Born in Clonmel, Ireland, he emigrated to Lower Canada as a child and was educated at the Collège Saint-Raphaël, where he began a life-long association with the Roman Catholic Sulpician order.
In November 1838, O'Sullivan was appointed the Chief Justice of the Court of Queen's Bench in Montreal, but died in March 1839 at the age of 54.
Other students in the class also went on to play leading roles in the nationalist politics of Lower Canada, such as Hugues Heney, André Jobin, and Jean-Moïse Raymond.
The Canadian regular and militia units and Mohawk warriors were under the command of Lieutenant Colonel de Salaberry.
They were outnumbered, but de Salaberry built up defensive positions with his forces protected by the dense woods, and trees and brushwood which they cut down.
[1][2] O'Sullivan was a lieutenant in a Beauharnois battalion of the Lower Canada militia, and served as aide-de-camp to de Salaberry.
[1][2] After the battle, a dispute arose about the role played by the Governor General, Sir George Prevost, and Major-General Louis de Watteville.
Neither Prevost nor de Watteville had been present at the battle, but stories began to spread that the victory was due to their leadership.
In response, a pseudonymous letter appeared in the Montreal Gazette on November 9, 1813, written by a "témoin oculaire" ("eye-witness"), confirming the impressive role and command decisions played by de Salaberry, and asserting that the victory was due entirely to the Canadians.
[2] After completing his courses at the Collège St-Raphaël, in 1805 O'Sullivan began his legal studies as an articled clerk with Denis-Benjamin Viger, a brilliant young lawyer and future joint-premier of the Province of Canada.
The Parti canadien members of the Assembly opposed the policies of the British governors, who generally favoured the English-speaking merchants and landholders.
During his time with Viger, O'Sullivan began writing articles for Le Canadien, a newspaper which supported the nationalist position.
[1][2] In 1814, O'Sullivan was elected to the two-member constituency of Huntingdon county, south of Montreal, alongside Austin Cuvillier, who would go on to be the first Speaker of the Legislative Assembly of the Province of Canada.
[1][2] In the Assembly, O'Sullivan tended to support the Parti canadien and his friend, James Stuart, which suited his reformist tendencies at that time.
However, he was more interested in issues of government administration and judicial matters than the battles over constitutional principles which increasingly occupied the Parti canadien.
[1][2] O'Sullivan had a lifelong connection with the French Sulpician order of Catholic priests, who had taught him at Collège St-Raphaël.
O'Sullivan gave advice on the civil and canon law aspects of the dispute to the person who brought the challenge.
The dispute began in January 1819, when John Molson, a prominent brewer and businessman, presented a petition to the Legislative Assembly calling for the creation of a third hospital, non-denominational, to operate in English and serve the English-speaking community of Montreal.
O'Sullivan was hit twice, including one wound that left a ball lodged close to his spine in an inoperable position.
[9] In November 1838, O'Sullivan was appointed Chief Justice of the Court of Queen's Bench for the district of Montreal, but only served for a single term in February 1839.
An autopsy found Caldwell's ball from the duel 20 years prior lodged against the middle of O'Sullivan's spine.