After completing his schooling, he worked in John Moody's auction business, becoming a partner in 1814.
Because he had not severed his ties with Moody by the time that the business failed in 1817, he lost all his possessions.
Stewart went on to complete his studies in law, was called to the bar in 1822 and set up practice in Amherst.
Stewart lost his seat in February 1838 after his election was appealed; however, the month before, he had been named to the province's Legislative Council.
Stewart was vocal in his opposition to responsible government for Nova Scotia.