Crew member: Speaking of dying a great death... Other crew member: Nice knowing you, Jacob! Crew member: We'll think of you often and fondly!
Maisie tries to join the Inevitable's crew, but Jacob (who by then has been told by Captain Crow that he wants him to take over as captain when he retires) tries gently to send her on her way:
Maisie: Right then, I'll talk to Captain Crow. There's a man with real authority. [...] Jacob: Hey, I have authority, all right? Maisie: You ain't captain, are ya? Jacob: No, but I am captain material. Maisie:[laughs] Captain "material"? [composes herself] Sorry, it just sounds funny. Jacob: I mean, I will be captain. Some day. Maisie: Well, I intend to get on that ship. So, if you don't mind, I'll take it up with Captain Now, not Captain Some Day.
As Jacob and Maisie make their first attempt to sail off of the island, a giant crab sneaks up on them:
Jacob: If we can make it to Rum Pepper Island, we'll be able to flag a ship. Dregmorr's thick with monsters, but don't worry. [the giant crab rises from the water behind him] If there's one of them within a mile of us, I'll sense it. [Maisie stares in terror at the giant crab. Jacob turns around.]May be a little off my game here.
Also, Red's completely unimpressed face throughout all of his attempts.
Jacob manages to break a spear in front of everyone during the finale... and discreetly admits to Maisie that it hurt like hell.
While traveling at sea on Red's back, Jacob tries to use a harpoon to catch some fish to eat... And fails miserably at it. He points out to Maisie that, while he is skilled with a harpoon, he's just not used to such small targets. Red then proceeds to help him out, as if to say "you're a great monster hunter alright, but you're hopeless as a fisherman".