Day served as a member of the Alberta legislature for the riding of Red Deer North in the between 1986 and 2000. In 1997 he was appointed Provincial Treasurer (Minister of Finance).
Despite not having a seat in Canada's House of Commons, on July 8, 2000, Day was elected leader of the Canadian federal political party the Canadian Alliance, replacing Preston Manning. He was subsequently elected as MP for the riding of Okanagan-Coquihalla, BC, in September 2000. He attracted attention during his first official news conference by turning up on a Jet Ski wearing a wetsuit.
One of his policies was famously satirized during the 2000 federal election campaign by the political satire troupe This Hour Has 22 Minutes. He had proposed to require the federal government to hold a referendum on any subject if 4% of the electorate signed a petition requesting this. The comedy show riposted by putting a petition on their website to hold a referendum to require Mr. Day to change his first name to Doris. Substantially more than 4% of the Canadian electorate signed the petition.
Day also ran into trouble with his remark that Canadian jobs were flowing south just like the Niagara River, when in fact the river flows north. He was also mocked for holding up a sign which said "No Two Tier Medicine" in large letters during the leadership debate. When informed that props were against the rules he claimed it was his lecture notes.
After the election Day ran into problems over the funding of his defense in a defamation of character lawsuit by Alberta taxpayers, and also over whether Day knew about a private investigator who had been hired by the Alliance to dig up dirt to smear the Liberals.
These and other issues lead to a split within the party ranks in 2001. Chuck Strahl[?] and Deborah Grey[?] led a group of dissident MPs who split off from the Canadian Alliance and sat next to the Tories in the House of Commons. Eventually Day agreed to resign, and in a leadership contest he lost badly and was replaced in March 2002 by Stephen Harper.
Day was also criticized when it was discovered that the Alberta government had paid $792,000 to settle a lawsuit filed against him. The lawsuit, filed by lawyer Lorne Goddard, arose as the result of a letter Day wrote criticizing Goddard for defending a pedophile. The rules governing Canadian jounalism forbid repeating libelous statements, but less discerning sources such as Frank Magazine[?] reported that in the letter Day accused Goddard of sharing the same interests of his pedophile client. Day was forced to settle the suit when it was realized that he could not win.
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