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).
In Toronto, Sheppard struggled on with his addictions, says Jodie Schlender, setting out to turn things around only after she’d gone. A lifelong cycling enthusiast, he found work amid the steel and glass towers of downtown Toronto, joining the hardbitten, anarchic subculture of bike messengers. It was a good fit. Sheppard’s innate toughness earned him respect. No one judged him based on his history. “This guy was genuinely trying,” says John Martin, a veteran courier who got to know Sheppard on the job. “He was struggling against a lot more crap than a lot of people have to deal with in life, and he was falling down from time to time. But he was a pleasant, polite, well-comported guy. I know for a fact he brought customers to his company because of that.”
Last Christmas, Sheppard’s life took another positive turn when he ran into Misty Bailey, an old school friend from Edmonton whom he’d long considered a kindred spirit. The two got engaged, and he seemed to be stabilizing. But Sheppard’s drinking soon reared its head, and the pair put off their nuptials indefinitely. “I was actually going to programs to get insight on his disorder,” Bailey recalls. On the night he was killed, Sheppard had fallen off the wagon following an eight-day stretch of sobriety, showing up at Bailey’s door and crashing in her bedroom. He was irritable when he woke, she says, and he stumbled out the door in anger. “I didn’t want him to go,” says Bailey. “But he was agitated, and I couldn’t really force him to do anything in that state. I just had to let him go.”
For such a high-flying couple, it was a decidedly low-key evening. Michael Bryant and his wife, Susan Abramovitch, were out on the town on Aug. 31 to celebrate their 12th wedding anniversary, but without much fanfare. They grabbed a couple of shawarmas and iced teas at a shabby takeout in Toronto’s Little Italy. Then they drove their black Saab convertible across the downtown to the neighbourhood known as the Beach, and took a romantic sunset stroll along Lake Ontario. At around 9 p.m., they made one final stop for baklavas at a family-run Greek pastry shop on the Danforth. Afterwards, they started back toward their midtown home, along construction-snarled Bloor Street, top down on a warm late-summer night.
Before his fateful encounter with Allan Sheppard, Bryant’s future prospects seemed limitless. At 43, he had recently abandoned an 11-year career in provincial politics, where he served as Ontario’s attorney general, minister of Aboriginal affairs and, most recently, minister of economic development, for a gig as head of Invest Toronto, the city’s new business-boosting agency. A sideways leap, but one that would put him in touch with all sorts of movers and shakers, and allow him to build for what many assumed was coming next—a run at the Ontario Liberal leadership, or perhaps a switch to federal politics.
No one has ever accused Bryant of lacking ambition. His resumé has all the hallmarks of a serial overachiever. The son of a lawyer and former mayor of Esquimalt, B.C., he moved east after undergrad in the late 1980s to study law at Osgoode Hall, finishing near the top of his class. He did an LL.M. at Harvard on a Fulbright scholarship, writing his thesis on conflicts between governments and native groups, and went on to teach at King’s College London, and the University of Toronto. He and Susan, now one of the country’s top entertainment lawyers, met while they were both clerking at the Supreme Court of Canada. “It was love at first sight for me,” Bryant said in 2004. “It took her a few more months to see the wisdom of our coupling.” The pair now have two children, Sadie, 6, and Louis, 4.
Tim Murphy, the former chief of staff for prime minister Paul Martin, struck up a friendship with Bryant when they were both working at a large Bay Street law firm in the mid-1990s. Murphy, who had just returned to practice after a stint as an Ontario MPP, immediately picked out Bryant as a political up-and-comer. “He was very smart and he cared about public policy,” says Murphy. Bryant was also a good communicator, and had a knack for finding mentors, including former Ontario premier David Peterson. “The guy was ambitious, but ambitious to do something—not be something,” says Murphy. “He liked to rock the boat and I think that’s a good thing in Canadian politics.”
Bryant made a splashy entry into public life as a 33-year-old in 1999, wresting a mid-Toronto seat away from Isabel Bassett, Conservative premier Mike Harris’s high-profile minister of culture. When Dalton McGuinty’s Liberals took power four years later, he became the youngest attorney general in the province’s history. And in a government that prides itself on beigeness, he quickly set himself apart with headline-grabbing initiatives like a ban on pit bulls, seizing and crushing cars involved in street racing, and a fight to impose severe parole restrictions on schoolgirl killer Karla Homolka.
If one had to chose an animal to describe Bryant, a bantam rooster might be the best fit. He is renowned for his fashion-plate ways (just days before the Bloor Street incident, he was showing off his jade green Paul Smith runners and matching Novesa Henley watch in the pages of the National Post). And although small in stature—around five foot eight—he’s not one to back down from a challenge. A boxer since the age of 10, Bryant still trains, although he no longer fights competitively. “He has very good skills,” says Adrian Teodorescu, a Toronto boxing coach who guided Lennox Lewis to a gold medal at the 1988 Seoul Olympics, and trained Bryant for a number of years. “But he’s very cool, very calm. Somebody with his body structure couldn’t be very aggressive. He’s about 140 lb.” (Teodorescu is facing his own legal troubles. Last December, he was charged with sexual assault, forcible confinement, threatening death and assault after a 21-year-old woman he had been training complained to police. He is currently free on bail.)
