Obviously the players were insured. Remember, one of the issues now is that the IOC is refusing to help subsidize the insurance.
And while they may have been naive, I don't think it was for the reason you suggest. The Canada Cup/World Cup was a joint venture with Hockey Canada, so they received less income due to splitting then than they would now having complete control.
But most importantly, the owners thought that going to the Olympics would have a noticeable effect on growing interest in the NHL brand, and therefore revenues. They have now gone to five Olympics, and I would expect have a lot of hard data today that they didn't then.
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