I definitely think there are times that Kipper was worn out.
I also agree that the pressure on Canadian teams is immense. But I also think that there is a cap disadvantage, due to the fact that the Canadian teams have to pay a premium to entice UFAs north of the border. It isn't a huge disadvantage, but it is definitely a headwind.
I also think that it is harder to be patient and play the long game in Canada - fans are way too impatient, and they and the media apply constant pressure on the GMs for change.
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