O'Leary has residences in Toronto and Boston. In a 2013 interview with Boston Magazine, O'Leary called Boston "home." In a video announcing his interest in the PC leadership he referred to the federal politicians "on Capitol Hill" that he was going to straighten out.  Any Grade 6 student knows our MPs convene on Parliament Hill.  His ignorance of not only Quebecois culture, but Canadian culture is astounding.  His strength is that he is tireless self-promoter. And, like the orange-haired vulgarian to the south who brags that he doesn't read books, O'Leary has been able to convince people that the acting part he plays in a TV series --  infallible, know-it-all businessman --  is the real Kevin.