He was a member of the Manitoba legislature from 1988 to 2003,[2] and a Cabinet Minister in the government of Progressive Conservative Premier Gary Filmon from 1990 to 1999.
McKenzie Co. Ltd.[1] Gilleshammer was easily re-elected in the 1995 general election, finishing over 2400 votes ahead of his nearest opponent.
[1] Shortly after Gilleshammer's appointment, the Manitoba Human Rights Commission ruled that the province who be required to provide health, dental and vision benefits to the partners of gay government workers.
Following a further cabinet shuffle on February 5, 1999, he was appointed to the high-ranking position of Minister of Finance, with responsibility for the Crown Corporations Public Review and Accountability Act.
[1] His pre-election budget offered increased spending in various fields, to be paid for by withdrawals on a government contingency fund (his critics referred to his as concealing a provincial deficit).