Skip to main content Skip to search Skip to search

History General

The Don

The Story of Toronto's Infamous Jail

by (author) Lorna Poplak

Dundurn Press
Initial publish date
Jan 2021
General, Public, Commercial & Industrial, Historical, Penology
  • Paperback / softback

    Publish Date
    Jan 2021
    List Price
  • eBook

    Publish Date
    Jan 2021
    List Price

Classroom Resources

Where to buy it


An in-depth exploration of the Don Jail from its inception through jailbreaks and overcrowding to its eventual shuttering and rebirth.

Conceived as a “palace for prisoners,” the Don Jail never lived up to its promise. Although based on progressive nineteenth-century penal reform and architectural principles, the institution quickly deteriorated into a place of infamy where both inmates and staff were in constant danger of violence and death. Its mid-twentieth-century replacement, the New Don, soon became equally tainted.

Along with investigating the origins and evolution of Toronto’s infamous jail, The Don presents a kaleidoscope of memorable characters — inmates, guards, governors, murderous gangs, meddlesome politicians, harried architects, and even a pair of star-crossed lovers whose doomed romance unfolded in the shadow of the gallows.

This is the story of the Don’s tumultuous descent from palace to hellhole, its shuttering and lapse into decay, and its astonishing modern-day metamorphosis.

Speaker's Book Award 2021 — Shortlisted | Brass Knuckles Award for Best Nonfiction Crime Book 2022 — Shortlisted

About the author

Lorna Poplak is a writer, editor, and researcher. She has served on the Toronto Community Council of the Society for Technical Communication (STC) and on the board of the Canadian Society of Children's Authors, Illustrators and Performers (CANSCAIP). She lives in Toronto.

Lorna Poplak's profile page


  • Short-listed, Brass Knuckles Award for Best Nonfiction Crime Book (Crime Writers of Canada)
  • Nominated, Heritage Toronto Book Award
  • Short-listed, Speaker's Book Award

Excerpt: The Don: The Story of Toronto's Infamous Jail (by (author) Lorna Poplak)


On December 31, 1977, the correctional services minister of Ontario rang out the old year with a sledgehammer blow to the cornerstone of an old building on the east side of the Don River in Toronto. He was not alone: another senior correctional services official and a well-known activist also took a crack at it. Watched by television crews, newspaper reporters, politicians, police officers, jail superintendents, and a few bemused members of the public, they finally managed to chip away a one-foot-square piece of stone from the building’s façade.

The target of all this negativity was the infamous Toronto Jail, also known as the Toronto gaol, the Don Jail, the Old Don, or, simply, the Don. It was not the first time that this institution, located at the northwest corner of Gerrard Street East and Broadview Avenue, had been assailed during its 113-year lifespan, but previous attacks had been verbal rather than physical. The jail had been variously called a “lion’s den,” a “black hole of Calcutta,” “Toronto’s Bastile [sic],” or worse. The correctional services minister liked to call it a “monument to human misery” in the “early barbaric” style.

Very occasionally, on the other hand, the Don Jail had been lauded as a veritable “palace for prisoners,” incorporating the finest and most progressive of correctional philosophies. This was certainly true in the mid-1800s, when the building was conceived and constructed.

The Don, Toronto’s fourth jail, opened its doors to its first reluctant residents in 1864, predating the Confederation of Canada by three years. It originally stood remote from the city on the “wrong” side of the Don River, the meandering and strategically significant waterway that spilled into Lake Ontario just east of where a tiny settlement had been established in 1793 by British colonists in what was then the newly formed province of Upper Canada.

In accordance with a Royal Proclamation of 1763 relating to the governance of Britain’s territorial possessions in North America, the legal system adopted in Upper Canada was English law.

When it came to criminal justice, did British law guarantee the fair and equitable treatment of those accused of committing an offence in Upper Canada? Not at all. In those days, it was all about crime and punishment. And the crime did not have to be very significant by modern standards to earn a very harsh penalty, one generally administered in full public view. Cursing or refusing to go to church could lead to corporal or physical punishment — flogging, branding, or being locked in wooden stocks for hours or days were the norm. Then there were the offences that were punishable by death. The list of capital crimes in Upper Canada in the early 1800s was a long one: prior to 1833, a person could receive the death penalty for killing (or even maiming) a cow, burning a stack of corn, or impersonating a pensioner. And, as was laid down in English law, capital punishment always meant death by hanging.

While the penalties generally involved public humiliation or shaming, there were, of course, also jails. Authorities needed a secure place to confine offenders pending the execution of their sentence. Primitive lockups have existed from early times; however, the idea of detention as punishment is more recent, largely influenced by the writings in the late 1700s and early 1800s of reformers, such as the British philanthropist John Howard, who were horrified by the appalling conditions they came across in penal institutions.

In 1792, an act was passed by the first Parliament of Upper Canada that called for the construction of a court house and jail in each district of the province, and another law in 1810 provided for the use of jails as houses of correction for “idle and disorderly” persons. By the mid1800s, two types of institution had emerged in Canada for the confinement of wrongdoers — or alleged wrongdoers.

