“I really don’t know why you’re interested in me and all this. Frankly, I don’t understand why anyone would even give a shit,” Holloway snaps. Sitting in the antiseptically clean kitchen of a spacious, well-appointed bungalow he shares with his long-time girlfriend and Milton, his cherished dog. Holloway looks ill at ease. A diminutive, middle-aged, and still powerfully built man with a thick mane of brown hair and a magnetic smile, he agrees to talk for the first time about his undercover work.

Holloway’s seeming reticence to discuss his past has a disingenuous ring to it. Beneath the taciturn veneer lies an adept performer who is acutely aware that one’s identity can be fashioned to conceal motives and the truth.

At first, Holloway plays the part of the reluctant, mildly irritated subject of a reporter’s interest, offering up halfhearted, cryptic answers. Eventually, his reserve fades and another, less calculated figure emerges. His storytelling becomes more fulsome, his cadence quickens until he catches himself almost delighting in recalling his escapades. Then, unexpectedly, Holloway pauses. His face becomes taut as he leans forward. “I remember a baby,” he says without a hint of affectation. “She was ten months old and about seventeen pounds. Her mom was a crackhead and giving a guy a blow job. I said, ‘Jesus, cover the kid up, she’s freezing.’ Her mom said she was asleep, but when I went to pick her up she was toast, starved to death.”

Holloway insists that his work was “never personal,” that he was paid to do a job with no emotional strings attached. But in recounting the story of the dead child, Holloway reveals something of himself—that his attitude toward the many casualties and culprits he encountered during his career was very much “personal” and it imbued all that he did as an instrument of the police.

Holloway was born in the coal-mining town of Sydney, Nova Scotia, in the late 1950s. His parents meandered through a spate of poorly paid jobs before heading to Toronto in 1965 in a futile search for a better life.

Holloway’s youth was unremarkable, save for losing the sight in his left eye owing to a friend’s schoolyard prank. It was his father’s volcanic temper—stoked by booze and poverty—that left the most enduring emotional scar. “It was rough,” he says, recalling the drunken tantrums and beatings. Holloway escaped into the thrilling world of comic books where heroes were forces for change and for good.

At seventeen, he abandoned home and school in pursuit of adventure and money. Holloway also discovered drugs. A long, disastrous addiction began with pot and hashish, and eventually turned to harder drugs. His fondness for a dope-fuelled good time was satisfied when he began working for rock bands that criss-crossed North America. The sex and drugs were plentiful and cheap.

Four years later, Holloway tired of the rock’n’roll lifestyle and, on a whim, took up jobs as a performing clown. He enjoyed hiding behind a painted-on face, discovering a gratifying sense of freedom in anonymity. During a stopover in Arkansas, Holloway met his future wife. The young couple returned to Canada and Holloway became a trucker. Later, when the marriage dissolved, Holloway moved to Barrie, a town just north of Toronto, where, by the early 1990s, he had helped build a successful trucking company that sustained his passion for fast cars, women, and, of course, drugs.

Holloway’s spending sprees attracted the attention of the Toronto-based Para-Dice Riders (pdr) biker club. At the time, some members of the pdr living in Barrie were also moonlighting as truckers and, like Holloway, they were regulars at local strip clubs. Holloway and the bikers gravitated to one another.

Cocaine was now Holloway’s drug of choice, and the pdr were his first suppliers. “I started and I couldn’t put it down,” he says. His habit mushroomed, reaching a $1,500-a-week price tag, the drugs consuming Holloway and, eventually, his business. Broke, he moved to Hamilton and fell more deeply into drugs, turning cocaine dealer for local doctors, lawyers, and businessmen to finance his own voracious habit. The precipitate descent from thriving entrepreneur to cocaine addict had occurred in less than a year. It was about to get worse.