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Just turned level 22, Level 16 sailing.
Hunting Navy ships for rum
(Rum for Gunner on Del Fuego, part of the Pearl crew quest, about 41% progress)
Sunk a frigate (about level 17) and scored Gentry out of the blue!
Sunk another galleon or frigate about 1 hour later and got Gentry again!!
Each time I was asked to maroon him at a wild island, which I did.
(and yes, I have sunk many, many different ships up to and including level 32)
So eventually he will pop up!
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