The first, jails, were generally smaller establishments, run by local or district authorities. In addition to serving as “holding tanks” for people on remand (that is, awaiting trial or sentencing), they housed offenders with short-term sentences or those appealing their sentences, as well as individuals waiting for transfer to a provincial or federal facility. As many of these inmates might be guilty of serious crimes such as armed robbery or murder, and as some of their stays turned out much longer than anticipated, it followed that jails were viewed as maximum-security facilities.

The second type, penitentiaries, were run by provincial and federal governments to house prisoners serving longer sentences. An act in Upper Canada in 1834 paved the way for the construction of the first Canadian penitentiary, which opened the following year at Portsmouth, near Kingston, and later became known as the Kingston Penitentiary. Besides imposing hard and often unproductive labour on offenders, early penitentiaries were designed to give them time, lots of time, to repent their actions through isolation, silence, and hefty doses of religious instruction.

The Don Jail, originally a joint venture between the City of Toronto and the County of York, belonged in the first category. By 1958, nearly a century after the Don’s opening, grossly inadequate conditions and chronic overcrowding in the antiquated building led to the addition of a new wing. This newer facility was officially called the Toronto Jail, but, predictably, it was nicknamed the New Don, and, eventually, the Don. Both jails were taken over by the province of Ontario in the late 1960s.

The pages that follow are not an academic treatise on penal philosophy or Canadian correctional institutions. Instead, they tell of the struggle in one small corner of the Canadian correctional system to negotiate the complicated and often contentious relations between a jail and the city that sprang up around it. The story of Toronto’s infamous Don jails raises thorny questions: How and why did the Old Don deviate so radically from the enlightened reformist principles that underpinned its architecture and original correctional practices? Did the jails protect individuals on both sides of the barred doors and windows? Did they in any way meet the requirements of a rapidly expanding city in an ever-changing world? And what should be done with a toxic artifact once it has outlived its original function?

Although attention will be paid to both jails, it is the original Don that, as the book’s cover so graphically illustrates, forms the main focus.

In addition to bringing to light the facts behind its location and construction, THE DON is the intertwining saga of the historic jail and the people who have occupied it during its one-hundred-and-fifty- plus years of existence. To quote American poet Henry Wadsworth Longfellow, “all houses wherein men have lived and died are haunted houses.” Many men — and women — have lived and died within the bleak precincts of the Don Jail. You will meet a large and diverse group of the spectres, both benevolent and malevolent, that haunt the unhallowed halls of this notorious place: the pitifully young and the old; the guardians and the guarded; the criminal, the innocent, and the mentally afflicted.


Ontario corrections minister Frank Drea was not granted his New Year’s wish for 1978. The fourth Toronto jail still stands on the east bank of the Don River, in the very heart of what is now the thriving urban community of Riverdale. Today, the building seems much diminished: a small, stone centre block with two wings, dwarfed by a multi-storey health centre on its western flank. For much of its existence, however, this controversial institution dominated the news, the skyline, and the consciousness of the city.

So this, too, is a story of Toronto, seen through the prism of the infamous jail that, since its inception in the mid-1800s, has left such an indelible mark on the city it has served.

Editorial Reviews

Lorna Poplak has written a fascinating history about Toronto's most notorious jail. The Don is recommended reading for anyone interested in true-crime or the dark-side of Toronto history.

Nate Hendley, author of The Boy on the Bicycle: A Forgotten Case of Wrongful Conviction in Toronto

Poplak is right to dwell on the many indictments of jail conditions throughout this book.


Canadian history buffs will savor the arcane criminal lore gathered here.

Publishers Weekly

This book documents the history of the Don, but also the history of the city of Toronto and thinking around incarceration. An informative read.

Jennifer Hollett, Executive Director, The Walrus

The Don is a breezily written book recommended for anyone interested in Toronto history, penology or criminology and a thoroughly well researched account of a jail which, in various states of repair and disrepair, housed tens of thousands of criminals and ne'er-do-wells in the Toronto area during its more than 150 years of existence. A must read for all true crime buffs!

James Dubro, author of Mob Rule and Dragons of Crime

The Don is an impeccably researched, detailed account of the history of Toronto's infamous jail and its inhabitants - some of whom orchestrated the most famous escapes in Canadian history. Lorna Poplak has given us an immensely readable, engaging and entertaining look at a significant piece of Toronto's past. The book comes alive as it describes the good intentions that surrounded the building of the jail, such as the rehabilitation and redemption of the inmates, through to, and including, a candid description of the reality of its often inhumane, fetid and over-crowded conditions. This is a must read for those interested in Toronto's criminal justice history.

Sandra Kingston, former crown attorney

Prodigiously researched.

Toronto Star

Lorna Poplak tells three stories in The Don: the history of Toronto's most famous/infamous prison; the evolving theories of incarceration and punishment through the jail's century-and-a-half life; and the shifting shape of the building and surrounding city. All well-told stories, populated by the extraordinary characters of jailors and jailed, hangmen and hanged, all confined within the long, grim history of the Don. A great read.

Joe Berridge, author of Perfect City

Related lists