That's... not at all what pain is, but I really have no room to complain about realism, considering the setting.

The biggest issue I have with your character is how he fits with the setting like oil in water. He's an edgy, sinister character more inherently immoral and sadistic than almost all of the franchise's [i]villains[/i], and you're trying to shoehorn him into fun pirate adventures on the open seas.