Sorry, I didn't have a black flag, so I just built one
Skills: Strategy, evasion, pick-pocket, sneaking, planning, negotiation, getting along with people, and leading
Xerxes was 12 when his parents died, killed by Lenfald soldiers. He was never explained why, but he assumed they must have committed a great crime. It was decided that he was to be taken care of by his aunt and uncle, but on the way there, Xerxes escaped 2 guards and fled into the woods. From that moment forward, he decided that he must learn to be smart in order to survive. He learned quickly that thievery required both skill and smarts. He practiced for hours upon hours the skill of it, and acquired as much information he could about the smarts of it.
Soon, when he was 15, he realized he could no longer learn from his peers. Since all of the other, more skilled and renowned outlaws where too hard to find, he went to the only place he could think to find outlaws: prison. Unfortunately, all of the best criminals (the ones that where caught at least) where in high security prison, so the only way in was by committing a crime and getting caught. Of course, Xerxes was smart enough to know that it would not be worth it to get caught just for information. So, using various contacts, he found a high-risk job that involved stealing a large sum of money. He made sure that the job would pay him even if he was caught. He arranged for the money to be given to him if they heard of either his release or escape, assuming he was caught (they didn't know he planned to be caught).
Xerxes then planned for days upon days for the job. When he completed his planning, he executed it perfectly. He stole the money, and used himself as bait to assure that his partner (name not mentioned) could escape with the money. He was then caught, and put in a very secured prison.
While in prison, Xerxes talked to every single criminal that he could, and asked them what their biggest mistakes where, what their trade secrets where, and what their regrets where. The other criminals saw ambition, and, having no hopes of ever leaving the prison, told him everything they knew. Xerxes absorbed everything that he could, and wrote everything he couldn't down on a small, leather journal that he smuggled in.
After 5 years in prison, when he was sure he had learned everything that he could, Xerxes escaped. No on knew how it was done, and knew only that it did. Ever since, he had been one of the smartest, most cunning criminals Roawia has ever seen.