I don't know what you mean by entitlement here. Did any of these American players refuse to play up to their contracts? Or did they simply tell these organizations that drafted them that they weren't going to extend/resign with them? Even Larkin could only submit a request to be traded, he can't actually enforce it. These franchises already get the better part of the first decade of these player's careers without any decision from the player, and the teams can trade these players for any reason before their UFA years. By the time any player is approaching UFA, he's either already been traded or has had team mates traded who had no say in the matter. They just had to pack up, move to another city, and start being loyal to some other franchise.
It's much more entitled to think a player who never chose your organization should be obligated to stay than it is for a player to make known that he doesn't want to stay with your organization past his current contract. If you want players to stay, build a competitive team. It's not like Americans, or anyone else, are requesting trades out of Montreal.
