A Head for Escape

When you’ve done the crime but don’t wanna do the time….

A head for escape
heading for escapeMaximum security is the most secure level of incarceration on the custodial confinement pyramid.  For 178 years, K P (Kingston Pen) was the pointy thing at the top of the maximum prison pyramid – one of those places where, when you checked in, you were checked out for a very (very!) long-ass time.

But, the human spirit is damn near indomitable, its feathery little wings an un-crushable ball of determination and will power.  In fact, (we only deal in facts here ma’am), the only thing unencumbered by some of the incarcerated is imagination – and as we all know, what an unequivocally inventive tool that can be! “When you ‘ain’t got nothin’, you got nothin’ to lose.”


One of the more infamous escapes from KP was executed by Norman ‘Red’ Ryan, a 28-year-old, who, in 1923, lit a fire in the prison exercise yard, threw a make-shift ladder against the wall and got busy scurrying to freedom. Ryan, who was armed with a pitch fork, ended up impaling one of the guards on his way out – a whole new twist to the ‘fork-you’ expression, to be sure.

Confiscated ‘home made weapons

250px content confiscated weaponsA vee-rrr-ee in-ter-est-ing Toronto twist to the story (decades before Toronto became known as the ‘6’) was the novice journalist who reported Red’s escape for the Toronto Star – one Ernest Hemingway. (You might have heard tell of him, yes?)

And what a great yarn ‘Red’ spun for the first-day-on-the-job-Hemingway.  Red, who fled to the States, became known as the Jesse James of Canada, avoiding capture and managing to stay on the ‘lam’ for a year, eventually giving himself away when he wrote a letter to K P’s warden, who, noticing the Minneapolis post mark, tracked Red down.  Not at all chagrined, Red did his best to charm his gaolers, all the while executing his second escape, and, subsequent recapture. Rehabilitation was just not Red’s thing – once paroled, Red took to donning disguises and robbing banks.  But he lost the public’s support for his Robin Hood persona when a police officer got shot whilst Red was robbing a Sarnia liquor store.  It was a very grey ending to Red’s uniquely entertaining outlaw career.

Tyrone ‘Ty’ Conn

The deck was stacked against Ty Conn from the second he took his first breath; his 15-year-old mother was not of maternal cloth and in fact, before Ty could actually say Mama, he was adopted by Belleville psychiatrist Dr. E. Bert Conn, who was extremely abusive to Ty – not to mention the good old doc’s wife – who was said to be mentally unstable. Suffice to say that in the 19 years between the time Ty was 9 and his death at 32, he was legally at large a mere 69 days.

Ty, who numbered 26 in the list of 28 KP escape attempts, was serving a looooong sentence for armed robbery, when on May 6th, 1999, he decided to go over the wall, literally. Hiding under a pile of Canada Post mailbags, (snail mail was still a ‘thing’ in the late ‘90’s! kids), Ty assembled his getaway gear; a ladder with homemade extension, a steel hook and a 12-metre canvas strip that doubled as a rope. Breaking out of the canvas shop loading bay, Ty, who already sussed out the changing of the guards, sprinted for a wall that was obstructed from tower view. Cunningly, he sprinkled cayenne pepper after himself to mask his scent and fool the sniff dogs.  Ty made it to Toronto where he hid out for two weeks before the cops tracked him down.

Because of his terrible upbringing and the fact that he had never physically harmed anyone in the execution of his crimes, Ty had major public sympathy on his side. “Come on, be honest; part of you is cheering for Tyrone Conn”, ran an article in the Kingston Whig-Standard.

It is not quite clear whether by intent or accident that Ty shot himself in the apartment he was holed up in, especially due to the fact he had forged sympathetic and public ties with journalists Theresa Burke and Linden MacIntyre of the Fifth Estate. These journalists went on to publish a book, Who Killed Ty Conn, Viking Press, 2000.  (A book well worth the read).

For more ‘on the lam’ yarns, check out Cece’s next blog when she ‘escapes’ to Martha’s Vineyard200px content me mask.