Thanks captain! It took me a while to find something I liked and thought appropriate to represent a true pirate. Pirates aren't meant to be pretty (OK, so we have one pretty pirate on board).
Now exactly what is in the image is a bit vague. To me it is a most unpleasant looking pirate with the black jolly roger flag in the background (over his shoulder) and a sea bird in flight behind the flag.
Is he carrying the flag? Is he ready to stake his territory with the flag (much like the astronauts on the moon)? I think so. The gesture with his thumb (to the pirate flag?) could be the answer to his victims' question "who are you"? The sea bird is smart enough to follow this/these most unpleasant pirate(s) knowing there will be a feast to pick from the bones left behind.
Or the flag+bird could just be a one-eyed mule or maybe a burnt giant cone... 8^)