After a longtime lurking, much overthinking, and too many bricklink orders, here's my sigfig: Johnny was unremarkable. His torso, bandana, and even his whiskered face were mass-produced. For some, this was a sign of something 'special', for Johnny it was not. He had crewed, without distinction, on rafts, schooners, runners, barracudas, and flagships. He'd served Broadside, Woodhouse, Redbeard, and Iron Hook. Yet such experience was to piracy as opera tickets were to acting. Johnny was a pirate by association, not participation or ability. He didn't even have a nickname, until last Tuesday...
Johnny paid to work a rum cart. Technically he was paid, but even unremarkable pirates can drink remarkably. He would consume today's wages by noon, and tomorrow's by closing time (which happened to be whenever he passed out.
That's where they found him.
After sobering up, and some gentle persuasion...
Johnny found himself the owner and figurehead of a new business enterprise. One whose profits he had no real access to. He was the cover for a torrent of dirty money, criminal underworkings, and shady businesses springing up all over the Brick Seas. Who were those using Johnny as an 'oilskin' against the inquiries of trade companies, treaties, councils, and governments? Johnny wasn't sure. He was remarkably uneasy. But at least oilskins didn't have to worry about staying dry...
Oilskin Johnny is the "Oilskin" (raincoat/unwitting front) for a group of sinister characters looking to launder money and avoid prosecution for other nefarious activities. Johnny will have a wide range of different businesses... hoping to have builds in each type of property as well as numerous different classes of ships.