When he first signed it, it seemed pretty obviously a 2 year deal with a trip to Robidas Island for year 3. But if he's still productive and wants to play, not everyone enjoys that all-expenses-paid vacation. For a guy who hasn't missed a game in the last 9 seasons, he doesn't exactly seem like the kind of guy who's going to walk away easily, especially if, as you mention, maybe he would like one more chance at that cup win.
If he still wants to play, I would guess the only spot he'd accept a deal to would be SJ, and they're pretty up against the cap as it is. I still think there's a pretty solid chance that he doesn't play for the Leafs next year for some reason, but I think it's far from assumed to be the case.