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Officials had hoped that by shutting down the oldest portion of the jail in 1977 and moving inmates into a more modern, adjoining building, they could dispel its image as a medieval dungeon.Peter Power/The Globe and Mail

It was no coincidence that the inspiration behind two-for-one jail credits originated at the Don Jail, a legendary correctional hellhole that predates Confederation.

Judges calculated that a day in the Don was worth at least two in most other prison settings, a ratio that prevailed for two decades until Prime Minister Stephen Harper's tough-on-crime agenda rolled it back.

Opened in 1864, it was the largest jail in North America at the time. Soon to be closed in favour of a massive new jail, it serves as a remand centre for defendants awaiting trial. A home to everyone from two-bit parole violators to terrorists and serial killers, the officially named Toronto Jail was also the first and last place Canada executed criminals.

Countless prisoners attested to its privations: from its rat-infested cellars and sliver-like cells to the dank gallows, where 34 men went to the hangman as their fearful confreres listened for the audible bang of the trapdoor.

"The Don is infamous," observed Douglas Olver, a senior Ontario correctional official who is writing a history of provincial jails. "No other jail has had anywhere close to the significant events that have taken place there."

Besides the executions, they include 70 murders, daring escapes and the shocking discovery a few years ago of 15 skeletons buried in an exercise yard. An unknown number of inmates have taken their own lives, including one condemned man who did a swan dive from the highest balcony of the rotunda.

Just 18 months remain before its denizens are transferred to the massive new 1,650-inmate facility located a few kilometres away, leaving the "new" Don to be demolished. The old Don will be preserved within a $100-million development by Bridgepoint Health.

In a rare visit to the location - officials were unable to recall the last time a journalist was allowed in - it wasn't hard to sense why the Don's name evokes shivers. Cold as a crypt and cavernously dark, echoes bounce off walls where prisoners once etched warnings and curses or crossed off their days with shaky Xs.

Officials had hoped that by shutting down the oldest portion of the jail in 1977 and moving inmates into a more modern, adjoining building, they could dispel its image as a medieval dungeon. It didn't work. The public and media failed to distinguish between the old and the new Don and, as recently as last month, Ontario Court Judge Melvyn Green noted in a judgment that, "circumstances at the Don Jail remain notorious."

To many officials, however, it is a bad rap.

"There has been an impression that conditions are so poor and individuals suffer so much that that they should get special credit for it," said Steve Small, Ontario's assistant deputy minister of correctional and community services. "You will see a totally different picture than what has been portrayed in the courts and in the media."

An ensuing tour showed that life in the new Don isn't a walk in the park, but bore out Mr. Small's contention when compared to the old Don - and then some.


The first thing that strikes a visitor to the 147-year-old jail is the odour - a none-too-savoury concoction of sweat and bodily waste.

"It's what we call our morning scent," said jail superintendent Rose Buhagiar. "The offenders have an unwritten rule that they don't flush during the night because of the noise."

One morning recently, the jail was 130 inmates over its capacity of 504. Approximately 70 cells were occupied by vulnerable inmates requiring special protection. Other ranges accommodated those with medical problems or special needs.

Violence can break out at any moment over the most trivial matter, Ms. Buhagiar said. "It could be that you spit on the floor," she said. "You took my extra piece of bread. You took too long in the shower. You didn't brush your teeth. It can be anything."

For the most part, life at the Don is a stifling affair. Roaming the corridor outside their cell block, tough guys give visitors the stink eye, wise guys hail guards and supervisors with an inside joke or epithet. The exercise yard is a featureless patch of asphalt surrounded by high walls. A small swatch of blue sky is obscured by mesh netting, erected to prevent outsiders from pitching in packages of drugs.

Until about five years ago, black inmates had a cell enclave known as Motown. Youthful offenders were housed on a range known as Kiddy Corner. Seasoned criminals who had done penitentiary time lived on the Pen Range.

The policy that helped maintain peace, however, also divided the jail into warring factions.

"When you identify them as a gang, it empowers them," Ms. Buhagiar said. "There is safety in numbers. So our philosophy now is to split them up. If we have three Hells Angels come in, we force them to live with the Malverns, Crips or whatever."

