has anyone ever achieved this? it is possible. I remember one time plundering a galleon that carried 30.000 gold. short while later another galleon with 25.000 gold. I didn't know what to think of it until much later I read in a forum that someone plundered 4 gallons worth over 100.000 between 2 towns the treasure fleet was traveling.
don't know if there are any real pirates! fans, but to me this must be the rarest thing to achieve in the game and I know no other place to talk about it