Roger

Born the fourth son of a wealthy family with many kids, Roger's childhood went largely ignored by his parents. Instead, he spent a lot of time with hired nannies and his siblings. Though his oldest brother was by far the most successful with his brawn and physical skill, it was his second eldest brother's witticism he looked up to the most. It was well known that this sharp-minded, charismatic teen could out-bargain any shopkeep and generally obtain anything he desired. Studying his brother's ways, Roger decided there was an unexplored, morally objectionable avenue yet to be taken. When he was twelve, he pulled off his first scam on a (seriously gullible) shopper in the market by exclaiming there was a fake money scandal about, and taking the shopper's coins as 'evidence'. Addicted to the thrill and the money, he continued to hone his craft, keeping his escapades secret and hiding his treasures.
War came to his region in his late teens. Abiding by the rules of one son per family draft, his eldest brother went off to fight and promptly died. His second eldest was already employed by the government, so it fell upon his third brother to take up the mantel. Sensing danger for his personal welfare, Roger attempted to obtain a job that would prevent him from joining the fight. With no diplomatic positions available, he started an apprenticeship with the local blacksmith and lasted about a week- physical labor was not his forte.
The news of his third brother's death arrived before Roger could find anything else. With no other options left, he gathered his secret treasures and left "to join the camp". He did not join the camp. Instead, he bartered with his treasures and gained passage with some traders to a different region where he would not be found.
Not long after they set off, they were accosted by pirates and taken prisoner. Melissa, the captain of these particular pirates, was inspecting prisoners and seemed not to be impressed with any of them- least of all Roger's smooth attempts to win her over. Fortunately for him, he caught the eye of Melissa's first mate, Guideon, who decided he rather liked him.
Roger now works primarily as a recruiter for Melissa's crew and his smooth tongue allows them to slip in and out of ports as Melissa desires. His knack for winning gambling games and running scams comes in handy whenever the crew is in need of a little extra funding- or a little extra fun when the crew feel like trying their chances at winning against him.