Original Text(~250 words)
I Strike the Jolly Roger I had scarce gained a position on the bowsprit when the flying jib flapped and filled upon the other tack, with a report like a gun. The schooner trembled to her keel under the reverse, but next moment, the other sails still drawing, the jib flapped back again and hung idle. This had nearly tossed me off into the sea; and now I lost no time, crawled back along the bowsprit, and tumbled head foremost on the deck. I was on the lee side of the forecastle, and the mainsail, which was still drawing, concealed from me a certain portion of the after-deck. Not a soul was to be seen. The planks, which had not been swabbed since the mutiny, bore the print of many feet, and an empty bottle, broken by the neck, tumbled to and fro like a live thing in the scuppers. Suddenly the HISPANIOLA came right into the wind. The jibs behind me cracked aloud, the rudder slammed to, the whole ship gave a sickening heave and shudder, and at the same moment the main-boom swung inboard, the sheet groaning in the blocks, and showed me the lee after-deck. There were the two watchmen, sure enough: red-cap on his back, as stiff as a handspike, with his arms stretched out like those of a crucifix and his teeth showing through his open lips; Israel Hands propped against the bulwarks, his chin on his chest, his hands lying open before him on...
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Summary
Jim finally boards the Hispaniola and discovers a grisly scene—two pirates have fought to the death in their drunken rage, leaving only the wounded Israel Hands alive. Despite being just a boy facing a dangerous pirate, Jim seizes the moment and declares himself captain of the ship. His first act is symbolic but powerful: he tears down the pirate flag and throws it overboard, officially ending Captain Silver's claim to the vessel. Hands, desperate and injured, agrees to help Jim sail the ship in exchange for food, drink, and medical care. They strike a deal—Jim will provide what Hands needs, and Hands will teach him to navigate the ship to North Inlet where they can safely beach it. As they sail along the coast, Jim feels the intoxicating rush of command and accomplishment. He's turned his desperate escape into a major victory, reclaiming the ship for the good guys. But Stevenson plants seeds of unease—Jim notices something disturbing in Hands' eyes, a calculating look that suggests the wounded pirate might not be as helpless or trustworthy as he appears. This chapter shows how sometimes the biggest opportunities come disguised as disasters, and how taking decisive action in chaotic moments can completely change your position. But it also warns us that desperate people are often the most dangerous, and that success can make us overconfident just when we need to be most careful.
That's what happens. To understand what the author is really doing—and to discuss this chapter with confidence—keep reading.
Terms to Know
Jolly Roger
The black pirate flag with skull and crossbones that ships flew to identify themselves as pirates. It was a symbol of lawlessness and rebellion against authority. When Jim tears it down, he's symbolically reclaiming legitimate control.
Modern Usage:
We still use this to mean any symbol of rebellion or defiance of rules, like when someone puts up a controversial flag or sign.
Bowsprit
The long pole that sticks out from the front of a sailing ship. It's a dangerous place to be during rough sailing because you can easily fall overboard. Jim climbs out on it to board the ship.
Modern Usage:
Any risky position you put yourself in to achieve a goal, like going out on a limb professionally or personally.
Mutiny
When crew members rebel against their captain and take control of the ship. It was considered one of the worst crimes at sea. The aftermath Jim sees shows how violent these takeovers could become.
Modern Usage:
Any organized rebellion against authority, from workplace uprisings against bad management to political revolutions.
Lee side
The side of the ship protected from the wind. It's the safer, calmer side during sailing. Jim uses it for cover as he explores the ship and assesses the situation.
Modern Usage:
Any protected position or safe space where you can observe and plan without being exposed to danger.
Scuppers
Drains on a ship's deck that let water flow overboard. When Jim sees a broken bottle rolling in them, it shows how chaotic and neglected the ship has become under pirate control.
Modern Usage:
We use this to describe any drainage system, but metaphorically it means the lowest point where unwanted things collect.
Handspike
A wooden bar used as a lever on ships for moving heavy objects. When Stevenson says the dead pirate is 'stiff as a handspike,' he's emphasizing how rigid the body has become.
Modern Usage:
Any tool used for leverage or prying, though we'd more commonly say someone is 'stiff as a board.'
Characters in This Chapter
Jim Hawkins
Protagonist taking command
Jim seizes control of a chaotic situation and declares himself captain of the ship. He shows remarkable courage and quick thinking for a young person, but also reveals some dangerous overconfidence as he begins to feel intoxicated by his sudden power.
Modern Equivalent:
The young employee who steps up during a crisis and suddenly finds themselves in charge
Israel Hands
Wounded antagonist
The only surviving pirate on the ship, injured and seemingly helpless. He agrees to help Jim sail the ship, but there are hints that he's more dangerous than he appears and may be planning something treacherous.
Modern Equivalent:
The coworker who seems defeated but is actually plotting their comeback
Red-cap
Dead pirate
Found dead on the deck, apparently killed in a drunken fight with other pirates. His death shows the violent chaos that erupted among the mutineers when left to their own devices without strong leadership.
Modern Equivalent:
The casualty of workplace drama who got caught in the crossfire
Why This Matters
Connect literature to life
This chapter teaches how to spot when normal hierarchies break down and new power structures emerge, plus how to recognize when someone's apparent weakness might be calculated positioning.
Practice This Today
This week, notice when your workplace or family has moments of confusion about who's in charge—watch who steps up and how others respond to their leadership attempts.
You have the foundation. Now let's look closer.
Key Quotes & Analysis
"I struck the colours and flung them overboard."
Context: Jim tears down the pirate flag after boarding the ship
This symbolic act represents Jim reclaiming the ship for legitimate authority. By removing the Jolly Roger, he's officially ending the pirates' claim to the vessel and asserting his own control.
