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The Don Jail at 550 Gerrard St. in Toronto

Charla Jones/The Globe and Mail

Overcrowded, degrading, racked with tension - the landmark Toronto (Don) Jail has long been synonymous with hard time. But a recent spasm of violence, culminating last weekend in the second homicide in two months behind its walls, suggest the aging lockup has become particularly volatile.

"It's not so much the numbers, it's the types," said one of the Don's corrections staff. "We have a 2010 generation of street thugs in a 1950s-generation jail. The mentality and the building do not match."

Bad press is nothing new to the Don.

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In 2003, a gunman who terrorized a downtown bar full of patrons was sentenced to just one day's incarceration when the sentencing judge ruled that the four months "dead time" he had spent there would be calculated on a three-for-one basis, instead of the customary two-for-one.

After hearing that Purnell Smith, 26, and two other men were squashed into a cell designed for a single occupant and that he slept on the floor with his head next to the toilet, Mr. Justice Richard Schneider called the Don "an embarrassment to the Canadian criminal justice system."

In a separate, related ruling the same year, Judge Schneider concluded that the fortress at Broadview Avenue and Gerrard Street East did not even comply with minimum standards set for prisoners by the United Nations.

Seven years later, the Don is back in the spotlight as homicide detectives probe the fatal weekend beating of Kevon Phillip, 24, the third act of extreme violence in two months to surface at the jail, whose inmates are chiefly awaiting either trial or sentencing, most commonly on drug charges.

In early November, Jeffrey Munro, 32, was also beaten to death at the Don, leaving three other inmates charged with first-degree murder.

And in the same week, Kevin Pereira, also 32, sustained serious injuries when he was attacked by a prisoner.

The newest victim, Mr. Phillips, was no stranger to the justice system.

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He had racked up a total of 25 convictions - seven for possession of property obtained by crime - and when he died in St. Michael's Hospital Saturday afternoon he was awaiting an immigration hearing and possible deportation to his native Jamaica.

No arrests have been made, and there was no immediate indication of what caused the deadly altercation or whether it was captured on surveillance videotape.

Police spent Sunday and yesterday interviewing inmates and jail guards.

But in the view of Eduardo Almeida of the Ontario Public Service Employees Union, one of the key elements in the violent attacks is not just overcrowding, with about 620 prisoners packed into a facility whose capacity is supposed to be 550, but also understaffing.

"If you have a high count of inmates and a low count of officers, that's when things like this occur," Mr. Almeida said on the weekend.

Cramped conditions are just one factor that make detention centres - Toronto has two others - more volatile than provincial or federal prisons.

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Another is the lack of programs.

A third is the no-tobacco rule, enforced across all penal facilities these days but felt acutely by defendants who have been recently arrested.

Many inmates, too, struggle with more serious types of drug withdrawal.

And looming over everything is the nail-biting uncertainty accompanying almost all prisoners awaiting trial.

"Some guys in there are just out of their minds with anxiety because they don't know what's going to happen to them and they're worrying about their families," said a Toronto police officer who has many times visited the Don, slated to close its doors in 2012 and be replaced by a new facility in Mimico.

And because most prisoners have access to newspapers, notoriety can worsen a prisoner's plight still further.

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Convicted bicycle thief Igor Kenk, for example, had a tough time in the Don, judging by the wound on his face and his dishevelled demeanour during one of his many court appearances.

So too did small-time hoodlum Ralph Scala, 37, the younger half of a father-and-son duo who inflicted widespread havoc on Toronto's Junction district before police arrested the pair and dispatched Mr. Scala to an eight-month spell in the Don.

He pleaded guilty to dozens of charges, he told The Globe and Mail, because he couldn't stand being in the Don any more.

"I have anxiety, I can't handle stress," he said. "I couldn't stay in there any more."

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