic mayor.

Still, with the Liberals’ tenuous hold on a minority government, Harper and Flaherty have a continuing stake in Ford’s fate. In March, when the prime minister came to town to break ground for the Island airport tunnel, he tried to give the beleaguered mayor a rhetorical boost with a personal testimonial on the joys of subways. At his side was Flaherty, who seems to feel responsible for the irrepressible Fords. During a meeting with the finance minister, one councillor recalls him telling her, “If you have any trouble with the boys, call me.”

When Rob Ford first ran for city council, even Doug Holyday wondered why he was the candidate, not his big brother, Doug, who was five years older, more gregarious and clearly the brains of the family. Today, Holyday has his own thoughts on the question. “I was always of the theory that Doug wanted to have his father and brother in politics,” he says, “because that gave him a freer hand to run the business.”

In the Ford family, business has always come first, and well before their father’s swift, devastating death from colon cancer in 2006, Doug Jr. had been handed the keys to that kingdom. Taking over as DECO’s president at 29, he expanded the company into the U.S., commuting every week to Chicago, where he established a foothold in the $15-billion North American label industry that has secured the family fortune—and thus the political franchise it helps underwrite.

As for that political franchise, few knew that the Fords had a long-term game plan. John Tory discovered it in 2003, when he was running for mayor against David Miller. Advised that he ought to seek out the blessing of Ford’s father, who was then regarded as the reigning power broker in Etobicoke, Tory arranged a lunch date with the retired MPP. When he arrived, he found Doug Sr. waiting to size him up along with Diane and all three of their burly blond sons. After an hour of pleasant chatter, Diane Ford got to the point. “She said, ‘Well, we think you’re a pretty good fellow and we’re going to support you for mayor,’ ” Tory recalls. “ ‘You can serve for a couple of terms and then it’ll be Robbie’s turn.’ ”

Tory was dumbfounded at that scenario. At the time, Rob Ford had already cemented his reputation as the odd man out on council, the lone obstructionist who voted against almost every motion and was widely dismissed as a buffoon. Ford’s colleagues would look on in trepidation whenever he rose to speak, bouncing from leg to leg with gathering fury, his voice rising as a tide of crimson flooded the flesh above his collar.

Six years later, when they tuned in to the mayoral debates, they were astounded by his transformation. Conservative campaign wizard Nick Kouvalis had bunked into a second-floor DECO boardroom, drilling Ford in focus and messaging techniques. Still, veteran councillor Pam McConnell was alarmed by his preternatural calm: “I thought, ‘What have they done to him?’ ” she says.