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They tried the drug using brother, that didn't work out too great. So they decided to go with the drug dealing brother[0] instead.

[0] https://www.theglobeandmail.com/news/toronto/globe-investiga...

The story goes that urban Toronto didn't vote for Ford, but the suburbs and the rest of the province is who he was targeting and they really responded to his populist platform. And there are enough people not living in Toronto DT to win him the election.

I wouldn't be too harsh on the Ontario voters; if the Conservatives had any bit of competence they would have been able to win the 2011 and 2014 elections easily. By 2018 the Liberals were about 10 years past their sell-by date. Few were particularly thrilled voting for Doug Ford but they felt their alternatives were worse. I didn't vote for Ford but at least understood the people that did.

Rob Ford was mayor of Toronto, Doug Ford is premier of Ontario.

Because the previous provincial leadership (Liberals Dalton McGuinty and Kathleen Wynne) performed poorly and caused a shift in political sentiment to the right. https://en.wikipedia.org/wiki/List_of_premiers_of_Ontario