Jack Sparrow was depressed in the 5th movie I think, I mean the Black Pearl represented freedom and all that he loves, but he didn’t have her for like 20 years, and that’s why he was drinking all the time, more than usual, and his “luck” was running out. Who knows how long he stayed on land, or went to sea on a small boat. I feel bad for him, I wish the movie kinda touched that subject a bit more