Will these players ever leave their teams?

I'd say theres a decent chance that half of them finish their careers with other teams, especially the goalies. If they wish to play to a later age they are usually used as trade bait to other teams who are desperately lacking a great starter or good backup. I would be almost convinced players like Datsyuk, Zetterberg, Crosby, Malkin, Ovechkin, Lecavalier, and the Sedins will finish their careers where they are now. They're all staples of the teams they are on. Toews and Kane might but Chicago has done a lot of wheeling and dealing with marquee players in the past.