Titles are the only thing that matter to me when I feel my team is a legit contender. If they're in a rebuilding phase and the team gets bounced from the playoffs, but shows sings they're moving in the right direction, I can live with that. But I absolutely don't want them to be stuck in a state of good-but-not-good-enough.
I'm for being loyal to a long time star that gave all he had for the team if he can still contribute to a contending team in a meaningful way. The player doesn't need to be go-to guy, but still have enough to put the team over with some help from a supporting cast.
I certainly would not keep him around for old times sake. If it means we are handicapping our team's chances to become relevant again, then he needs to go.