Francis Lewis (1850-)
His mom died in child birth, so Francis spent all of his early life with his father. At first the crew of The Stalker were not to keen on the baby/toddler on their ship (what true sailing man wants to be seen walking the deck with an infant?) As he grew a little older he was readily accepted, as much for his hard work as for his fearless stupidity; a drunk six year old is truly a funny sight. By the end of the Opium Wars, young Francis was as much a smuggler as anyone else on the ship.
He was also chasing the "Midnight Oil". It's not a good idea for a drug runner to get hooked on the product, but Francis was young, naive, and the other sailors were not above peer power; besides he wasn't an addict in any way, and you need someone to test the product. Everyone looked the other way when it came to this particular transgression, but the sailors all said they'd step in if Francis went too far.
With the end of the Opium Wars there wasn't as much of a need for smugglers in the Far East. The Stalker pulled odd jobs where it could; even honest work when it had too. It was a dull time punctuated only with the death of the senior Lewis. The death of his father sent Francis deeper down the rabbit hole than he'd ever been. Sober, he knew he didn't want to be in anywhere near the Far East, and The Stalker ended up in the Caribbean.
The Stalker's arrival in the Caribbean could not have been better timed. Cuba was fighting the Spanish for independence, and American civilians were supplying arms. There's lots of money in guns, and only half the risk with the U.S. Navy looking the other way. (Just like in the Opium Wars.) The money was pouring in, and his drug habit was well under control until the U.S.S. Maine blew sky high. With the Teddy Roosevelt getting his way, the Cubans wouldn't be needing Lewis' arms to fight the Spanish that much longer...
Staring fifty in the eyes, Francis thought retirement seemed like a grand idea; he'd saved up a fair amount of money, now it was time to enjoy life. Francis passed on command of The Stalker to his first mate Bernard, and settled in the North East U.S. It was a peaceful existence, an economic depression sure, but much better than the building tension over in Europe. A peaceful decade until some Serb shot an Archduke.
He tried to resist the call to adventure, he really did, but some "businessmen" found out about his past, and that left Francis with little choice. On the plus side his "partners" did get him a brand new ship. Christened Juliet, she was more than a match for anything on the seas except the most modern military vessels.
Unfortunately, there were plenty of modern military ships in the Atlantic, and the most dangerous of those were bellow the waves not cresting the waves. Germany's unrestricted U-boat warfare drove Francis off the deep end. The "Midnight Oil" became an ever more common ritual, as well as copious amounts of drinking; thanks to that instead of having made money, by the end of the war, Francis owed a fair amount to his partners.
He still owes them money, and tires to close the gap by making booze runs from Canada to New York. (He's making some progress. He's such a steady customer, and a good employee, that the mob has all but forgiven his interest payments [it'd be no good for Francis to off himself while still making them money]) When he's not at sea, he's baked out of his mind, still trying to forget the horror and stress of German U-Boats. It's been an interesting 75 years, but Francis Lewis is not ready for another adventure...