The Don's sole purpose is to act as a holding tank for a vast spectrum of accused criminals awaiting trial.

"All the provincial joints have changed," observed one inmate charged with armed robbery and assault. "There are no more programs. It's no fun now. You are being punished, and it's not a good time."

Then again, perhaps it's all about the life you are used to. "Honest to God, it's easy inside here," said a 42-year-old offender. "Outside is hell. I like my freedom, but on the outside, I've got to sell a certain amount of drugs or get a certain amount of money. I feel a gun on me or I get manhandled by a bunch of kids. Here, I don't worry about anything."


What possible future could there be for a crumbling jail that is home to the ghosts of uncounted wretches who lived and died in desolation? With some prodding from architects with a vision, Bridgepoint Health saw the potential of a plan to incorporate the old Don Jail into a modern hospital.

Halfway through its overhaul, the old jail will eventually house three floors of administrative offices. Construction workers with PCL Construction are at work on every level of the spectacular, Baroque-style building, skillfully incorporating stone carvings, cells and pitted brick walls into lobbies, boardrooms and offices.

Paul Sapounzi, a lead architect with the Ventin Group, which is involved with the facility's restoration, said it was not altogether easy to persuade Bridgepoint executives that a jail with an unremittingly bleak history could become a warm, comfortable workplace.

"There is a sacredness to this place," Mr. Sapounzi enthused. "It has been so private for 150 years. This building was designed as kind of a palace - they just happened to put a jail into it."

Workers chuckle about some of the surprises they encountered in the early stages of their work. A homeless person had created an elaborate roost for himself in the governor's quarters in the jail's attic. Murals painted by long-dead inmates were discovered on basement walls. Skeletons buried in a prison yard had to be excavated and identified.


In one notorious escape, inmates obtained a soap impression of a careless guard's skeleton key. Late at night, they gained entry to the execution chamber and used part of the gallows' trap-door mechanism to loosen mortar in the walls and escape.

In another escape, Norman (Slippery) Neal used a hacksaw in 1923 to cut through his cell bars, a door in the corridor and a barred window. The jail governor of the day - a harsh and uncompromising man named G. Hedley Basher - ordered a massive search and Mr. Neal was recaptured.

Members of the notorious Boyd Gang also broke out of the Don in 1952 using a hacksaw one of them had concealed in his wooden leg. Soon after being recaptured, the foursome escaped again by cutting through two sets of bars. Two of the men were ultimately sent to Kingston Penitentiary. The other two, who had killed a police officer while they were at large, were executed in 1952.

Shortly before the noose was draped around his neck, one of them asked a guard whether it was true that hanging guaranteed an instant death. For him, it didn't. He took 44 minutes to die.


In its heyday, the prevailing ethic at the Don Jail was simple - prison should be a harsh and intimidating experience that no sane person would want to repeat.

To that end, the last thing an offender saw as he entered the Don from the outside world was a mawkish stone figure of Father Time carved into the stone above the front door of the jail. Inside the jail, numerous wrought-iron serpents and dragons emerge from the dark, connecting walls to balconies and catwalks.

Floggings were conducted on the floor of its central rotunda, with inmates watching the gruesome spectacle from the balconies. The families of debtors were often imprisoned in adjoining cells as extra punishment. For a long time, talking was prohibited.

The cells of the old Don were stunningly narrow and often double bunked. The toilet was a bucket.

For all its privations, however, nothing compared to the execution chamber as a lesson for persistent ne'er-do-wells. The chamber was a dank room located just off the midpoint of a death-row cell block. To add to the horror, the odd botched hanging would cause a gory decapitation.

The last executions to take place in Canada - those of Lucas and Ronald Turpin - took place in the Don Jail in 1962. The chamber still remains largely untouched despite renovations going on throughout the building.

"It's always feels cold in there," a member of the construction team observed with a shudder.

Editor's Note: Diamond and Schmitt Architects designed the adaptation of the Don Jail in Toronto. Ventin Group is involved in its restoration. Incorrect information appeared in print on April 20 and in an earlier online version of this story. This version has been corrected.

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