Pirate legendaries!

Throwing my hat into the ring for a leader pirate, not sure what species but the general idea is just a normal dude with really high luck and charisma that compulsively lies and is sarcastic. They've accidentally become the leader of a large pirate group. Someone asked them where they got a bag of chips from and they sarcastically replied that they stole it. Everything went down hill from there. Now a decade or so later they're the leader of large group of pirates and don't really know what they're doing.

I feel like it might be too silly but I figure you miss all the shots you don't take.