Toronto’s “Mink Mile” was designed for gawking. A two-block stretch of Bloor Street West populated with the kind of high-end retailers—Cartier, Prada, Chanel, Tiffany—whose imposing prices strictly limit the hoi polloi to window shopping. Close to several luxury hotels and fine restaurants, it’s a favoured hunting ground for paparazzi when the film festival rolls into town. But since the night of Aug. 31, a new and far grimier attraction has emerged—a grey Canada Post mail collection box. Bouquets of cheap flowers surround its battered legs. Scrawled courier slips and handwritten Post-it notes cover the sides and top. Expressions of sympathy and anger at the violent death of Darcy Allan Sheppard, a 33-year-old bike courier. “R.I.P. A helluva way to die,” reads one. “Heaven’s got lots of bike lanes,” says another.
The incident, an all-too-common big-city dispute between a cyclist and a motorist that somehow escalated into a confrontation that saw Sheppard clinging to the car as it bashed him against trees, lampposts and finally the mailbox, before he fell into the road and was run over, was shocking enough. But the fact that the driver was Ontario’s former attorney general, Michael Bryant, makes it all the harder to comprehend. The 43-year-old, touted as a rising political star and perhaps future premier, has been charged with criminal negligence and dangerous operation of a motor vehicle causing death, and faces a maximum penalty of life in prison. And the question of whether the pillar of the community is guilty of an unconscionable act of road rage, or himself a victim of violent attack at the hands of the cyclist, is the debate consuming the city, sparking angry, traffic-blocking protests by bike advocates, incredulous cocktail party chatter, and an all-out media frenzy.
Only fate—or a fertile literary imagination—could have brought such a disparate pair together. A troubled young man who lived on society’s margins crossing paths with a striving power broker on a patch of Canada’s richest real estate. Two very different stories, one tragic result, and an ending that has yet to be written.
“He came out of nowhere.”
That time-worn recollection has been applied to many an ill-fated cyclist, and if Michael Bryant uttered it the night of Aug. 31, he could hardly have spoken truer words. Allan Sheppard was a living epitome of Canada’s invisible underclass, a rootless man with little in the way of family, bouncing between cities, struggling against his own weaknesses to gain control of his world. Friends spoke of him turning things around. But the night he died fit all too well into the broader pattern of his history: he had drunk his way out of his girlfriend’s good graces. Then, on his way out her door, he’d had a run-in with the police, creating a scene that ended with the cops ordering him in not so many words to move along.
The exchange has become of a peg of sorts for those trying to come to terms with Sheppard’s death. One neighbour said Sheppard was so drunk he’d fallen off his bike just before the two officers arrived at the scene. In several media interviews, Sheppard’s girlfriend, Misty Bailey, said she implored the officers to drive him back to an apartment he’d rented after moving out of her place a few weeks earlier. “He was definitely drunk,” the 30-year-old told Maclean’s. “I’ve seen lots of times when they were willing to take someone somewhere. So why not go that extra mile?”
Yet Sheppard’s record with law enforcement officials suggests he might have been just as pleased to take himself away. With 61 outstanding arrest warrants in his home province of Alberta, he would hardly have considered a ride across town with two cops an attractive option. The police, for their part, judged him sober enough to ride—and their own switchboard too busy for them to waste time ferrying home drunks. “We’re Toronto police, not Toronto taxi,” snapped Sgt. Tim Burrows, a traffic officer, in one interview.
Whatever the explanation for how he wound up on the road, Sheppard’s state at that point—alone, probably drunk and almost certainly unhappy—was sadly emblematic of his life. A Metis from the Edmonton area, he was the child of an alcoholic mother and was quickly placed in foster care. As a preschooler, he was adopted by a family only to find himself back in foster care a few years later, say friends. A charismatic youth with a quick wit and a piercing gaze, he had no trouble making friends and, later, attracting girls. But drug and alcohol addiction dogged him all the way, and responsibility was never his forte. By the time he met Bailey, Sheppard had fathered four children he never supported and whose mothers he contacted only sporadically.
That trail of personal destruction has made him a difficult figure for some people to mourn. Trudy Schlender, the great-grandmother of Sheppard’s youngest child, admits she “didn’t shed any tears” when she heard of his demise. Yet her granddaughter Jodie, whom Schlender had raised herself, still harbours fond memories of him, noting that he’d called her last May to ask about his son. It was the first time he’d expressed interest in the child, she said, adding: “I’d never intended for us to lose touch.”
The two had met in 2002 while Jodie was waitressing at a bar in the mountain town of Hinton, Alta., where Sheppard was working as a disc jockey. They struck up a relationship but soon became heavy drug users, Jodie acknowledges, travelling often to Edmonton to supply their habits, and later hitchhiking across the country to Toronto. “We kind of just lived every day for every day,” she says. A few months on, in May 2004, Jodie came back to Hinton broke and six months pregnant. “We sent her the ticket to get out of there, and I’m glad we did,” says Trudy, 70. “She came home with nothing more than a pair of socks and underwear and the clothes on her back. I don’t have a good word to say about him.”
It was during their time in Alberta that Sheppard allegedly struck upon a scheme to raise money, stealing cheques that he made out to himself and then cashed. The Alberta warrants for fraud and property crimes related mainly to this scam. Evidently, they were not serious enough for authorities in that province to have him sent home (warrants for minor offences are typically enforceable only within the area where they occurred; if police want a suspect sent from another province, they have to pick up the tab for travel).
