Prologue

ROB AND ME

On the morning of my grade eight graduation, as families headed home from church for a traditional Sunday breakfast before the afternoon ceremony, I spotted Duncan O’Neill alone on a bench, a brown lunch bag at his side. Duncan had joined our class towards the end of the year, a big kid two years too old for the grade. He wasn’t part of anybody’s world, accepted by neither the popular kids who weren’t so smart nor the smart kids who weren’t so popular.

“A boy in my class is sitting over there by himself,” I said to my mother.

“Ask if he wants to come to our house for breakfast,” she responded right away.

Duncan was happy to join us. He said many times how much he liked the bacon and eggs, each time quickly adding that his mother sometimes made him a breakfast just like this.

I barely knew Duncan and never saw him again after that day. Why he had popped into my thoughts was a mystery until I recognized the similarity to another big kid who didn’t fit in when he arrived at Toronto city council, late in 2000. This one was often loud and aggressive, but I thought I recognized in him a shy, awkward kid who seemed painfully alone.

If Rob Ford had been my grade eight classmate and my mother had seen him sitting without a friend, she would have said, “Ask if he wants to come to our house for breakfast.” Rob would have happily joined us. He would have said many times how much he liked the bacon and eggs, each time quickly adding that his mother sometimes made him a breakfast just like this.

Rob Ford didn’t know my mother. But when she died, in 2007, he drove from Etobicoke to North York on a Friday night. He entered the funeral home quietly and, after paying his respects, left the same way.

—

I do not doubt reports of Rob Ford’s monstrously bad behaviour. Nor would I deny that a beast lurks within, released by alcohol and drugs. My friends often ridiculed and demonized Ford at the same time, as if you couldn’t heap enough scorn on a creature like him. My observation that Rob had many sides to him, and that there must be reasons for the way he was, only irritated them. They saw him as stupid and dangerous, an ignorant buffoon. They wanted him to be simply that. They were uncomfortable with my empathy for the man. Maybe they thought it eroded my belief that Rob Ford was unfit to be mayor. It didn’t. I was the city councillor who thought up the motions that took away Ford’s powers as mayor of Toronto—and made sure they passed a council vote—in November 2013. I took no pleasure in it—quite the opposite—but believed it had to be done.

For two months afterwards, when I passed Ford in the hall, he met my “Hey Rob” with a menacing glare. Then, during the January 2014 council meeting, I watched with apprehension as Rob slid from his seat and walked deliberately towards mine. He was holding a sheet of paper, which he thrust in front of me. Rob’s expression, unreadable at first, became a half smile.

The paper was a football pool, with a spot for me to fill in my picks. He wanted me to play again. “Don’t get me wrong,” he said, making it clear that our football friendship wouldn’t protect me from political payback. “I’m taking you out in the next election. I’m going to smoke you.”

—

The football pool was a holdover from the ten years when we sat two seats apart on Toronto council, before Rob became mayor. He represented the mostly working-class area of north Etobicoke, I the more affluent North York community of Willowdale. When newly elected first-time councillors arrive at the beginning of each term, most are barely visible for the first few months. Not so with Rob Ford. He invited immediate comparisons to the late comedian Chris Farley, whose earnest buffoonery produced one misadventure after another. When Ford exploded from his seat to denounce his spendthrift colleagues, I had a front-row view. Proximity to Ford so rattled one councillor that he changed seats. I was always more curious than anything else. What was beneath all that anger?

Between outbursts, Rob sat silently, seemingly detached from everything and everyone around him. “We need to find a way to relate to this guy,” Councillor Joe Mihevc suggested one day. My seatmate since 1999, Joe was the sort who fostered relationships with nearby councillors. The big guy to our left was hard to reach. But we’d noticed Rob’s obsession with football, and so we started a pool and invited him to join us. Rob never realized that Joe and I knew nothing about the game because, against all odds, our random picks consistently beat his more informed choices.

When he paid us our winnings, we’d tell him we were donating his money to left-wing causes. He loved that kind of boyish pushing and shoving, and gave the same back the few times he won. One year, he clobbered us in the Super Bowl pool and never let us forget it. He would happily endure weeks of losses for a single day of victory.

Apart from council meetings and a few lunches, Rob and I spent little time together. But I was his football pool buddy, which was not a small thing in his life, I came to realize. After he was elected mayor in 2010, and council divided itself into hostile factions, our football bets ended. Bumping into him at a function more than a year into his mayoralty, I bemoaned the loss of disposable income from my winnings.

The day after, my executive assistant told me, “The mayor’s office is calling, he wants your football picks.” Another staff member stopped me: “The mayor’s staff is e-mailing. They need your picks.” Taking a washroom break, I encountered a senior Ford staffer at the next urinal. “Councillor,” he said, “would you please get in your football picks. The mayor is making us crazy.”

