Fairclough was elected to the incoming New Democrat government of Piers McDonald in the 1996 Yukon general election. He ran successfully in the rural New Democrat stronghold of Mayo-Tatchun, succeeding retiring New Democrat MLA Danny Joe. Before entering territorial politics, Fairclough had been Chief of the Little Salmon/Carmacks First Nation. Fairclough served in McDonald's Cabinet from 1996-2000 as Minister of Renewable Resources, Minister responsible for the Yukon Housing Corporation, and the Minister responsible for the Yukon Liquor Corporation.
30th Legislative Assembly
Fairclough was re-elected as a member of the New Democrats in the 2000, but that election saw his party reduced to Official Opposition status. Fairclough became interim leader of the New Democrats when Trevor Harding, the previous interim leader, decided to resign politics. Harding had succeeded New Democrat leader Piers McDonald, who had been defeated on election night. Fairclough ultimately ran for leadership of the New Democrats, but withdrew. Former Whitehorse Centre MLA Todd Hardy, who had lost his seat in the 2000 election, was elected leader in 2002.
31st Legislative Assembly
Fairclough was elected in 2002 Yukon election, again as part of the Official Opposition. He was appointed Official Opposition critic for Health and Social Services and Public Schools. He also shared critic portfolios on Finance and First Nations relations. However, he was later expelled in 2006 from the New Democrat caucus by leader Todd Hardy when it was discovered that he and his colleague, Kluane MLA Gary McRobb, were publicly consulting constituents about considering quitting the New Democrats for the Liberals due to Hardy's isolated decision-making and a lack of faith in his leadership. Fairclough had also insisted upon Hardy calling a leadership race, but Hardy had refused. Fairclough and McRobb soon joined the Liberal caucus, reducing Hardy's New Democrats to third party status and elevating the Yukon Liberal Party to Official Opposition. The move prompted the New Democrats to table legislation preventing MLAs from crossing the floor without an ensuing election, but the legislation was never adopted. Fairclough served as the Liberal environment critic for the rest of the session.
32nd Legislative Assembly
Fairclough was comfortably re-elected in his riding in the 2006 Yukon election, capturing half the vote. McRobb too was re-elected, and the Liberals retained their Official Opposition status under a Yukon Partymajority government. During the 32nd legislature, Fairclough served as opposition critic for Health and Social Services, Community Services, Education, the Public Service Commission, the Yukon Liquor Corporation, and the Yukon Housing Corporation. He also functioned as the Liberals' whip. Fairclough announced his intention to seek re-election in his riding of Mayo-Tatchun in the 2011 Yukon election, but was defeated in his attempt by the New Democrat's Jim Tredger. Fairclough finished in third behind the New Democrats and the Yukon Party.
Personal life
Fairclough was once again re-elected Chief of the Little Salmon/Carmacks First Nation after his departure from territorial politics in 2011. He served one term prior to being defeated in 2016. During his second tenure as Chief, he was a vocal critic of the territorial and federal governments' attempts to amend the Yukon Environment and Socio-Economic Assessment Act to reduce the power of Yukon First Nations under Bill S-6. Fairclough argued that the proposed changes undermined the spirit of the First Nations' final agreements. The victorious Liberal campaigns of Yukon PremierSandy Silver and Prime Minister Justin Trudeau ultimately committed to repealing Bill S-6 in the 2016 Yukon election and the 2015 federal election, respectively.