In Today's Words:
I took down their flag and threw it in the trash - this place is under new management now.
"I'm cap'n here by rights."
Context: Jim declares his authority to Israel Hands
This shows Jim's growing confidence and sense of authority, but also hints at dangerous overconfidence. He's claiming leadership based on moral right rather than experience or strength.
In Today's Words:
I'm in charge here now, and I have every right to be.
"There was something in his eyes that made me distrust him."
Context: Jim observes Israel Hands while they make their deal
Stevenson plants seeds of suspicion about Hands' true intentions. Jim's intuition is warning him that this seemingly helpless man might be more dangerous than he appears.
In Today's Words:
Something about the way he looked at me gave me the creeps.
Intelligence Amplifier™ Analysis
The Road of Opportunity in Chaos
Disrupted systems create temporary leadership opportunities for those bold enough to act decisively, but success can breed dangerous overconfidence.
Thematic Threads
Class
In This Chapter
Jim, a working-class boy, claims authority over a ship and commands a grown pirate through decisive action rather than birthright
Development
Evolved from early class anxiety to active class transcendence through competence and courage
In Your Life:
Your background doesn't disqualify you from leadership when you're the one willing to step up and take responsibility.
Identity
In This Chapter
Jim transforms from frightened stowaway to ship's captain in a single bold moment of self-declaration
Development
Progressed from passive identity confusion to active identity creation through decisive action
In Your Life:
Sometimes you become who you need to be by acting like that person first, not by waiting to feel ready.
Power
In This Chapter
Jim discovers that real power comes from taking decisive action in moments of vacuum, not from formal authority
Development
Evolved from observing others' power struggles to actively seizing power when opportunity presents itself
In Your Life:
True authority often belongs to whoever is willing to take responsibility and act when others hesitate.
Trust
In This Chapter
Jim must navigate a dangerous alliance with Hands, recognizing both the necessity and the risks of trusting desperate people
Development
Developed from naive trust through betrayal to strategic, cautious cooperation
In Your Life:
When you're in a position of strength, desperate people will make deals they plan to break later.
Growth
In This Chapter
Jim experiences the intoxicating rush of command and accomplishment, but Stevenson hints at the dangers of overconfidence
Development
Progressed from passive learning to active mastery, now facing the challenges that come with success
In Your Life:
Your biggest victories can set you up for your biggest mistakes if success makes you stop being careful.
Modern Adaptation
When the Promotion Goes Sideways
Following Jim's story...
Jim walks into the startup office Monday morning to find chaos—the CTO and head of sales had a massive blowout Friday night, both quit via angry emails, and half the development team called in sick. The charismatic CEO who recruited Jim is nowhere to be found, just a note saying he's 'handling investors.' Jim realizes the product demo for their biggest potential client is Thursday, and nobody's in charge. While other interns panic or make excuses to leave early, Jim starts making calls—organizing the remaining developers, coordinating with the client, even accessing the CEO's calendar to reschedule non-essential meetings. By Tuesday, people are looking to him for direction. He moves into the CTO's office and starts running daily standups. The power feels intoxicating—at seventeen, he's essentially running a tech company. But something bothers him about how easily the CEO disappeared during the crisis, and how quickly that same CEO praises Jim's 'initiative' when he finally returns Wednesday with a big smile and vague explanations.
The Road
The road Jim Hawkins walked in 1883, Jim walks today. The pattern is identical: chaos creates leadership vacuums, and those who act decisively can claim power—but success in crisis often blinds us to ongoing dangers.
The Map
This chapter provides a navigation tool for recognizing when systems collapse and how to step into leadership roles. Jim learns to act quickly when authority structures fail, but also to stay alert when things seem too easy.
Amplification
Before reading this, Jim might have waited for someone else to take charge during the office crisis, missing his chance to prove himself. Now he can NAME the leadership vacuum, PREDICT that decisive action will be rewarded, and NAVIGATE the opportunity while staying wary of people who benefit from chaos.
You now have the context. Time to form your own thoughts.
Discussion Questions
- 1
What exactly happens when Jim boards the Hispaniola, and how does he respond to finding himself alone with the wounded Israel Hands?
analysis • surface - 2
Why does Jim's act of tearing down the pirate flag matter so much, and what does it accomplish beyond just removing a piece of cloth?
analysis • medium - 3
Think about times when normal rules broke down at your workplace, school, or in your family. Who stepped up to take charge, and how did that change their position permanently?
application • medium - 4
If you found yourself in Jim's position—suddenly in charge during a crisis but dealing with someone you couldn't fully trust—how would you balance taking command with staying safe?
application • deep - 5
What does this chapter reveal about how power actually works in real life, especially the difference between official authority and the kind that emerges during chaos?
reflection • deep
Critical Thinking Exercise
Map Your Crisis Leadership Moment
Think of a time when normal order broke down around you—a family emergency, workplace crisis, or community problem. Write about who stepped up to take charge and what they did to claim that leadership role. Then identify a current situation in your life where there's a leadership vacuum waiting to be filled.
Consider:
- •Look for moments when people were confused and looking for direction
- •Notice what specific actions turned someone from follower into leader
- •Pay attention to symbolic gestures that declared new authority
Journaling Prompt
Write about a leadership opportunity you see right now in your life. What would be your equivalent of 'tearing down the pirate flag'—the decisive action that would signal you're taking charge?
Coming Up Next...
Chapter 26: The Cat and Mouse Game
As the story unfolds, you'll explore to recognize when someone is trying to manipulate you through misdirection, while uncovering staying alert and thinking ahead can save your life in dangerous situations. These lessons connect the classic to contemporary challenges we all face.