Commentary
Olivia Chow was elected Mayor of Toronto in the June 26 byelection. The former NDP MP/city councillor earned 269,372 votes (37.16 percent), edging out former city councillor Ana Bailão (235,175 votes, 32.46 percent). The two conservative candidates, former Toronto police chief Mark Saunders (62,167 votes, 8.59 percent) and former Toronto Sun columnist Anthony Furey (35,899 votes, 4.96 percent), finished third and fourth respectively.
Therein lies an interesting political puzzle. Why is it so difficult for a conservative to be elected mayor in Canada? 
Toronto is a liberal and progressive city. Hence, candidates running on a centre to centre-left platform have a much greater chance of electoral success. This is especially true after Toronto became a federated municipality in 1953. The majority of its mayors—Allan Lamport (Liberal), Philip Givens (Liberal), John Sewell (Independent/Socialist), Art Eggleton (Liberal), June Rowlands (Liberal), Barbara Hall (Independent, former NDP), David Miller (Independent, former NDP) and Chow—fit within this ideological mindset….