I started by figuring out what adventures he had been on and what different types of environments he'd been exposed too. I added sunspots to his back because he probably works long days under a blazing sun. He would probably get wet a lot too, which means if not cared for properly the leather he's wearing would dry out and crack! Orcs aren't famous for their cleanliness so making the wounds look infected was kind of a no-brainer.
I painted the bandana it to look like it was drenched in old dried blood, maybe someone used his bandana to stop the bleeding the last time he was wounded or maybe it's just someone else's...
The tattoo was inspired by early Polynesian designs. I did a lot of research into what different styles of tattooing would be around during the golden age of piracy irl and the fact is that there wasn't much else (apart from the Polynesian Maori tribal stuff) available at the time. So maybe he was marooned on a jungle island and lived with a tribe of savages for a couple years?
I swapped the icon around his neck for a bird skull, undoubtedly a trusted companion that passed away before his time. Heartbroken he now wears the skull around his neck to always be close to what's left of his friend.
I had a lot of fun painting this, thanks for checking it out!
/Max - Stockholm Warpaint