It's just. Both okay
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Maybe it was stupid to think he could outrun time on a pirate ship, sail away from one island and take Riku and run to another and expect that to bring back everything that was lost; haul in the heavy anchors they all dragged in their wake in the course of a day.
But he’s Sora, and he's done more impossible things than this. So he’s going to try.
(The boys finally get to go to the Caribbean together, even if they had to die and come back first--but hey, better late than never? Post-KH III)