I'm not Canadian, but I am a hockey fan (I'm from Grand Forks...hockey fans will know where that is; no one else will). Oh yes, I know who Don Cherry is. I suspect Canadians love him not so much for his commentary but for his gruff-but-avuncular personality, as well as his flair. He's that knowledgable, older sort who gets so worked up that he sometimes confuses himself.
There's a former player of his who lives near me, and whe helmets first became mandated, this player was a rookie and so had to wear one. He wore one to his first practice, and Cherry screamed at him something like "take that helmet off, you pussy!" I get the feeling that Cherry, himself, took a puck or two to the noggin.
(This is a strange story, as Cherry has been one of the most outspoken advocates for softening the boards of Canadian rinks to make them safer for the players.)