In October 1798, John Sullivan was sent to the town gallows on King St. E. The unfortunate crook, an illiterate tailor, had been convicted of passing a forged banknote worth three shillings and ninepence, slightly less than a dollar, and conspiring with a friend, Michael Flannery, to have it cashed.

Unfortunately for the pair, the hasty scheme was quickly uncovered. Flannery fled to the United States, leaving Sullivan to take the fall. Though it was Flannery who had concocted the idea and actually made the forged note, Sullivan was the one who had tried to use it. In the eyes of the judge, that alone was enough to warrant death by hanging.

In the 1790s, jail for the town of York was located on the south side of King, just east of Yonge, where the King Edward Hotel is today. It was a simple wooden structure with room for only a few prisoners, surrounded by a high fence.

Capital punishment was permitted by law (in fact, it was considered a suitable punishment for roughly 120 different crimes, according to author Peter Vronsky,) but up to that point no-one had been sentenced to death since the founding of the town a few years earlier in 1793.

For that reason, there were no trained executioners available to dispatch Sullivan. A fellow prisoner at the King St. jail was eventually convinced to do the job in exchange for $100 and an early release.

On Oct. 11, 1798, Sullivan was walked to the hanging yard within the prison walls. A crowd of several hundred had gathered to watch the spectacle.

"People celebrated as if it were a public holiday," writes author Terry Boyle in Hidden Ontario: Secrets from Ontario's Past. "A huge crowd of men, women, and children congregated by the gallows, and there stood Sullivan waiting to be hanged."

The noose tied and the audience waiting in nervous silence, the freelance executioner sprung the trap, dropping Sullivan through the floor. The rope yanked tight and snapped, according to historian Mike Filey, sending a confused Sullivan tumbling to the ground.

Undeterred, guards scooped the temporarily reprieved prisoner off the ground and returned him to the top of wooden scaffold while the executioner hurriedly reset the gallows.

The rope held the second time.

Follow Chris Bateman on Twitter at @chrisbateman.

Image: "Jail (1799-1827), King St. E., s. side, at Leader Lane," Toronto Public Library, JRR 711