Long John Silver is relating the tale of the night he lost his leg and Pew lost his sight, during a sea voyage with Flint as captain. The surgeon that amputated him, one of the pirate Roberts’ men, was hanged at Corso Castle. Now, Silver says, much of the good old men are scattered and weakened—before he died, Pew had become a beggar and robber and nearly starved. But Silver tells the youngest hand that he is smart and worth talking to frankly. Jim is appalled that Silver is flattering the boy in exactly the same way Silver had spoken to and flattered himself.
Only now does it become entirely clear what Silver’s relationship to piracy is: he is a pirate himself, who has traveled on pirate ships with Pew, Flint, and (presumably) Billy Bones. Jim is almost more offended by Silver’s obvious manipulation of the young crewman (which makes his kindness towards Jim that much more inauthentic) than by his boasting about evil deeds.
Silver says that “gentlemen of fortune” live roughly and dangerously, but it’s worth it when they leave a cruise with hundreds of pounds. He, though, is careful with his money, hiding it to be safe. Now he’s given it to his wife: soon she’ll sneak off to meet him—but where, he won’t tell. While gentlemen of fortune are wary of trusting people, he says, he has a certain way about him.
Silver seems to enjoy his role as leader and lecturer. While he is a pirate himself, he’s careful to distinguish himself from the others—he has managed to be so successful precisely because he is both deceitful and, when he finds it useful, trusting.
Jim has realized that “gentleman of fortune” means simply a pirate, and that he’s witnessing perhaps the last honest crewman aboard being corrupted by Silver’s flattery. Jim then hears the voice of Israel Hands, who asks how long they’ll to lie in wait—he’s sick of Captain Smollett. But Silver tells him not to act until he gives the word—they need someone to steer the course. Instead he’ll finish with “them” on the island: he’s seen too many plots failed because of hurry.
By piecing together what Silver is sharing with the other members of the crew, Jim is able to understand the high stakes of the conversation and what it means for him and the others. They have until reaching Treasure Island, he realizes: then the planned mutiny will begin. This passage also introduces the important meaning of “gentleman of fortune”—as pirates, these men of the sea are deeply affected both by fate and chance (“fortune”) and the desire for wealth (the other meaning of “fortune”).
Another hand asks what they’ll do with the others once on the island—abandon them there or kill them—and Silver says he prefers death, if only to prevent the chance of them testifying at trial later. He claims Trelawney for himself. Then he asks the young sailor for an apple. Jim is terrified he’ll be discovered, but immediately Hands suggests they drink rum instead.
Silver’s cruelty and lack of concern for other people is evident here: he’s willing to do everything he can in order to survive, including killing off all those who might stand in the way of his own freedom. Jim, in turn, has enjoyed some good fortune of his own in escaping discovery.
Jim also hears Hands whisper to Silver that a few crewmen still haven’t been brought over to their side. Suddenly the voice of the look-out cries, “Land ho!”
Just as Jim is attempting to come to terms with what he’s heard, the moment of arrival (and mutiny) approaches.