Tyrone Conn’s escape from Kingston Penitentiary

Tyrone connA decade ago, Canada’s federal prison service was humiliated when a wily bank robber clambered over the 10-metre high stone wall of the country’s oldest, seemingly most secure penitentiary, and vanished into the darkness, leaving behind cheering sex killers and pedophiles who were his prison mates. The conditions in which that escape was possible exist again today at some of the country’s highest security prisons.

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Tyrone Conn was 32 years old, serving a 47-year prison sentence at maximum-security Kingston Penitentiary when he staged a spectacular escape on May 7, 1999. His cunning, patience and ingenuity, coupled with a series of stunning security failures, made the breakout from the Big House possible (use the interactive aerial view of Kingston Pen above to understand the escape). Conn was the first prisoner to make it over the wall of Kingston Pen in 41 years. He scampered over the east wall sometime between 3 a.m. and 5 a.m., using a ladder he jury-rigged to greater height and a 42-foot length of canvas strapping and grappling hook he fashioned from a piece of steel rebar. The nearest guard tower, a squat observation post at the southeast corner of the prison, had been empty since 11 p.m. the night before. Had a guard been on duty, he or she likely would have had a clear view of the escape in progress, and, armed with a rifle, would have been equipped to stop it. The tower had been unstaffed on the overnight shift for several years, a victim of management budget cuts, despite the protests of prison staff. After the escape, prison managers reinstated 24-hour-a-day, seven-day-a-week staffing of four perimeter watch towers at Kingston Pen, a prison that holds psychopathic sex killers like Paul Bernardo. Conn’s escape also was successful because two inmate accomplices on his cellblock spent the evening of May 6 moving a dummy in and out of his cell bunk before regular head counts. At the time, Conn was hidden in a canvas shop, assembling his escape gear. The dummy wasn’t discovered until after 7 a.m., when a search of the prison was ordered after a staff member arriving for work noticed the canvas strapping dangling from the outside of the east wall.

There are eight perimeter observation towers at maximum-security Millhaven Institution, just west of Kingston, Ontario. The Haven holds some of the country’s toughest bikers, gang members and contract killers. Just one of the eight towers is staffed on the overnight shift from 11 to 7. Recently, managers at the prison reduced the number of armed security patrols around the perimeter of the prison from two to one. The patrols were conducted by a guard in a truck with an automatic rifle and a handgun, who remains in constant contact with a central command post that monitors video cameras and motion detectors. The cut was made over the protests of prison workers (more on the staffing controversy in my Whig-Standard account of the Conn escape).

At medium-security Collins Bay Institution in Kingston, which also houses bank robbers and murderers, none of the four corner guard towers is staffed on the overnight shift from 11 to 7.

Similar conditions exist at many federal prisons across the country, following the Correctional Service’s implementation of a new staffing model April 1, over the objections of front-line prison workers. Staff say security has been sacrificed by penny-pinching bosses.

Ty Conn’s breakout was embarrassing for senior Corrections officials, who deserved much of the blame for fostering a culture at Kingston Pen that made the escape possible, front-line staff say. The internal inquiry into Conn’s escape and the resulting report (reproduced below in full)documents dozens of security failures at the prison. Many prison workers insist that the final report was a whitewash, meant to protect prison managers and senior Corrections staff. It chronicles the genius of Conn’s escape plot. It does not address one lingering question – who helped him? Police who investigated the escape are nearly certain that an accomplice in a car was waiting outside the prison in a nearby neighbourhood to spirit Conn quickly out of Kingston. That person has never been identified.

Conn died, of an apparent self-inflicted gunshot, roughly two weeks after his escape.

Here is the internal Corrections report on the escape, obtained under Access to Information law:

» Want to know more?  Read the excellent book, Who Killed Ty Conn, by Linden MacIntyre and Theresa Burke

Here’s the full text of my Kingston Whig-Standard story, published in May 2009:

In 45 years living at the same King Street address, Irene Hogarth has never really had a problem with the 500 or so “boys” who live next door.

“They’re very good neighbours,” says the 83-year-old, smiling.

“They don’t run across our property,” she says. “It’s probably safer here than anywhere.”

The answer may surprise some, given that Hogarth’s neighbours are some of the country’s worst sex offenders, child molesters and killers who are imprisoned at maximum- security Kingston Penitentiary.

Despite the pedigree of her neighbours, Hogarth and her husband raised a three-child brood here, beginning in 1963. The children were five, nine and 11 when the family moved in.

“Kids accept things,” she says. She’s accustomed to being asked breathlessly what it’s like to live next to the country’s oldest federal penitentiary.

“I say it’s just fine,” she says.

Hogarth’s property abuts the eastern edge of the 8.6-hectare federal complex and is close enough that, with a good windup, a thrower could heave a ball from her yard over the 10-metre-high east stone wall of the prison.

