Spacing Toronto's Adam Bunch has a great post up explaining how William Lyon Mackenzie, leader of the abortive 1837 rebellion, fled for his like (and had hope for the future) with the help of a pirate.
William Lyon Mackenzie ran for his life. His rebellion had failed. It was a disaster. His rebel army was crushed on Yonge Street. His headquarters at Montgomery’s Tavern were burned to the ground north of Eglinton. Some of his men were already dead. Others would soon be hanged for treason. Just a few years earlier, Mackenzie had been the first Mayor of Toronto. Now, he was the city’s most wanted fugitive. The Lieutenant Governor was offering a £1000 reward for his capture. So Mackenzie was forced to flee the city he loved, smuggled through the countryside by his supporters as gangs of angry Loyalists searched for him. He ran all the way south to Niagara, getting rowed across the river just a few minutes ahead of the men who had come to arrest him. He was lucky to escape Canada with his life. He would spend the next decade living in exile.
But Mackenzie wasn’t ready to give up. Not yet. His failed rebellion in Toronto was just the beginning. Now, he and his supporters would launch a war against the British government in Canada, hoping a series of bloody border raids would spark a full-scale democratic revolution. It would last a year — for pretty much all of 1838. We call it the Patriot War.
And the rebel’s admiral in that war was a man by the name of Pirate Bill Johnston. He was a smuggler, a spy, a veteran of the War of 1812 on both sides and, weirdly, an IRS agent. The rebel mayor was the most wanted man on the western shore of Lake Ontario. But the pirate admiral Bill Johnston would soon be the most wanted man in the east.
He’d been born in Trois Rivières, but he grew up just outside Kingston. And it was there that he would make his name as a young smuggler. By the time he was in his early 20s, Johnston was the captain of his own ship. He sailed his schooner through the labyrinth of islands at the spot where the St. Lawrence River meets Lake Ontario. We call them the Thousand Islands — but there are actually almost two thousand of them. It was the perfect spot to be a smuggler. Johnston would make runs through the confusing warren of islands, bringing contraband goods across the river from the United States. And he wasn’t alone. Some estimates say that as much as 90% of all the tea in Upper Canada had been smuggled into the province to avoid paying taxes — and plenty of the rum, too.