“You bloody idiot, you know better than to mix yer liquors!”
Kage Baker, The Life of the World to Come
Characters in the Company series have a peculiar look at history. The future depicted in the novels is bland. Past times is where interesting stuff happened: cowboys, Indians, and of course pirates. To truly understand pirates, you need to mix yer liquors. To write about pirates, you need to behave like a bloody idiot. You need, to have a HAT.
Pirates or Ninjas?
The clash of these super-memes is one of the most fundamental oppositions in culture, along with Dionysian vs Apollonian, Elves vs Dwarves, Elephant vs Hippopotamus. Kage Baker definitely sided with the pirates. The yarrr she brought into the world is manifest in one of the main characters in the series. For Alec, every day is Talk Like a Pirate Day. (Sadly, one of his twin brothers leans more on the ninja side.) Do you want to play the part of the good little boy, or do you want to be the rebel? Alec tries to be both, but his heart is true to the Jolly Roger.
Pirates have history.
This is not the first stage in life. You become a pirate, you are not born one. And escaping the rule of law, embracing freedom, is a conscious choice; nobody is forced into the pirate life. In a game based on the Company series, I would like to see players questioning rules and choosing to rebel. What would those pirates face? A totalitarian machine based on the most comprehensive surveillance system ever devised.
The decision to raise the Jolly Roger should come from the players; it should not even be introduced as a viable option. If players feel like using the good boy system, let them do it. And if they don't behave, let them be pirates.
Just send ninjas.