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Previously a town councillor and deputy mayor of Inuvik, Roland was first elected to the Legislative Assembly in the 1995 Northwest Territories general election, after defeating the incumbent candidate Fred Koe.
Prior to seeking election as member of the Legislative Assembly of the Northwest Territories, Braden worked extensively with Charles "Bud" Drury, a former federal cabinet minister, who was assigned to look at further constitutional development in the Northwest Territories.
In the 1891 Northwest Territories election, he ran as an unsuccessful candidate for a seat to the Legislative Assembly of the Northwest Territories for the riding of South Qu'Appelle.