The T Dot's First Hanging by Adam Bunch

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 totally shitfaced 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.

Photo: Toronto's first jail

Adam Bunch is the Editor-in-Chief of The Little Red Umbrella and the creator of The Toronto Dreams Project. You can read the rest of his posts here or follow him on Twitter here.

This post originally appeared on the Toronto Dreams Project Historical Ephemera Blog, which tells stories about the history of Toronto, including tales of bank robbers, duels and 100 year-old fish. You can read more highlights from it here, or visit it yourself here.