As he recovers, the Captain continues with his urge to drink. Pleading for a drink from Jim, the Captain tries all the techniques possible to convince him to serve him a drink: From reminding Jim about the regular wage he earned from him, to befriending him and calling him his matey'. Jim refused all of his requests, as the doctor had advised against it. Refusing to listen to Jim, the Captain goes on a boasting spree giving examples of the deadly places he has been to, the terrifying men he has encountered and how he had lived on rum. He calls it his meat, drink, and wife. He tells Jim that he is experiencing withdrawal symptoms and that strange images are haunting him regularly. He also offers Jim a bribe of one gold guinea. Jim gets quite offended by this offer.
Finally, after seeing how upset and agitated the Captain has become, Jim worries about the Captain disrupting the other patrons of the Inn, Jim gets him a drink on the condition that the Captain will repay all the money he owes his father. Regaining his original composure after downing the rum he refuses to stay in bed for a week. He manages to get up from the bed with Jim's help and tells him that if he stayed at the Inn for long they'd have the Black Spot' on him. But he soon realizes he is too weak to go and settles down in bed.
He also kept on grumbling about many things which Jim doesn't understand. Except the term Black Spot' which he hears three times in succession and also that the the bad men' are after his sea chest. Jim also finds out that the Captain was the first mate of the legendary pirate Old Captain Flint and he is the only one who knows the place where his treasure is buried. During his conversation, Jim is asked to be wary of the seafaring man with one leg.
On asking what the Black Spot' is, Jim is again confused with the Captain's reply. He drowns himself in deep slumber after taking his medication.
That evening, Jim's father dies, adding to the pain and distress Jim was already going through. The Captain takes to heavy drinking, after regaining his strength despite the warnings. He starts singing and shouting in the house while the others are mourning their loss. This scarcely alarms Jim for he knows by now what to expect of the Captain.
The gloomy air at the inn has more surprises in store. On a foggy afternoon, Jim notices a stranger, a blind beggar approaching the Inn. The man asks Jim which part of the country he is in. After finding out where he is, he politely requests Jim to lead him into the Inn. Once inside, his tone changes and he orders Jim to take him to the Captain and threatens to break Jim's arm if he doesn't. The blind man instructs Jim on how he should be introduced and asks him to do it the very same way. On doing so, Jim sees the fear of death written on the Captain's face.
In Jim's presence, a business deal takes place between the blind man and the Captain, where the blind man passes something from his hand to the Captain's. After releasing Jim's hand from his clutch, he leaves quickly without help. The Captain gets up quickly from his bed mumbling "Ten O'clock, six hours..." and unable to complete the sentence falls flat of the floor, never to get up again. Although Jim has never liked the Captain, he cries at his death.
Stevenson builds up the tension in this chapter. Jim refuses to provide alcohol to the Captain. To which, he curses the doctor and starts boasting about his dreadful experiences. When nothing seems to work on Jim, the Captain tries to bribe him. Jim is quiet offended at this for he feels he has been wrongly judged. His presence of mind to refuse the bribe and the fact that he asks for the money owed to his father deserves shows Jim's maturity. This quality displays the sense of objectiveness of the boy, making Jim a character to be dealt with seriously.
This chapter also builds the character of Captain Bill as a eccentric drunk who is trying to save himself and his sea chest from a possible attack.
Jim, amidst this turmoil, goes through an emotional upheaval when his father passes away.
Stevenson also introduces us to another character - the blind beggar. A horrible-looking figure who is arrogant and cruel despite his handicap.
An interesting point to note is that when the number of characters are increasing and the plot is getting complex, Bill dies of heart attack, leaving us with ample amount of questions like who is the blind man ? Why did he visit Bill? What was the business that took place between the dead and the blind man? What was the paper that the blind man gave to the Captain?
Jim recalls that he had cried at the death of the Captain despite his dislike for him. This indicates that Jim is emotionally sensitive and, in this way, Stevenson ends the chapter with the right emotional touch.