Ten years ago, that wall proved no match for a wily resident of the “big house.”

Hogarth recalls a visitor on the morning of May 7, 1999.

“A prison guard came to the door and said to me that someone had gotten out and was my car still here,” she recalls.

Her car had not been stolen. She was given a handbill that included a photo of a hazel-eyed, brown-haired 32-year-old man.

It was much too late for that door-to-door canvass of the neighbourhood to do any good.

By that time, Tyrone Conn, a crook once described in court as a “modern-day Houdini” because of his ability to escape, had fled west, out of the city, after he scaled the wall.

Conn was serving a 47-year sentence for bank robbery.

“I believe somebody was waiting to pick him up,” says Sgt. Rick Labrash, the Kingston Police officer who investigated the escape.

Labrash was then assigned to a special police unit that probes penitentiary-related crime.

Although there is no definitive proof, Labrash believes an accomplice in a car was waiting to spirit Conn out of the city immediately.

“It appears that he ran toward Alwington Place, ripped open an envelope and spread cayenne pepper to throw off the dogs,” Labrash says.

The car may have been parked in the Alwington neighbourhood just east of the prison or perhaps as far east as the Tett complex, adjacent to the prison service’s regional headquarters.

Labrash says there was evidence that Conn ran east along the waterfront to his rendezvous.

If the accomplice could be found today, he or she could still face a criminal charge of aiding an escape.

It’s also believed that Conn stopped first in Belleville and visited his mother, before making his way to Toronto.

Roughly two weeks after the escape, he died of an apparently self-inflicted gunshot wound.


His daring breakout humiliated the prison service. It was the first over-the-wall breach at KP in 41 years. It led to a major overhaul of security procedures and equipment at Kingston Penitentiary.

“It would be very difficult for an inmate to escape [today] from Kingston Penitentiary,” said Theresa Westfall, who has been warden of the 174-year-old prison for almost two years.

“We’ve got so many different security measures in place, that if one security measure isn’t working 100%, then another measure will catch it.”

Razor wire and motion detectors were added to the top of the stone wall that encircles the prison complex. Those features weren’t in place a decade ago, so when Conn attached a grappling hook to a conduit along the top of the wall, no one was alerted.

The union representing prison security staff had often complained that the institution needed the wire and detectors.

“Management said, ‘That’s ridiculous, we don’t need anything like that,’ ” recalls Phil Whaley, who retired in 2000 after a 31-year career as a guard at Kingston Pen.

He served several terms on the local union executive and squared off often against managers.

In 1999, budget cuts meant that managers were looking for ways to reduce security, he said, over the protests of staff.

The prison service also had adopted a kinder, gentler attitude in which inmates were to be given more freedom.

“The old ways were thought to be too restrictive,” Whaley says.

There was no means, for instance, of tracking inmate movement inside the compound. A pass system had long been phased out.

“They popped up in all sorts of weird places,” Whaley says.

“It was ridiculous.”

Westfall says now inmates must be escorted if they leave the main cellblock building.

“That wasn’t the case when the escape took place,” she says. Overall, movement is far more restrictive and controlled today, Westfall says.

High-definition video surveillance cameras also have been installed throughout the complex, giving staff a real-time view of inmate activity.

Another victim of budget cuts a decade ago was the 24-hour staffing of perimeter watch towers, the squat sentry posts along the wall where guards armed with rifles watch over the compound.

Conn knew that at 11 p. m. each night, a guard who occupied the tower at the southeast corner of the prison went off shift. No one replaced the sentry.

It’s believed Conn went over the wall sometime between 3 and 5 a. m., at a point not far from the southeast tower.

Corrections reinstated continuous staffing of four sentry towers after the escape.

There are eight perimeter watch towers surrounding maximum- security Millhaven Institution just west of Kingston, where gang leaders and killers are housed. On the overnight shift from 11 p. m. to 7 a. m., one of the towers is staffed.

Medium-security Collins Bay Institution in Kingston has four perimeter towers that remain empty overnight.

As it did a decade ago, the union representing security staff is battling management over these staffing decisions.

“We’re seeing a lot of reductions in staffing at our facilities,” says Jason Godin, regional president of the Union of Canadian Correctional Officers. “Now it’s just coming down to dollars and cents.”

He believes an embarrassing report by the auditor general is partly to blame for the budget squeeze.

Staff fear the cuts create an atmosphere similar to the one that allowed Conn to escape.

“Could this happen again? You’re damn right it could happen again,” Godin says.

He says a number of cuts took effect across the country on April 1.

“There have been a number of efforts to scale back posts,” he says.

At Millhaven, the number of armed security vehicles patrolling the complex was reduced from two to one.

