Background
Medcalf was born in Delgany, County Wicklow, Ireland, in 1803 and moved to Upper Canada in 1819 with his parents, William and Martha Medcalf, and seven siblings.
Medcalf was born in Delgany, County Wicklow, Ireland, in 1803 and moved to Upper Canada in 1819 with his parents, William and Martha Medcalf, and seven siblings.
They lived on the Big Otter Creek in Bayham, Ontario. In 1823, Medcalf relocated to Philadelphia in the United States, where he began working as a blacksmith and millwright. He opened the Don Foundry and Machine Shop in 1847, which specialized in the production of agricultural machinery and steam engines.
Between 1854 and 1862, he held master positions at various Orange Order lodges in Toronto, and was a lodge grand master of Canada West in the period 1862-1864.
lieutenant was his lodge service that led him to Toronto politics and his successful election as alderman of Saint Lawrence Ward in 1860 and Saint David"s Ward in 1863, 1867 and 1868. In 1864 he ran in the election for Mayor of Toronto in opposition to the incumbent mayor John George Bowes.
Between 1867 and 1873, the mayor was selected by Toronto City Council rather than by popular vote, but when the electoral system was restored in 1874 he was re-elected for another two terms until he was defeated by the Conservative member Angus Morrison in 1876. He also ran for election in 1871 in the Toronto East district, but was defeated by Matthew Crooks Cameron.
Medcalf"s nickname in politics was "Old Squaretoes", a reference to his foundry work boots, an image he used to promote his "rags-to-riches story".
Medcalf died on March 26, 1880 in Toronto, aged 77.