Hallowe'en is coming.

 In addition to coming up on Remembrance Day, we are also coming up on Hallowe'en. In that (ahem) spirit I thought I would share with you a few of the stories of Toronto's rather gruesome past, some of which I told last year when I was doing my virtual history walks.

So, without further ado, here is the story of Toronto's first execution.

Let’s start off the evening with the story of John Sullivan, an illiterate tailor living somewhere in muddy York in the 1790’s, then a backwash of immense proportions.

Downtown York- now Toronto- in 1793, painted by Elizabeth Simcoe, wife of Lieutenant governor john Graves Simcoe.

One night in October, 1798, John Sullivan was drinking at a local establishment with his friend Michael Flannery, a man who had some education and was known for reciting bits of Latin proverbs, thus earning him the nickname of Latin Mike. The two ran out of money but not out of thirst, but Flannery, who was a printer, came up with a cunning plan: he would forge a banknote. And so he created a note for 3 shillings and nine pence, worth about 24 cents, and he gave it to Sullivan who passed it off to the barkeep.

Shockingly, it was quickly realized that someone was trying to hand off the late 18th century equivalent of monopoly money, only not as authentic, and the authorities were summoned. Flannery immediately fled and made his way to the United States as fast as he could, and so it was Sullivan who was left behind to take the fall.

And it would be a literal fall, with a very abrupt stop. At that time, forgery was one of approximately 120 crimes that could result in a sentence of Capital Punishment. And thus, even though the amount of money involved was minute, even by the standards of the time, the judge felt the sentence was merited as he passed judgement with the words “Sullivan, may all who behold you, and who shall hear of your crime, and of your unhappy fate, take warning from your example… [I] recommend to you to employ the few days that shall be allowed, of a life spent in wickedness, in humble and fervent prayer to almighty God…”

Sullivan was taken to the brand new York Jail a tiny wooden structure that could hold as many as three prisoners which was surrounded by high stake walls and had a heavy door that stood on the South side of King Street just East of Yonge, where the King Edward Hotel now stands.

The original jail. No idea what the small inset picture is.

In front of the fence stood the hanging yard, as hanging was a public spectacle that often drew very large crowds back then. School children were sometimes taken to public executions, as it was thought that it would be salutary and encourage morality in them to know what happens to wrong doers and ne’er do wells. And thus, a large crowd of several hundred people (an impressive number for a town of considerably less than 500) gathered outside the jail on October 11th, 1798, for the purpose of seeing John Sullivan breathe his last.

However, behind the scenes there was a slight problem. Sullivan’s was to be the first execution in Toronto history, and since there had never been any need for an executioner prior to this time, they didn’t have one. Nor had they any one any experience with being a hangman, and while the authorities had no difficulty in sentencing a man to death and the crowds could not wait to see such a sentence carried out, no wanted to do it themselves. But, fortunately, another prisoner, known only by his last name of McKnight, was willing to do the job for an early release and 100 pounds.

(For those keeping score, they are releasing a man and paying him one hundred pounds to kill a man who passed off a note for 24 pennies.)

And thus Sullivan was lead out to the scaffold, said his last words, the noose was tied, and McKnight did his job. Only Sullivan tumbled to the ground, still alive, utterly failing to provide a salutary moral example to the waiting crowd.

Undeterred, Sullivan was picked up, dusted off, presumably asked if he had any last Last Words, and had the noose placed around his neck a second time- and promptly tumbled to the ground for the second time.

Once again, he was picked up and taken back to the hanging spot. And here he spoke what were to be his true last words. “For God’s sake, McKnight, I hope you get it right this time.”

And, at last, McKnight did.