2 Ideas

[League]

Following on that, I have a new idea for liar's dice (pirate's dice I think it was called though, scuffle my ruff or not...): you can go to World's End, and play Davy Jones for loot; if you win, well, you're increasing your bank quite bountifully; if you lose, well, let's just say you have some service to serve.

While you have a service with Jones to fulfill, they could make it so that you get no loot or reduced loot, or so that you get your health halved for as long as you have a service. The second is probably way better, as it encourages you to go out to sea to hurry up the service. Or to go back and work your way down with the dice again, savvy?

(Service is merely sinking ships, sending people to the locker in place of yerself.)

[MacIronhawk]

Taking a ship if you win?
Uh...no...
Maybe if you have to sail it and not for much money.
You sound like my friend who wants to play POTCO.
But liar's dice that'd be a fun game!