Skip to main content

If there's a way to escape from behind bars, it's likely been tried in Kingston.

"Foxy Freddie" Caddedu, serving life for murder, took the contortionist route in 1981, dropping 20 pounds to jam his 5-foot-7 body into a small hole cut from a glued-together stack of food trays, and sneaking out of prison via the kitchen. Norman "Red" Ryan went for distraction, setting fire to the prison horse stables in 1923, before hopping the wall with his accomplices.

In 1999, Ty Conn, the last prisoner to successfully escape from the Kingston Penitentiary, fooled the guards with a dummy in his bed, and scrambled to freedom with a homemade ladder and grappling hook.

Escapees have even gone by water, stealing the prison boat and making a break for the United States, not far from where the Olympic torch entered Kingston by sailboat yesterday morning. In fact, some of the most interesting people to pass through this city have been the people most desperate to leave it. Kingston is the prison capital of Canada, with eight correctional facilities, including the infamous Kingston Pen, which was built in 1834, and has been home to some of the country's most notorious criminals.

Many of Kingston's prominent limestone landmarks were built with stones from the prison quarry. The history of the city's great escapes - and its prisons' cruellest punishments - has been carefully catalogued in the stately former warden's home, now a museum, on the hill overlooking the Pen.

"The ingenuity side of this story is pretty impressive," says David St. Onge, the museum's curator.

One shelf holds a collection of dummy heads used in escape attempts - the hair made from barber shavings, the neck with a mop head, the skin with medical gauze and flour, all proceeds of the underground trade in the prison. In a case across from the infamous orange meal trays, Mr. St. Onge points out a crossbow engineered from toothbrushes and kitchen tongs, which, when tested by guards, was accurate to 12 metres.

"If you look closely, you can see he's actually plucked his own hair for the cross hairs. "

But the back rooms of the museum show the darker side of Canada's prison past. From the mid-1800s, there's the "strapping bench," whose name explains its purpose, and the "box," a cramped coffin with a few breathing holes into which mainly female prisoners were locked for misbehaving. The museum even has an old-fashioned version of water torture, in which a prisoner was seated, with a barrel locked around his face, while icy water was poured through it - that was used 350 times in the prison in the late 1850s, Mr. St. Onge says, until an American prisoner died of a heart attack and it was banned in Kingston.

Prison history also speaks to human nature - both inside and out, observes Mr. St. Onge, who has worked at the museum for 25 years. "It's a yardstick to see how we've evolved, what we left behind."

Until the late 1800s, parents brought their children for tours of the prison, to stare at the inmates who were then locked in dark, tiny cells, with a straw bed and a bucket for a toilet. "You'd pay 25 cents a person, and gatekeepers would take you through," he says. "It was written into the rules that inmates were not allowed to look at the crowd passing through or risk being charged." The visit came complete with souvenirs - the museum has a candy dish with a picture of the penitentiary stamped upon it. (Today, the most popular item in the museum gift shop is a diaper shirt that reads: "I spent 9 months on the inside.")

Based on wardens' journals, letters and records, Mr. St. Onge says there have been 27 successful escapes from the penitentiary - involving various gangs of prisoners - and countless others foiled. (On an anniversary of Mr. Conn's escape, one inmate tried to throw a milk crate attached to a rope over the wall - he couldn't throw high enough, so he gave up and was soon caught by the guards.) A couple of inmates have even tried to break back in, including a young sailor in the 1800s who returned to jail over 11 shillings he stole from the warden's safe.

Of all successful breakouts, only three men are presumed to have made it clear, safely assuming new identities. None of the three would still be living today. The aforementioned Mr. Caddedu and Mr. Ryan were recaptured trying to rob banks; Mr. Conn died in an apparent suicide when he was cornered by police in Toronto. But one treasured artifact is the tidy, five-page letter that Mr. Ryan mailed to one of the guards, from "the Land of the Free," apologizing for punching him during the escape.

"I was rather sorry it was yourself that I had to tackle," he wrote. "However I admire your pluck. ... Hope you were not hurt too much." And the reason he gave for his escape? The lousy food.



DAYS 47, 48 & 49








Report an error

Editorial code of conduct