Late in 2013, after I’d initiated the removal of his powers, the Ford brothers were watching football in the “mancave” at Deco, the family label business, when Doug needled Rob for not retaliating against me. “I kicked him out of the football pool,” Rob replied, as if that made us even. After he invited me back the following January, the bets were accompanied by an unusual amount of bravado, mostly about what he was going to do to me in the next municipal election. “I’m giving you a heads-up. You fucked with me, now I’m coming after you. I’ve got a guy who’s going to take you out.” It was as if I had embarrassed him in front of the other kids and he needed to show them he could get right up and push me down.

In the fifteen years I’ve known Rob Ford, most of our conversations have started with football or hockey and branched out from there. The topics were limited and discussions tended to be short and to the point. But they showed a man struggling to do the best he could. During Sunday morning calls to sort out the pool picks, we’d talk about the challenges of fatherhood, or his plans to become mayor. Later, as he suffered through addiction, his mood could swing wildly. When I made the mistake of once joking that I could have tricked him by altering the point spread for that week’s games, his face turned red and he became cold and menacing.

“You fuck with me, bro, you won’t do it twice. I’ll be knocking on your door.”

Then, when I least expected it, he’d show warmth. As we waited for the elevator one day, I told him I was insulted he hadn’t included me in the Top 10 list of councillors he wanted defeated in the October 2014 election. “That’s because I’ve already got my best guy against you,” he said. As Rob wound himself up, his brother came along, not realizing I was the instigator.

“Okay, Rob,” Doug Ford admonished, in a rare moment of playing the peacemaker.

“Buddy, I’m taking you out like a cheap date,” Rob continued to rant at me.

“Rob, okay, okaaay!” Doug tried again.

Something in the exchange triggered a different Rob. He suddenly grew concerned that I’d be unemployed if his candidate defeated me. “You don’t need to worry,” Rob said reassuringly. “You won’t have trouble finding a job. You’re a smart guy, an educated guy. You’ll be on the radio or write a book or something.”

—

Rob Ford showed the world many faces, all real but none really him. He is a jumble of contradictions: attention seeker and shy loner; bully and kind-hearted friend; a savvy politician who can’t comprehend much of what happens around him; the self-proclaimed “best mayor this city has ever had” and the guy with such low self-esteem that he’ll stare at the floor to avoid eye contact.

But the Rob Ford I know best is none of these. At some point, the ten-year-old inside him made friends with my ten-year-old self. We were the sort of friends who didn’t visit one another after school but looked for each other at recess.

“He has a special relationship with you,” his brother Doug told me several times. “I don’t fucking understand it.”

Neither did I. Not until it struck me how few people tried to connect with the person beneath the protective layers.

“I think Rob doesn’t have any friends, and you’re probably one of the closest friends he has,” Nick Kouvalis, his former campaign manager and chief of staff, told me. “You can talk football, with a little side wager. You can have lunch with him maybe. He doesn’t have anyone like that. He has people who will do things with him—but they want something from him. They want his money. They want his connections. They want something from him.”

On his forty-fifth birthday, Rob was in rehab, so I made him a collection of music from the year he was born. The song list began with “Gimme Shelter” and ended optimistically with “Here Comes the Sun.” When Rob phoned to say thanks, he spoke so warmly it took me a few seconds to recognize who it was.

Several times, I tried to persuade Rob to let that Rob Ford speak with me for this book. He apologetically offered multiple reasons for saying no. His political supporters who “hated” me wouldn’t like it; he had to wait till after the election; since big US networks and screenwriters wanted his story, there was no way he could give it to me. And the biggest reason: “Dougie says not to.”

—

Rob Ford appears simple but is easily the most complicated person I’ve ever known. Every time I thought I had him mostly figured out, he’d surprise me again. Then I began seeing the patterns within the contradictions, the predictable amid the inexplicable. I wondered about the childhood that produced such a troubled adult. As my football buddy became international news, I was astounded at the lack of effort spent explaining Rob Ford’s behaviour rather than merely chronicling it. Since abandoning journalism for politics more than thirty years ago, I hadn’t written much of anything. But I decided that Rob Ford’s story needed to be told, and it didn’t look as though anybody else was going to tell it.

In August 2014, on the final day of his last council meeting as mayor, I went over to Rob to talk football and elections, trying to stay within his comfort zone. But he was in the mood for real conversation.

Documents had been released a day earlier depicting him as a sometimes drunken football coach who mistreated his players. That contradicted how Rob saw himself: a caring coach who expressed it by teaching his players how to win, tolerating neither weakness nor failure.

“It hurt me deeply,” he said of the published reports, touching his chest, more sad than angry. “I was bawling to my brother.” He seemed barely interested in a new poll showing he had moved back into second place in the mayor’s race, a near-impossible feat for any politician with even half his misdeeds.

I asked him what quality in him explained his continued popularity among at least a third of the population. “I think it’s because they see you as an average guy,” I suggested, wanting his reaction to a term he had often used to describe himself.

“You think,” he said sternly, like a teacher knowing I could do better. “You don’t think.”

Uncharacteristically, Rob looked me straight in the eye. “An average guy,” he repeated. “There is no such thing as an average guy.”