Jim was put to work night away when he is asked to deliver a note addressed to Long John Silver. Jim is overjoyed as he gets an opportunity to go outdoors. He finds his way to the Spy-glass and finds a tall, strong, smiling hunk with one good leg and the other cut off close to his hip, cheering the people at the inn. Jim is relieved to find that Long John is not the same person whom the Captain had feared as he had none of the characteristics of a buccaneer. He appeared to be a very respectable man and did not fit any of the images of a buccaneer that Jim had imagined in his dreams. Jim approaches Long John Silver and hands him the note. Just then he sees a familiar face rushing out of the Spy-glass. Jim is sure he recognizes the person as Black Dog and he informs Long John Silver about him. Long John doesn't recognize him. He cross checks with Tom Morgan, who was drinking with him. But he states that doesn't know him either. Even through Long John doesn't recognize Black Dog by name, he admits that he had see him with a blind man named Pew. He asks Ben to locate Black Dog and tells Jim that they will keel-haul him.
Long John then diverts Jim's attention and involves him in a conversation. Suddenly he bursts into laughter. Though Jim joins him, he doesn't get the joke. Later he figures out that Long John is laughing at himself and blaming himself for the loss of money-as Black Dog hadn't paid for his drink-and that he should takes up Jim's position as a cabin boy in the ship.
Silver gets friendly with Jim and him that they'll make a good company and they do. Jim finds him very informative as he talks about various ships and the work taking place on them as they walk down to the hotel where the Squire is staying. Long John Silver tells the Squire about the incident at Spy-glass and departs. He nods an O.K. in a seaman's style when he is asked to be on board with the crew by four. Dr. Livesey and the Squire appreciate Long John's personality and proceed towards the ship to make an inspection, along with Jim.
In this chapter Jim is sent on an individual assignment though not a big task to talk about. This is for the first time that Jim is asked to be on his own. His job as a crew member of the Hispaniola has begun. Jim enjoys his walk through the docks. The moment he enters the Spy-glass and comes face to face with the man to whom he has to deliver the note-the Sea Cook Long John Silver-Jim is reminded of the strange description of Billy Bones. The clean looks and cheerful attitude of Long John Silver convinces Jim that he is not the man whom the Captain feared.
Jim gets a glimpse of Black Dog rushing out of the inn. He tells the Silver about him. But Silver does not recognize him or at least pretends not to. And after inquiring with Tom Morgan, who is drinking with him, he makes sure that he didn't know him either. Jim's suspicion about the Sea Cook, after finding Black Dog at the Spy-glass, is strengthened. But Long John's calm and tactful behavior overshadows Jim's suspicions. Silver, however, does admit that he had seen Black Dog with a blind man named Pew. Jim slowly starts to like Long John when he laughs at himself for his foolishness of not billing Black Dog. He laughs at his irresponsible attitude and tells Jim that he should also work as cabin boy. Jim finds Long John more than just a cook. He finds him to be very informative about ships, the sea and the seafaring men. Long John also takes a liking towards him and teaches him the complicated nautical phrases till Jim is able to repeat it by himself. This not only brings out Jim's enthusiasm but also shows that he gets along well with his elders. Jim, on his side observes that Long John is an enthusiastic and disciplined man.
The reader may note that Stevenson brings in excitement to the story when he introduces Long John Silver. The reader wonders, just like Jim, if he is the same seafaring man with one leg.' The reintroduction of Black Dog, though briefly, fires up the reader's suspicion about Long John. But Stevenson doesn't reveal much at this stage. On the contrary, he tries to make Long John likeable in Jim's eyes, making the reader all the more doubtful about Jim's perceptive ability.
So after introducing the seafaring man with one leg in this chapter, Stevenson makes sure that the reader's eagerness to know about him has increased.