Born in 1933,[2] MacAskill is a graduate of the Nova Scotia Institute of Technology where he obtained an interprovincial plumbing certificate.[3] For over 20 years, he operated his own plumbing and heating business in Englishtown, Nova Scotia.[3] MacAskill entered provincial politics in 1988, defeating Progressive Conservative incumbent Fisher Hudson to become the MLA for Victoria.[4] He was re-elected in 1993[5] and served as a backbencher in John Savage's government. On July 18, 1997, MacAskill was appointed to the Executive Council of Nova Scotia as Minister of Natural Resources.[6][7] Following his re-election in the 1998 election,[8] MacAskill retained the Natural Resources portfolio.[9] He was re-elected to a fourth term as MLA in the 1999 election,[10] and did not seek re-election in 2003.[11][12]