Has Crosby ever commented on future plans (i.e. playing away from PIT)? Probably a stupid question because if he's ever commented, I can't imagine him saying other than wanting to finish his career in PIT....regardless of what he might really think. That said, I get the sense he would want to stay in PIT, play his career with only 1 team....I'm guessing the PIT fans would feel the same way as well. It's not really a stain on someone's career or anything, but I'm always biased towards guys that stick to one franchise their entire careers.
If he hadn't already won 3 Cups, perhaps he'd feel that is one piece he's missing and look to potentially go somewhere with a chance (i.e. Bourque)....but that won't be a scenario.
I'm guessing the organization would let Crosby decide here....if he wants to finish his career as a Penguin, I have to imagine the organization honors that wish.