In fairness he's been in a no-win situation his whole life in terms of personality. The "tall poppy syndrome" in Canada required him to be even more humble and down the middle than even hockey culture does, because while people loved him, they were also ready to pounce on any slip up. Look at the response when he got married. To an American!
The man was the most sought after endorser, and he wanted to protect that, understandably. Rick Reilly talks about how they kept having to edit out stuff from the book, because while it made for great reading, he couldn't have that in there and have his image tarnished. The only time he has really taken a stand was in the 2002 Olympics.
Had he been an American he could have gotten away with being more outspoken, and whatnot. But he's not, and unfortunately, the same people who say they want to see more opinions/personality/etc., are the same people who will jump on him when he says something they don't like. So, why bother?