There is no evidence that O'Leary has any political ability and none that he would make a good PM. Trump doesn't make much sense in the US but at least he's a celebrity in a celebrity culture. Canada doesn't have a celebrity culture

O'Leary was born in 1954, he's 62 and part of that older generation.  His early education  in English was in Quebec but he went to high school in Ontario. His family moved around a lot outside of Canada. Most of his university education and subsequent working life has been outside the province. I don't know him personally but see no evidence of his contempt for the French language and culture. Like most Anglos of that period he didn't learn French because not having the language was no hindrance to success.  It is now.  Had he been born a decade later, it's likely he would have learned French.