Previously, two separate vehicles, each driven by an armed guard, circled the compound continuously. The driver is in constant radio contact with a central command post.

Godin says managers have not been able to explain how one vehicle will be backed up in the event of an emergency.


A significant failing in Conn’s escape was his ability to trick KP staff into believing he was in his cellblock throughout the evening of May 6.

Beginning at roughly 3 p. m., he was hidden inside a canvas shop where inmates repaired mailbags. Conn had sneaked into the shop after lunch that day.

When the shop closed just after 3 p. m. and was locked, staff did not realize that Conn was hiding in a semi-secure area.

While Conn assembled his escape gear in the shop, two inmate accomplices on his cellblock in the prison’s G range were moving a dummy in and out of his cell bunk.

The crude apparatus was constructed the night before the escape. A shoebox served as torso and paper towel rolls served as an arm and leg.

There was no head.

The limbs and torso were wrapped in towels and hockey pads were placed at the joints.

The dummy was dressed in a T-shirt and track pants. It was positioned in his bunk so that seen from outside the cell, part of the torso and a bent knee and elbow were visible.

The head of the ‘person’ on the bunk wasn’t visible because Conn began using a headboard on his bed several weeks earlier. A guard passing his cell could not see his head.

For weeks, Conn began lying on his bunk in the same position that the dummy would later assume.

Thirty minutes before each formal count, the dummy was positioned in Conn’s bed by his accomplices. After each count, the dummy was disassembled and hidden, so it wouldn’t be discovered.

The accomplices also changed the lighting in the cell and moved objects around throughout the evening to give the appearance someone was there.

They had one other clever trick. A speaker was hidden in the dummy, connected to a microphone of a nearby accomplice. If a staff member tried to speak to Conn, the accomplice could answer.

The audio ruse wasn’t used.

Five head counts were conducted between 4:30 p. m. and 5 a. m. the next day, but the dummy was not discovered until after 7 a. m., giving Conn a headstart of several hours.

Several prison staff were disciplined, but Whaley says that retribution and the official investigation report were a cover for management failings.

For years middle managers and top bosses had refused to enforce strict security protocols and had refused to back front-line security staff as they tried to enforce the rules, Whaley says.

“Some people just gave up,” he says.

Staff morale sank, basic security became lax and a mood of apathy settled in.

“It was bad,” Whaley says.

By 10:30 p. m., all of Kingston Pen’s roughly 400 inmates were locked into their cells for the night.

Conn was, by then, completing several projects inside the canvas shop.

Labrash, of Kingston Police, documented the work in detail.

Conn disassembled a storage cabinet, salvaging pieces of angle iron. He used those to extend an 11-foot-long stepladder to 18 feet, six inches.

He retrieved a 42-foot-long piece of canvas strapping he had hidden in the shop.

“He looped that strapping through a metal ring that he sewed shut,” Labrash says.

Conn bent a 16-inch-long piece of metal rebar so that one end formed a grappling hook.

Then he waited, watching from the second-storey vantage point until a guard who patrolled the yard with a dog was out of the area.

Then it was a simple matter of breaking open the poorly secured second-storey doors to the shop. Labrash believed Conn pushed out his jury-rigged ladder, which was easily tall enough to allow him to descend 17 feet to the ground.

He dashed south into the inmate exercise yard to a point where the inner stone wall was 23 feet, six inches high.

By standing on top of his ladder, the five-foot-nine convict was easily able to reach the top of the wall to attach his grappling hook and shimmy down the outside.

At 7:05 that morning, an employee arriving for work at the stores building noticed the canvas strapping hanging from the east wall. The alarm was sounded.

At 7:18 a. m., the headless dummy was found in Conn’s cell bunk.

“I was surprised that it was as easy as it as for this individual,” Labrash says.


Thirty-three inmates escaped from federal prisons across Canada last year, all from minimum-security institutions.

The year of Conn’s escape, he was among 114 escapees.

In August last year, two inmates at Kingston Penitentiary got onto the roof of the prison’s recreation building unseen and threw a line and grappling hook to the west wall.

The afternoon escape attempt was detected before they got to the wall. The convicts gave up.

In 1995, two inmates escaped from the main cellblock of the prison, in part because a guard mistook a dummy for an inmate during an evening head count.

The inmates were recaptured by 9 p. m. in the prison yard.

An internal investigation report concluded that some security practices had “slipped” because of ongoing renovations at the prison and that “physical security was in question.”

“We’ve got so many up-to-date security measures now that would prevent an escape from happening from Kingston Penitentiary,” says Warden Westfall.

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1 thought on “Tyrone Conn’s escape from Kingston Penitentiary

  1. i just want to know why there was no guard on that and seeing what was going on just wondering why ? i also want to know what do they make the fake bodys out of?

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