Perhaps I’m old fashioned, but I like seeing a player finish his career on the roster of the team with which he played the majority of his years. From a fan’s perspective, a special kind of identity builds between a player and a team when the one has been associated with the latter over a long period of time, let alone what that relationship means to both parties involved. It’s a shame when that identity has to be shattered.
That doesn’t mean I’m not sympathetic to certain situations, such as when Ray Bourque requested a trade and was sent from the Bruins to the Avalanche or when Karl Malone signed with the Lakers. I completely understand an aging star seeking a championship to complete his career wanting to move to a team in contention. Such deals are rarely about money–sometimes the player even ends up earning less than he would have elsewhere–and all about that last chance at finally winning.