But Bryant’s unbridled energy and high media profile—the Queen’s Park press gallery once jokingly gave him the cocker spaniel award for his propensity to “rub up” against them—started to be viewed with suspicion in some quarters. In 2007, McGuinty shuffled him to Aboriginal Affairs, a move widely perceived as a demotion, although Bryant won kudos for closing the books on the Ipperwash affair and his handling of another land dispute in Caledonia. And his re-elevation to Economic Development in 2008 came amidst rumours that he was thinking of bolting for Bay Street. When Bryant left government this past May—just weeks after giving a shoot-from-the-hip speech on the economy—his welcome had pretty much worn out. “There’s no doubt his style chafed a lot of people the wrong way,” says a senior Ontario Liberal, comparing Bryant to famed Edmonton Oilers agitator Ken “The Rat” Linseman. “If he was on your team you loved him, if not, you hated him.”
But whatever political ill will existed, among Bryant’s friends and acquaintances there is almost universal sympathy for the position he now finds himself in. Bernie Finkelstein, the founder of True North records and a longtime friend, says he was appalled by the tragedy, and flabbergasted by the initial suggestions that Bryant was somehow to blame. “Of all the people I know, he’s last on the list of someone who would be prone to road rage,” says Finkelstein, a client of Susan’s for more than 15 years. “They’re a lovely couple. Very smart and dedicated to their kids. And he’s a very caring person.”
Finkelstein says he is sure there must be more to the story. Appearances can be deceiving. The flashy Saab convertible, for example, was used, purchased for just $5,000. Finkelstein remembers Bryant proudly showing it off after a dinner on College Street last summer. “It was pretty cool,” he says ruefully. “Such a beautiful car for that kind of money.”
If Sheppard was in a poor frame of mind when he left Bailey’s neighbourhood, he was probably ready to snap by the time he rode west down Bloor Street near Bay, past the shops of Yorkville. He’d already developed a short fuse when it came to dealing with motorists, having been injured last year when one side-swiped him. Fellow couriers who attended a memorial service last weekend in Toronto recalled him as an outright “hater” of cars.
Security camera footage suggests the confrontation began after Bryant’s car clipped Sheppard’s rear tire. What words flew in the instant that followed may never be known (or, more accurately, only Bryant’s version will be). But a number of witnesses were on hand for the horrific spectacle that followed. Sheppard got off his bike and walked back to the car, several said, slamming his backpack onto its hood. He yelled angrily and then—just as the convertible lurched and tried to speed away—he grabbed onto the driver’s side mirror. One man, 23-year-old Raajiv Rajadurai, recalled Sheppard being dragged down the street, sparks flying off his cycling shoes as his feet skidded across the pavement.
Within seconds, the car had swung into the oncoming lane—swerving past trucks parked along the yellow line near a construction site. Several witnesses described it bumping up onto the sidewalk as if the driver were deliberately trying to scrape the man off the side of his vehicle. “There were trees and posts and newspaper boxes. The tires were screeching,” witness Josh Harlan told the Toronto Star. “Suddenly it was clear to me whoever was dragging on the side of the car was in mortal danger.” Others thought Sheppard was attacking the driver, or might have grabbed hold of the steering wheel, sending the car out of control.
Which of these narratives takes hold is now critical to Bryant’s future. If the former attorney general was being attacked, or even felt threatened, a court may well find his reaction proportional, even if it ultimately resulted in the death of Allan Sheppard, says Jonathan Rosenthal, a prominent Toronto defence lawyer. “The Crown will have to prove beyond a reasonable doubt that Bryant was negligent, and I think they’re going to have a very hard time. We know that the guy was drunk, and facing charges, and was perhaps behaving violently.” Indeed, if the police forensic investigation were to find Sheppard’s fingerprints on the steering wheel, Rosenthal says he doubts the matter will even go to trial.
Suffice to say, Bryant and his allies are already working to shape perceptions of the tragedy and its principal players. He has proclaimed his innocence and, two days after being charged, hired Marie Heinen, a top-rung Toronto defence lawyer most recently in the news for getting former NHL agent David Frost acquitted on charges of sexually exploiting junior hockey players. Bryant also retained Navigator Inc., a public relations firm former prime minister Brian Mulroney employed during the Oliphant inquiry.
The latter move raised eyebrows even among some of Bryant’s former political allies, who saw it as transparently self-serving. “Using Mulroney’s controversial mouthpiece in a case like this?” said one Liberal who knows Bryant. “Not smart.” But it has already paid dividends: instead of emerging bleary-eyed and dishevelled from police headquarters, Bryant appeared shaven and clad in a pressed suit for his first session before the cameras; his statement offered sympathy to Sheppard’s family without acknowledging responsibility.
The effect was both dignifying and humanizing, and slowly but surely—as witness accounts of the confrontation emerged—news coverage drifted in Bryant’s favour. A steady drip of details from Sheppard’s spotty past didn’t hurt. Nor did some well-placed facts about Bryant’s movements before the crash. One city paper published details of his evening with Abramovitch under the sympathetic headline: “Enchanted evening, until the drive home.”
Whether that benign spin will be enough to rescue Bryant’s political career is another matter. More than a mere matter of traffic safety, Sheppard’s death seemed to stir some deep-rooted sense of unfairness, giving the cycling protests an undertone of social justice. “It’s symbolic because you can’t get anybody at a higher status than Bryant,” said Serge, a 24-year-old cycle messenger who attended a rally near the site of the incident, and asked to not have his last name printed. “Allan, well, he was like me—pretty much the bottom of the barrel in terms of what’s defined as success.”
Of course, what passes between two angry men on a street can have precious little to do with social station—not least when they’ve never met each other before. Given the facts as they now stand, Bryant may well receive exoneration in a criminal court of law. His trial in the court of public opinion has only just begun.
Looking for more?
Get the best of Maclean's sent straight to your inbox. Sign up for news, commentary and analysis.