The T Dot's First Hanging

It seems that sometime around the turn of the 1800s, when our city was still just a town only a few years old, John Sullivan and Michael Flannery went out one night and got drunk together. Sullivan was an Irish tailor and they called Flannery "Latin Mike" because he liked to recite Latin proverbs, which I guess was a thing back then. At some point their drunk asses must have run out of money, because Latin Mike decided to forge a bank note worth about three shillings so that Sullivan could use it to buy more booze. Shockingly, their plan backfired and while Latin Mike managed to escape and fled to the States, Humphrey Sullivan landed in Toronto's first jail, sentenced to death. Which, you know, seems a little harsh.

The jail was brand new, built on the orders of the slave-owning gambling addict/politician, Peter Russell, who was running the young town while Lieutenant Governor John Simcoe (the dude who founded Toronto) was back in England, slowly dying. The "gaol" was built on King Street, where the King Edward hotel is now (there's a plaque) and as you may have guessed from the drawing above, it was a little wooden building with a log fence. Inside, there was just enough room for three prisoners and it seems that while Sullivan was there it was filled to capacity. Next door to him was John Small, on trial for having recently killed the Attorney-General in the city's first duel. And in the other cell was a Mr. McKnight. When the officials running Sullivan's execution ran into trouble finding someone willing to do the actual executing, it was McKnight they convinced to do it in return for $100 and a pardon.

McKnight, however, was not awesome at hanging people. He screwed up the first attempt. And then the second. By the third, even Sullivan was getting impatient, saying something along the lines of: "McKnight, I hope to goodness you've got the rope all right this time."

He did.

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A version of this story will appear in The Toronto Book of the Dead Coming September 2017 Pre-order from Amazon, Indigo, or your favourite bookseller

There seems to be some confusion about a few of this story's details, like whether John Sullivan's real name might have been Humphrey, but I've mostly cobbled that all together from The Toronto Story and Jarvis Collegiate's startlingly informative website, which are both fantastic. They've also got lots more about Peter Russell and John Simcoe and the city's first duel, which are all so getting their own posts sometime. (Update: I've written the Peter Russell post here.)