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Neban, Remmy, Darkhart, Timmy, and Tormentans all seem to offer good loot. I do think that lower level pirates do have a better chance of getting good loot, due to the fact that they can fight enemies that are a higher level than them. This probably has an effect on the loot they get. I got a rare cannon ram (the one with extra explosive range) on my lv 21 pirate (he was probably lv 18 or so at the time) and I can never get any rare sea/cannon charms.
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