One man, Joseph Shepard (one “p”), with two North York places named in his honour with different spellings. There’s the 14-floor federal government office building, The Joseph Shepard Building, 4900 Yonge St. It’s just north of Sheppard Avenue (two “p’s.”) also named after him. Why this happened is unknown.

Ironically, the government building’s namesake was a rebel against the government of his era.

Born in 1765 in New Hampshire, Shepard came to North York as a young man. He became very prosperous – he owned a farm, sawmill and grain mill and was a land developer.

Fighting with British colonial forces against invading Americans during the War of 1812 he was badly injured in the Battle of York, April 27,1813 at Fort York, which was supposed to defend York (now Toronto), then the capital of Upper Canada.

During the fighting the fort’s gunpowder magazine exploded and Shepard’s left leg was shattered. The 2,700 American troops defeated the greatly outnumbered 750 British, Canadian, and affiliated Ojibwa fighters. Shepard received a land grant as compensation.

By Bob Olsen Toronto Star file photo
A populist, he was an early supporter of Upper Canada’s political reform movement against the tight knit wealthy, intermarried British colonials’ “Family Compact’s” grip, the people he had fought alongside during the war. He died May 3, 1837, six months before the 1837 Upper Canada Rebellion began. In a front-page obituary in his newspaper, The Constitution, rebel leader William Lyon Mackenzie wrote: “Mr. Shepard’s countenance was open and manly — he was remarkably good natured — his stature was six feet, and he was stout built in proportion.”

He and his wife Catherine had four sons and four daughters. All the sons participated in the rebellion. The rebels used their farm on what is now Burndale Avenue, near Yonge and Sheppard, as a rallying place and hideout. When government forces set fire to the house, Catherine doused it with buckets of water. The house still exists.

The Dictionary of Canadian Biography says: “Joseph Shepard worked to take political power away from the non-elected minority and it is not surprising that his family tried to follow the principles he had established.”