After his father's death in 1816, Stewart and his family, consisting of his recently widowed mother, grandmother, uncle, and nine siblings, emigrated to Upper Canada.
[1] As a young man, Stewart began working for a merchant in Montreal and gained experience in the lumber trade.
In 1835, while in London, Stewart presented submissions to the British government on behalf of Bytown residents and Montreal merchants, arguing for the need for navigational improvements to the Ottawa River.
Three years later, in 1838, he gave testimony in the British Parliament about the feasibility of a water route linking Lake Huron to the Ottawa River.
[1] Although initially prosperous, Stewart suffered financial losses in the mid-1840s as a result of a glut in timber and drop in prices.
He eventually left the timber trade and concentrated on his extensive farm operations, as well as acquiring considerable landholdings in Bytown, and in the neighbouring counties of Carleton and Renfrew.
[1] During the time of the Shiners' War, a conflict between French-Canadian and Irish lumbermen, he helped form the Association for the Preservation of the Peace.
Three other candidates followed, also announcing their intention to stand for election, but the situation changed in late September, when Sydenham paid a short visit to Bytown.
Stewart immediately issued two public protests, accusing the returning officer of partisanship in favour of Derbishire, but did not contest the outcome further.
In 1843, Draper accepted an appointment to the Legislative Council, the upper house of the provincial parliament, vacating his seat in the Assembly.
Stewart contested the resulting by-election, and at one point was escorted to Russell by a brigade of uniformed volunteer firemen from Bytown.
He was criticised for drawing the town boundaries to exclude his own farming property, making it subject to lower tax rates.