Mun Note: This is an excerpt from a piece done on Discord with @tidefated, in which Charles is discussing how he met Jack Rackham and Anne Bonny, and as he is not the best story teller it has – a certain charm to it that I feel my usual headcanon voice doesn’t capture. 

This is the raw form, of Charles himself sharing the tale. It was prompted by someone noting the dramatically different personalities of the trio, and a seeming curiosity on how the dynamic could have formed. 

He could tell the man was digging, if subtly. Charles debated internally, before he spoke rather honestly on the topic. “He’s got Anne. They’re a package deal – you don’t get one without the other, and it was Anne who caught my attention first. She was quiet, silent as a fucking grave, but she had these eyes,” He raised his hand to his own, pointed off with two fingers as if indicating something. “Eyes that looked wide and wild at the world, and I recognized them. I’d seen eyes like that before, so I sent a test. Sent a man toward what looked like her weak spot.”

He looked over at Edward then, even as he confessed, “Jack could have died the same day I saw him, for what I saw in those eyes, if I’d been wrong. But I wasn’t. Never seen a girl kill a man so efficiently in my life. And Jack? Damn fuck didn’t even move. Just watched, and when she was done, got up, checked the man over—and walked right on up to me like somehow that body told him everything. Asked me what I wanted, bold as fucking brass. Said I needed crew. He said, lucky me. They needed a ship.”

Charles huffed again, looking back, the fondness in his features genuine despite the stark nature of the tale. “Since then, I can’t say how many times Anne’s killed for the crew. Killed for me, or for Jack. But I can say Jack’s got a way of winning wars without fighting. He can make the most dogged of fucks listen. He’s saved people a lot of time, a lot of energy. He saves lives with that wit of his. Pulled me back from some wild shit over the years. Helped me find my feet when I didn’t want to stand anymore." 

Charles fell quiet then, before shrugging a little. "He’s got the wit to run real business, to go legit, but he doesn’t. He doesn’t cause Anne’s running from something, and until she’s ready to stop, Jack’ll stay on the account, and in some strange way, protect her just like she protects him.”